Azelaic acid (nonanedioic acid) [CAS 123-99-9; InChIKey BDJRBEYXGGNYIS-UHFFFAOYSA-N; Reaxys,

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Results

HO

OH

1. Query O

Date

353 reactions in 2016-03-15 06h:19m:32s (EST) Reaxys

O

Search as: As drawn

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HO

OH

HO OH

O

O

Rx-ID: 23054283 View in Reaxys 1/353 Yield 97 %

Conditions & References 6 : Example 6 [Composition of Polyester] By using the effect of the hafnium (IV) compound as an esterification catalyst, the synthesis of polyester shown in Table 3 was studied (S. R. Sandler and W. Karo, Polymer Synthesis, 2nd ed. (Academic Press: San Diego, 1992) Vol.1, Chapter 2). A Soxhlet tube filled with dried molecular sieves 4A (about 1.5 g) was connected to the top of a 5 ml eggplant flask contained with a teflon coated magnetic stirrer, and a cooling tube was further attached over said Soxhlet tube.

10 mmol of hydroxycarboxylic acid, 2 ml of o-xylene and 0.2 mol percent of hafnium chloride (IV).bul.(THF)2were added and heating reflux was conducted in the argon for 24 hours. After the reaction, a solution wherein the mixture solution was dissolved into 30 ml of chloroform was poured into 150 ml of acetone while being stirred. The white precipitation that was produced, was collected by filtration, and dried under reduced pressure. Furthermore, by the same method, 10 mmol of dicarboxylic acid, 10 mmol of diol, 2 ml of o-xylene and 0.2 mol percent of hafnium chloride (IV).bul.(THF)2 were added and heating reflux was conducted in the argon for 24 hours. After the reaction, the mixture solution was dissolved in 200 ml of chloroform, and 30 ml of methanol was added. The mixture solution was concentrated, the white precipitation thus produced was collected by filtration, and dried under reduced pressure. [0028] The results are shown in Table 3. In Table 3, the following are shown: the yield represents isolated yield; DP stands for the degree of polymerization; DP and the number average molecular weight (Mn) are values obtained by 1H NMR; the weight-average molecular weight (Mw) is the value wherein gel permeation column chromatography (two columns of Two linear TSKgel-GMXXL (Tosoh Corporation) connected in series were used) is conducted to 0.2percent by weight of the generated polymer in THF at 40° C., with polystyrene as a standard; the value in parenthesis for HO [CO(CH2)11O]nH is a value of thermal polymerization condensation in the absence of catalyst; the various values for polyester in the bottom line are the values obtained by using 1 mol percent of hafnium chloride (IV).bul.(THF)2 and conducting the reaction for 4 days. These results revealed that the hafnium chloride (IV).bul.(THF)2 is useful as a catalyst for polycondensation reaction in the method for preparing polyester using ω-hydroxycarboxylic acid or the method for preparing polyester using α,ω-aliphatic dicarboxylic acid and α, ω-aliphatic diol. [TABLE-US-00003] TABLE 3 isolated yield polyester (percent) DPMn .x. 104 Mw .x. 104 HO[CO(CH2)9O]nH 95 >200 1.82 3.40 [>3.40]HO[CO(CH2)11O]nH 97 >200 2.77 7.24 [>3.96] (88) (45) -[0.89)] -HO[CO(CH2)2CO2(CH2)6O]nH 98 >200 2.24 3.87 [>4.00]HO[CO(CH2)7CO2(CH2)10O]nH 97 >200 2.69 5.83 [>6.52] 96 >200 1.34 6.51 [>6.09] With molecular sevies 4A, [HfCl4(thf)2] in o-xylene, Time= 24h, Heating / reflux Patent; Ishihara, Kazuaki; Yamamoto, Hisashi; US2004/15005; (2004); (A1) English View in Reaxys

96 %

6 : Example 6 [Composition of Polyester] By using the effect of the hafnium (IV) compound as an esterification catalyst, the synthesis of polyester shown in Table 3 was studied (S. R. Sandler and W. Karo, Polymer Synthesis, 2nd ed. (Academic Press: San Diego, 1992) Vol.1, Chapter 2). A Soxhlet tube filled with dried molecular sieves 4A (about 1.5 g) was connected to the top of a 5 ml eggplant flask contained with a teflon coated magnetic stirrer, and a cooling tube was further attached over said Soxhlet tube.

10 mmol of hydroxycarboxylic acid, 2 ml of o-xylene and 0.2 mol percent of hafnium chloride (IV).bul.(THF)2were added and heating reflux was conducted in the argon for 24 hours. After the reaction, a solution wherein the mixture solution was dissolved into 30 ml of chloroform was poured into 150 ml of acetone while being stirred. The white precipitation that was produced, was collected by filtration, and dried under reduced pressure. Furthermore, by the same method, 10 mmol of dicarboxylic acid, 10 mmol of diol, 2 ml of o-xylene and 0.2 mol percent of hafnium chloride (IV).bul.(THF)2 were added and heating reflux was conducted in the argon for 24 hours. After the reaction, the mixture solution was dissolved in 200 ml of chloroform, and 30 ml of methanol was added. The mixture solution was concentrated, the white precipitation thus produced was collected by filtration, and dried under reduced pressure. [0028] The results are shown in Table 3. In Table 3, the following are shown: the yield represents isolated yield; DP stands for the degree of polymerization; DP and the number average molecular weight (Mn) are values obtained by 1H NMR; the weight-average molecular weight (Mw) is the value wherein gel permeation column chromatography (two columns of Two linear TSKgel-GMXXL (Tosoh Corporation) connected in series were used) is conducted to 0.2percent by weight of the generated polymer in THF at 40° C., with polystyrene as a standard; the value in parenthesis for HO [CO(CH2)11O]nH is a value of thermal polymerization condensation in the absence of catalyst; the various values for polyester in the bottom line are the values obtained by using 1 mol percent of hafnium chloride (IV).bul.(THF)2 and conducting the reaction for 4 days. These results revealed that the hafnium chloride (IV).bul.(THF)2 is useful as a catalyst for polycondensation reaction in the method for preparing polyester using ω-hydroxycarboxylic acid or the method for preparing polyester using α,ω-aliphatic dicarboxylic acid and α, ω-aliphatic diol. [TABLE-US-00003] TABLE 3 isolated yield polyester (percent) DPMn .x. 104 Mw .x. 104 HO[CO(CH2)9O]nH 95 >200 1.82 3.40 [>3.40]HO[CO(CH2)11O]nH 97 >200 2.77 7.24

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[>3.96] (88) (45) -[0.89)] -HO[CO(CH2)2CO2(CH2)6O]nH 98 >200 2.24 3.87 [>4.00]HO[CO(CH2)7CO2(CH2)10O]nH 97 >200 2.69 5.83 [>6.52] 96 >200 1.34 6.51 [>6.09] With molecular sevies 4A, [HfCl4(thf)2] in o-xylene, Time= 24h, Heating / reflux Patent; Ishihara, Kazuaki; Yamamoto, Hisashi; US2004/15005; (2004); (A1) English View in Reaxys

HO

OH O

HO

HO

O

O

Z O

Rx-ID: 9872452 View in Reaxys 2/353 Yield

Conditions & References

86 %, 82 % With cetylpyridinium peroxotungstophosphate, hydrogen peroxide in water, Time= 1h, T= 80 °C Pai; Tolstikov; Berdnikova; Kustova; Khlebnikova; Selivanova; Shangina; Kostrovskii; Russian Chemical Bulletin; vol. 54; nb. 8; (2005); p. 1847 - 1854 View in Reaxys 86.1 %, 81.5 %

With H3[PW12O40], hydrogen peroxide, 1-hexadecylpyridinium bromide in water, Time= 5h, T= 85 °C , Green chemistry, Reagent/catalyst, Temperature, Concentration Godard, Anais; De Caro, Pascale; Thiebaud-Roux, Sophie; Vedrenne, Emeline; Mouloungui, Zephirin; JAOCS, Journal of the American Oil Chemists' Society; vol. 90; nb. 1; (2013); p. 133 - 140 View in Reaxys

75 %, 74 % Ozonolysis of oleic acid (1). General procedure General procedure: At ozone generator output 40 mmol O3/h through a solution of 1.41 g (5.0 mmol) of oleic acid 1 in 25 mL of anhydrous alcohol or 20 mL of anhydrous THF or 25 mL of a mixture AcOH–CH2Cl2, 1 : 5, at 0 °C was bubbled ozone-oxygen mixture till 5.5 mmol of ozone was consumed. The reaction mixture was flushed with argon and then it was treated by two procedures. a. At 0 ° 1.20 g (17.3 mmol) of NH2OH·HCl was added, the mixture was stirred at room temperature till disappearance of peroxides (iodine-starch test). The solvent was distilled off, the residue was dissolved in CHCl3 (50 mL), the obtained solution was washed with H2O (2 × 15 mL), dried over Na2SO4, and evaporated.

Ozonolysis in a mixture of acetic acid and dichloromethane. By method b after chromatographing 1.86 g of residue (SiO2, petroleum ether–tert-butyl methyl ether, 2 : 1) we obtained 0.60 g (75percent) of nonanoic acid 3 and 0.64 g (74percent) of nonanedioic acid 2, whose IR, 1H and 13C NMR spectra were identic to those previously described [17].

Stage 1: With oxygen, ozone, T= 0 - 20 °C Stage 2: With semicarbazide-hydrochloride in methanol, T= 0 °C , Solvent, Reagent/catalyst Ishmuratov, G. Yu.; Yakovleva; Botsman; Legostaeva, Yu. V.; Nazarov; Baidimirov; Russian Journal of Organic Chemistry; vol. 51; nb. 5; (2015); p. 610 - 614 View in Reaxys 64 %, 35 % 11 :(Reference Example 11)An oxygen-containing compound was produced using a batch reaction process.First, oleic acid (0.565 g, 2.00 mmol) was added to a 50 mL stainless steel autoclave, and 28 g of a high-pressure carbon dioxide solution of high-purity ozone containing 2.7 mmol of ozone was supplied from an ozone supply device to give 6.5 MPa at 15°C.After stirring for 10 minutes, the temperature was increased to 140°C to give 22 MPa, and stirring while heating was conducted for 15 minutes.After the reaction, the autoclave was cooled with ice, and the pressure was reduced; subsequently, the contents were treated with diazomethane, and the reaction mixture was analyzed by gas chromatography using biphenyl as an internal standard. The results confirmed that azelaic acid was obtained in a yield of 64percent, and nonanoic acid was obtained in a yield of 35percent.

With ozone in carbon dioxide, Time= 0.416667h, T= 15 - 140 °C , p= 48754.9 - 165017Torr , Autoclave Patent; Utsunomiya University; EP2399897; (2011); (A1) English View in Reaxys

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51.5 - 52.7 %

1 :Example 1; Oxidative Ozonolysis of Oleic Acid; A micro falling-film reactor was used for the first part of the reaction, the reaction of ozone and oleic acid. The system consisted of 64 channels with a channel width and a channel depth of 300 μm and a channel length of 75 mm. The channels were operated in parallel and were etched through for educt input and product removal. The cooling channels corresponded in their diameter to the reaction channels. By virtue of the construction of the microreactor, contact between gas and liquid took place solely in the cooled region. The reaction was carried out in countercurrent, although co-current operation is also possible. Technical oleic acid with the following composition was used for the ozonolysis: 5percent palmitoleic acid (C16:1-FA), 69percent oleic acid (C18:1-FA), 13percent linoleic acid (C18:2-FA), 1percent linolenic acid (C18:3-FA) and 1percent gadoleic acid (C20:1). The other constituents were generally fatty acids with a chain length of C12 to C20. To dilute the reactants, the technical oleic acid was mixed with pelargonic acid in a ratio of 1:2. Owing to their instability, the ozonization products were directly reacted and cleaved with oxygen in microreactors. In such a fixed-bed microreactor consisting of 50 parallel, 70 mm-long reaction channels, with a diameter of 600 μm, with 25 μm thick filters at the outlet of the microchannels, providing for retention of the catalyst powder, having particle diameters of 50 to 80 μm, using zeolite activated with manganese, as described in International Published Application WO 95/21809 A1, the reaction was carried out at 95° C., the reactor being heated with thermal oil. In view of the residence time required, two reactors of this type were arranged in tandem.

The reactors for the second reaction step were operated in co-current (trickle flow) with oxygen, the mass ratio between ozonization products and oxygen being adjusted to 90:10. However, countercurrent operation is also possible. In all tests, ca. 0.3 Nl/h oxygen was used per reactor. The heat of reaction was dissipated through the thermal oil. Both reaction steps were carried out continuously. The first reaction step took place at 20° C. 0.1 ml/min. of the liquid fatty acid mixture was used. The quantity of starting gas was varied according to the ozone concentration and the unreacted ozone was catalytically destroyed. The ozonolysis of technical oleic acid was carried out in the first microreaction system. In the second microreaction system, the ozonization products formed were cleaved under the effect of oxygen to form a mixture, with the principal constituents being azelaic and pelargonic acid. The results are set out in Table 1 (recording the mean values of three measurements). The yield of azelaic acid is based on the total input of the technical oleic acid used, i.e., including the saturated constituents. The volume/time yield is based on the empty volumes of the reactors used. The reaction mixture was analyzed by GC. Only minute traces of oleic acid were detected, so that the conversion under the selected conditions in the first reaction step can be regarded as a full conversion. After leaving the second oxidation reactor, ozonides could no longer be detected either. To monitor the GC analyses, relatively large quantities, from repeated test runs, were worked up as follows: the pelargonic acid was first distilled off and the azelaic acid was extracted with water and crystallized, yellowish crystals being obtained. After a recrystallization step, white crystals were obtained. The melting point was between 103° and 105° C., i.e., close to that of pure azelaic acid. GC analysis revealed purities of 97to 99percent. The yield of azelaic acid, based on the quantity of technical oleic acid used, was between 51.5 and 52.7percent of the theoretical and, by virtue of the excellent dissipation of heat, was almost independent of the ozone concentration in the starting gas. The yield, and hence the selectivity, for azelaic acid exceeded those of conventional processes for the selected starting composition. TABLE 1 Test results (variation of the ozone concentration in the first reaction stage, oxidation under identical conditions at 95° C. in a fixed-bed microreactor) Parameter 1 2 3 4 5 Ratio of oleic to 1:2 1:2 1:2 1:2 1:2 pelargonic acid [kg/kg] Starting fatty acid 0.1 0.1 0.1 0.1 0.1 [ml/min] c(ozone) in the starting 2 5 7 10 13 gas [percent] Starting gas [NI/h] 8.5 3.4 2.4 1.7 1.3 Temperature [° C.] 20 20 20 20 20 Pressure [bar] 1.3 1.3 1.3 1.3 1.3 Residence time [s] 120 120 120 120 120 Yield of azelaic acid [percent] 51.5 52.1 52.5 52.7 52.3 Volume/time yield 1.12 1.13 1.14 1.14 1.13[t * h-1 * m-3]* Volume/time yield 0.26 0.26 0.27 0.27 0.27[t * h-1 * m-3]** *Yield of azelaic acid, based on the volume of the falling-film absorber **Yield of azelaic acid, based on the volume of the falling-film absorber and the two following oxidizers With ozone, zeolite activated with manganese, T= 95 °C , Product distribution / selectivity Patent; Gutsche, Bernhard; Franzen, Stefan; Kloeker, Markus; US2007/276165; (2007); (A1) English View in Reaxys With sodium periodate, ruthenium trichloride in water, acetonitrile, Time= 2h, T= 20 °C , Product distribution, Further Variations: Solvents, reaction time Zimmermann, Francois; Meux, Eric; Mieloszynski, Jean-Luc; Lecuire, Jean-Marie; Oget, Nicolas; Tetrahedron Letters; vol. 46; nb. 18; (2005); p. 3201 - 3203 View in Reaxys With potassium permanganate in supercritical carbon dioxide, T= 34.99 °C , p= 91509.2Torr , Kinetics, Temperature Sparks, Darrell L.; Antonio Estevez; Hernandez, Rafael; Green Chemistry; vol. 11; nb. 7; (2009); p. 986 - 993 View in Reaxys With Ru(acetylacetonate)3, dipicolinic acid,, water, hydrogen peroxide in tert-butanol, Time= 24h, T= 80 °C Behr, Arno; Tenhumberg, Nils; Wintzer, Andreas; RSC Advances; vol. 3; nb. 1; (2013); p. 172 - 180

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View in Reaxys 10 : EXAMPLES 1 TO 12 0151] The tests described below illustrate the reaction for oxidation of oleonitrile (ON) and also, by way of comparison, that of oleic acid (OA) and of methyl oleate (MO) by means of aqueous hydrogen peroxide, of varying the reaction parameters, i.e. the H2O2 content of the solution injected, and the injection molar ratios and flow rates, at a constant set temperature (70° C.) and under atmospheric pressure. [0152] 100 g of fatty compound and 1.1 g of tungstic acid (H2WO4; Merck 98percent) are introduced into a 250 cm3 jacketed reactor comprising a mechanical stirrer, and then stirred and heated at 70° C., said temperature being maintained by circulation of thermostatic water. The aqueous hydrogen peroxide is then added in weight contents which are variable according to the tests, via a peristaltic pump at variable addition speeds according to the tests. The reaction is stopped after 6 h, the aqueous phase is separated for analysis. The remaining organic phase is washed several times with hot water until aqueous hydrogen peroxide has disappeared from the washing water. [0153] The fatty substrates introduced come from the following sources: The fatty substrates introduced come from the following sources: [0154] oleonitrile (ON): Arkema with C16:0: 3percent, C18:0: 9.7percent, C18:1: 84.7percent, C18:2: 1percent (percent by weight). [0155] oleic acid (OA): Oleon Radiacid 0210 (C18:1: 72percent, C18:2: 9percent by weight) [0156] methyl oleate (MO): Aldrich Grade Technique (C18:1: 70percent by weight) [0157] The operating conditions and the results obtained are given in table 1 hereinafter, in which “molar ratio” denotes the H2O2/fatty compound molar ratio and NA denotes the presence (Y) or the absence (N) of nonanoic acid, characteristic of the cleavage of the molecule. [TABLE-US-00001] TABLE 1 operating conditions and results ExamFlow Initial Final ple [H2O2] Molar rate iodine iodine No. Substrate (percent) ratio g/min value value NA 1 ON 50 6 0.24 98 4 Y 2 ON 50 4 0.48 98 30 Y 3 ON 50 6 0.48 98 41 Y 4 ON 35 4 0.34 98 37 N 5 ON 50 4 0.48 98 32 Y 6 MO 35 1.8 0.128 91 74 N 7 MO 50 4 0.48 91 80 N 8 MO 50 4 0.48 91 87 N 9 OA 35 1.8 0.128 86 9 N 10 OA 50 2.7 0.5 86 9 Y 11 OA 35 1.8 0.256 86 33 N 12 OA 50 6 0.48 86 26 Y [0158] The oleonitrile oxidation reaction makes it possible to substantially reduce the iodine value of the medium (see example 1) marking the disappearance of the double bonds (formation of diols or cleavage). The H2O2 concentration has an influence on the cleavage of the molecule treated (compare examples 1, 2, 3 and with example 4) resulting in heminitrile formation. [0159] The methyl oleate oxidation reaction results only in a very low conversion of the double bonds regardless of the operating conditions. This oleic acid derivative is not therefore suitable for the formation of diacids by oxidative cleavage. [0160] The oleic acid oxidation reaction allows a reduction in the iodine value of the medium (examples 9 to 12) and the formation of diacids, with a suitable H2O2 concentration.

With hydrogen peroxide, tungsten(VI) trioxide hydrate in water, Time= 6h, T= 70 °C , p= 760.051Torr , Concentration Patent; ARKEMA FRANCE; Brandhorst, Markus; Couturier, Jean-Luc; Dubois, Jean-Luc; US2013/345388; (2013); (A1) English View in Reaxys 1 : EXAMPLE 1 In Situ Preparation of the Phase-Transfer Catalyst EXAMPLE 1 In Situ Preparation of the Phase-Transfer Catalyst In a method of oxidative molecular cleavage of a fatty compound and of preparation of carboxylic acids (especially azelaic acid (COOH-(CH2)7-COOH) and pelargonic acid (CH3-(CH2)7-COOH)) according to the invention, a fatty acid composition comprising oleic acid is first prepared from a sunflower oil having a high content of oleic acid (ARTERRIS, Toulouse, France). Enzymatic hydrolysis of the sunflower oil is carried out, during which 22.5 kg of sunflower oil are placed in contact with a solution of a lipase (Lyven, Colombelles, France) of Candida cylindracea in distilled water (20.1 kg) with magnetic stirring at 40° C. for 5 hours. A fatty acid preparation is formed, the composition of which, determined by gas chromatography, is given in Table 1 below.TABLE 1 Fatty acid Composition by mass, percent Oleic acid, C18:1 87.6 Linoleic acid, C18:2 4.7 Palmitic acid, C16:0 3.5 Stearic acid, C18:0 3.1 Capric acid, C10:0 0.2 Others 0.9 21 g of this fatty acid preparation comprising 65 mmol of oleic acid are placed in a 250 ml three-necked round-bottomed flask equipped with a cooler, a mechanical stirrer and a heating device. There are added dropwise 2 ml of an aqueous solution of a quaternary ammonium salt (3.36 mmol) selected from the group formed of tetrabutylammonium chloride (n-Bu4NCl, Sigma Aldrich, Saint-Quentin Fallavier, France), tetrabutylammonium bromide (n-Bu4NBr, Sigma Aldrich, Saint-Quentin Fallavier, France), N-cetylpyridinium chloride monohydrate (C5H5N(n-C16H33)3Cl, H2O, Sigma Aldrich, Saint-Quentin Fallavier, France), Nmethyl-N,N,N-trioctylammonium chloride (CH3N(n-C8H17)3Cl, Sigma Aldrich, Saint-Quentin Fallavier, France), which is better known by the name "aliquat 336", and N,N,N,N-tetraoctylammonium chloride (N(n-C8H17)4Cl, Sigma Aldrich, Saint-Quentin Fallavier, France). An emulsion of the oleic acid and the solution of the quaternary ammonium salt is formed by mechanical stirring of the resulting mixture.There are prepared by mixing and stirring at ambient temperature for 30 minutes 4 g (1.2 mmol) of tungstophosphoric acid (H3PW12O40.15.4H2O) and 34 ml of 30percent oxygenated water (325.0 mmol) in 5 ml of distilled water. The solution of tungstophosphoric acid is added to the emulsion of the oleic acid and the quaternary ammonium salt. The addition of the solution of tungstophosphoric acid to the three-necked flask containing the emulsion is carried out dropwise over a period of 5 minutes. After addition of the solution of tungstophosphoric acid to the emulsion, the reaction mixture is heated to a temperature of 60° C. The reactor is placed and maintained under mechanical stirring (400 rpm) at a temperature of 85° C. and at atmospheric pressure for a period of

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5 hours, and the reactor is then allowed to cool to ambient temperature again. The pH of the reaction mixture is adjusted to a value of pH=1 by addition of one volume of an aqueous solution of hydrochloric acid at a concentration of 4 mol/ l.In order to separate the carboxylic acids formed and the catalyst, one volume of ethyl acetate is added to the acidic mixture at pH=1 and then the reaction mixture is placed at a precipitation temperature (Tprecip, ambient temperature or temperature below 4° C.) so as to form a precipitate of the catalyst. The precipitate formed is washed with ethyl acetate. The aqueous phase containing the salts is separated from the organic phase in a separating funnel and is then washed with ethyl acetate. The different organic phases are combined, dried over ammonium sulfate and evaporated under reduced pressure.The samples obtained are analyzed and quantified by gas chromatography by means of a Varian chromatograph coupled to a flame ionization detector (FID) and equipped with a capillary column (L 50 m, 0.25 mm, particle size 25 -m) for analysis of the fatty acid methyl esters. The mobile phase is helium (Air liquide, France) at a pressure of 1034 hPa (15 psi) at the head of the capillary column. The temperature of the injector and of the detector is 250° C. The temperature of the oven containing the column is maintained at 100° C. for 5 minutes and is then increased gradually to 180° C. at a rate of 5° C./minute over 10 minutes and is finally increased gradually to 250° C. at a rate of 10° C./minute over 5 minutes and maintained at that temperature for 43 minutes.For the purposes of analysis, a solution of each sample is prepared at a concentration of 10 mg/ml in methyl tert-butyl ether (MTBE). The fatty acids are converted into methyl esters by treatment with trimethylsulfonium hydroxide. Pentadecanoic acid at a concentration of 2 mg/ml is added as internal standard. The results are presented in Table 2 below, in which Tprecip is the precipitation temperature, AZA percent and PEA percent represent the value of the synthesis and extraction yield of azelaic acid and pelargonic acid, respectively, relative to the starting oleic acid.TABLE 2 PEA, Catalyst prepared in situ Tprecip AZA, percent percent (n-Bu4N)3{PO4[WO(O2)2]4}; (A) 4° C. 77.6 80.9 (n-Bu4N)3{PO4[WO(O2)2]4}; (A) RT 72.9 73.9 (C5H5N(n-C16H33))3{PO4[WO(O2)2]4}; (B) 4° C. 81.5 86.1 (C5H5N(n-C16H33))3{PO4[WO(O2)2]4}; (B) RT 71.8 70.9 (CH3N(n-C8H17)3)3{PO4[WO(O2)2]4}; (C) 4° C. 78.5 82.0 (CH3N(n-C8H17)3)3{PO4[WO(O2)2]4}; (C) RT 71.3 77.2 ((n-C8H17)4N)3{PO4[WO(O2)2]4}; (D) 4° C. 73.2 76.5 An improved yield is observed for a precipitation of the catalyst carried out at a temperature of +4° C. in comparison with a precipitation of the catalyst carried out at ambient temperature.

With tungstophosphoric acid *15.4 H2O, 1-hexadecylpyridinium chloride, hydrogen peroxide in water, Time= 5h, T= 85 °C , p= 760.051Torr , Reagent/catalyst, Temperature, Concentration Patent; INSTITUT NATIONAL DE LA RECHERCHE AGRONOMIQUE; INSTITUT NATIONAL POLYTECHNIQUE DE TOULOUSE; Godard, Anaïs; Thiebaud Roux, Sophie; De Caro, Pascale; Vedrenne, Emeline; Mouloungui, Zéphirin; US2014/371487; (2014); (A1) English View in Reaxys 2 : Extraction of a Diacid (Azelaic Acid: AZ) from a Reaction Mixture R2 Via the Oxidative Cleavage of Oleic Acid The reaction for the oxidative cleavage of oleic acid is performed in a similar manner to that for the oxidative cleavage of oleonitrile (replacement with oleic acid). The oleic acid used is Oleon at a purity of 75percent. The reaction takes place at 70° C. without a stream of air and with 144percent pure H2O2 relative to the pure oleic acid. Table 5 below gives the composition of the oleic acid cleavage solution and its extract with 58/42 acetic acid (AA)/water (weight ratio).

With hydrogen peroxide, T= 70 °C Patent; ARKEMA FRANCE; Brandhorst, Markus; US2015/299107; (2015); (A1) English View in Reaxys 91 %Chro- Oxidative Cleavage in a Single Step mat., 69 In a 250-mL round-bottom flask equipped with a condenser, tungstic acid (0.283 g, 1.13 mmol) was suspended in %Chromat. aqueous solution of H2O2 (60 percent w/w, 51.2 g,904 mmol) and the system was stirred at 343 K. Oleic acid (36.3 mL, 113 mmol) was added as soon as complete dissolution of tungstic acid was observed. The reaction mixture was stirred under reflux. After 8 h, the mixture was allowed to cool down to room temperature and cool water (50 mL) was added. The reaction mixture was extracted with hot ethyl acetate (4 × 100 mL). The combined organic layers were dried with anhydrous sodium sulfate and evaporated under reduced pressure. The products were analyzed by 1H NMR without further purification of the crude material and by GC after derivatization (tr AA = 11 min, tr PA = 4.2 min, tr DSA = 20 min).

With hydrogen peroxide, tungsten(VI) trioxide hydrate in water, Time= 8h, Reflux Benessere, Vincenzo; Cucciolito, Maria E.; De Santis, Augusta; Di Serio, Martino; Esposito, Roberto; Ruffo, Francesco; Turco, Rosa; Journal of the American Oil Chemists' Society; vol. 92; nb. 11-12; (2015); p. 1701 - 1707 View in Reaxys

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OH

HO

HO O

OH O

OH

O

Rx-ID: 207241 View in Reaxys 3/353 Yield

Conditions & References With Catalyst M-Chromium oxide, sulfuric acid Bennett; Gudgeon; Journal of the Chemical Society; (1938); p. 1679 View in Reaxys With potassium permanganate, acetone Bougault; Schuster; Journal de Pharmacie et de Chimie; vol. <8> 15; (1932); p. 6; Chem. Zentralbl.; vol. 103; nb. I; (1932); p. 1890 View in Reaxys Oxidative Cleavage in Two Steps In a 250-mL round-bottom flask equipped with a condenser, tungstic acid (0.040 g, 0.160 mmol) was suspended in aqueous solution of H2O2 (60 percent w/w, 1.36 g, 24 mmol), and the system was stirred at 343 K. Oleic acid (5.1 mL, 16 mmol) was added as soon as complete dissolution of tungstic acid was observed. After 2 h, the mixture was allowed to cool down to room temperature and NaOCl (4.5 percent active Cl2, 150 mL, 95.4 mmol) was added. The system was stirred at room temperature for 2 h, and pH was then adjusted to 1 using aqueous hydrochloric acid solution (37 percent w/w). The reaction mixture was extracted with ethyl acetate (4 × 200 mL). The combined organic layers were dried with anhydrous sodium sulfate and evaporated under reduced pressure. The products were analyzed by 1H NMR without further purification of the crude material and through GC after derivatization (tr AA = 11 min,tr PA = 4.2 min).

With sodium hypochlorite in water, Time= 2h, T= 20 °C Benessere, Vincenzo; Cucciolito, Maria E.; De Santis, Augusta; Di Serio, Martino; Esposito, Roberto; Ruffo, Francesco; Turco, Rosa; Journal of the American Oil Chemists' Society; vol. 92; nb. 11-12; (2015); p. 1701 - 1707 View in Reaxys

N HO

OH

N

–O

N

O

2

2 H

H

–O

O– O

O

O

N

N

O O N

Zn 2+ Zn 2+

Rx-ID: 36693976 View in Reaxys 4/353 Yield 53 %

Conditions & References 2.4. Synthesis of complex [Zn(pmbm)(aze)]n (3) A mixture of Zn(AC)2·2H2O (21.9 mg, 0.1 mmol), pmbm (24.6 mg, 0.1 mmol) and H2tpa (16.6 mg, 0.1 mmol) was stirred in ethanol-water-methanol mixed solvent (7 mL, v/v/v: 3/2/2).

The pmbm ligands were bought from the company of Jinan Henghua. Then aqueous NH3 solution (25percent, 10 d) was dropped into the mixture to give a clear solution under ultrasonic treatment.

The resultant solution was allowed to evaporate slowly in darkness at room temperature for several days to give paleyellow crystals of 1 With ammonium hydroxide in methanol, ethanol, water, T= 20 °C , Sonication Hao, Hong-Jun; Du, Ming-Yue; Wang, Dan-Feng; Sun, Cheng-Jie; Wang, Zhan-Hui; Huang, Rong-Bin; Zheng, Lan-Sun; Journal of Molecular Structure; vol. 1048; (2013); p. 124 - 129 View in Reaxys

HO

Z O

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HO HO

OH

N

HO

HO

O

N

O

OH

O

O

Rx-ID: 40448428 View in Reaxys 5/353 Yield

Conditions & References

66 %, 46 %, 45 %, 26 %

Ozonolysis of oleic acid (1). General procedure General procedure: At ozone generator output 40 mmol O3/h through a solution of 1.41 g (5.0 mmol) of oleic acid 1 in 25 mL of anhydrous alcohol or 20 mL of anhydrous THF or 25 mL of a mixture AcOH–CH2Cl2, 1 : 5, at 0 °C was bubbled ozone-oxygen mixture till 5.5 mmol of ozone was consumed. The reaction mixture was flushed with argon and then it was treated by two procedures. a. At 0 °C 1.20 g (17.3 mmol) of NH2OH·HCl was added, the mixture was stirred at room temperature till disappearance of peroxides (iodine-starch test). The solvent was distilled off, the residue was dissolved in CHCl3 (50 mL), the obtained solution was washed with H2O (2 × 15 mL), dried over Na2SO4, and evaporated. Ozonolysis in a mixture of acetic acid and dichloromethane. By method a after chromatographing 1.62 g of residue (petroleum ether–tert-butyl methyl ether, 2 : 1) we obtained 0.36 g (46percent) of nonanoic acid 3, 0.36 g (45percent) of nonanal oxime 6, 0.61 g (65percent) of nonanedioic acid 2, and 0.25 g (26percent) of 9-(hydroxyimino)nonanoic acid 4.

Stage 1: With oxygen, ozone, T= 0 - 20 °C Stage 2: With hydroxylamine hydrochloride in methanol, T= 0 °C , Solvent, Reagent/catalyst Ishmuratov, G. Yu.; Yakovleva; Botsman; Legostaeva, Yu. V.; Nazarov; Baidimirov; Russian Journal of Organic Chemistry; vol. 51; nb. 5; (2015); p. 610 - 614 View in Reaxys

N O –O

N

Cu 2+ 4 HO

OH

N

O

N

N

O

O 2

O

H H

O–

O

N

N

O

O–

N

N Cu 2+

Rx-ID: 34186470 View in Reaxys 6/353 Yield 76 %

Conditions & References Synthesis of 2 a mixture of Co(NO3)2·6H2O (145 mg, 0.5 mmol), Aze (94 mg, 0.5 mmol), L (105 mg, 0.5 mmol) was dissolved in 8 mL distilled water. The pH value was adjusted to 6.0 with 1 M NaOH solution. The resulting mixture was sealed in a 25 mL teflon-lined stainless steel vessel and heated at 160 °C for 3 days in an oven and then slowly cooled to room temperature. Purple block-shaped crystals of 1 were obtained in 62percent yield (based on Co). Similar procedures to complex 1 were performed except that Co(NO3)2·6H2O was replaced by Cu(NO3)2·4H2O (122 mg, 0.5 mmol). Blue block-shaped crystals of 2 were obtained in 76percent yield (based on Cu). Elemental analysis(percent): Calcd. for (2): C 54.83, H 5.26, N 12.18. Found: C 54.87, H 5.20, N 12.12. IR (KBr): ν (cm−1)=3101.77(w) 2926.02(w) 2851.51(w) 1572.00(s) 1527.32(s) 1498.16(w) 1399.95(m) 1305.83(m) 1266.82(w) 1238.64(w) 1142.78(w) 1061.80(m) 959.98(m) 835.21(m) 654.04(w) in water, Time= 72h, T= 160 °C , pH= 6 Zhao, Fang-Hua; Che, Yun-Xia; Zheng, Ji-Min; Inorganic Chemistry Communications; vol. 24; (2012); p. 200 - 204 View in Reaxys O

O

O

N

concentrated H2 SO4

HO

HO

H

O O

H

OH O

O

Rx-ID: 25118336 View in Reaxys 7/353 Yield 88%

Conditions & References 6 : EXAMPLE 6 EXAMPLE 6

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5 g of cyclohexanonepropionitrile are hydrolyzed to cyclohexanonepropionic acid by heating under reflux with 20 ml of a 1:1 solution of acetic acid/concentrated hydrochloric acid for 3 hours.

The mixture is extracted with CH2 Cl2, and the separated acid is mixed with 1.7 g of 59percent H2 O2.

The solution is added to 25 ml of methanol containing 2 ml of concentrated H2 SO4, and the process is carried out as described under example 5.

A cyclohexanonepropionic acid conversion of 65percent is obtained, with an azelaic acid yield of 88percent with respect to the converted product.

With hydrogenchloride, acetic acid in methanol Patent; Brichima S.p.A.; US4322547; (1982); (A1) English View in Reaxys

O

Z O

HO

OH O

HO

O

OH O

O

O

O

Rx-ID: 33974653 View in Reaxys 8/353 Yield

Conditions & References 2 :Example 2Ozonolysis and Oxidation with Addition of Acid20 g of a 0.182 molal solution of methyl oleate (95percent pure) in a solvent mixture of propionic acid and water (15 equivalents based on moles of double bond) were initially charged in a two-neck flask with gas inlet tube and reflux condenser. The feed gas, consisting of 5percent by volume of oxygen in carbon dioxide was passed through an ozone generator at a flow rate of 40 ml/min. The ozone generator was set to maximum power. The ozone-containing gas mixture was passed into the reaction mixture with stirring. The offgas stream was passed by means of gas wash bottles into a 5percent aqueous potassium iodide solution. After 60 minutes, the substrate was converted, and the gas introduction was then stopped. According to GC analysis, the reaction mixture has a content of 39.5percent of 9-nonanal and 38.2percent of methyl 9-oxononanoate.After adding hydrogen peroxide (0.454 g of a 30percent aqueous solution) and sulphuric acid (0.019 g, 95percent) the reaction mixture was then heated to 100° C. in an oil bath. After 75 minutes, nonanal and methyl 9-oxononanoate were converted completely to the respective carboxyl compounds. GC analysis: 40.22percent pelargonic acid, 38.50percent azelaic acid derivative (21.90percent monomethyl azelate+16.6percent azelaic acid) (FID signal, figure in area percent, uncorrected).

Stage 1: With ozone in water, propionic acid, Time= 1h Stage 2: With dihydrogen peroxide, sulfuric acid in water, propionic acid, Time= 1.25h, T= 100 °C Patent; Evonik Degussa GmbH; US2012/245375; (2012); (A1) English View in Reaxys

N O

N O–

6H O Co 2+ 2

HO

OH

N

O 2

O

N

O

N

O–

O–

N

O

N

O

N

N Co 2+

Rx-ID: 34186469 View in Reaxys 9/353 Yield 62 %

Conditions & References Synthesis of 1 a mixture of Co(NO3)2·6H2O (145 mg, 0.5 mmol), Aze (94 mg, 0.5 mmol), L (105 mg, 0.5 mmol) was dissolved in 8 mL distilled water. The pH value was adjusted to 6.0 with 1 M NaOH solution. The resulting mixture was sealed in a 25 mL teflon-lined stainless steel vessel and heated at 160 °C for 3 days in an oven and then slowly cooled to room temperature. Purple block-shaped crystals of 1 were obtained in 62percent yield (based on Co). Elemental analy-

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sis(percent): Calcd. for (1): C 55.39, H 5.31, N 12.30. Found: C 55.32, H 5.37, N 12.35. IR (KBr): ν (cm−1)=3090.22(w) 2924.75(w) 2852.10(w) 1557.14(s) 1532.62(s) 1419.69(m) 1307.62(w) 1275.12(w) 1251.67(w) 1128.82(w) 1069.87(m) 960.52(m) 834.93(m) 737.03(w) 661.19(w) 538.24(w). in water, Time= 72h, T= 160 °C , pH= 6 Zhao, Fang-Hua; Che, Yun-Xia; Zheng, Ji-Min; Inorganic Chemistry Communications; vol. 24; (2012); p. 200 - 204 View in Reaxys O– N

O N

N

Cd 2+ 4 HO

OH

N

O

N

O

O 2

O

H H

O–

N

N

O N

N O–

O Cd 2+

3H O 2

Rx-ID: 34186471 View in Reaxys 10/353 Yield

Conditions & References

54 %

Synthesis of 1 a mixture of Co(NO3)2·6H2O (145 mg, 0.5 mmol), Aze (94 mg, 0.5 mmol), L (105 mg, 0.5 mmol) was dissolved in 8 mL distilled water. The pH value was adjusted to 6.0 with 1 M NaOH solution. The resulting mixture was sealed in a 25 mL teflon-lined stainless steel vessel and heated at 160 °C for 3 days in an oven and then slowly cooled to room temperature. Purple block-shaped crystals of 1 were obtained in 62percent yield (based on Co).Similar procedures to complex 1 were performed except that Co(NO3)2·6H2O was replaced by Cd(NO3)2·4H2O (154 mg, 0.5 mmol). Colourless needle-like crystals of 3 were obtained in 54percent yield (based on Cd). Elemental analysis(percent): Calcd. for (3): C 44.81, H 5.37, N 9.95. Found: C 44.87, H 5.31, N 9.99. IR (KBr): ν (cm−1)=3406.91(w) 3120.02(w) 2930.00(w) 2855.30(w) 1533.50(s) 1411.82(s) 1307.13(m) 1247.47(w) 1134.13(w) 1068.50(m) 961.07(m) 840.98(w) 646.25(w). in water, Time= 72h, T= 160 °C , pH= 6 Zhao, Fang-Hua; Che, Yun-Xia; Zheng, Ji-Min; Inorganic Chemistry Communications; vol. 24; (2012); p. 200 - 204 View in Reaxys

H

OH

Z O

HO

OH

OH O

O

H

OH

O OH

Rx-ID: 34771545 View in Reaxys 11/353 Yield 60.8 %, 83.2 %

Conditions & References With H3[PW12O40], dihydrogen peroxide, 1-hexadecylpyridinium bromide in water, Time= 5h, T= 85 °C , Green chemistry Godard, Anais; De Caro, Pascale; Thiebaud-Roux, Sophie; Vedrenne, Emeline; Mouloungui, Zephirin; JAOCS, Journal of the American Oil Chemists' Society; vol. 90; nb. 1; (2013); p. 133 - 140 View in Reaxys 9 : EXAMPLE 9 Oxidative Cleavage of Ricinoleic Acid EXAMPLE 9 Oxidative Cleavage of Ricinoleic Acid A treatment as described in Example 1 of oxidative molecular cleavage of ricinoleic acid (or (9cis)-12-hydroxyoctadeca-9-enoic acid) obtained from the hydrolysis of castor oil is carried out, in which catalyst (B) is formed in situ in a molar proportion of 2percent. The initial quantity of ricinoleic acid is 14 mmol and the initial quantity of H2O2 is 163 mmol (30percent).The temperature is 85° C., the reaction time is 5 hours and the stirring speed is 400 rpm.The oxidative molecular cleavage of the ricinoleic acid leads to the formation of a diacid (azelaic acid, AZA) and of a monoacid (3-hydroxynonanoic acid), which are extracted in ethyl acetate.Azelaic

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acid and 3-hydroxynonanoic acid are obtained with yields of 83.2percent and 60.8percent, respectively, for a rate of conversion of ricinoleic acid of 99.9percent.

With tungstophosphoric acid *15.4 H2O, 1-hexadecylpyridinium chloride, dihydrogen peroxide in water, Time= 5h, T= 85 °C Patent; INSTITUT NATIONAL DE LA RECHERCHE AGRONOMIQUE; INSTITUT NATIONAL POLYTECHNIQUE DE TOULOUSE; Godard, Anaïs; Thiebaud Roux, Sophie; De Caro, Pascale; Vedrenne, Emeline; Mouloungui, Zéphirin; US2014/371487; (2014); (A1) English View in Reaxys

O

HO

OH O

HO O

O

O HO

Rx-ID: 34771548 View in Reaxys 12/353 Yield 87.3 %, 86.5 %

Conditions & References With H3[PW12O40], dihydrogen peroxide, 1-hexadecylpyridinium bromide in water, Time= 5h, T= 85 °C , Green chemistry Godard, Anais; De Caro, Pascale; Thiebaud-Roux, Sophie; Vedrenne, Emeline; Mouloungui, Zephirin; JAOCS, Journal of the American Oil Chemists' Society; vol. 90; nb. 1; (2013); p. 133 - 140 View in Reaxys 7 : EXAMPLE 7 Oxidative Cleavage of 9,10-Epoxyoctadecanoic Acid EXAMPLE 7 Oxidative Cleavage of 9,10-Epoxyoctadecanoic Acid 9,10-Epoxyoctadecanoic acid is prepared according to a method described in "Salimon et al., (2009), European Journal of Scientific Research, 32(2), 216-222" and in which 71 mmol of oleic acid are treated with freshly prepared performic acid at ambient temperature for 3 hours with magnetic stirring (400 rpm). A white powder of 9,10-epoxyoctadecanoic acid (51 mmol) is obtained, with a degree of purity of 65percent and a yield of 72percent.A treatment of oxidative molecular cleavage of the 9,10-epoxyoctadecanoic acid is carried out, in which catalyst (B) is formed in situ in a molar proportion of 2percent. The initial quantity of 9,10-epoxyoctadecanoic acid is 51 mmol and the initial quantity of H2O2 is 255 mol (30percent). The initial molar ratio 9,10epoxyoctadecanoic acid/H2O2 is 1/5, the temperature is 85° C., the reaction time is 5 hours and the speed of rotation of the mechanical stirrer is 400 rpm.The rate of conversion "TC" of 9,10-epoxyoctadecanoic acid, "AZA percent" and "PEA percent", which represent the value of the synthesis yield of azelaic acid and pelargonic acid, respectively, relative to the starting 9,10-epoxyoctadecanoic acid, are given in Table 7 below.TABLE 7 Catalyst (B) prepared in situ TC, percent AZA percent PEA percent (C5H5N(n-C16H33))3{PO4[WO(O2)2]4} 98.9 86.5 87.3 With tungstophosphoric acid *15.4 H2O, 1-hexadecylpyridinium chloride, dihydrogen peroxide in water, Time= 5h, T= 85 °C Patent; INSTITUT NATIONAL DE LA RECHERCHE AGRONOMIQUE; INSTITUT NATIONAL POLYTECHNIQUE DE TOULOUSE; Godard, Anaïs; Thiebaud Roux, Sophie; De Caro, Pascale; Vedrenne, Emeline; Mouloungui, Zéphirin; US2014/371487; (2014); (A1) English View in Reaxys

OH

O HO

HO

OH

OH O

OH

O

O

Rx-ID: 35370398 View in Reaxys 13/353 Yield 50 %

Conditions & References 8 : Oxidative Cleavage of 9,10-dihydroxy-octadecanedioic acid EXAMPLE 8 Oxidative Cleavage of 9,10-dihydroxy-octadecanedioic acid 1.04 g (3 mmol) of pure 9,10-dihydroxy-octadecanedioic acid was added to 8.6 mL (9.45 mmol) of a solution of bleach at 1.11 mol·L-1 (Aldrich Ref 81070).

After 5 h at room temperature, the aqueous phase was acidified with 37 wt. percent HCl. Azelaic acid was obtained by decanting and then filtration and was washed with cold water.

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Azelaic acid was obtained at a yield of 50percent in the form of a white solid.

M.p.=107° C., FTIR analysis, 1H, 13C NMR in CDCl3 and GC/MS of the methyl diester comply with the literature.

With sodium hypochlorite, Time= 5h, T= 20 °C , Reagent/catalyst Patent; UNIVERSITE CLAUDE BERNARD LYON I; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; Lemaire, Marc; Favre-Reguillon, Alain; Paquit, Bénédicte; Claude, Sylvain; Raoul, Yann; US2013/131379; (2013); (A1) English View in Reaxys

O O

HO

E

OH

O

OH

O

O

O

O

O

O

Rx-ID: 35688314 View in Reaxys 14/353 Yield

Conditions & References 2 :Example 2: Oxidative cleavage of (E)-dimethyl 9-octadecenedioate with added acetic acid Tungstic acid (0.0188 g) was dissolved at 60°C in a mixture of aqueous phosphoric acid (1 .50 mL of a stock solution containingl .4443 g 85percent H3P04 per liter) and aqueous 70percent hydrogen peroxide (1 .60 mL). A test tube was charged with methyltrioctylammonium chloride (0.0081 g), (E)-dimethyl 9-octadecenedioate (0.4271 g), and acetic acid (0.3015 g). The test tube, equipped with a stirring bar and a punctured septum, was placed in an oil bath of 85°C and stirred. This led to the formation of a liquid. To the test tube was added 1.10 mL of the tungstic acid in hydrogen peroxide solution (cooled to room temperature). The mixture was stirred at maximum speed overnight at 85°C. To the reaction mixture was added CD3OD (5 mL), and the solution was analyzed by proton NMR. This showed high yield formation of a mixture of methyl azelate and azelaic acid. Work up by addition of CH2CI2 (100 mL), drying over Na2S04 and evaporation afforded a white powder (0.50 g), which according to proton and carbon NMR in DMSO-d6 consisted of a mixture of methyl azelate and azelaic acid with traces of impurities With phosphoric acid, dihydrogen peroxide, Aliquatreg; 336, tungsten(VI) trioxide hydrate, acetic acid in water, T= 60 - 85 °C , Reagent/catalyst Patent; DSM IP ASSETS B.V.; ALSTERS, Paulus, Lamburtus; WO2013/92353; (2013); (A1) English View in Reaxys

OH

HO

HO O

OH O

OH

O

HO O

Rx-ID: 37626836 View in Reaxys 15/353 Yield

Conditions & References

86 %, 99 % With 1 wt Au/Al2O3, oxygen, sodium hydroxide in water, Time= 4.33333h, T= 80 °C , p= 3750.38Torr , Autoclave, Inert atmosphere Kulik, Anna; Martin, Andreas; Pohl, Marga-Martina; Fischer, Christine; Koeckritz, Angela; Green Chemistry; vol. 16; nb. 4; (2014); p. 1799 - 1806 View in Reaxys

HO

HO

OH

N O

O

O

Rx-ID: 4672637 View in Reaxys 16/353 Yield 90 %

Conditions & References With sulfuric acid, Time= 6h, T= 100 °C Cotarca; Delogu; Maggioni; Nardelli; Bianchini; Sguassero; Synthesis; nb. 3; (1997); p. 328 - 332 View in Reaxys

90 %

With sulfuric acid, Time= 6h, T= 100 °C Cotarca, Livius; Delogu, Pietro; Nardelli, Alfonso; Maggioni, Paolo; Bianchini, Roberto; Sguassero, Stefano; Alini, Stefano; Dario, Roberto; Clauti, Giuliano; Pitta, Giorgio; Duse, Gianpaolo; Goffredi, Fabrizio; Organic Process Research and Development; vol. 5; nb. 1; (2001); p. 69 - 76

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View in Reaxys 6 : azelaic acid EXAMPLE 6 azelaic acid 83.5 g of 8-cyanooctanoic acid dissolved in 300 ml of dimethyl ether ethylene glycol are heated to 130° C. for 4 hours in the presence of 50g of 40percent caustic soda.

After cooling, the reaction mixture is diluted with water, then acidified to pH 5 with diluted sulfuric acid, and then the precipitated solid is filtered.

After drying, 92 g of azelaic acid with a m.p. of 107° C. are obtained. in anhydrous ethylene glycol dimethyl ether Patent; Industrie Chimiche Caffaro, S.p.A.; US5872267; (1999); (A1) English View in Reaxys Patent; Industrie Chimiche Caffaro S.P.A.; US5917067; (1999); (A1) English View in Reaxys 6.a : azelaic acid EXAMPLE 6a azelaic acid 84.5 g of 8-cyanooctanoic acid are heated to 130° C. for 10 hours in the presence of 250 ml of concentrated sulfuric acid.

After cooling, the reaction mixture is diluted with water and ice and the solid crystalline precipitate is filtered.

After drying, one obtains 90 g of azelaic acid with a m.p. of 107° C. in sulfuric acid Patent; Industrie Chimiche Caffaro S.P.A.; US5917067; (1999); (A1) English View in Reaxys

hydrous cobalt chloride

H2 WO4

Z

HO

H

O O

H

Z O

HO

OH O

O

Rx-ID: 25519060 View in Reaxys 17/353 Yield 70%

Conditions & References 4 : EXAMPLE 4 EXAMPLE 4 Using the same apparatus as in Example 1, 100 g of crude oleic acid (80percent purity) containing 9percent linoleic acid and 0.75 g of H2 WO4 is added.

The stirred mixture is brought to 60°-65° C. and 28 g of 60percent w/w H2 O2 is added.

The H2 O2 is gradually added over about 30 mins in order to maintain the temperature between 65°-75° C. Once the addition of H2 O2 is completed the mixture is left at that temperature for 1.5 hours.

The crude reaction product so obtained is charged into an stirred 500 ml autoclave containing 150 ml of water and 1.0 g of hydrous cobalt chloride.

The autoclave is then pressurised with 65 atm of air and the temperature is raised to 70° C. The reaction mixture is treated according to the way described in example 1 obtaining 42 g of azelaic acid (yield=70percent) and 30.9 g of pelargonic acid (yield=69percent). in water Patent; Novaol S.r.l.; US5714623; (1998); (A1) English View in Reaxys

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HO

HO O

OH O

O

Rx-ID: 29534772 View in Reaxys 18/353 Yield 96 %

Conditions & References With sodium periodate, RuCl3*2.9H2O in water, Time= 0.5h, T= 20 °C , Sonication Rup, Sandrine; Sindt, Michele; Oget, Nicolas; Tetrahedron Letters; vol. 51; nb. 23; (2010); p. 3123 - 3126 View in Reaxys

HO

OH O

HO

O

Z O

Rx-ID: 206050 View in Reaxys 19/353 Yield 80 %

Conditions & References With potassium permanganate Zuo, Jiaqing; Li, Shaojun; Bouzidi, Laziz; Narine, Suresh S.; Polymer; vol. 52; nb. 20; (2011); p. 4503 - 4516 View in Reaxys

21 %

With oleate hydratase from S. maltophilia in aq. buffer, Time= 2h, T= 35 °C , pH= 8, Enzymatic reaction Song, Ji-Won; Lee, Jung-Hoo; Bornscheuer, Uwe T.; Park, Jin-Byung; Advanced Synthesis and Catalysis; vol.

356; nb. 8; (2014); p. 1782 - 1788 View in Reaxys With acetic acid, T= 90 °C , bei der Ozonisierung Patent; Rieche; DE565158; (1931); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 445 View in Reaxys With sulfuric acid, T= 0 - 8 °C , Beim Erhitzen des Reaktionsprodukts mit konz. HNO3 in Gegenwart von MnO2 auf 110-120grad Patent; Nopco Chem. Co.; US2426954; (1944) View in Reaxys Kuerzinger; ; vol. 5; (1954); p. 825,826 View in Reaxys beim Ranzigwerden Scala; Chem. Zentralbl.; vol. 69; nb. I; (1898); p. 439 View in Reaxys With oxygen, anhydrous cobalt diacetate, acetic acid, T= 65 °C Patent; Swern; Knight; US2572892; (1949) View in Reaxys With potassium permanganate, water Golendeew; ; vol. 11; nb. 3; (1955); p. 5,10; ; (1958); p. 16274 View in Reaxys Coleman; Swern; Journal of the American Oil Chemists' Society; vol. 35; (1958); p. 675 View in Reaxys With nitric acid, T= 200 °C Patent; Tallow Research Inc.; US2773095; (1952)

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View in Reaxys bei der Oxydation durch Luftsauerstoff am Licht Ciamician; Silber; Chemische Berichte; vol. 47; (1914); p. 642; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 23 I; (1914); p. 116 View in Reaxys bei der Oxydation durch N2O4 Jegorow; Journal fuer Praktische Chemie (Leipzig); vol. <2>86; (1912); p. 539 View in Reaxys With nitric acid, T= 40 - 75 °C Patent; du Pont de Nemours and Co.; US2560156; (1947) View in Reaxys With potassium permanganate, water Golendeew; ; vol. 11; nb. 3; (1955); p. 5,10; ; (1958); p. 16274 View in Reaxys Coleman; Swern; Journal of the American Oil Chemists' Society; vol. 35; (1958); p. 675 View in Reaxys 3 : Example 3 Example 3 The following reagents were added to the apparatus used in Example 1: 100 g of crude oleic acid (purity = 80percent, linoleic acid content = 9.9percent), 167 cm3f 35percent H2 2 2.0g of H2O4nd 2.0g of Arquad 2HT (registered trade mark).

The mixture was heated to 100-104°C with stirring and was kept at that temperature for 6 h.

Upon completion of the test, the aqueous phase was separated and the organic phase was subjected to continuous extraction with water at 95°C. The aqueous phases were cooled to 5°C and then filtered to produce 41.6g of azelaic acid.

Patent; Novaol S.r.l.; EP621861; (1997); (B1) english View in Reaxys With ozone, Time= 2h, T= 150 °C Kadhum, Abdul Amir H.; Wasmi, Bilal A.; Mohamad, Abu Bakar; Al-Amiery, Ahmed A.; Takriff, Mohd S.; Research on Chemical Intermediates; vol. 38; nb. 2; (2012); p. 659 - 668 View in Reaxys 2.1 With potassium permanganate Shabanian, Meisam; Mirzakhanian, Zeinab; Basaki, Nemat; Khonakdar, Hossein Ali; Faghihi, Khalil; Hoshyargar, Faegheh; Wagenknecht, Udo; Thermochimica Acta; vol. 585; (2014); p. 63 - 70 View in Reaxys

H

OH

Z

HO

OH O

O

O OH

Rx-ID: 207063 View in Reaxys 20/353 Yield 20.0 %

Conditions & References With potassium hydroxide, potassium permanganate in water, Time= 0.5h, T= 75 °C

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Narasimhan; Kothawade; Pharande; Mourya; Dhake; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 42; nb. 11; (2003); p. 2828 - 2834 View in Reaxys With nitric acid Hall; Reid; Journal of the American Chemical Society; vol. 65; (1943); p. 1467 View in Reaxys With potassium hydroxide, potassium permanganate Murai; Hamano; ; vol. 17; nb. 3; (1940); p. 138; ; (1941); p. 4621 View in Reaxys Hill; McEwen; View in Reaxys With NH4VO3, nitric acid Ischanina et al.; ; nb. 42; (1957); p. 30; ; (1959); p. 1138 View in Reaxys With nitric acid Carmichael; Journal of the Chemical Society; vol. 121; (1922); p. 2549 View in Reaxys Day; Kon; Stevenson; Journal of the Chemical Society; vol. 117; (1920); p. 645 View in Reaxys Kiliani; Chemische Berichte; vol. 54; (1921); p. 465; Chemische Berichte; vol. 61; (1928); p. 1163 View in Reaxys Baker; Ingold; Journal of the Chemical Society; vol. 123; (1923); p. 125,130 View in Reaxys Verkade; Hartman; Coops; Recueil des Travaux Chimiques des Pays-Bas; vol. 45; (1926); p. 379; Verslag van de Gewone Vergadering van de Afdeling Natuurkunde, Koninklijke Nederlandse Akademie van Wetenschappen; vol. 33; p. 767; Chem. Zentralbl.; vol. 96; nb. I; (1925); p. 1281 View in Reaxys Verkade; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 138; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 200 View in Reaxys With alkaline permanganate Hill; McEwen; Organic Syntheses; vol. 13; (1933); p. 4 View in Reaxys Kuerzinger; ; vol. 5; (1954); p. 825,826 View in Reaxys With dinitrogen tetraoxide Jegorow; Journal fuer Praktische Chemie (Leipzig); vol. <2>86; (1912); p. 539 View in Reaxys

HO

OH O

HO

O

Z O

Rx-ID: 9872440 View in Reaxys 21/353 Yield 75 %

Conditions & References With sodium periodate, ruthenium trichloride in water, ethyl acetate, acetonitrile, Time= 2h Zimmermann, Francois; Meux, Eric; Mieloszynski, Jean-Luc; Lecuire, Jean-Marie; Oget, Nicolas; Tetrahedron Letters; vol. 46; nb. 18; (2005); p. 3201 - 3203

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View in Reaxys

HO

HO O

OH O

HO O

O

Rx-ID: 29534770 View in Reaxys 22/353 Yield

Conditions & References

98 %, 62 % With sodium periodate, RuCl3*2.9H2O in water, Time= 8h, T= 20 °C , Sonication Rup, Sandrine; Sindt, Michele; Oget, Nicolas; Tetrahedron Letters; vol. 51; nb. 23; (2010); p. 3123 - 3126 View in Reaxys

O

O O

O

HO

OH O

HO

OH

HO

O

OH O

Rx-ID: 4697040 View in Reaxys 23/353 Yield

Conditions & References

2 %, 92 %

With sodium tetrahydroborate in tetrahydrofuran, Time= 120h, T= 23 °C Benitez, Pilar; Delgado, Ana; Farrera, Joan-Anton; Ribo, Josep M.; Synthetic Communications; vol. 27; nb. 10; (1997); p. 1697 - 1702 View in Reaxys

87 %, 6 %

With sodium tetrahydroborate in tetrahydrofuran, Time= 6h, T= 65 °C Benitez, Pilar; Delgado, Ana; Farrera, Joan-Anton; Ribo, Josep M.; Synthetic Communications; vol. 27; nb. 10; (1997); p. 1697 - 1702 View in Reaxys

HO

HO

E O

OH O

O

HO O

Rx-ID: 5090815 View in Reaxys 24/353 Yield

Conditions & References

79 % Chro- With dihydrogen peroxide, methyltrioctylammonium tetrakis(oxodiperoxotungsto)phos in water, Time= 5h, T= 85 °C mat., 82 % Antonelli, Ermanno; D'Aloisio, Rino; Gambaro, Mario; Fiorani, Tiziana; Venturello, Carlo; Journal of Organic Chromat.

Chemistry; vol. 63; nb. 21; (1998); p. 7190 - 7206 View in Reaxys 82 % Chro- With dihydrogen peroxide, methyltrioctylammonium tetrakis(oxodiperoxotungsto)phos in water, Time= 5h, T= 85 °C mat., 79 % Antonelli, Ermanno; D'Aloisio, Rino; Gambaro, Mario; Fiorani, Tiziana; Venturello, Carlo; Journal of Organic Chromat.

Chemistry; vol. 63; nb. 21; (1998); p. 7190 - 7206 View in Reaxys

HO

OH

Z O

O

O

Rx-ID: 2114683 View in Reaxys 25/353 Yield 73.5 %

Conditions & References With sodium hydroxide in water, Time= 6h, T= 330 - 350 °C , autoclave Zakharkin, L. I.; Guseva, V. V.; Kaverin, V. V.; Yur'ev, V. P.; Journal of Organic Chemistry USSR (English Translation); vol. 23; nb. 6; (1987); p. 1201 - 1202; Zhurnal Organicheskoi Khimii; vol. 23; nb. 6; (1987); p. 1328 - 1329 View in Reaxys

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HO

N

N

OH O

O

Rx-ID: 4672393 View in Reaxys 26/353 Yield 88 %

Conditions & References With water, Time= 48h, Rhodococcus rhodochrous AJ270 Meth-Cohn, Otto; Wang, Mei-Xiang; Chemical Communications; nb. 11; (1997); p. 1041 - 1042 View in Reaxys

88 %

With potassium phosphate buffer, Rhodococcus sp. AJ270, Time= 48h, T= 30 °C Meth-Cohn, Otto; Wang, Mei-Xiang; Journal of the Chemical Society - Perkin Transactions 1; nb. 21; (1997); p. 3197 - 3204 View in Reaxys

HO

OH HO

O

Yield 62 %

OH OH

O

poly(glycerol-azelaic acid), Mn = 2316 Da, polydispersity index 1.30, degree of polymerization 4.9; monomer(s): azelaic acid; glycerol Rx-ID: 11037917 View in Reaxys 27/353

Conditions & References With Ti(OC4H9)4, Time= 16h, T= 100 - 150 °C , p= 1.12511Torr Wyatt, Victor T.; Nunez, Alberto; Foglia, Thomas A.; Marmer, William N.; JAOCS, Journal of the American Oil Chemists' Society; vol. 83; nb. 12; (2006); p. 1033 - 1039 View in Reaxys

O O

Z

Z

O O O O

Z

O

O O

HO

OH

O O

O

O

HO

OH O

O

O

HO O

HO

O

Rx-ID: 29638369 View in Reaxys 28/353 Yield

Conditions & References 1 :Example 1Oxidation reaction was carried out with the use of a catalyst system containing 30percent hydrogen peroxide water (oxidant) (13.2 equivalents), sodium tungstate and hydrogen sulfate methyltrioctylammonium (0.15 equivalents each), sulfuric acid (0.37 mmol), and distilled water (1 ml) for triolein (1.0 g). As a result, the yield of nonanoic acid, which is monocarboxylic acid, was 87percent. In addition, the yield of azelaic acid was 19percent. The remaining product was triazelain when the reaction was terminated. Accordingly, it has been revealed that an oxidation reaction

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of triolein with hydrogen peroxide is a selective reaction, and that a reaction in which oxidation cleavage of an olefin portion results in generation of carboxylic acid proceeds in a preferential manner. The reaction formula is shown below.

With sulfuric acid, dihydrogen peroxide, sodium tungstate, [Me(n-C8H17)3N]HSO4 in water, Time= 20h, T= 90 °C , Product distribution / selectivity Patent; TOYOTA JIDOSHA KABUSHIKI KAISHA; US2010/210873; (2010); (A1) English View in Reaxys

HO

O O O

OH

O

O

O

O

Rx-ID: 2026468 View in Reaxys 29/353 Yield

Conditions & References

70 %

With oxygen, sodium t-butanolate in diethyl ether, water, Time= 4h, Ambient temperature Karim, Mohammad R.; Sampson, Paul; Journal of Organic Chemistry; vol. 55; nb. 2; (1990); p. 598 - 605 View in Reaxys

HO

OH

HO OH

O

O

poly(decamethylene azelate), degree of polymerization gt; 200, M&n=2.69E4, Mw=5.83E4; monomers: azelaic acid; 1,10-dec‐ anediol Rx-ID: 9121565 View in Reaxys 30/353 Yield

Conditions & References

97 %

With [HfCl4(thf)2] in o-xylene, Time= 24h, Heating Ishihara, Kazuaki; Nakayama, Masaya; Ohara, Suguru; Yamamoto, Hisashi; Tetrahedron; vol. 58; nb. 41; (2002); p. 8179 - 8188 View in Reaxys

H

OH

Z

O OH OH O

O

HO

OH

OH HO

O

H

O

O OH

Rx-ID: 10173344 View in Reaxys 31/353 Yield 84 %, 84 %, 4 %

Conditions & References With cetylpyridinium peroxotungstophosphate, dihydrogen peroxide in water, Time= 1h, T= 80 °C Pai; Tolstikov; Berdnikova; Kustova; Khlebnikova; Selivanova; Shangina; Kostrovskii; Russian Chemical Bulletin; vol. 54; nb. 8; (2005); p. 1847 - 1854 View in Reaxys

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HO

OH O

O

FeCl3.6H2O

O Fe 2+ O–

O

O–

Rx-ID: 29602128 View in Reaxys 32/353 Yield

Conditions & References 5.i : i) i) Iron Azelate 1 270 mg of FeCl3.6H2O (1 mmol, Aldrich, 99percent) and 188 mg (1 mmol) of azelaic acid (Aldrich, 99percent) are dispersed in 5 ml of distilled water.

The whole is left in a 23 ml Teflon body placed in a Paar metallic bomb for 3 days at 100° C. The solid is recovered by filtration and washed with acetone.

200 mg of solid are suspended in 50 ml of absolute ethanol with stirring for 5 hours to activate it.

The solid is recovered by filtration.

The particle size measured by light scattering is >1 micron (1500 nm). in ethanol, water Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - CNRS-; UNIVERSITE DE VERSAILLES SAINT-QUENTIN-EN- YVELINES; US2010/226991; (2010); (A1) English View in Reaxys 10.e : e) e) Iron Azelate 1 270 mg of FeCl3.6H2O (1 mmol, Aldrich, 99percent) and 188 mg (1 mmol) of azelaic acid (Aldrich, 99percent) are dispersed in 5 ml of distilled water.

The whole is left in a 23 ml Teflon body placed in a Paar metal bomb for 3 days at 100° C. The solid is recovered by filtration and washed with acetone.

200 mg of the solid are suspended in 50 ml of absolute ethanol with stirring for 5 h in order to activate it.

The solid is recovered by filtration.

The particle size measured by light scattering is >1 micron (1500 nm). in ethanol, water Patent; Centre National De La Recherche Scientifique - CNR S; US2011/52650; (2011); (A1) English View in Reaxys

HO

OH O

2H 2 2H H

2H

2H

2H

2H 2H 2H 2H 2H

2H

O

2H 2H 2 2H H

O

2H

2H

2H

2H

2H 2H 2H

HO

OH

OH O

2H

2H 2 H

2H 2H

2H

O

Rx-ID: 37454986 View in Reaxys 33/353 Yield

Conditions & References

74 %, Ca. 1 With NaOD, 10 platinum on carbon, water-d2, Time= 144h, T= 220 °C , p= 17251.7Torr , Inert atmosphere, Autoclave g Darwish, Tamim A.; Luks, Emily; Moraes, Greta; Yepuri, Nageshwar R.; Holden, Peter J.; Jamesa, Michael; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 56; nb. 9-10; (2013); p. 520 - 529 View in Reaxys

O HO O

O O

HO

OH

HO

HO OH

O

O

O

O

Rx-ID: 37626837 View in Reaxys 34/353 Yield 28 %

Conditions & References With 1 wt Au/Al2O3, oxygen, sodium hydroxide in water, Time= 4.33333h, T= 80 °C , p= 3750.38Torr , Autoclave, Inert atmosphere

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Kulik, Anna; Martin, Andreas; Pohl, Marga-Martina; Fischer, Christine; Koeckritz, Angela; Green Chemistry; vol. 16; nb. 4; (2014); p. 1799 - 1806 View in Reaxys

HO

OH

HO

Z

O HO

O

O

Z O

Rx-ID: 206623 View in Reaxys 35/353 Yield

Conditions & References Ozonisierung Boeeseken et al.; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 623 View in Reaxys 8 : EXAMPLE 8 Oxidative Cleavage of Linoleic Acid (LNA) EXAMPLE 8 Oxidative Cleavage of Linoleic Acid (LNA) A treatment of oxidative molecular cleavage of linoleic acid ((9cis,12cis)-octadeca-9,12-dienoic acid, LNA) is carried out according to tests no. 1 and no. 2, in which catalyst (B) is formed in situ in linoleic acid (LNA). The molar proportion LNA/H2O2/catalyst is specified in Table 8 below. The value "LNA percent" represents the molar fraction of linoleic acid converted in the reaction. The values "HA percent" and "AZA percent" represent the value of the synthesis and extraction yield of the hexanoic monoacid (HA) and the azelaic diacid (AZA), respectively, relative to the starting linoleic acid (LNA). The temperature is 85° C., the reaction time is 5 hours and the stirring speed is 400 rpm.TABLE 8 Test no. 1 Test no. 2 LNA, mmol 60 22 H2O2, mmol 350 220 LNA/ H2O2 1/5.8 1/10 Cat (B), mmol 1.2 0.9 LNA/Cat (B) 1/50 (0.02percent) 1/25 (0.04percent) LNA percent 100 100 HA percent 47.7 60.7 AZA percent 41.0 49.8 With tungstophosphoric acid *15.4 H2O, 1-hexadecylpyridinium chloride, dihydrogen peroxide in water, Time= 5h, T= 85 °C Patent; INSTITUT NATIONAL DE LA RECHERCHE AGRONOMIQUE; INSTITUT NATIONAL POLYTECHNIQUE DE TOULOUSE; Godard, Anaïs; Thiebaud Roux, Sophie; De Caro, Pascale; Vedrenne, Emeline; Mouloungui, Zéphirin; US2014/371487; (2014); (A1) English View in Reaxys

O

HO

OH

OH

O

OH

O

Rx-ID: 251628 View in Reaxys 36/353 Yield 22 %

Conditions & References With recombinant escherichia coli BL21(DE3), Tween 81 in aq. buffer, Time= 2h, T= 35 °C , pH= 8, Enzymatic reaction Song, Ji-Won; Lee, Jung-Hoo; Bornscheuer, Uwe T.; Park, Jin-Byung; Advanced Synthesis and Catalysis; vol.

356; nb. 8; (2014); p. 1782 - 1788 View in Reaxys Oxydation Shukow; Schestakow; Chem. Zentralbl.; vol. 74; nb. I; (1903); p. 525 View in Reaxys

HO

OH O

O

N

N

(v5) (v5)(v5)

(v5)

(v5)

CH –

(v10) Fe 2+ (v5) – (v5)CH (v5)

N

HO

(v4)

2

2 OH

O O

(v4)

(v5)

(v10)

N

(v5) (v5)

CH –

(v4)

(v5)

Fe 2+

(v5) (v5)(v5)

CH –

(v4)

(v5)

Rx-ID: 27515640 View in Reaxys 37/353

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Yield >99 %

Conditions & References in methanol, 1:1 mixt. ground for 5 min, dissolved in methanol; crystd.

Braga, Dario; Giaffreda, Stefano Luca; Grepioni, Fabrizia; Chemical Communications; nb. 37; (2006); p. 3877 3879 ; (from Gmelin) View in Reaxys

O

O

HO

OH

HO

OH

OH

O

OH

O

O

Rx-ID: 206312 View in Reaxys 38/353 Yield

Conditions & References With nitric acid Patent; I.G. Farbenind.; DE745642; (1939); View in Reaxys Asahina; Takimoto; Yakugaku Zasshi; vol. 49; (1929); p. 1023; dtsch. Ref. S. 157; ; (1930); p. 1346 View in Reaxys With NH4VO3, bei Siedetemperatur Hall; Reid; Journal of the American Chemical Society; vol. 65; (1943); p. 1467 View in Reaxys Patent; Du Pont de Nemours and Co.; US2269998; (1940) View in Reaxys

oleic acid ozonide

HO

OH O

O

Rx-ID: 6331678 View in Reaxys 39/353 Yield

Conditions & References With potassium hydrogensulfite Molinari; Barozi; Chemische Berichte; vol. 41; (1908); p. 2795 View in Reaxys With sodium hydroxide, silver(l) oxide, T= 90 °C Asinger; Chemische Berichte; vol. 75; (1942); p. 670,671; Chemische Berichte; vol. 77/79; (1944); p. 78 View in Reaxys With water Molinari; Soncini; Chemische Berichte; vol. 39; (1906); p. 2739 View in Reaxys Harries; Tuerk; Chemische Berichte; vol. 39; (1906); p. 3737 View in Reaxys Harries; Tank; Chemische Berichte; vol. 40; (1907); p. 4556 View in Reaxys Harries; Franck; Chemische Berichte; vol. 42; (1909); p. 455 View in Reaxys With aqueous alkali Molinari; Soncini; Chemische Berichte; vol. 39; (1906); p. 2739 View in Reaxys

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O

O

N N

HO

OH O

O

O N N

N

N

N O

N

N

O N

N

N

O N

N

N O

N

O

N N O

N

O N

N

N

N

N

O

O

O

O

N

N

N

N

N

N N O

O OH

O

N

O

N

O

O

N

O

N

N O

N

O N

O

N

OH

N N

N

N N

N

N

N

N

O

O

Rx-ID: 29845037 View in Reaxys 40/353 Yield

Conditions & References With UO2(NO3)26H2O in water, T= 200 °C Thuery, Pierre; Inorganic Chemistry; vol. 49; nb. 19; (2010); p. 9078 - 9085 View in Reaxys

HO

OH O

6 H

O

O

H2

O

N+

O– O

O

O–

Zn 2+ O–

Zn 2+

O–

Rx-ID: 39620748 View in Reaxys 41/353 Yield

Conditions & References

Ca. 52 %

in water, Time= 24h, T= 200 °C , Autoclave Tamames-Tabar; Imbuluzqueta; Guillou; Serre; Miller; Elkam; Horcajada; Blanco-Prieto; CrystEngComm; vol.

17; nb. 2; (2015); p. 456 - 462 View in Reaxys

HO

OH O

O

O

Z O

Rx-ID: 206523 View in Reaxys 42/353 Yield

Conditions & References With sulfuric acid, T= 0 - 8 °C , Beim Erhitzen des Reaktionsprodukts mit konz. HNO3 in Gegenwart von MnO2 auf 110-120grad Patent; Nopco Chem. Co.; US2426954; (1944) View in Reaxys Reaction Steps: 2 1.1: dihydrogen peroxide / tungsten(VI) trioxide hydrate / water / 62 °C / 75.01 - 150.01 Torr 1.2: 3.5 h / 60 °C / 15001.5 Torr 2.1: water / 6 h / 100 °C With water, dihydrogen peroxide, tungsten(VI) trioxide hydrate in water

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Patent; NOVAMONT S.P.A.; BIESER, Arno; BORSOTTI, Giampietro; DIGIOIA, Francesca; FERRARI, Adriano; PIROCCO, Alessandro; WO2011/80297; (2011); (A1) English View in Reaxys

HO

HO

OH

heptyloic acid

N O

O

O

Rx-ID: 17321866 View in Reaxys 43/353 Yield

Conditions & References Reaction Steps: 2 1: 90 percent / H2 / 5percent Pd/C / benzene / 50 °C / 6080 Torr 2: 90 percent / conc. aq. H2SO4 / 6 h / 100 °C With sulfuric acid, hydrogen, palladium on activated charcoal in benzene Cotarca; Delogu; Maggioni; Nardelli; Bianchini; Sguassero; Synthesis; nb. 3; (1997); p. 328 - 332 View in Reaxys

H

2

HO

OH

O N

O

H

H

H

Ag2O

O

N

O O–

O 2 Ag+ –O

2

O

3

N

N

H O

H

Rx-ID: 32012931 View in Reaxys 44/353 Yield

Conditions & References

81 %

With NH4OH in methanol, water, Sonication; soln. in mixed solvent 1:1 was treated under ultrasonic irradiation at ambient temp., then aq. NH3 soln. was dropped, soln. was allowed to evaporate slowly in darkness at ambient temp. for several days; ppt. was sepd., washed with cold MeOH and Et2O; elem. anal.

Sun, Di; Liu, Fu-Jing; Hao, Hong-Jun; Huang, Rong-Bin; Zheng, Lan-Sun; Journal of Molecular Structure; vol.

1004; nb. 1-3; (2011); p. 313 - 318 ; (from Gmelin) View in Reaxys

OH

HO

HO O

O

OH

H 18O

18OH

O

OH O

H 18O

18OH 18O

O

O

H 18O

OH O

O

Rx-ID: 37626835 View in Reaxys 45/353 Yield

Conditions & References With 1 wt Au/Al2O3, sodium hydroxide, (18)O2 in water, T= 80 °C , p= 375.038Torr , Autoclave, Inert atmosphere, Reflux, Reagent/catalyst Kulik, Anna; Martin, Andreas; Pohl, Marga-Martina; Fischer, Christine; Koeckritz, Angela; Green Chemistry; vol. 16; nb. 4; (2014); p. 1799 - 1806 View in Reaxys –O

HO

OH

O

2

3 H

H O

O

O Pb2+

O

Pb2+

O

O–

O– (v0)

(v0)

Yield 96 %

Rx-ID: 27383015 View in Reaxys 46/353

Conditions & References in water, High Pressure; placed in a bomb, heated to 220°C (3 h), held for 3 h; cooled to room temp. (3 h), crysts., washed (water), air dried; elem. anal.

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Plater, M. John; De Silva, Ben; Gelbrich, Thomas; Hursthouse, Michael B.; Higgitt, Catherine L.; Saunders, David R.; Polyhedron; vol. 22; nb. 24; (2003); p. 3171 - 3179 ; (from Gmelin) View in Reaxys

N

HO

N

OH

O–

NH

O

O–

O

2H O 2

O

HN

O

Cl 2Cu N

N 4

Cu 2+

H O

H

Rx-ID: 28324951 View in Reaxys 47/353 Yield 58 %

Conditions & References With HCl in water, High Pressure; mixt. was placed in digestion bomb, HCl was added to pH=4.7, heated at 150°C for 24 h, cooled slowly in air to 25°C; ppt. was isolated, washed with water; elem. anal.

Mallika Krishnan, Subhashree; Supkowski, Ronald M.; LaDuca, Robert L.; Journal of Molecular Structure; vol.

891; nb. 1-3; (2008); p. 423 - 428 ; (from Gmelin) View in Reaxys

O

HO

OH

O

O

OH

O

Rx-ID: 207853 View in Reaxys 48/353 Yield

Conditions & References With potassium permanganate, acetone, beim Verseifen des sodaloeslichen Reaktionsprodukts Brady; Journal of the American Chemical Society; vol. 61; (1939); p. 3466 View in Reaxys

8.9-dihydroxy-eicosane-dicarboxylic acid-(1.20)-di‐ methyl ester of mp: 99 degree HO

OH O

8.9-dihydroxy-eicosane-dicarboxylic acid-(1.20)-di‐ methyl ester of mp: 77 degree

HO

OH O

O

O

Rx-ID: 6983572 View in Reaxys 49/353 Yield

Conditions & References With ethanol, periodic acid, Oxydieren der entstandenen Aldehyde mit Peressigsaeure bei 85grad und Verseifen Ross; Gebhart; Gerecht; Journal of the American Chemical Society; vol. 67; (1945); p. 1276 View in Reaxys

HO

OH

HO

N

poly(ester-amide)-5, Mn(100/(yE-3))= 2500; Monomer(s):5hydroxy-2-amino benzothiazole, dibasic acid chloride

NH 2

O

S

O

Rx-ID: 9640582 View in Reaxys 50/353 Yield

Conditions & References With sodium hydroxide, citric acid triamide in 1,2-dichloro-ethane, Time= 2h, T= 50 - 60 °C Patel; Desai; Heterocyclic Communications; vol. 10; nb. 2-3; (2004); p. 203 - 208 View in Reaxys

–O

HO

OH O

O

O

O

2

Co 2+

4 H

O Co 2+

–O

H

O– 4

O

H O

H

Rx-ID: 27210216 View in Reaxys 51/353

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Yield

Conditions & References

84 %

in ethanol, water, addn. of ligand soln. (in H2O/EtOH=1:4) to slight excess of Co-salt, refluxing for 2 h (pptn.); cooling to room temp., filtration, washing (EtOH, ether), drying in air;elem. anal.

Geraghty, Majella; McCann, Malachy; Devereux, Michael; McKee, Vickie; Inorganica Chimica Acta; vol. 293; nb.

2; (1999); p. 160 - 166 ; (from Gmelin) View in Reaxys O–

O

HO

OH

O N

O

2 Ag+

H

2

–O

H

O

Ag2O

N

O

2

N

N

3

H O

H

Rx-ID: 32120888 View in Reaxys 52/353 Yield

Conditions & References

46 %

With NH3 in methanol, ammonia, aq. NH3; Sonication; stirring mixt. of Ag2O, bipyridine and azelaic acid in methanol/ water (1/4) under sonication at room temp. for 15 min, addn. of aq. ammonia, slow evapn. at room temp. for several ds; isolation of crystals, washing with cold methanol and diethyl ether, elem. anal.

Luo, Geng-Geng; Wu, Dong-Liang; Liu, Li; Xia, Jiu-Xu; Li, Dong-Xu; Dai, Jing-Cao; Xiao, Zi-Jing; Journal of Molecular Structure; vol. 1005; nb. 1-3; (2011); p. 172 - 177 ; (from Gmelin) View in Reaxys

N

11

O

N

O

C

11

C

HO

OH

Rx-ID: 33244245 View in Reaxys 53/353 Yield

Conditions & References Stage 1: With sodium hydroxide, Time= 0.0833333h, T= 140 °C Stage 2: With hydrogenchloride in water Best, Marcel; Gifford, Andrew N.; Kim, Sung Won; Babst, Ben; Piel, Markus; Roesch, Frank; Fowler, Joanna S.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 55; nb. 1; (2012); p. 39 - 43 View in Reaxys

N

14

O

N

O

C

14

C

HO

OH

Rx-ID: 33244247 View in Reaxys 54/353 Yield

Conditions & References Stage 1: With sodium hydroxide, Time= 0.0833333h, T= 140 °C Stage 2: With hydrogenchloride in water Best, Marcel; Gifford, Andrew N.; Kim, Sung Won; Babst, Ben; Piel, Markus; Roesch, Frank; Fowler, Joanna S.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 55; nb. 1; (2012); p. 39 - 43 View in Reaxys

O

OH O

O

HO

OH O

O

Rx-ID: 34712866 View in Reaxys 55/353 Yield

Conditions & References 1 :The following substances were fed continuously to a CSTR with a working capacity of 80 l, equipped with stirrer and with an adequate temperature regulation system: methyl oleate (technical purity approximately 85percent; flow rate 10 kg/h); an aqueous solution of hydrogen peroxide at 60percent (flow rate 2.3 kg/h); tungstic acid (H2WO4) (flow rate 48 g/h). The reaction was conducted at a constant temperature of 62° C. under vacuum (absolute pressure of 0.10-0.20*105 Pa) to evaporate the water fed together with the hydrogen peroxide; the evaporated gas was collected and condensed (approximately 1 kg/h of water).FIG. 3 shows the hydrogen peroxide over-all concentration during step a).As can be seen in FIG. 3, the over-all hydrogen peroxide concentration in the reactor was constant at about 1.5 g/ kg.The intermediate product containing vicinal diols was continuously discharged from the reactor and fed to step b)

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by means of a gear pump, adjusted to maintain a constant level in the reactor, with a flow rate of approximately 11.4 kg.Step b)Step b) was performed in a jet loop reactor with a working capacity of 80 l equipped with a 3 m3/h recirculation pump and heat exchanger. The intermediate product of step a) was continuously fed with a flow rate of 11.4 kg/h together with: cobalt acetate (Co(CH3COOH)2.4H2O, dissolved at 1.5percent in an aqueous current (approximately 2 kg/h); pressurized air (20*105 Pa; flow rate 12 to 15 kg/h). The air flow rate was adjusted to maintain a constant O2 content (approximately 10percent) at the reactor outlet.The reaction was conducted at 60° C., keeping constant the reaction volume to 50 l. The reaction time was about 3.5 h.The reaction mixture of step b) was continuously discharged from the jet loop reactor and fed to a decanter to separate the oily phase from the aqueous phase. Approximately 13 kg/h of oily product was obtained.Step (c)The separated oily phase was dried and degassed, and then transferred to a distillation column which allowed fractioning of the monocarboxylic acids, to separate the pelargonic acid from the lighter monocarboxylic acids. The main component of the lighter monocarboxylic acids fraction (byproducts of the oxidative cleavage reaction) was octanoic acid.Approximately 3.8 kg/h of vapor phase containing monocarboxylic acids (raw pelargonic acid), of which 3.5 kg/h are pelargonic acid with a titer of over 99percent, was obtained. The 3.8 kg/h current of raw pelargonic acid contained approximately 3.3percent of octanoic acid.An organic current of approximately 9 kg/h, containing as major component mono-methyl azelate, together with methyl palmitate, methyl stearate and esters of methyl dihydroxy stearate, was extracted from the bottom of the distillation column.Said organic current was then continuously fed to an emulsifier together with 18 kg/h of water. The emulsion was hydrolyzed by feeding it to three consecutive columns filled with acid ion exchange resin and heated at the temperature of 100° C. The total reaction time was 6 h.Each column was provided with a fractionating column on the top, to separate 1.1 kg/h of methanol from water. Approximately 8.5 kg/h of carboxylic acids were obtained from the bottom of the column, of which about 4.3 kg was azelaic acid.

With water, Time= 6h, T= 100 °C , Industry scale, Product distribution / selectivity Patent; Novamont S.p.A.; US2012/302778; (2012); (A1) English View in Reaxys O

HO O

O

N+

OH

N+

O –O

2H

O O–

O

N+

N+

O–

Rx-ID: 1627481 View in Reaxys 56/353 Yield

Conditions & References in water Breslow, Ronald; Rajagopalan, Raghavan; Schwarz, Joshua; Journal of the American Chemical Society; vol. 103; nb. 10; (1981); p. 2905 - 2907 View in Reaxys

O

HO

OH

OH

HO

O

O

O

O

Rx-ID: 31189197 View in Reaxys 57/353 Yield

Conditions & References 1.c :Step (c); The separated oily phase was dried and degassed, and then transferred to a distillation column which allowed fractioning of the monocarboxylic acids, to separate the pelargonic acid from the lighter monocarboxylic acids.

The main component of the lighter monocarboxylic acids fraction (byproducts of the oxidative cleavage reaction) was octanoic acid.Approximately 3.8 kg/h of vapor phase containing monocarboxylic acids (raw pelargonic acid), of which 3.5 kg/h are pelargonic acid with a titer of over 99percent, was obtained. The 3.8 kg/h current of raw pelargonic acid contained approximately 3.3percent of octanoic acid.An organic current of approximately 9 kg/h, containing as major component mono-methyl azelate, together with methyl palmitate, methyl stearate and esters of methyl dihydroxy stearate, was extracted from the bottom of the distillation column.Said organic current was then continuously fed to an emulsifier together with 18 kg/h of water. The emulsion was hydro lyzed by feeding it to three consecutive columns filled with acid ion exchange resin and heated at the temperature of 100°C. The total reaction time was 6 h.Each column was provided with a fractionating column on the top, to separate 1.1 kg/h of methanol from water. Approximately 8.5 kg/h of carboxylic acids were obtained from the bottom of the column, of which about 4.3 kg was azelaic acid.

With water, Time= 6h, T= 100 °C , Product distribution / selectivity Patent; NOVAMONT S.P.A.; BIESER, Arno; BORSOTTI, Giampietro; DIGIOIA, Francesca; FERRARI, Adriano; PIROCCO, Alessandro; WO2011/80297; (2011); (A1) English

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View in Reaxys N

HO

OH

Ag2O

HO

O

O N

OH

2 Ag+ H

HH

O

–O

O–

O

H

7

O

H

2 N

N

Rx-ID: 33571863 View in Reaxys 58/353 Yield 48 %

Conditions & References With NH3 in methanol, ammonia, aq. NH3; Sonication; stirring mixt. of silver oxide, pyridine deriv. and azelaic acid in methanol/water (1:1) under sonication at room temp. for 20 min, addn. of aq.ammonia; slow evapn. at room temp. in dark for several ds, collecting crystals, washing with methanol and diethyl ether, elem. anal.

Luo, Geng-Geng; Zhu, Rui-Min; He, Wei-Jun; Li, Ming-Zhi; Zhao, Qing-Hua; Li, Dong-Xu; Dai, Jing-Cao; Journal of Molecular Structure; vol. 1021; (2012); p. 84 - 88 ; (from Gmelin) View in Reaxys

HO

OH

N

N

O

S

S

O

HO

OH

H 2N

NH 2

O

O

Rx-ID: 35342321 View in Reaxys 59/353 Yield

Conditions & References With ammonia in water, acetonitrile, T= 50 °C , Sonication Su, Hai-Feng; Xue, Lan; Li, Yun-Hua; Lin, Shui-Chao; Wen, Yi-Mei; Huang, Rong-Bin; Xie, Su-Yuan; Zheng, LanSun; Journal of the American Chemical Society; vol. 135; nb. 16; (2013); p. 6122 - 6129 View in Reaxys

HO

S

N

OH O

N

S

O

HO

OH

H 2N

NH 2

O

O

Rx-ID: 35342325 View in Reaxys 60/353 Yield

Conditions & References With ammonia in water, acetonitrile, T= 50 °C , Sonication Su, Hai-Feng; Xue, Lan; Li, Yun-Hua; Lin, Shui-Chao; Wen, Yi-Mei; Huang, Rong-Bin; Xie, Su-Yuan; Zheng, LanSun; Journal of the American Chemical Society; vol. 135; nb. 16; (2013); p. 6122 - 6129 View in Reaxys

OH

OH

O

HO

OH

OH OH

OH

O

O

Rx-ID: 207887 View in Reaxys 61/353 Yield

Conditions & References With sodium hydroxide, potassium chlorate, T= 180 - 200 °C Eckert; Monatshefte fuer Chemie; vol. 38; (1917); p. 5

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View in Reaxys With alkaline permanganate Hazura; Monatshefte fuer Chemie; vol. 8; (1887); p. 267 View in Reaxys

O

OH

OH

OH

HO

OH

HO OH

OH

O

OH

O

Rx-ID: 208155 View in Reaxys 62/353 Yield

Conditions & References With sodium hydroxide, potassium chlorate, T= 180 - 200 °C Eckert; Monatshefte fuer Chemie; vol. 38; (1917); p. 5 View in Reaxys With potassium permanganate Goldsobel; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 42; (1910); p. 56; Chem. Zentralbl.; 1910 I. 1231 View in Reaxys

castor oil

HO

OH O

O

Rx-ID: 6331669 View in Reaxys 63/353 Yield

Conditions & References With potassium hydroxide, Ansaeuern mit Schwefelsaeure die Fettsaeuren in Freiheit; Waschen und Trocknen. Loesen in 4prozentige Kalilauge, Behandeln mit Wasser und Kaliumpermanganat. Erhitzen auf 90grad nach Verlauf Maquenne; Bulletin de la Societe Chimique de France; vol. <3>21; (1899); p. 1061 View in Reaxys With nitric acid Carmichael; Journal of the Chemical Society; vol. 121; (1922); p. 2549 View in Reaxys Day; Kon; Stevenson; Journal of the Chemical Society; vol. 117; (1920); p. 645 View in Reaxys Kiliani; Chemische Berichte; vol. 54; (1921); p. 465; Chemische Berichte; vol. 61; (1928); p. 1163 View in Reaxys Baker; Ingold; Journal of the Chemical Society; vol. 123; (1923); p. 125,130 View in Reaxys Arppe; Justus Liebigs Annalen der Chemie; vol. 124; (1862); p. 86 View in Reaxys Verkade; Hartman; Coops; Recueil des Travaux Chimiques des Pays-Bas; vol. 45; (1926); p. 379; Verslag van de Gewone Vergadering van de Afdeling Natuurkunde, Koninklijke Nederlandse Akademie van Wetenschappen; vol. 33; p. 767; Chem. Zentralbl.; vol. 96; nb. I; (1925); p. 1281 View in Reaxys Verkade; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 138; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 200 View in Reaxys With alkaline permanganate Hill; McEwen; Organic Syntheses; vol. 13; (1933); p. 4 View in Reaxys With ozone Noorduyn; Recueil des Travaux Chimiques des Pays-Bas; vol. 38; (1919); p. 327 View in Reaxys

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threo-9,10-dihydroxy-octadecanoic acid

HO

OH O

O

Rx-ID: 6331681 View in Reaxys 64/353 Yield

Conditions & References With sodium hydroxide, T= 475 °C Patent; Kessler Chem.Corp.; US2625558; (1950) View in Reaxys With NH4VO3, nitric acid Asahara; Tomita; ; vol. 2; (1953); p. 105; ; (1954); p. 11341 View in Reaxys

(v12)

H –H C

ClCl 2+Zr

(v4)(v5)H (v5)H (v5) (v5) H

H

(v5) H

H H– C H

(v5) (v5) (v5) (v4)

(v4)–

2 O Na +

O O–

O–

O–

O

HC

2

O

O–

(v3) 4+

Zr

Rx-ID: 26320144 View in Reaxys 65/353 Yield 69 %

Conditions & References in chloroform, water, Zr-compound in chloroform; Na-compound in aq. soln.; discoloration at 290°C; Carraher, C. E.; European Polymer. J.; vol. 8; (1972); p. 215 - 220 View in Reaxys vol. Zr: Org.Verb.; 5, page 72 - 73 ; (from Gmelin) View in Reaxys

HO

OH O

6 H

O

O

H2

O

N+

O– H 2N

H

O–

O

–O

NH 2

O– H 2N 2 NH 2 O

H

O

Ni 2+

Ni 2+

Rx-ID: 27203903 View in Reaxys 66/353 Yield 90 %

Conditions & References in water, byproducts: HNO3; aq. soln. of azelaic acid and hydrazine hydrate added to metal nitrate soln.; ppt. collected, washed (water, ethanol, ether), air dried; elem. anal.

Yasodhai; Govindarajan; Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry; vol. 30; nb. 4; (2000); p. 745 - 760 ; (from Gmelin) View in Reaxys

HO

OH O

O

H 2N

H O

NH 2

Cd 2+ O 2

H

O–

–O

O– Cd 2+

N O

O

O H 2N

NH 2

Rx-ID: 27205874 View in Reaxys 67/353 Yield 85 %

Conditions & References in water, byproducts: HNO3; aq. soln. of azelaic acid and hydrazine hydrate added to metal nitrate soln.; ppt. collected, washed (water, ethanol, ether), air dried; elem. anal.

Yasodhai; Govindarajan; Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry; vol. 30; nb. 4; (2000); p. 745 - 760 ; (from Gmelin) View in Reaxys

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O O

O H O O

H

H O

O OH

O

H N

H 2N

NH OH

NH

O

O O

H

HO

OH O

NH 2

H N

HO

O

O

NH 2

O H

O

HN

H HO

O

H

OH

Rx-ID: 29894685 View in Reaxys 68/353 Yield

Conditions & References With hydrogenchloride, water in 1,4-dioxane, Time= 4h, T= 80 °C Zhao, Hu-Yi; Wu, Fu-Kai; Qiu, Ying-Kun; Wu, Zhen; Jiang, Yong-Tao; Chen, Ji-Yong; Journal of Asian Natural Products Research; vol. 12; nb. 9; (2010); p. 793 - 800 View in Reaxys

OH Z

E

E

Z

OH O

HO

OH

HO

HO

OH

OH

O

O

O

O

O

Rx-ID: 31086530 View in Reaxys 69/353 Yield

Conditions & References Stage 1: With ozone in dichloromethane, Time= 0.25h, T= -78 °C Stage 2: With formic acid, dihydrogen peroxide in dichloromethane, Time= 0.25h, T= 20 °C Hitora, Yuki; Takada, Kentaro; Okada, Shigeru; Ise, Yuji; Matsunaga, Shigeki; Journal of Natural Products; vol.

74; nb. 5; (2011); p. 1262 - 1267 View in Reaxys O

N

HO

OH O

O

Rx-ID: 36639680 View in Reaxys 70/353 Yield

Conditions & References Reaction Steps: 4 1: CHPCA / hexane / 3.5 h / 40 - 50 °C 2: 500 - 550 °C / |Inert atmosphere 3: hydrogen; 5 palladium on charcoal / toluene / 50 °C / 6080.41 Torr 4: sulfuric acid / 6 h / 100 °C With sulfuric acid, 5 palladium on charcoal, CHPCA, hydrogen in hexane, toluene, 1: |Baeyer-Villiger Ketone Oxidation Cotarca, Livius; Delogu, Pietro; Nardelli, Alfonso; Maggioni, Paolo; Bianchini, Roberto; Sguassero, Stefano; Alini, Stefano; Dario, Roberto; Clauti, Giuliano; Pitta, Giorgio; Duse, Gianpaolo; Goffredi, Fabrizio; Organic Process Research and Development; vol. 5; nb. 1; (2001); p. 69 - 76

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View in Reaxys Reaction Steps: 4 1: CHPCA / hexane / 3.5 h / 40 - 50 °C 2: 600 °C / |Inert atmosphere 3: hydrogen; 5 palladium on charcoal / toluene / 50 °C / 6080.41 Torr 4: sulfuric acid / 6 h / 100 °C With sulfuric acid, 5 palladium on charcoal, CHPCA, hydrogen in hexane, toluene, 1: |Baeyer-Villiger Ketone Oxidation Cotarca, Livius; Delogu, Pietro; Nardelli, Alfonso; Maggioni, Paolo; Bianchini, Roberto; Sguassero, Stefano; Alini, Stefano; Dario, Roberto; Clauti, Giuliano; Pitta, Giorgio; Duse, Gianpaolo; Goffredi, Fabrizio; Organic Process Research and Development; vol. 5; nb. 1; (2001); p. 69 - 76 View in Reaxys O HO

OH O

O

Rx-ID: 36639691 View in Reaxys 71/353 Yield

Conditions & References Reaction Steps: 5 1: cyclohexylamine; 4-methoxy-phenol; acetic acid / 2 h / 70 - 130 °C 2: CHPCA / hexane / 3.5 h / 40 - 50 °C 3: 500 - 550 °C / |Inert atmosphere 4: hydrogen; 5 palladium on charcoal / toluene / 50 °C / 6080.41 Torr 5: sulfuric acid / 6 h / 100 °C With sulfuric acid, 5 palladium on charcoal, CHPCA, hydrogen, cyclohexylamine, acetic acid, 4-methoxy-phenol in hexane, toluene, 2: |Baeyer-Villiger Ketone Oxidation Cotarca, Livius; Delogu, Pietro; Nardelli, Alfonso; Maggioni, Paolo; Bianchini, Roberto; Sguassero, Stefano; Alini, Stefano; Dario, Roberto; Clauti, Giuliano; Pitta, Giorgio; Duse, Gianpaolo; Goffredi, Fabrizio; Organic Process Research and Development; vol. 5; nb. 1; (2001); p. 69 - 76 View in Reaxys Reaction Steps: 5 1: cyclohexylamine; 4-methoxy-phenol; acetic acid / 2 h / 70 - 130 °C 2: CHPCA / hexane / 3.5 h / 40 - 50 °C 3: 600 °C / |Inert atmosphere 4: hydrogen; 5 palladium on charcoal / toluene / 50 °C / 6080.41 Torr 5: sulfuric acid / 6 h / 100 °C With sulfuric acid, 5 palladium on charcoal, CHPCA, hydrogen, cyclohexylamine, acetic acid, 4-methoxy-phenol in hexane, toluene, 2: |Baeyer-Villiger Ketone Oxidation Cotarca, Livius; Delogu, Pietro; Nardelli, Alfonso; Maggioni, Paolo; Bianchini, Roberto; Sguassero, Stefano; Alini, Stefano; Dario, Roberto; Clauti, Giuliano; Pitta, Giorgio; Duse, Gianpaolo; Goffredi, Fabrizio; Organic Process Research and Development; vol. 5; nb. 1; (2001); p. 69 - 76 View in Reaxys N

O

O

HO

OH O

O

Rx-ID: 36639697 View in Reaxys 72/353 Yield

Conditions & References Reaction Steps: 3 1: 500 - 550 °C / |Inert atmosphere 2: hydrogen; 5 palladium on charcoal / toluene / 50 °C / 6080.41 Torr 3: sulfuric acid / 6 h / 100 °C With sulfuric acid, 5 palladium on charcoal, hydrogen in toluene

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Cotarca, Livius; Delogu, Pietro; Nardelli, Alfonso; Maggioni, Paolo; Bianchini, Roberto; Sguassero, Stefano; Alini, Stefano; Dario, Roberto; Clauti, Giuliano; Pitta, Giorgio; Duse, Gianpaolo; Goffredi, Fabrizio; Organic Process Research and Development; vol. 5; nb. 1; (2001); p. 69 - 76 View in Reaxys Reaction Steps: 3 1: 600 °C / |Inert atmosphere 2: hydrogen; 5 palladium on charcoal / toluene / 50 °C / 6080.41 Torr 3: sulfuric acid / 6 h / 100 °C With sulfuric acid, 5 palladium on charcoal, hydrogen in toluene Cotarca, Livius; Delogu, Pietro; Nardelli, Alfonso; Maggioni, Paolo; Bianchini, Roberto; Sguassero, Stefano; Alini, Stefano; Dario, Roberto; Clauti, Giuliano; Pitta, Giorgio; Duse, Gianpaolo; Goffredi, Fabrizio; Organic Process Research and Development; vol. 5; nb. 1; (2001); p. 69 - 76 View in Reaxys

O

Cl O

O

HO

OH O

O O

O

O

O O

OH O

Rx-ID: 1958738 View in Reaxys 73/353 Yield 35 %

Conditions & References With sodium tetrahydroborate Kallury, R. Krishnamohanrao; Krull, Ulrich J.; Thompson, Michael; Journal of Organic Chemistry; vol. 52; nb. 24; (1987); p. 5478 - 5480 View in Reaxys

inactive,high-melting ψ.ι-dioxy-stearic acid

HO

OH O

O

Rx-ID: 6331675 View in Reaxys 74/353 Yield

Conditions & References With potassium hydroxide, potassium chlorate, T= 200 - 220 °C Eckert; Monatshefte fuer Chemie; vol. 38; (1917); p. 5 View in Reaxys

6H O Co 2+ 2

HO

OH

O 2

O

N

O

H 2N

H

O–

O

NH 2

–O

O– Co 2+ O

H

O H 2N 2 NH 2

O

Rx-ID: 27143821 View in Reaxys 75/353 Yield 83 %

Conditions & References in water, byproducts: HNO3; aq. soln. of azelaic acid and hydrazine hydrate added to metal nitrate soln.; ppt. collected, washed (water, ethanol, ether), air dried; elem. anal.

Yasodhai; Govindarajan; Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry; vol. 30; nb. 4; (2000); p. 745 - 760 ; (from Gmelin) View in Reaxys

HO

OH O

O–

O 2

O

N O

Zn 2+

H 2N

H O

NH 2

–O

O– H 2N O

H

NH 2

O Zn 2+

Rx-ID: 27206816 View in Reaxys 76/353 Yield 80 %

Conditions & References in water, byproducts: HNO3; aq. soln. of azelaic acid and hydrazine hydrate added to metal nitrate soln.; ppt. collected, washed (water, ethanol, ether), air dried; elem. anal.

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Yasodhai; Govindarajan; Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry; vol. 30; nb. 4; (2000); p. 745 - 760 ; (from Gmelin) View in Reaxys

N

O

HO

OH O

O

O

N NHHO 2

O O

OH

NH 2

Rx-ID: 32831087 View in Reaxys 77/353 Yield

Conditions & References in methanol, Time= 18h, T= 20 °C , Heating Thompson, Laura J.; Voguri, Raja S.; Male, Louise; Tremayne, Maryjane; CrystEngComm; vol. 13; nb. 12; (2011); p. 4188 - 4195 View in Reaxys

HO

9(or 10)-chloro-10(or 9)-hydroxy-octadecanoic acid

OH O

O

Rx-ID: 6331668 View in Reaxys 78/353 Yield

Conditions & References With sodium hydroxide, T= 380 °C Patent; Swift and Co.; US2791607; (1955) View in Reaxys

HO

pelargonyl-azelaamic acid

OH O

O

Rx-ID: 6331680 View in Reaxys 79/353 Yield

Conditions & References With hydrogenchloride, T= 100 °C Spieckermann; Chemische Berichte; vol. 29; (1896); p. 813 View in Reaxys

HO

OH O

O 2

O

O N

Pb2+

O– (v0)

O

O Pb2+ O–

O– (v0)

Rx-ID: 27383016 View in Reaxys 80/353 Yield

Conditions & References in methanol, ethanol, water, warmed (40°C) solns. (Pb salt in ethanol/methanol/water, acid in ethanol) mixed, cooled with a water bath to ca. 22°C; crysts. washed (water/ethanol, ethanol), air dried; elem. anal.

Plater, M. John; De Silva, Ben; Gelbrich, Thomas; Hursthouse, Michael B.; Higgitt, Catherine L.; Saunders, David R.; Polyhedron; vol. 22; nb. 24; (2003); p. 3171 - 3179 ; (from Gmelin) View in Reaxys in water, T= 70 °C Otero, Vanessa; Sanches, Diogo; Montagner, Cristina; Vilarigues, Mrcia; Carlyle, Leslie; Lopes, Joo A.; Melo, Maria J.; Journal of Raman Spectroscopy; vol. 45; nb. 11-12; (2014); p. 1197 - 1206 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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N 6

HO

–O

H O

OH

H

N O

NH

O

O

O

Cl 2Ni

N

H N

O–

N

H O

Ni 2+

H

Rx-ID: 28780737 View in Reaxys 81/353 Yield 47 %

Conditions & References in water, High Pressure; hydrothermal synthesis; NiCl2, 4,4'-dipyridylamine, azelaic acid added to distd. H2O; heated in a sealed Teflon-lined stainless steel autoclave at 120°C for 48 h; cooled to ambient temp.; filtered; washed with distd.

H2O, acetone; dried in air; elem. anal.

Shyu, Eric; Krishnan, Subhashree Mallika; Supkowski, Ronald M.; LaDuca, Robert L.; Polyhedron; vol. 28; nb.

8; (2009); p. 1437 - 1446 ; (from Gmelin) View in Reaxys N 6

HO

–O

H O

OH

N O

NH

O

O

O

Cl 2Co

N

H N

O–

H

N H

Co 2+

O

H

Rx-ID: 28780739 View in Reaxys 82/353 Yield 50 %

Conditions & References in water, High Pressure; hydrothermal synthesis; CoCl2, 4,4'-dipyridylamine, azelaic acid added to distd. H2O; heated in a sealed Teflon-lined stainless steel autoclave at 120°C for 48 h; cooled to ambient temp.; filtered; washed with distd.

H2O, acetone; dried in air; elem. anal.

Shyu, Eric; Krishnan, Subhashree Mallika; Supkowski, Ronald M.; LaDuca, Robert L.; Polyhedron; vol. 28; nb.

8; (2009); p. 1437 - 1446 ; (from Gmelin) View in Reaxys

HO

HO

OH O

O

O

Rx-ID: 667440 View in Reaxys 83/353 Yield

Conditions & References With vanadium containing H2SO4, nitric acid, T= 70 °C Patent; Henkel and Cie.; DE728507; (1940); View in Reaxys

HO

HO O

OH O

O

Rx-ID: 731748 View in Reaxys 84/353 Yield

Conditions & References With vanadium containing H2SO4, nitric acid, T= 70 °C Patent; Henkel and Cie.; DE728507; (1940); View in Reaxys

pelargonylazelaamic acid

HO

OH O

O

HO O

Rx-ID: 6965217 View in Reaxys 85/353 Yield

Conditions & References With hydrogenchloride, T= 100 °C Spieckermann; Chemische Berichte; vol. 29; (1896); p. 813

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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View in Reaxys

HO

Z O

HO

OH O

HO

HO O

O

O O

Rx-ID: 9775057 View in Reaxys 86/353 Yield

Conditions & References

35 %, 3 %, With water, ozone, Time= 0.000833333h, T= 24.85 °C , p= 760Torr , Product distribution, Further Variations: thickness 3% of educt layer Katrib, Yasmine; Martin, Scot T.; Hung, Hui-Ming; Rudich, Yinon; Zhang, Haizheng; Slowik, Jay G.; Davidovits, Paul; Jayne, John T.; Worsnop, Douglas R.; Journal of Physical Chemistry A; vol. 108; nb. 32; (2004); p. 6686 6695 View in Reaxys O

O 14

Br

C

Br

HO

OH

Rx-ID: 33244248 View in Reaxys 87/353 Yield

Conditions & References Reaction Steps: 3 1: isopropyl alcohol / 15 h / Reflux 2: potassium hydroxide / dimethyl sulfoxide / 0.08 h / 140 °C 3: sodium hydroxide / 0.08 h / 140 °C With potassium hydroxide, sodium hydroxide in dimethyl sulfoxide, isopropyl alcohol Best, Marcel; Gifford, Andrew N.; Kim, Sung Won; Babst, Ben; Piel, Markus; Roesch, Frank; Fowler, Joanna S.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 55; nb. 1; (2012); p. 39 - 43 View in Reaxys O

O 14

C

Br

HO

N

OH

Rx-ID: 33244252 View in Reaxys 88/353 Yield

Conditions & References Reaction Steps: 2 1: potassium hydroxide / dimethyl sulfoxide / 0.08 h / 140 °C 2: sodium hydroxide / 0.08 h / 140 °C With potassium hydroxide, sodium hydroxide in dimethyl sulfoxide Best, Marcel; Gifford, Andrew N.; Kim, Sung Won; Babst, Ben; Piel, Markus; Roesch, Frank; Fowler, Joanna S.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 55; nb. 1; (2012); p. 39 - 43 View in Reaxys

N

NH 2

O HO

N

O

H N

N

OH O

Rx-ID: 33648544 View in Reaxys 89/353 Yield

Conditions & References Reaction Steps: 2

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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1.1: thionyl chloride; triethylamine / chloroform / 3 h / Inert atmosphere; Reflux 1.2: 20 °C / Inert atmosphere 2.1: ethyl acetate / 1080 h With thionyl chloride, triethylamine in chloroform, ethyl acetate Aakeroey, Christer B.; Panikkattu, Sheelu V.; Dehaven, Baillie; Desper, John; Crystal Growth and Design; vol.

12; nb. 5; (2012); p. 2579 - 2587 View in Reaxys

N

NH 2

O

O

O N

HO

N H

OH

N

Rx-ID: 33648551 View in Reaxys 90/353 Yield

Conditions & References Reaction Steps: 2 1.1: thionyl chloride; triethylamine / chloroform / 3 h / Inert atmosphere; Reflux 1.2: 20 °C / Inert atmosphere 2.1: ethyl acetate With thionyl chloride, triethylamine in chloroform, ethyl acetate Aakeroey, Christer B.; Panikkattu, Sheelu V.; Dehaven, Baillie; Desper, John; Crystal Growth and Design; vol.

12; nb. 5; (2012); p. 2579 - 2587 View in Reaxys

N O

O

O

O

N HO

N H

OH

N

OH

Rx-ID: 33648558 View in Reaxys 91/353 Yield

Conditions & References Reaction Steps: 2 1.1: thionyl chloride; triethylamine / chloroform / 3 h / Inert atmosphere; Reflux 1.2: 20 °C / Inert atmosphere 2.1: ethyl acetate With thionyl chloride, triethylamine in chloroform, ethyl acetate Aakeroey, Christer B.; Panikkattu, Sheelu V.; Dehaven, Baillie; Desper, John; Crystal Growth and Design; vol.

12; nb. 5; (2012); p. 2579 - 2587 View in Reaxys

N O HO

N

O

H N

N

OH O

HO

O

Rx-ID: 33648563 View in Reaxys 92/353 Yield

Conditions & References Reaction Steps: 2 1.1: thionyl chloride; triethylamine / chloroform / 3 h / Inert atmosphere; Reflux 1.2: 20 °C / Inert atmosphere 2.1: ethyl acetate / 1080 h With thionyl chloride, triethylamine in chloroform, ethyl acetate Aakeroey, Christer B.; Panikkattu, Sheelu V.; Dehaven, Baillie; Desper, John; Crystal Growth and Design; vol.

12; nb. 5; (2012); p. 2579 - 2587 View in Reaxys

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H 2N

HO I

NH 2

OH O

I

NHHN

O

Rx-ID: 37866175 View in Reaxys 93/353 Yield

Conditions & References Reaction Steps: 5 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethylene glycol dimethyl ether; water / 18 h / 85 °C / |Inert atmosphere 2.1: ammonium chloride; trimethylaluminum / toluene / 17 h / |Inert atmosphere; |Reflux 2.2: 4 h / 0 - 20 °C 3.1: hydrogenchloride / water; tetrahydrofuran / 3 h / 0 - 20 °C 4.1: sodium hydroxide; water / 0.08 h / 0 °C 5.1: dimethyl sulfoxide With hydrogenchloride, tetrakis(triphenylphosphine) palladium(0), water, trimethylaluminum, sodium carbonate, ammonium chloride, sodium hydroxide in tetrahydrofuran, ethylene glycol dimethyl ether, water, dimethyl sulfoxide, toluene Kusukawa, Takahiro; Tanaka, Syugo; Inoue, Kouta; Tetrahedron; vol. 70; nb. 26; (2014); p. 4049 - 4056 View in Reaxys

N

N

H 2N

HO

NHHN

NH 2

OH O

O

Rx-ID: 37866195 View in Reaxys 94/353 Yield

Conditions & References Reaction Steps: 4 1.1: ammonium chloride; trimethylaluminum / toluene / 17 h / |Inert atmosphere; |Reflux 1.2: 4 h / 0 - 20 °C 2.1: hydrogenchloride / water; tetrahydrofuran / 3 h / 0 - 20 °C 3.1: sodium hydroxide; water / 0.08 h / 0 °C 4.1: dimethyl sulfoxide With hydrogenchloride, water, trimethylaluminum, ammonium chloride, sodium hydroxide in tetrahydrofuran, water, dimethyl sulfoxide, toluene Kusukawa, Takahiro; Tanaka, Syugo; Inoue, Kouta; Tetrahedron; vol. 70; nb. 26; (2014); p. 4049 - 4056 View in Reaxys H 2N

NHHN

NH 2

HO B

N

HO

OH

HO O

O

Rx-ID: 37866213 View in Reaxys 95/353 Yield

Conditions & References Reaction Steps: 5 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / ethylene glycol dimethyl ether; water / 18 h / 85 °C / |Inert atmosphere 2.1: ammonium chloride; trimethylaluminum / toluene / 17 h / |Inert atmosphere; |Reflux 2.2: 4 h / 0 - 20 °C 3.1: hydrogenchloride / water; tetrahydrofuran / 3 h / 0 - 20 °C

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4.1: sodium hydroxide; water / 0.08 h / 0 °C 5.1: dimethyl sulfoxide With hydrogenchloride, tetrakis(triphenylphosphine) palladium(0), water, trimethylaluminum, sodium carbonate, ammonium chloride, sodium hydroxide in tetrahydrofuran, ethylene glycol dimethyl ether, water, dimethyl sulfoxide, toluene Kusukawa, Takahiro; Tanaka, Syugo; Inoue, Kouta; Tetrahedron; vol. 70; nb. 26; (2014); p. 4049 - 4056 View in Reaxys

O

O HN

O NHHN

H 2N

O

NHHN

NH 2

NH

HO

OH O

O

Rx-ID: 37866232 View in Reaxys 96/353 Yield

Conditions & References Reaction Steps: 3 1: hydrogenchloride / water; tetrahydrofuran / 3 h / 0 - 20 °C 2: sodium hydroxide; water / 0.08 h / 0 °C 3: dimethyl sulfoxide With hydrogenchloride, water, sodium hydroxide in tetrahydrofuran, water, dimethyl sulfoxide Kusukawa, Takahiro; Tanaka, Syugo; Inoue, Kouta; Tetrahedron; vol. 70; nb. 26; (2014); p. 4049 - 4056 View in Reaxys

H 2N

NHHN

2 NH 2HCl

H 2N

HO

NHHN

NH 2

OH O

O

Rx-ID: 37866250 View in Reaxys 97/353 Yield

Conditions & References Reaction Steps: 2 1: sodium hydroxide; water / 0.08 h / 0 °C 2: dimethyl sulfoxide With water, sodium hydroxide in dimethyl sulfoxide Kusukawa, Takahiro; Tanaka, Syugo; Inoue, Kouta; Tetrahedron; vol. 70; nb. 26; (2014); p. 4049 - 4056 View in Reaxys

HO

O

HO

OH O

O

O

Rx-ID: 37888736 View in Reaxys 98/353 Yield

Conditions & References With Escherichia coli oxidoreductase in aq. phosphate buffer, pH= 6, Enzymatic reaction Otte, Konrad B.; Kittelberger, Jens; Kirtz, Marko; Nestl, Bettina M.; Hauer, Bernhard; ChemCatChem; vol. 6; nb.

4; (2014); p. 1003 - 1009 View in Reaxys

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–O

O–

–O

2 Ag+ O

O

O

HN 3

O–

2 Ag+ O

HN

N

3.5H O 2

NH

3

N

NH

N

N

Rx-ID: 37916939 View in Reaxys 99/353 Yield

Conditions & References in neat (no solvent), T= 150 °C , Inert atmosphere Han, Lu-Lu; Zhang, Xi-Ying; Chen, Jiang-Shan; Li, Zhong-Hui; Sun, Dao-Feng; Wang, Xing-Po; Sun, Di; Crystal Growth and Design; vol. 14; nb. 5; (2014); p. 2230 - 2239 View in Reaxys

HO

OH O

HO

O

Z O

HO

HO

HO

O

O

O

O O

Rx-ID: 38770156 View in Reaxys 100/353 Yield

Conditions & References With ozone in water Pfrang, Christian; Sebastiani, Federica; Lucas, Claire O. M.; King, Martin D.; Hoare, Ioan D.; Chang, Debby; Campbell, Richard A.; Physical Chemistry Chemical Physics; vol. 16; nb. 26; (2014); p. 13220 - 13228 View in Reaxys NH

HO

S

O

O

OH O

2H

H 2N

O

N H

NHHO 2

O

Rx-ID: 41412478 View in Reaxys 101/353 Yield

Conditions & References Reaction Steps: 2 1: water 2: water With water in water Janczak, Jan; Crystal Growth and Design; vol. 15; nb. 10; (2015); p. 5097 - 5111 View in Reaxys

O O

OH

E OH

O

HO

OH O

O

HO

E O

OH

OH

Rx-ID: 9686167 View in Reaxys 102/353 Yield

Conditions & References With air, T= 37 °C , Product distribution, Further Variations: time dependence Balamraju, Yuvaraju N.; Sun, Mingjiang; Salomon, Robert G.; Journal of the American Chemical Society; vol. 126; nb. 37; (2004); p. 11522 - 11528 View in Reaxys

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O

N+ HH

H

O

Cl Y Cl

O–

–O

H

4

H

2 O

Cl

2

O–

(v3)

Y3+

H

O–

3 O

O

Rx-ID: 26888807 View in Reaxys 103/353 Yield

Conditions & References With water in water, addn. of the ammonium salt to a hot soln. of YCl3, pptn. (pH 5.5-6.0), heating (0.5 h, 333-343 K); washing with water, drying to constant weight (303 K), elem. anal.

Brzyska, W.; Ozga, W.; Journal of Thermal Analysis; vol. 36; (1990); p. 441 - 454 ; (from Gmelin) View in Reaxys

(v1) F–

2 (v1)

HO

OH O

(v1) F–

4

O

–F

(v1)

N

(v4)

–F

-1 (v4) B3+ F–F–

O

N

(v4) N (v7) (v7)N (v4) (v4) Mo2+Mo2+ (v4) (v4) B3+ N N F–F– N (v1) (v1)N (v4) (v4)(v4)

N

(v1) (v1) O–

N (v1)

–O

2+Mo

Mo2+

(v1)

O

Rx-ID: 27233169 View in Reaxys 104/353 Yield

Conditions & References in acetonitrile, (N2); gentle heating for 1 h, concn.; addn. of CH2Cl2 or hexane. pptn.

Whelan, Elizabeth; Devereux, Michael; McCann, Malachy; McKee, Vickie; Chemical Communications; nb. 5; (1997); p. 427 - 428 ; (from Gmelin) View in Reaxys N

HO

Cd 2+ 2

OH NH

O

6

O

O O

N

–O

H

O– Cl OO

H

H N

O– N O

O

N 2

Cd 2+

H O

H

Rx-ID: 28780738 View in Reaxys 105/353 Yield 30 %

Conditions & References in water, High Pressure; hydrothermal synthesis; Cd(ClO4)2, 4,4'-dipyridylamine, azelaic acid added to distd. H2O; heated in a sealed Teflon-lined stainless steel autoclave at 120°C for 48 h; cooled to ambient temp.; filtered; washed with distd. H2O, acetone; dried in air; elem. anal.

Shyu, Eric; Krishnan, Subhashree Mallika; Supkowski, Ronald M.; LaDuca, Robert L.; Polyhedron; vol. 28; nb.

8; (2009); p. 1437 - 1446 ; (from Gmelin) View in Reaxys

O HO

O

OH

OH

2HO

O O

OH

O

O

O O

OH

Rx-ID: 32963123 View in Reaxys 106/353 Yield

Conditions & References in N,N-dimethyl-formamide, Time= 12h, T= 30 °C

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Subhapriya; Vijayakumar; Madhu Mohan; Vijayanand; Molecular Crystals and Liquid Crystals; vol. 537; (2011); p.

36 - 50 View in Reaxys

O

HO

OH O

O

O OH

O OH

OH 2HO

O

O O

Rx-ID: 32963124 View in Reaxys 107/353 Yield

Conditions & References in N,N-dimethyl-formamide, Time= 12h, T= 30 °C Subhapriya; Vijayakumar; Madhu Mohan; Vijayanand; Molecular Crystals and Liquid Crystals; vol. 537; (2011); p.

36 - 50 View in Reaxys

O HO

OH

O O

O

OH

O OH

OH 2HO

O

O O

Rx-ID: 32963125 View in Reaxys 108/353 Yield

Conditions & References in N,N-dimethyl-formamide, Time= 12h, T= 30 °C Subhapriya; Vijayakumar; Madhu Mohan; Vijayanand; Molecular Crystals and Liquid Crystals; vol. 537; (2011); p.

36 - 50 View in Reaxys

O

HO

OH O

O

O OH

O OH

OH 2HO

O

O O

Rx-ID: 32963126 View in Reaxys 109/353 Yield

Conditions & References in N,N-dimethyl-formamide, Time= 12h, T= 30 °C Subhapriya; Vijayakumar; Madhu Mohan; Vijayanand; Molecular Crystals and Liquid Crystals; vol. 537; (2011); p.

36 - 50 View in Reaxys

O

HO

OH O

O

O OH

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O OH

OH 2HO

O

O O

Rx-ID: 32963127 View in Reaxys 110/353 Yield

Conditions & References in N,N-dimethyl-formamide, Time= 12h, T= 30 °C Subhapriya; Vijayakumar; Madhu Mohan; Vijayanand; Molecular Crystals and Liquid Crystals; vol. 537; (2011); p.

36 - 50 View in Reaxys

O

HO

OH O

O

O OH

O OH

OH 2HO

O

O O

Rx-ID: 32963128 View in Reaxys 111/353 Yield

Conditions & References in N,N-dimethyl-formamide, Time= 12h, T= 30 °C Subhapriya; Vijayakumar; Madhu Mohan; Vijayanand; Molecular Crystals and Liquid Crystals; vol. 537; (2011); p.

36 - 50 View in Reaxys

O

HO

OH O

O

O OH

2 O OH

OH HO

O

O O

Rx-ID: 32963129 View in Reaxys 112/353 Yield

Conditions & References in N,N-dimethyl-formamide, Time= 12h, T= 30 °C Subhapriya; Vijayakumar; Madhu Mohan; Vijayanand; Molecular Crystals and Liquid Crystals; vol. 537; (2011); p.

36 - 50 View in Reaxys

HO

O

OH

–O

O 2

H O

O

O

–

O

–

N+

N+

Rx-ID: 33863965 View in Reaxys 113/353 Yield

Conditions & References in water, pH= 8 Duan, Qunpeng; Xia, Wei; Hu, Xiaoyu; Ni, Mengfei; Jiang, Juli; Lin, Chen; Pan, Yi; Wang, Leyong; Chemical Communications; vol. 48; nb. 68; (2012); p. 8532 - 8534 View in Reaxys in tetrahydrofuran, Inert atmosphere

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Gotor, Raul; Costero, Ana M.; Gavina, Pablo; Gil, Salvador; Parra, Margarita; European Journal of Organic Chemistry; nb. 8; (2013); p. 1515 - 1520 View in Reaxys H

2

HO

O

OH

H

O

O Ca 2+

O

O

O–

CaCl 2

O–

Rx-ID: 39348595 View in Reaxys 114/353 Yield

Conditions & References in water, T= 70 °C Otero, Vanessa; Sanches, Diogo; Montagner, Cristina; Vilarigues, Mrcia; Carlyle, Leslie; Lopes, Joo A.; Melo, Maria J.; Journal of Raman Spectroscopy; vol. 45; nb. 11-12; (2014); p. 1197 - 1206 View in Reaxys H

4

HO

O

OH

H

O

O Mn2+

O

O

O–

Cl 2Mn

O–

Rx-ID: 39348596 View in Reaxys 115/353 Yield

Conditions & References in water, T= 70 °C Otero, Vanessa; Sanches, Diogo; Montagner, Cristina; Vilarigues, Mrcia; Carlyle, Leslie; Lopes, Joo A.; Melo, Maria J.; Journal of Raman Spectroscopy; vol. 45; nb. 11-12; (2014); p. 1197 - 1206 View in Reaxys H

HO

O

OH

H

O

O Cd 2+

O

O

O–

CdCl 2

O–

Rx-ID: 39348600 View in Reaxys 116/353 Yield

Conditions & References in water, T= 70 °C Otero, Vanessa; Sanches, Diogo; Montagner, Cristina; Vilarigues, Mrcia; Carlyle, Leslie; Lopes, Joo A.; Melo, Maria J.; Journal of Raman Spectroscopy; vol. 45; nb. 11-12; (2014); p. 1197 - 1206 View in Reaxys

HO

OH

O

O

Cl 2Zn

O

Zn 2+ O–

O

O–

Rx-ID: 39348601 View in Reaxys 117/353 Yield

Conditions & References in water, T= 70 °C Otero, Vanessa; Sanches, Diogo; Montagner, Cristina; Vilarigues, Mrcia; Carlyle, Leslie; Lopes, Joo A.; Melo, Maria J.; Journal of Raman Spectroscopy; vol. 45; nb. 11-12; (2014); p. 1197 - 1206 View in Reaxys –O

HO

OH

O

2

Cu 2+

O

O Cu 2+

O

O

H

H

O–

O–

O

Rx-ID: 39348602 View in Reaxys 118/353 Yield

Conditions & References in water, T= 70 °C Otero, Vanessa; Sanches, Diogo; Montagner, Cristina; Vilarigues, Mrcia; Carlyle, Leslie; Lopes, Joo A.; Melo, Maria J.; Journal of Raman Spectroscopy; vol. 45; nb. 11-12; (2014); p. 1197 - 1206

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View in Reaxys

O

E

O

E

O

HO

O O

OH

O

O

O

Rx-ID: 797114 View in Reaxys 119/353 Yield

Conditions & References With methanol, diethyl ether, sodium methylate, Hydrieren des Reaktionsprodukts an Palladium/Kohle in Aethanol und Erwaermen des erhaltenen Esters mit aethanol.Kalilauge und anschliessend mit konz.wss.Salzsaeure Acker; Anderson; Journal of Organic Chemistry; vol. 24; (1959); p. 1162 View in Reaxys

HO

ν.ι-dioxy-stearic acid

OH O

O

Rx-ID: 6331665 View in Reaxys 120/353 Yield

Conditions & References With potassium carbonate Le Sueur; Journal of the Chemical Society; vol. 79; (1901); p. 1313 View in Reaxys With permanganate(VII) ion Edmed; Journal of the Chemical Society; vol. 73; (1898); p. 630 View in Reaxys

O

O

N

Co 2+ –O

O– 4

N

O

H O

H

O

N

O

–

O

(v4) (v4) N N(v6) 2+ Co (v4) (v4)

N

O–

O

10

H

H

(v4) (v4) N

N

–

11.5 O

(v4) (v4) N N(v6) 2+ Co (v4) (v4)

O–

O

H

N

O

N

(v4) (v4) N

N

H

H

O

H

Rx-ID: 27192704 View in Reaxys 121/353 Yield 21 %

Conditions & References in ethanol, water, addn. of excess of phen to Co-complex suspn. (in H2O/EtOH=1:4), refluxing for 3 h; concn. (vac.), crystn., filtration, washing (EtOH), drying in air; elem.anal.

Geraghty, Majella; McCann, Malachy; Devereux, Michael; McKee, Vickie; Inorganica Chimica Acta; vol. 293; nb.

2; (1999); p. 160 - 166 ; (from Gmelin) View in Reaxys

HO

F

Cl

OH H 2N 2 O

HO

OH

HO F

O

O

O

Rx-ID: 174613 View in Reaxys 122/353 Yield

Conditions & References With diethyl ether, magnesium, anschliessend mit wss.Schwefelsaeure Pattison; Howell; Journal of Organic Chemistry; vol. 21; (1956); p. 879 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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HO

E

E

E

O

HO

OH O

HO O

O

Rx-ID: 3721379 View in Reaxys 123/353 Yield

Conditions & References With maleic anhydride, potassium permanganate, 1.) C6H6, reflux, 5 h, Yield given. Multistep reaction Husain, Shahid; Ahmad, Moghis U.; Osman, S. M.; Phytochemistry (Elsevier); vol. 19; (1980); p. 75 - 78 View in Reaxys

HO

oleic acid ozonide peroxide

OH O

O

Rx-ID: 6331677 View in Reaxys 124/353 Yield

Conditions & References With water Harries; Tuerk; Chemische Berichte; vol. 39; (1906); p. 3737 View in Reaxys Harries; Thieme; Justus Liebigs Annalen der Chemie; vol. 343; (1905); p. 357; Chemische Berichte; vol. 39; (1906); p. 2844 View in Reaxys

O

O– H

O

O

O–

O

H

Mn2+

O

O–

Mn2+

O–

Rx-ID: 27445125 View in Reaxys 125/353 Yield

Conditions & References in neat (no solvent), Kinetics, byproducts: H2O; sample dehydration on heating at 10 K/min in Ar or CO2 or air flow at 200 ml/min (dehydration temp. range 56-148°C); TG, DTA Suzuki, Yukihiko; Thermochimica Acta; vol. 255; (1995); p. 155 - 170 ; (from Gmelin) View in Reaxys

N H

6

HO

O

OH O

O

N

H

N

Cl 2Ni

N N N HO 0.5 –O

O–

OH 6 O

O

5 O

N

O

N 2 Cl –

2

OH –

8H O 2

7 Ni 2+

Rx-ID: 34313788 View in Reaxys 126/353 Yield

Conditions & References T= 180 °C Zhao, Fang-Hua; Che, Yun-Xia; Zheng, Ji-Min; Crystal Growth and Design; vol. 12; nb. 10; (2012); p. 4712 - 4715,4 View in Reaxys

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–O

H N

O

N

HO

OH

H

H

Ag2O

O

O

O–

2 Ag+

O

O

HN 3

N N H

N

NH

3.5H O 2

N

Rx-ID: 37916944 View in Reaxys 127/353 Yield

Conditions & References

35 %

Time= 73h, T= 30 - 180 °C , pH= 4.07- 4.14, Autoclave Han, Lu-Lu; Zhang, Xi-Ying; Chen, Jiang-Shan; Li, Zhong-Hui; Sun, Dao-Feng; Wang, Xing-Po; Sun, Di; Crystal Growth and Design; vol. 14; nb. 5; (2014); p. 2230 - 2239 View in Reaxys

HO

α-eleostearic acid diozonide

OH O

O

Rx-ID: 6331664 View in Reaxys 128/353 Yield

Conditions & References With water Majima; Chemische Berichte; vol. 42; (1909); p. 678 View in Reaxys

HO

2.8-dimethyl-nonanedioic acid

OH O

O

Rx-ID: 6331667 View in Reaxys 129/353 Yield

Conditions & References T= 200 °C Haworth; Perkin; Journal of the Chemical Society; vol. 65; (1894); p. 104; Chemische Berichte; vol. 26; (1893); p.

2249 View in Reaxys

Chinese wax

HO

OH O

O

Rx-ID: 6331670 View in Reaxys 130/353 Yield

Conditions & References With nitric acid Buckton; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1857); p.

303 View in Reaxys

HO

elaidic acid ozonide peroxide

OH O

O

Rx-ID: 6331672 View in Reaxys 131/353 Yield

Conditions & References With water Harries; Thieme; Justus Liebigs Annalen der Chemie; vol. 343; (1905); p. 357; Chemische Berichte; vol. 39; (1906); p. 2844 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

47/102

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HO

heptane-tetracarboxylic acid-(1.1.7.7)-tetraethyl ester

OH O

O

Rx-ID: 6331673 View in Reaxys 132/353 Yield

Conditions & References With potassium hydroxide, Beim Erhitzen der nicht naeher beschriebenen Saeure auf 180grad Grunfeld; Annales de Chimie (Cachan, France); vol. <10> 20; (1933); p. 304,367 View in Reaxys

HO

higher fatty acids of coconut oil

OH O

O

Rx-ID: 6331674 View in Reaxys 133/353 Yield

Conditions & References With nitric acid Wirz; Justus Liebigs Annalen der Chemie; vol. 104; (1857); p. 271 View in Reaxys

HO

keratin

OH O

O

Rx-ID: 6331676 View in Reaxys 134/353 Yield

Conditions & References With potassium permanganate Lissizin; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 62; (1909); p. 226 View in Reaxys

HO

trioleyne ozonide

OH O

O

Rx-ID: 6331682 View in Reaxys 135/353 Yield

Conditions & References With potassium hydroxide Molinari; Fenaroli; Chemische Berichte; vol. 41; (1908); p. 2790 Anm.1 View in Reaxys

castor oil

HO

OH O

azelaic acid and suberic acid

O

Rx-ID: 6726255 View in Reaxys 136/353 Yield

Conditions & References With nitric acid Harries; Thieme; Justus Liebigs Annalen der Chemie; vol. 343; (1905); p. 357; Chemische Berichte; vol. 39; (1906); p. 2844 View in Reaxys

oleate of sodium

HO

OH O

pelargonaldehyde ; pelargonic acid

O

Rx-ID: 6730429 View in Reaxys 137/353 Yield

Conditions & References With water, ozone Harries; Thieme; Justus Liebigs Annalen der Chemie; vol. 343; (1905); p. 357; Chemische Berichte; vol. 39; (1906); p. 2844

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View in Reaxys

HO

linolenic acid ozonide peroxide

OH O

semialdehyde of/the/ azelaic acid

O

Rx-ID: 6731241 View in Reaxys 138/353 Yield

Conditions & References With water Erdmann,E.; Raspe; Chemische Berichte; vol. 42; (1909); p. 1337 View in Reaxys

O

O

Bi3+

potassium azelate

O–

O–

(v0) (v1)

O -1 H

Rx-ID: 8231672 View in Reaxys 139/353 Yield

Conditions & References With Bi(NO3)3, ethanol, [14C]-D-(-)-Mannitol, water Lauter; Jurist; Christiansen; Journal of the American Pharmaceutical Association (1912-1977); vol. 21; (1932); p.

1280; Chem. Zentralbl.; vol. 104; nb. I; (1933); p. 2081 View in Reaxys

HO

HO

OH

OH O

O

O

Rx-ID: 22328916 View in Reaxys 140/353 Yield

Conditions & References Reaction Steps: 3 1: ozone 2: permanganate; water; alcohol 3: Cr2O3-H2SO4 With Catalyst M-Chromium oxide, ethanol, sulfuric acid, water, permanganate(VII) ion, ozone Kerschbaum; Chemische Berichte; vol. 60; (1927); p. 907 View in Reaxys Reaction Steps: 3 1: ozone 2: permanganate; water; alcohol 3: Cr2O3-H2SO4 With Catalyst M-Chromium oxide, ethanol, sulfuric acid, water, permanganate(VII) ion, ozone Kerschbaum; Chemische Berichte; vol. 60; (1927); p. 907 View in Reaxys

O

O

HO

Ce O

OH 6

O

O

N O

4+

2

2 Ce 4+

3

NH +4

–O

4.5

O–

H O

H

O–

H 2O2( 2-)

Rx-ID: 26808609 View in Reaxys 141/353 Yield

Conditions & References in not given, stoich. amts. of educts, pH 2.2 to 2.3; filtering, washed with dild. soln. of azelaic acid, dried in air Merkusheva, S. A.; Skopik, N. A.; Serebrennikov, V. V.; Radiokhimiya; vol. 10; (1968); p. 718 - 719; Radiokhimiya; vol. 10; (1968); p. 731 - 738 ; (from Gmelin) View in Reaxys in not given, stoich. amts. of educts, pH 2.2 to 2.3; filtering, washed with dild. soln. of azelaic acid, dried in air

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vol. Sc: MVol.D5; 1.2.10.2, page 179 - 181 ; (from Gmelin) View in Reaxys

O

N+

3

H

2

O– Sc 3+

O–

H

O

O

O

N+ HH

O

–

O–

O

O–

–O

H

3

O

H

2 Sc 3+

Rx-ID: 26839935 View in Reaxys 142/353 Yield

Conditions & References in not given, pH 5.9 vol. Sc: MVol.D5; 1.2.10.1, page 178 - 179 ; (from Gmelin) View in Reaxys in not given Kurpiel, R.; Brzyska, W.; Zesz. Nauk. Politech. Slask. Chem.; vol. 677; (1981); p. 155 - 163; C.A.; vol. 98; (1983); p.

190859 ; (from Gmelin) View in Reaxys 2+ 2 O Cu

O

O

0.82 O–

H O

–O

2 O Na +

O

H O

O–

H 3O3( 3-)

Cu 2+

O– 0.46

H

O–

2

H

H 2.36O2.36( 2.36-)

Rx-ID: 27212876 View in Reaxys 143/353 Yield

Conditions & References in water, Cu2(OH)3(OOCCH3)*H2O dispersed into aq. soln. of the sodium dicarboxylate at room temp. for 1 d and for 2 ds with fresh dicarboxylate soln. to exchange the acetate ion; ppt. washed with alcohol, dried at 40 °C Hornick; Rabu; Drillon; Polyhedron; vol. 19; nb. 3; (2000); p. 259 - 266 ; (from Gmelin) View in Reaxys

O HO O

Mn2+ O

O

O– H

O–

OH

O–

O

O–

H

O Mn2+

Rx-ID: 27470675 View in Reaxys 144/353 Yield

Conditions & References in water, pptn. on Mn-salt reacting with org. acid soln. in 10percent excess at 70°C, crystn. on soln. allowing to stand overnight at room temp.; crystals filtration, washing (H2O, EtOH/H2O 2:1, ether), drying by pressing gently between filter papers, storing over silica gel in desiccator;elem. anal.; optical microscopy, XRD Suzuki, Yukihiko; Thermochimica Acta; vol. 255; (1995); p. 155 - 170 ; (from Gmelin) View in Reaxys

HO

OH O

O

O

O

–O

O–

10

N N N (v4) Co 2+ (v4) N N (v4) (v4) N

O

(v4) (v4)(v6)

O

–O

H

O–

11.5 O

H

N N N (v4) Co 2+ (v4) N N (v4) (v4) N

(v4) (v4)(v6)

H O

H

Rx-ID: 31838837 View in Reaxys 145/353

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Yield

Conditions & References Reaction Steps: 2 1: water; ethanol 2: water; ethanol in ethanol, water Geraghty, Majella; McCann, Malachy; Devereux, Michael; McKee, Vickie; Inorganica Chimica Acta; vol. 293; nb.

2; (1999); p. 160 - 166 View in Reaxys

O

O E

HO

OH

E OH

O

O

Rx-ID: 84896 View in Reaxys 146/353 Yield

Conditions & References With hydrogenchloride, Beim Hydrieren der nicht naeher beschriebenen 5-Oxo-hepten-(1)-dicarbonsaeure-(1.7) an Kupferchromit in Wasser bei 250grad und 150 at Patent; Thueringische Zellwolle A.G.; DE765970; (1941); View in Reaxys

O

HO

OH

O

O

OH

O

Rx-ID: 207687 View in Reaxys 147/353 Yield

Conditions & References With ozone Haller; Brochet; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 150; (1910); p. 500 View in Reaxys

HO

OH O

OH

HO

O

OH O

O

Rx-ID: 248597 View in Reaxys 148/353 Yield

Conditions & References With hydrogen iodide v.Pechmann; Chemische Berichte; vol. 37; (1904); p. 3821 View in Reaxys

HO

OH O

HO

O

O

Rx-ID: 251542 View in Reaxys 149/353 Yield

Conditions & References With alkaline KMNO4 Arnaud; Hasenfratz; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 152; (1911); p. 1604 View in Reaxys

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O O HO

OH O

O

O

E N

O O HO

OH 2 O

O

O E N

Rx-ID: 1627478 View in Reaxys 150/353 Yield

Conditions & References in pyridine Kato, Takashi; Fujishima, Akira; Frechet, Jean M. J.; Chemistry Letters; nb. 6; (1990); p. 919 - 922 View in Reaxys

HO

dioxystearic acid

OH O

HO

O

O

Rx-ID: 6965206 View in Reaxys 151/353 Yield

Conditions & References With alkaline permanganate Edmed; Journal of the Chemical Society; vol. 73; (1898); p. 630 View in Reaxys

threo-9,10,18-trihydroxy-octadecanoic acid methyl ester O

HO

OH

O

O OH

O

O

O

O

Rx-ID: 6992260 View in Reaxys 152/353 Yield

Conditions & References With chromic acid, acetone Meakins; Swindells; Journal of the Chemical Society; (1959); p. 1044,1046 View in Reaxys

O

OH

HO

OH O

O

Rx-ID: 22329560 View in Reaxys 153/353 Yield

Conditions & References Reaction Steps: 2 1: permanganate; water; alcohol 2: Cr2O3-H2SO4 With Catalyst M-Chromium oxide, ethanol, sulfuric acid, water, permanganate(VII) ion Kerschbaum; Chemische Berichte; vol. 60; (1927); p. 907 View in Reaxys

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H

2 H

O

O

O

N+ HH

O–

–O

O–

–O

2 Sc 3+

O

3

Rx-ID: 37306758 View in Reaxys 154/353 Yield

Conditions & References Reaction Steps: 2 1: not given in not given Kurpiel, R.; Brzyska, W.; Zesz. Nauk. Politech. Slask. Chem.; vol. 677; (1981); p. 155 - 163; C.A.; vol. 98; (1983); p.

190859 View in Reaxys NH

S

O

O

NH

S

O

O 2H

H 2N

N H

NHHO 2

H 2N

OH

N H

NHHO 2

O

Rx-ID: 41412488 View in Reaxys 155/353 Yield

Conditions & References With water Janczak, Jan; Crystal Growth and Design; vol. 15; nb. 10; (2015); p. 5097 - 5111 View in Reaxys

HO

OH

HO

O

OH O

HO

O

O O

Rx-ID: 239406 View in Reaxys 156/353 Yield

Conditions & References With Catalyst M-Chromium oxide, sulfuric acid Kerschbaum; Chemische Berichte; vol. 60; (1927); p. 907 View in Reaxys

HO

OH O

HO

HO O

O

O

Rx-ID: 251543 View in Reaxys 157/353 Yield

Conditions & References With hexane, ozone, Zersetzen des Reaktionsprodukts mit Wasser Harries; Chemische Berichte; vol. 40; (1907); p. 4906; Chemische Berichte; vol. 41; (1908); p. 1227 View in Reaxys

O

O

HO

OH

HO

OH O

OH

O

O

O

Rx-ID: 254113 View in Reaxys 158/353 Yield

Conditions & References With nitric acid Asahina; Takimoto; Yakugaku Zasshi; vol. 49; (1929); p. 1023; dtsch. Ref. S. 157; ; (1930); p. 1346 View in Reaxys

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53/102

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O

O

O

HO

HO

OH

OH

O O

O

O

Rx-ID: 846556 View in Reaxys 159/353 Yield

Conditions & References With sodium hydroxide, hydrazine hydrate Stetter; Coenen; Chemische Berichte; vol. 87; (1954); p. 869,871 View in Reaxys

O

O

O

O O–

OH

O

HO HO

2 O Na +

O OH

O–

O O

N

OH O

O

OH HO

HO

N

OH O

O

O

O O

OH

HO

O

O O O

OH

Rx-ID: 5067843 View in Reaxys 160/353 Yield

Conditions & References With phosphate buffer, pH= 5.5, ion pair formation Matschiner; Neubert; Wohlrab; Skin Pharmacology; vol. 8; nb. 6; (1995); p. 319 - 325 View in Reaxys

O

Br

HO

O

OH

Br

O

O

Rx-ID: 6331666 View in Reaxys 161/353 Yield

Conditions & References With magnesium v.Braun; Sobecki; Chemische Berichte; vol. 44; (1911); p. 1926 View in Reaxys

air

HO

cobalt oleate

OH O

O

O

Z O

HO

higher-melting 9.10-dihydroxy-stearic acid methyl ester O

lower-melting 9.10-dihydroxy-stearic acid methyl ester Rx-ID: 7080172 View in Reaxys 162/353

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54/102

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Yield

Conditions & References T= 65 °C Swern et al.; Journal of the American Chemical Society; vol. 67; (1945); p. 1134 View in Reaxys

HO

OH O

NH 2

O

O

N

NH 2

N

N H

O

-1 HO

NH 2

NH 2

N

N H

OH N

Rx-ID: 31912854 View in Reaxys 163/353 Yield

Conditions & References in methanol Carvalho, Simao P.; Wang, Ruiyao; Wang, Haotian; Ball, Brian; Lebel, Olivier; Crystal Growth and Design; vol.

10; nb. 6; (2010); p. 2734 - 2745 View in Reaxys

H 2N

HO

Cl

N

O

OH

NH 2

O

N

O

N HO

O NH 2

OH H 2N

Cl

N

Rx-ID: 33579096 View in Reaxys 164/353 Yield

Conditions & References in methanol, Time= 48h Delori, Amit; Galek, Peter T. A.; Pidcock, Elna; Jones, William; Chemistry - A European Journal; vol. 18; nb. 22; (2012); p. 6835 - 6846 View in Reaxys

N O HO

O

OH

O

O

HN O

N HO

O

N H

OH

N

N

Rx-ID: 33648568 View in Reaxys 165/353 Yield

Conditions & References in ethyl acetate Aakeroey, Christer B.; Panikkattu, Sheelu V.; Dehaven, Baillie; Desper, John; Crystal Growth and Design; vol.

12; nb. 5; (2012); p. 2579 - 2587 View in Reaxys N

HO

O

OH HN

O

O

N

O

H N

O HO

N

OH O

N

Rx-ID: 33648569 View in Reaxys 166/353

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Yield

Conditions & References in ethyl acetate, Time= 1080h Aakeroey, Christer B.; Panikkattu, Sheelu V.; Dehaven, Baillie; Desper, John; Crystal Growth and Design; vol.

12; nb. 5; (2012); p. 2579 - 2587 View in Reaxys

N

O

N

HO

O

OH

O N

HN

N

S N

O

O

O

O N O

N

HN

N

S

0.5 HO

O

N

O

N

O

OH

O

Rx-ID: 37224134 View in Reaxys 167/353 Yield

Conditions & References in methanol Sanphui, Palash; Tothadi, Srinu; Ganguly, Somnath; Desiraju, Gautam R.; Molecular Pharmaceutics; vol. 10; nb.

12; (2013); p. 4687 - 4697 View in Reaxys H 2N

HO

NHHN

NH 2

H 2N

NHHN

NH 2

OH HO

O

OH

O O

O

Rx-ID: 37866264 View in Reaxys 168/353 Yield

Conditions & References in dimethyl sulfoxide Kusukawa, Takahiro; Tanaka, Syugo; Inoue, Kouta; Tetrahedron; vol. 70; nb. 26; (2014); p. 4049 - 4056 View in Reaxys

HO

OH

HO

H 2N O

OH

H 2N O

O

O

Rx-ID: 40342665 View in Reaxys 169/353 Yield

Conditions & References in water Lavi, Avi; Segre, Enrico; Gomez-Hernandez, Mario; Zhang, Renyi; Rudich, Yinon; Journal of Physical Chemistry A; vol. 119; nb. 19; (2015); p. 4336 - 4346 View in Reaxys

HO

OH O

O

HO

N H

N H

OH O

O

Rx-ID: 40342670 View in Reaxys 170/353 Yield

Conditions & References in water

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Lavi, Avi; Segre, Enrico; Gomez-Hernandez, Mario; Zhang, Renyi; Rudich, Yinon; Journal of Physical Chemistry A; vol. 119; nb. 19; (2015); p. 4336 - 4346 View in Reaxys

HO

OH O

HO

N

OH

N O

O

O

Rx-ID: 40342674 View in Reaxys 171/353 Yield

Conditions & References in water Lavi, Avi; Segre, Enrico; Gomez-Hernandez, Mario; Zhang, Renyi; Rudich, Yinon; Journal of Physical Chemistry A; vol. 119; nb. 19; (2015); p. 4336 - 4346 View in Reaxys

HO

OH O

NH 2

O

NH

H N

S

S

O

O

NH 2

H 2N

NH

N H

NHHO 2

OH

Rx-ID: 41412479 View in Reaxys 172/353 Yield

Conditions & References in water Janczak, Jan; Crystal Growth and Design; vol. 15; nb. 10; (2015); p. 5097 - 5111 View in Reaxys

HO

Z O O

HO

OH

HO

HO

HO OH

O

O

O

O

O

Rx-ID: 5192696 View in Reaxys 173/353 Yield

Conditions & References With dihydrogen peroxide, WO3, silica gel in tert-butyl alcohol, Time= 5h, Heating, Catalytic oxidation, Product distribution, Further Variations: Catalysts Noureddini; Kanabur; JAOCS, Journal of the American Oil Chemists' Society; vol. 76; nb. 3; (1999); p. 305 - 312 View in Reaxys

O HO

H

H

potassium hydroxide

O

O

O

HO

OH O

HO

O

α-oxy-α-n-octyl-sebacic acid O

ψ,ι-dioxy-stearic acid Rx-ID: 6965222 View in Reaxys 174/353 Yield

Conditions & References T= 160 °C , Schmelzen Nicolet; Jurist; Journal of the American Chemical Society; vol. 44; (1922); p. 1140 View in Reaxys

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O HO

HO

E

OH

OH O

O

O

Rx-ID: 207766 View in Reaxys 175/353 Yield

Conditions & References Ozonspaltung Ruzicka; Plattner; Widmer; Helvetica Chimica Acta; vol. 25; (1942); p. 1090 View in Reaxys Reaction Steps: 2 1: dihydrogen peroxide; formic acid / dichloromethane / 8 h / 0 - 40 °C 2: sodium hypochlorite / 5 h / 20 °C With sodium hypochlorite, formic acid, dihydrogen peroxide in dichloromethane Patent; UNIVERSITE CLAUDE BERNARD LYON I; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; Lemaire, Marc; Favre-Reguillon, Alain; Paquit, Bénédicte; Claude, Sylvain; Raoul, Yann; US2013/131379; (2013); (A1) English View in Reaxys

O N OH

O HN HO

HO

OH O

O

OH O

HO O

O

NH

OH O

O HO

Rx-ID: 1573621 View in Reaxys 176/353 Yield

Conditions & References With ammonium sulfate, dipotassium hydrogenphosphate, potassium dihydrogenphosphate, magnesium sulfate in water, Time= 168h, T= 28 °C , Alcaligenes sp.; further pyridine compounds Ohsugi, Masahiro; Inoue, Yasuko; Takami, Keiko; Namikawa, Mayumi; Agricultural and Biological Chemistry; vol. 45; nb. 8; (1981); p. 1879 - 1880 View in Reaxys

O

O

H

3 –O

O–

O

O

H

O

O–

–O

2 Sc 3+

2 Sc 3+

3

Rx-ID: 26838713 View in Reaxys 177/353 Yield

Conditions & References 40 to 170°C vol. Sc: MVol.D5; 1.2.10.1, page 178 - 179 ; (from Gmelin) View in Reaxys Kurpiel, R.; Brzyska, W.; Zesz. Nauk. Politech. Slask. Chem.; vol. 677; (1981); p. 155 - 163; C.A.; vol. 98; (1983); p.

190859 ; (from Gmelin) View in Reaxys

olive oil

HO

OH O

O

Rx-ID: 6331679 View in Reaxys 178/353 Yield

Conditions & References beim Ranzigwerden

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Scala; Chem. Zentralbl.; vol. 69; nb. I; (1898); p. 439 View in Reaxys

HO

KMnO4

OH

OH O

O

Rx-ID: 6800052 View in Reaxys 179/353 Yield

Conditions & References Hill; Carothers; Journal of the American Chemical Society; vol. 55; (1933); p. 5031,5034 View in Reaxys Hill; Journal of the American Chemical Society; vol. 57; (1935); p. 1132 View in Reaxys

HO

convolvulinoloic acid

OH

HO NH 2

O

O

O

Rx-ID: 6972959 View in Reaxys 180/353 Yield

Conditions & References und Erwaermen des oeligen Oxims der κ-Oxo-pentadecylsaeure mit konz.Schwefelsaeure und nachfolgendes Erhitzen mit 48prozentiger Bromwasserstoffsaeure im Rohr auf 170grad Asahina; Akasu; Yakugaku Zasshi; nb. 523; (1925); p. 4; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 915 View in Reaxys

HO

OH O

O 3

N+

O

O–

O–

O

O

H

3 Sc 3+

–O

O–

O

H

2 Sc 3+

Rx-ID: 26811334 View in Reaxys 181/353 Yield

Conditions & References Turova, L. I.; Serebrennikov, V. V.; Trudy Tomskogo Gosudarstvennogo Universiteta; vol. 240; (1973); p. 135 - 137; C.A.; vol. 80; (1974); p. 70252 View in Reaxys vol. Sc: MVol.D5; 1.2.10.1, page 178 - 179 ; (from Gmelin) View in Reaxys

O

E

E

O

E

KMnO4

O

HO

OH O

O

Rx-ID: 6800054 View in Reaxys 182/353 Yield

Conditions & References Kass; Nichols; Burr; Journal of the American Chemical Society; vol. 63; (1941); p. 1061 View in Reaxys

HO

aqueous KOH-solution

oxygen

O

HO

OH O

O

OH

O

Rx-ID: 7058236 View in Reaxys 183/353 Yield

Conditions & References T= 130 °C , p= 73550.8Torr Treibs; Rothe; Chemische Berichte; vol. 84; (1951); p. 370,375 View in Reaxys

O

E

E

O

KMnO4

O

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HO

OH O

HO O

O

Rx-ID: 7064785 View in Reaxys 184/353 Yield

Conditions & References Kass; Burr; Journal of the American Chemical Society; vol. 61; (1939); p. 1063 View in Reaxys

O

OH H

OH

H

OH

HO

chromic acid

OH O

O

HO O

Rx-ID: 6965204 View in Reaxys 185/353 Yield

Conditions & References T= 110 °C , optically active erythro-9.10-dihydroxy-stearic acid from castor oil Toyama; Ishikawa; Bulletin of the Chemical Society of Japan; vol. 11; (1936); p. 737,740 View in Reaxys

HO

E

oxygen

cobalt elaidate

O

OH O O

HO

OH

HO

HO OH

O

O

O

O

O racemate

Rx-ID: 7065423 View in Reaxys 186/353 Yield

Conditions & References T= 55 - 80 °C Ellis; Biochemical Journal; vol. 30; (1936); p. 758 View in Reaxys

O HO H

OH

H

OH

H

H

HO

H

HO

H

–O

O

4

O

OH

Pb4+

racemate

HO

OH O

O

malondialdehyde

O

Rx-ID: 7080421 View in Reaxys 187/353 Yield

Conditions & References T= 37 °C Nunn; Smedley-Maclean; Biochemical Journal; vol. 29; (1935); p. 2744 View in Reaxys

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OH O

HO

HO

OH

OH

HO OH

O

O

O

O

O

O

O

HO

HO

OH

HO

OH

OH

O

O

O

O

Rx-ID: 2056768 View in Reaxys 188/353 Yield

Conditions & References

0.824 (unit not given), 0.110 (unit not given), 0.020 (unit not given)

With nitric acid in pentamethylene, Time= 0.166667h, other temperature, other concentration of HNO3;, Product distribution Chevilenko, I. S.; Preobrazhenskii, V. A.; Medvedeva, V. F.; Kaimina, N. D.; J. Appl. Chem. USSR (Engl. Transl.); vol. 55; nb. 11; (1982); p. 2742 - 2746,2492 - 2495 View in Reaxys

O

HO

O

OH

dodecane-dicarboxylic acid-(1.12)

OH

O

O

O

Rx-ID: 7075160 View in Reaxys 189/353 Yield

Conditions & References T= 15 °C , Elektrolysiert man das Kaliumsalz zusammen mit Kaliumsalz des Malonsaeuremonoaethylesters an Platinelektroden und verseift.Electrolysis Carmichael; Journal of the Chemical Society; vol. 121; (1922); p. 2549 View in Reaxys

O

nickel O O

HO

OH

HO

dodecane-dicarboxylic acid-(1.12)

OH

O

O

O

Rx-ID: 7075161 View in Reaxys 190/353 Yield

Conditions & References T= 100 - 105 °C , darauffolgenden Oxydation mit Kaliumpermanganat in Aceton.Hydrogenation, linolenic acid ethyl ester Hildlitch; Vidyarthi; Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences; vol. 122; (1929); p. 555,562; Chem. Zentralbl.; vol. 100; nb. I; (1929); p. 2163 View in Reaxys

H

OH

Z

N2O4

fuming hydrochloric acid

O OH

HO

OH O

heptyloic acid

O

Rx-ID: 7077102 View in Reaxys 191/353 Yield

Conditions & References T= 130 - 140 °C , bei nacheinanderfolgender Einw. im Rohr

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Jegorow; Journal fuer Praktische Chemie (Leipzig); vol. <2>86; (1912); p. 539 View in Reaxys

O

hydrogen

nickel

O O

HO

OH

HO

undecane-dicarboxylic acid-(1.11)

OH

O

O

O

dodecane-dicarboxylic acid-(1.12) Rx-ID: 7089050 View in Reaxys 192/353 Yield

Conditions & References T= 100 - 105 °C , darauffolgenden Oxydation mit alkal.Kalimpermanganat-Loesung.Hydrogenation, linolic acid methyl ester Hildlitch; Vidyarthi; Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences; vol. 122; (1929); p. 555,562; Chem. Zentralbl.; vol. 100; nb. I; (1929); p. 2163 View in Reaxys

HO

Z O

HO

OH O

HO

HO

O

O

O

O O

Rx-ID: 32124538 View in Reaxys 193/353 Yield

Conditions & References With Titanium(IV) oxide, Time= 24h, UV-irradiation, Mechanism Rathousky, Jiri; Kalousek, Vit; Kolar, Michal; Jirkovsky, Jaromir; Bartak, Petr; Catalysis Today; vol. 161; nb. 1; (2011); p. 202 - 208 View in Reaxys

HO

OH

HO

I O

OH

OH

H

O

O

O

Rx-ID: 6800038 View in Reaxys 194/353 Yield

Conditions & References T= 180 °C v. Pechmann; Sidgwick; Chemische Berichte; vol. 37; (1904); p. 3819 View in Reaxys

O

Cl

H

O

HO

OH

amalgamated zinc

HO

OH O

O

O

Rx-ID: 6800047 View in Reaxys 195/353 Yield

Conditions & References Kochen Brown; Farmer; Biochemical Journal; vol. 29; (1935); p. 635,636 View in Reaxys Mannich; Chemische Berichte; vol. 74; (1941); p. 565,568 View in Reaxys

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O

OH

OH

OH

alkaline permanganate

HO OH

OH

OH O

HO

OH

HO OH

O

O

O

Rx-ID: 6800868 View in Reaxys 196/353 Yield

Conditions & References T= 0 - 20 °C , isolinusinic acid Green; Hilditch; Journal of the Chemical Society; (1937); p. 767 View in Reaxys

O

OH

OH

OH

KMnO4

HO OH

OH

diluted KOH

OH O

HO

OH

HO OH

O

O

O

Rx-ID: 6800869 View in Reaxys 197/353 Yield

Conditions & References T= 0 - 20 °C , linusinic acid Green; Hilditch; Journal of the Chemical Society; (1937); p. 766 View in Reaxys

O

HO

KMnO4

Z O

HO

OH O

HO O

O

Rx-ID: 6965211 View in Reaxys 198/353 Yield

Conditions & References Reaktion der Methylester oder Aethylester; Verseifung Shorland; de la Mare; Biochemical Journal; vol. 39; (1945); p. 246 View in Reaxys Baliga; Hilditch; Journal of the Chemical Society; (1949); p. Spl.91,94 View in Reaxys Green; Hilditch; Stainsby; Journal of the Chemical Society; (1936); p. 1751 View in Reaxys

O

OH H

OH

H

OH

H O

HO

OH O

H

O

KO H

KClO3

HO O

Rx-ID: 6965213 View in Reaxys 199/353

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Yield

Conditions & References T= 200 - 220 °C Eckert; Monatshefte fuer Chemie; vol. 38; (1917); p. 5 View in Reaxys

O HO

oxygen O

alcoholic KOH

OH

HO

OH O

HO O

O

Rx-ID: 6965215 View in Reaxys 200/353 Yield

Conditions & References T= 18 °C , Oxidation Morrell; Phillips; Journal of the Society of Chemical Industry, London; vol. 57; (1938); p. 246,247 View in Reaxys

OH HO

oxygen O

alcoholic KOH

O

HO

OH O

HO O

O

Rx-ID: 6965216 View in Reaxys 201/353 Yield

Conditions & References T= 18 °C Morrell; Phillips; Journal of the Society of Chemical Industry, London; vol. 57; (1938); p. 246,247 View in Reaxys

HO

OH O

O

O

Z O O

HO OH

lower-melting (+--threo-)9.10-dihydroxystearic acid

peroxide/s

O

Rx-ID: 7084576 View in Reaxys 202/353 Yield

Conditions & References T= 120 °C , Autoxydation ohne Katalizator Gunstone; Hilditch; Journal of the Chemical Society; (1945); p. 841 View in Reaxys

O

H

N O

HO

O O

OH

H

HO

O

O

Rx-ID: 7154498 View in Reaxys 203/353 Yield

Conditions & References T= 60 °C Stoll; Rouve; Helvetica Chimica Acta; vol. 30; (1947); p. 1833

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View in Reaxys

HO

HO O

OH O

O

Rx-ID: 202542 View in Reaxys 204/353 Yield

Conditions & References bei der Ozonspaltung, lower-melting form Collaud; Helvetica Chimica Acta; vol. 26; (1943); p. 1067 View in Reaxys bei der Ozonspaltung Chuit et al.; Helvetica Chimica Acta; vol. 9; (1926); p. 1086 View in Reaxys

OH

O

–O

HO OH O

O

4

HO

Pb4+

OH O

OH

O

Rx-ID: 254991 View in Reaxys 205/353 Yield

Conditions & References Nunn; Smedley-Maclean; Biochemical Journal; vol. 29; (1935); p. 2744 View in Reaxys

HO

Z O

O HO

O

OH

OH O

O

OH O

O

Rx-ID: 1893630 View in Reaxys 206/353 Yield

Conditions & References Time= 120h, T= 30 °C , biotransformation of its esters, Sarcina lutea ICR2010, Product distribution Blank, Wolfgang; Takayanagi, Hiroko; Kido, Toshiko; Meussdoerffer, Franz; Esaki, Nobuyoshi; Soda, Kenji; Agricultural and Biological Chemistry; vol. 55; nb. 10; (1991); p. 2651 - 2652 View in Reaxys

HO

E

O

KMnO4

HO

OH O

O

O

Rx-ID: 6800055 View in Reaxys 207/353 Yield

Conditions & References Hilditch; Longenecker; Journal of Biological Chemistry; vol. 122; (1938); p. 501 View in Reaxys

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OH HO

O

HO

S OO

OH O

HO O

O

Z O

Rx-ID: 6965203 View in Reaxys 208/353 Yield

Conditions & References T= 0 - 5 °C , dann Oxydieren des Reaktionsprodukts mit HNO3 in Gegenwart von MnO2 bei 115-120grad Patent; Nopco Chem.Co.; US2426954; (1944) View in Reaxys

OH

HO

HO

Cl

H

E N

O

OH O

O

HO

HO

γ-hexyl-butyrolactone

NH 2 O

α-hexyl-trimethyleneimine Rx-ID: 6968022 View in Reaxys 209/353 Yield

Conditions & References T= 190 °C Goldsobel; Chemische Berichte; vol. 27; (1894); p. 3123 View in Reaxys

E

aqueous alkaline KMnO4

E HO

Z O O

HO

OH

HO

HO OH

O

O

O

O

Rx-ID: 7067069 View in Reaxys 210/353 Yield

Conditions & References T= 0 °C , Product distribution Green; Hilditch; Journal of the Chemical Society; (1937); p. 767 View in Reaxys

HO

Z O

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O HO

O OH HO

HO

HO

H

O

H

OH H

O

HO

OH

H

OH

O

OH

racemate

racemate

Rx-ID: 206051 View in Reaxys 211/353 Yield

Conditions & References T= 120 °C , durch geblasenes Waloel katalysierten Autoxydation Skellon; Journal of the Society of Chemical Industry, London; vol. 50; (1931); p. 383T; Journal of the Chemical Society; (1848); p. 347 View in Reaxys

O

Br

O

KMnO4

E

O

Na2CO3

Br

HO

OH O

HO O

O

Rx-ID: 6965214 View in Reaxys 212/353 Yield

Conditions & References Entbromen mit Zink in Methanol, Verseifen mit heisser verd. KOH und Hydrieren in Gegenwart von Platinoxyd in Eisessig McKay; Bader; Journal of Organic Chemistry; vol. 13; (1948); p. 80 View in Reaxys H N

HO

Cl

H O

O

HO

OH O

O H

HO

H

O

O

H N

Rx-ID: 7053345 View in Reaxys 213/353 Yield

Conditions & References T= 100 °C Spieckermann; Chemische Berichte; vol. 29; (1896); p. 813 View in Reaxys

O Cl

OH

OH

OH

Cl

Cl

Cl

H

OH

HO

OH O

H O

HO

O

O

OH

OH

KClO3

OH

HO O

Rx-ID: 7058959 View in Reaxys 214/353 Yield

Conditions & References T= 180 - 200 °C , Linusinsaeure reagiert Eckert; Monatshefte fuer Chemie; vol. 38; (1917); p. 5

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View in Reaxys

OH Cl

Cl

Cl

Cl

OH

O H

OH

HO O

OH O

OH

KClO3

H O

OH

OH

HO O

O

Rx-ID: 7064818 View in Reaxys 215/353 Yield

Conditions & References T= 180 - 200 °C , sativic acid Eckert; Monatshefte fuer Chemie; vol. 38; (1917); p. 5 View in Reaxys

Z O

E HO

KMnO4

Na2CO3

Z O

HO

OH O

HO

O

O

O

HO

OH

O

Rx-ID: 7067082 View in Reaxys 216/353 Yield

Conditions & References T= 0 °C Farmer; van den Heuvel; Journal of the Chemical Society; (1936); p. 1811 View in Reaxys

HO

OH O

HO

O

Z O

Rx-ID: 206769 View in Reaxys 217/353 Yield

Conditions & References Ozonspaltung und nach der Oxydation der in Benzin unloeslichen Fraktion mit KMnO4 Takano; ; vol. 36; (1933); p. 549,551; Chem. Zentralbl.; vol. 105; nb. I; (1934); p. 2513 View in Reaxys Toyama; Tsuchiya; ; vol. 37; (1934); p. 17,19,20; Chem. Zentralbl.; vol. 105; nb. I; (1934); p. 2677 View in Reaxys OH O

HO

OH O

HO

O

Z O

Rx-ID: 207764 View in Reaxys 218/353

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Yield

Conditions & References Ozonisierung Ruzicka; Plattner; Widmer; Helvetica Chimica Acta; vol. 25; (1942); p. 1090 View in Reaxys

O O O O

Z O O

HO

OH

HO

HO

HO OH

O

O

O

O

O

Rx-ID: 1538279 View in Reaxys 219/353 Yield

Conditions & References With hydrogenchloride, potassium hydroxide, potassium permanganate, sodium periodate, multistep reaction: 1.)

210-220 deg C, 2 h, 2.) EtOH, 23 deg C, 16 h, 3.) 23 degC, 20h; reaction with ethyl elaidate; addition of maleic anhydride to esters of mono-unsaturated fatty acids, formation of 1:1 adducts, oxidative cleavage of products formed, Product distribution Holmberg, Krister; Johansson, Jan-Allan; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 36; nb. 7; (1982); p. 481 - 486 View in Reaxys

O O

O

E O

O O

HO

OH

HO

HO

HO OH

O

O

O

O

O

Rx-ID: 1538281 View in Reaxys 220/353 Yield

Conditions & References With hydrogenchloride, potassium hydroxide, potassium permanganate, sodium periodate, multistep reaction: 1.)

210-220 deg C, 2 h, 2.) EtOH, 23 deg C, 16 h, 3.) 23 deg C, 20 h; reaction with ethyl oleate; addition of maleic anhydride to esters of mono-unsaturated fatty acids, formation of 1:1 adducts, oxidative cleavage of products formed, Product distribution Holmberg, Krister; Johansson, Jan-Allan; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 36; nb. 7; (1982); p. 481 - 486 View in Reaxys

HO

chromic acid

O

OH O

O

Rx-ID: 6331671 View in Reaxys 221/353 Yield

Conditions & References Ruzicka; Brugger; Helvetica Chimica Acta; vol. 9; (1926); p. 403 View in Reaxys

OH

OH

O OH

OH

alkaline permanganate

OH

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HO

OH O

O

Rx-ID: 6800044 View in Reaxys 222/353 Yield

Conditions & References Hazura; Monatshefte fuer Chemie; vol. 8; (1887); p. 267 View in Reaxys

O O

H2 C

OH

HO

chromium trioxide

C H2

OH O

O

Rx-ID: 6800050 View in Reaxys 223/353 Yield

Conditions & References Ruzicka; Stoll; Schinz; Helvetica Chimica Acta; vol. 9; (1926); p. 250,260; Helvetica Chimica Acta; vol. 11; (1928); p. 671 Anm. 3, 685 View in Reaxys Patent; Naef and Co.; DE441273; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 109 View in Reaxys

KMnO4

HO

OH O

O

Rx-ID: 6800051 View in Reaxys 224/353 Yield

Conditions & References in sodaalkal. Loesung v. Braun; Deutsch; Schmatloch; Chemische Berichte; vol. 45; (1912); p. 1255 View in Reaxys Reformatski; Grischkewitsch-Trochimowski; Semenzow; Chemische Berichte; vol. 44; (1911); p. 1885 View in Reaxys

H

OH

Z

nitric acid

O OH O

HO

OH

HO OH

O

O

O

Rx-ID: 6800870 View in Reaxys 225/353 Yield

Conditions & References Baker; Ingold; Journal of the Chemical Society; vol. 123; (1923); p. 125,130 View in Reaxys Verkade; Hartman; Coops; Recueil des Travaux Chimiques des Pays-Bas; vol. 45; (1926); p. 379; Verslag van de Gewone Vergadering van de Afdeling Natuurkunde, Koninklijke Nederlandse Akademie van Wetenschappen; vol. 33; p. 767; Chem. Zentralbl.; vol. 96; nb. I; (1925); p. 1281 View in Reaxys Verkade; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 138; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 200 View in Reaxys

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OH O

H

OH

chromic acid

O

HO

OH

HO

O O

O

O

Rx-ID: 6961516 View in Reaxys 226/353 Yield

Conditions & References Spielman; Journal of Biological Chemistry; vol. 106; (1934); p. 88,93 View in Reaxys

HO

O

E

permanganate

O

HO

HO

OH O

O

O

Rx-ID: 7067066 View in Reaxys 227/353 Yield

Conditions & References Hilditch; Houlbrooke; Analyst (Cambridge, United Kingdom); vol. 53; p. 253,256; Chem. Zentralbl.; vol. 99; nb. II; (1928); p. 503 View in Reaxys

O

permanganate

HO

OH O

O

Rx-ID: 7541356 View in Reaxys 228/353 Yield

Conditions & References nachfolgend Oxydation mit Natriumhypobromit Ruzicka; Helvetica Chimica Acta; vol. 9; (1926); p. 247 View in Reaxys

O

Br

HO

E

HO

OH O

Br

O

Rx-ID: 255577 View in Reaxys 229/353 Yield

Conditions & References Ozonolyse Toyama; Tsuchiya; ; vol. 38; (1935); p. 363; Chem. Zentralbl.; vol. 107; nb. I; (1936); p. 990 View in Reaxys

O HO

OH

HO

E OH

OH O

O

Rx-ID: 255579 View in Reaxys 230/353 Yield

Conditions & References bei der Oxydation Reinger; Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 32; p. 129; Chem. Zentralbl.; vol. 93; nb. III; (1922); p. 127 View in Reaxys

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71/102

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Br

Br

Br

HO

OH

E Br

OH O

O

O

Rx-ID: 257780 View in Reaxys 231/353 Yield

Conditions & References Ozonolyse Toyama; Tsuchiya; ; vol. 38; (1935); p. 38; Chem. Zentralbl.; vol. 107; nb. I; (1936); p. 990 View in Reaxys N

N S

S

O

HO

E

OH

OH S N

O

S

O

N

Rx-ID: 259576 View in Reaxys 232/353 Yield

Conditions & References bei der Ozonolyse und bei der Abspaltung der Rhodan-Reste aus dem erhaltenen Rhodanin und Oxydation mit KMnO4 Toyama; Tsuchiya; ; vol. 38; (1935); p. 35; Chem. Zentralbl.; vol. 107; nb. I; (1936); p. 990 View in Reaxys

HN

O

O

O

O

HO N

OH

OH

HO OH

O

O

O

O

Rx-ID: 5423375 View in Reaxys 233/353 Yield

Conditions & References Barger; Journal of the Chemical Society; vol. 97; (1910); p. 467,469 View in Reaxys Barger et al.; Helvetica Chimica Acta; vol. 16; (1933); p. 90,93 View in Reaxys

O

HO N

HO

OH

OH

O

O

O

Z O

Rx-ID: 6800039 View in Reaxys 234/353 Yield

Conditions & References Arppe; Justus Liebigs Annalen der Chemie; vol. 124; (1862); p. 86 View in Reaxys Laurent; Annales de Chimie (Cachan, France); vol. <2> 66; (1837); p. 155,166 View in Reaxys

HO

HO

(v4)

OH

O

O

O

O

O

O

Rx-ID: 6800042 View in Reaxys 235/353 Yield

Conditions & References Chuit et al.; Helvetica Chimica Acta; vol. 10; (1927); p. 118 View in Reaxys

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72/102

2016-03-15 06:32:16

HO

chromic acid

OH O

HO

O

Z O

Rx-ID: 6800048 View in Reaxys 236/353 Yield

Conditions & References Edmed; Journal of the Chemical Society; vol. 73; (1898); p. 630 View in Reaxys

N

HO

KOH-solution

N

OH O

O

Rx-ID: 6800056 View in Reaxys 237/353 Yield

Conditions & References Ssolonina; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 29; (1897); p. 414; Chem. Zentralbl.; vol. 68; nb. II; (1897); p. 849 View in Reaxys

HO

potassium permanganate

OH O

HO

O

Z O

Rx-ID: 6800058 View in Reaxys 238/353 Yield

Conditions & References Saizew,A.; Journal fuer Praktische Chemie (Leipzig); vol. <2>33; (1886); p. 310; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 17; (1885); p. 426 View in Reaxys

H

OH

Z

potassium permanganate

HO

OH O

O

O OH

Rx-ID: 6800059 View in Reaxys 239/353 Yield

Conditions & References Maquenne; Bulletin de la Societe Chimique de France; vol. <3>21; (1899); p. 1061 View in Reaxys

sodium periodate O

Z O

potassium permanganate

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

potassium carbonate

73/102

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HO

aqueous tert-butyl alcohol

OH O

O

HO O

Rx-ID: 6965221 View in Reaxys 240/353 Yield

Conditions & References v.Rudloff; Canadian Journal of Chemistry; vol. 34; (1956); p. 1413,1414 View in Reaxys

Cl

Cl

Z

Cl O

Z O

HO

OH O

O

HO

O

O

O

O

Rx-ID: 7064816 View in Reaxys 241/353 Yield

Conditions & References Ozonisierung und Zersetzung des Ozonids mit Wasser bei 98grad Arcus; Smedley-Maclean; Biochemical Journal; vol. 73; (1943); p. 2,5 View in Reaxys

HO

OH

Cr2O3-H2SO4

O

HO

OH O

azelaaldehydic acid

O

Rx-ID: 7069326 View in Reaxys 242/353 Yield

Conditions & References Kerschbaum; Chemische Berichte; vol. 60; (1927); p. 907 View in Reaxys O

OH

sodium dichromate

HO

HO

OH O

decene-(8)-carboxylic acid-(1)

O

Rx-ID: 7073280 View in Reaxys 243/353 Yield

Conditions & References Chuit et al.; Helvetica Chimica Acta; vol. 9; (1926); p. 1086 View in Reaxys

HO

O

HO

OH O

O

trimer(ic) azelaaldehydic acid

O

Rx-ID: 7088756 View in Reaxys 244/353 Yield

Conditions & References Aufbewahren an der Luft King; Journal of the Chemical Society; (1938); p. 1827; Journal of the Chemical Society; (1942); p. 219,389 View in Reaxys

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74/102

2016-03-15 06:32:16

O O Cl

Cl

Cl

Cl

HO

OH

HO OH

O

O

O

Rx-ID: 61110 View in Reaxys 245/353 Yield

Conditions & References nachfolgend Oxydation mit Natriumhypobromit Ruzicka; Helvetica Chimica Acta; vol. 9; (1926); p. 247 View in Reaxys

HO

Br

H C–

O

HO

O

OH

Na + O

O

O

O

O

Rx-ID: 234980 View in Reaxys 246/353 Yield

Conditions & References und Kochen mit konz.HCl Gaubert; Linstead; Rydon; Journal of the Chemical Society; (1937); p. 1977 View in Reaxys N S

HO

HO

E O

OH O

S

O

HO O

N

Rx-ID: 258823 View in Reaxys 247/353 Yield

Conditions & References bei der Ozonolyse, und weitere Oxydation mit KMnO4 Toyama; Tsuchiya; ; vol. 38; (1935); p. 35; Chem. Zentralbl.; vol. 107; nb. I; (1936); p. 990 View in Reaxys

H

HO

H

OH

O

O O

O

O

O

Rx-ID: 5412469 View in Reaxys 248/353 Yield

Conditions & References Anderlini; Gazzetta Chimica Italiana; vol. 24 I; (1894); p. 475 View in Reaxys

HO

Cl

OH

H N

N

O

O

Rx-ID: 6800037 View in Reaxys 249/353 Yield

Conditions & References Ssolonina; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 29; (1897); p. 414; Chem. Zentralbl.; vol. 68; nb. II; (1897); p. 849 View in Reaxys

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75/102

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O

OH

O

HO N

OH

OH

O

H

O

O

OH

Rx-ID: 6800040 View in Reaxys 250/353 Yield

Conditions & References Ulrich; ; (1867); p. 547 View in Reaxys

O

HO

HO N

OH

OH

O

O

O

O

Rx-ID: 6800041 View in Reaxys 251/353 Yield

Conditions & References Krafft; Chemische Berichte; vol. 11; (1878); p. 1414; Chemische Berichte; vol. 29; (1896); p. 2233,2237 View in Reaxys

Cl

Cl

Cl

Cl

HO

E

HO

(v4)

OH

O

O

O

O

O

O

Rx-ID: 6800043 View in Reaxys 252/353 Yield

Conditions & References Zersetzung des Ozonids mit Wasser Chuit et al.; Helvetica Chimica Acta; vol. 10; (1927); p. 118 View in Reaxys

O

H

HO OH O

O O

H

HO

alkali

OH O

OH

O

Rx-ID: 6800045 View in Reaxys 253/353 Yield

Conditions & References Maruyama; Suzuki; Proceedings of the Imperial Academy (Tokyo); vol. 7; (1931); p. 379; Chem. Zentralbl.; vol. 103; nb. I; (1932); p. 2307 View in Reaxys

HO

Cl

OH O

O

HO

amalgamated zinc

H O

OH O

O

Rx-ID: 6800046 View in Reaxys 254/353 Yield

Conditions & References Reduktion Lukes; Sorm; Collection of Czechoslovak Chemical Communications; vol. 13; (1948); p. 586 View in Reaxys

O

HO

OH

chromic acid O

HO

OH O

O

Rx-ID: 6800049 View in Reaxys 255/353 Yield

Conditions & References Krafft; Seldis; Chemische Berichte; vol. 33; (1900); p. 3573 View in Reaxys

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76/102

2016-03-15 06:32:16

O OH H

HO HO

O

HO

KMnO4

H

OH O

O

racemate

Rx-ID: 6800053 View in Reaxys 256/353 Yield

Conditions & References Bougault; Schuster; Journal de Pharmacie et de Chimie; vol. <8> 15; (1932); p. 6; Chem. Zentralbl.; vol. 103; nb. I; (1932); p. 1890 View in Reaxys

O

Br

M g

Br

HO

OH O

O

Rx-ID: 6800057 View in Reaxys 257/353 Yield

Conditions & References und Einw. des Reaktionsproduktes mit CO2 v.Braun; Sobecki; Chemische Berichte; vol. 44; (1911); p. 1923 View in Reaxys

HO

HO

chromic acid O

OH O

O

OH H

O

Rx-ID: 6800579 View in Reaxys 258/353 Yield

Conditions & References Gruen; Wirth; Chemische Berichte; vol. 55; (1922); p. 2218 View in Reaxys

HO

HO

permanganate O

OH O

O

O

OH H

Rx-ID: 6800580 View in Reaxys 259/353 Yield

Conditions & References Gruen; Wirth; Chemische Berichte; vol. 55; (1922); p. 2218 View in Reaxys

OH HO

alkaline permanganate

OH O

OH

HO

OH O

HO

O

OH O

O

Rx-ID: 6800845 View in Reaxys 260/353 Yield

Conditions & References Nagel; Chemische Berichte; vol. 60; (1927); p. 609 View in Reaxys

OH

diluted Cr2O3-H2SO4

HO OH O

OH

HO

OH O

O

HO

OH O

O

Rx-ID: 6800846 View in Reaxys 261/353

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77/102

2016-03-15 06:32:16

Yield

Conditions & References Nagel; Chemische Berichte; vol. 60; (1927); p. 609 View in Reaxys

H

OH

Z

alkaline permanganate

O OH O

HO

OH

HO OH

O

O

O

Rx-ID: 6800867 View in Reaxys 262/353 Yield

Conditions & References Stosius; Wiesler; Biochemische Zeitschrift; vol. 111; (1920); p. 5 View in Reaxys

O OH H

HO HO

KOH-solution

H

permanganate

racemate O

HO

OH

HO OH

O

O

O

Rx-ID: 6800871 View in Reaxys 263/353 Yield

Conditions & References in der Waerme Lapworth; Mottram; Journal of the Chemical Society; vol. 127; (1925); p. 1987 View in Reaxys

O

O

OH

chromic acid

OH OH O

HO

OH

HO

ι-keto-stearic acid

OH

O

O

O

Rx-ID: 6800909 View in Reaxys 264/353 Yield

Conditions & References Shukow; Schestakow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 35; (1903); p. 19; Chem. Zentralbl.; vol. 74; nb. I; (1903); p. 825 View in Reaxys Shukow; Schestakow; Journal fuer Praktische Chemie (Leipzig); vol. 67; p. 414 View in Reaxys

HO

O

sodium hypobromite

HO

OH O

O

O

Br

Br

Br

Br

Rx-ID: 6949479 View in Reaxys 265/353

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78/102

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Yield

Conditions & References van Romburgh; ; vol. 20; (1911); p. 195 View in Reaxys

HO

H

HO

H

OH

HO

O

O

O

O

O

Rx-ID: 6959677 View in Reaxys 266/353 Yield

Conditions & References bei der Ozonisierung des Natriumsalzes und Nachoxydation der Aldehyde und Aldehydsaeuren mit Permanganat, 11elaidic acid Bertram; Biochemische Zeitschrift; vol. 197; (1928); p. 438 View in Reaxys Boeeseken; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 634 Anm.14 View in Reaxys

OH

O

Cr2O3-H2SO4

OH OH

OH

HO

OH O

HO O

O

Rx-ID: 6959680 View in Reaxys 267/353 Yield

Conditions & References high-melting λ.ι.λ-trioxy-stearic acid Asahina; Ishida; Yakugaku Zasshi; nb. 481; (1922); p. 1; Chem. Zentralbl.; vol. 93; nb. III; (1922); p. 126 View in Reaxys

O

O

E

potassium permanganate

O

HO

OH O

HO O

O

Rx-ID: 6959683 View in Reaxys 268/353 Yield

Conditions & References Toyama; ; vol. 30; p. 155; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 2744 View in Reaxys Armstrong; Hilditch; Journal of the Society of Chemical Industry, London; vol. 44; (1925); p. 182 T; Chem. Zentralbl.; vol. 96; nb. II; (1925); p. 576 View in Reaxys

O

HO

potassium permanganate O

HO

OH O

O

HO O

Rx-ID: 6959684 View in Reaxys 269/353 Yield

Conditions & References der Methylester Toyama; ; vol. 30; p. 155; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 2744 View in Reaxys Armstrong; Hilditch; Journal of the Society of Chemical Industry, London; vol. 44; (1925); p. 182 T; Chem. Zentralbl.; vol. 96; nb. II; (1925); p. 576 View in Reaxys

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79/102

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HO

potassium permanganate

alkali

O

HO

OH O

HO O

O

Rx-ID: 6959685 View in Reaxys 270/353 Yield

Conditions & References 11-elaidic acid Boeeseken; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 634 Anm.14 View in Reaxys

HO

KMnO4 O

HO

OH O

HO

κ.λ-dioxy-stearic acid O

O

Rx-ID: 6959686 View in Reaxys 271/353 Yield

Conditions & References Fokin; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 44; (1912); p. 658; Chem. Zentralbl.; vol. 83; nb.

II; (1912); p. 2058 View in Reaxys

O OH H

HO HO

HO

Cr2O3-H2SO4

H

OH O

O

HO O

racemate

Rx-ID: 6965205 View in Reaxys 272/353 Yield

Conditions & References in der Hitze Asahina; Ishida; Yakugaku Zasshi; nb. 481; (1922); p. 1; Chem. Zentralbl.; vol. 93; nb. III; (1922); p. 126 View in Reaxys

O

H2O2, 3 percent

HO O

O

HO

OH O

HO O

O

Rx-ID: 6965207 View in Reaxys 273/353 Yield

Conditions & References Boeeseken; Lichtenbelt; Milo; van Marlen; Recueil des Travaux Chimiques des Pays-Bas; vol. 30; (1911); p. 146 View in Reaxys

OH

Z Br

HO

OH O

O

KMnO4

O

HO O

Rx-ID: 6965208 View in Reaxys 274/353 Yield

Conditions & References Maruyama; Suzuki; Proceedings of the Imperial Academy (Tokyo); vol. 7; (1931); p. 379; Chem. Zentralbl.; vol. 103; nb. I; (1932); p. 2307

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80/102

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View in Reaxys

potassium permanganate

alkali

HO O

HO

OH O

HO O

O

Rx-ID: 6965220 View in Reaxys 275/353 Yield

Conditions & References Gruen; Wittka; ; vol. 32; (1925); p. 258; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 619 View in Reaxys

Cr2O3-H2SO4 HO O O

HO

OH

HO

HO OH

O

O

O

O

Rx-ID: 6965226 View in Reaxys 276/353 Yield

Conditions & References Simon; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 180; (1925); p. 1406 View in Reaxys Gruen; Wittka; ; vol. 32; (1925); p. 258; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 619 View in Reaxys

O

O

O

O

O O

HO

alcoholic KOH-solution

O

OH O

O

O

O

O

Rx-ID: 7041093 View in Reaxys 277/353 Yield

Conditions & References Zerfallen bei 200grad Haworth; Perkin; Journal of the Chemical Society; vol. 65; (1894); p. 104; Chemische Berichte; vol. 26; (1893); p.

2249 View in Reaxys

alkaline permanganate HO

Z O

HO

OH O

O

HO

HO

O

ψ.ι-dioxy-stearic acid O

O

OH

Rx-ID: 7054680 View in Reaxys 278/353 Yield

Conditions & References Edmed; Journal of the Chemical Society; vol. 73; (1898); p. 630 View in Reaxys

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Saizew,A.; Journal fuer Praktische Chemie (Leipzig); vol. <2>33; (1886); p. 310; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 17; (1885); p. 426 View in Reaxys

HO

E

alkaline permanganate

O

HO

OH O

HO

HO

ψ.ι-dioxy-stearic acid O

O

O

O OH

Rx-ID: 7054681 View in Reaxys 279/353 Yield

Conditions & References Saizew,A.; Journal fuer Praktische Chemie (Leipzig); vol. <2>33; (1886); p. 315 View in Reaxys Edmed; Journal of the Chemical Society; vol. 73; (1898); p. 630 View in Reaxys

O

OH

OH

OH

HO

KMnO4

HO OH

OH

OH O

OH

O

HO O

Rx-ID: 7058883 View in Reaxys 280/353 Yield

Conditions & References Linusinsaeure und Isolinusinsaeure reagiert Goldsobel; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 42; (1910); p. 56; Chem. Zentralbl.; 1910 I. 1231 View in Reaxys

O OH H

HO HO

KO H

H

racemate

HO

OH O

HO

glycidic acid of mp: 78.5-79 degree O

O

Rx-ID: 7076329 View in Reaxys 281/353 Yield

Conditions & References Le Sueur; Journal of the Chemical Society; vol. 79; (1901); p. 1315 View in Reaxys

H

OH

Z

alkaline KMnO4

O OH

HO

OH

trioxystearic acid

O O

O

Rx-ID: 7088906 View in Reaxys 282/353 Yield

Conditions & References Rassow; Angewandte Chemie; vol. 26; (1913); p. 318

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View in Reaxys

O

O

O

permanganate

O

HO

OH O

O

O

O

Rx-ID: 7976385 View in Reaxys 283/353 Yield

Conditions & References Majima; Chemische Berichte; vol. 55; (1922); p. 205 View in Reaxys

O E

OH OH

E

permanganate

alkali

O

HO

OH

HO OH

O

O

O

Rx-ID: 7976833 View in Reaxys 284/353 Yield

Conditions & References van Romburgh; van Veen; Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences; vol. 32; p. 693; Chem. Zentralbl.; vol. 100; nb. II; (1929); p. 2785 View in Reaxys

Na +

O

water

ozone

Z O–

HO

OH O

O

HO O

Rx-ID: 8316919 View in Reaxys 285/353 Yield

Conditions & References Harries; Thieme; Justus Liebigs Annalen der Chemie; vol. 343; (1905); p. 357; Chemische Berichte; vol. 39; (1906); p. 2844 View in Reaxys

O

O

HO

OH

OH O

HO

O

HO O

O

Rx-ID: 63509 View in Reaxys 286/353 Yield

Conditions & References Boeeseken; Slooff; Recueil des Travaux Chimiques des Pays-Bas; vol. 49; (1930); p. 97; Chem. Zentralbl.; vol. 100; nb. II; (1929); p. 716 View in Reaxys

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83/102

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E

HO

OH

HO

O O

E HO

O

O

O

Z O

Rx-ID: 206167 View in Reaxys 287/353 Yield

Conditions & References bei der Ozonspaltung Eibner; Rossmann; ; vol. 35; (1928); p. 197; Chem. Zentralbl.; vol. 101; nb. I; (1930); p. 2653 View in Reaxys

HO

E

E

HO

E

OH

HO

O O

O

O

O

O

Rx-ID: 206172 View in Reaxys 288/353 Yield

Conditions & References bei der Ozonspaltung Eibner; Rossmann; ; vol. 35; (1928); p. 197; Chem. Zentralbl.; vol. 101; nb. I; (1930); p. 2653 View in Reaxys

HO O

HO

OH

HO

O O

O

O

Rx-ID: 249338 View in Reaxys 289/353 Yield

Conditions & References beim Ozonisieren und Zersetzung des Ozonids mit Wasser Toyama; ; vol. 30; p. 155; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 2744 View in Reaxys

E

E

HO

OH

Z Br

O

HO

OH O

O

O

O

OH

HO O

Rx-ID: 257675 View in Reaxys 290/353 Yield

Conditions & References Maruyama; Suzuki; Proceedings of the Imperial Academy (Tokyo); vol. 8; (1932); p. 488; Chem. Zentralbl.; vol. 105; nb. II; (1934); p. 2065 View in Reaxys

HO

HO

(v4)

OH

O

OH

O

O

O

O

O

H

O

Rx-ID: 6800578 View in Reaxys 291/353 Yield

Conditions & References Gruen; Wirth; Chemische Berichte; vol. 55; (1922); p. 2218 View in Reaxys

OH

O

O

HO N

OH

OH

O

OH

OH

O

HO OH

O

O

O

Rx-ID: 6800866 View in Reaxys 292/353

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84/102

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Yield

Conditions & References Asahina; Shimidzu; Yakugaku Zasshi; nb. 479; (1922); p. 2; Chem. Zentralbl.; vol. 93; nb. I; (1922); p. 976 View in Reaxys

Cl

Cl

Cl

Cl

alkaline KMnO4

(v4)

O

O

O

O

HO

OH

10-oxo-nonadecanedioic acid (1.19)

HO OH

O

O

O

O

Rx-ID: 6800910 View in Reaxys 293/353 Yield

Conditions & References Ruzicka et al.; Helvetica Chimica Acta; vol. 15; (1932); p. 1466 View in Reaxys

OH HO

alkaline permanganate

OH O

OH

O

O

HO

HO

OH

OH O

HO

O

OH O

Rx-ID: 6801465 View in Reaxys 294/353 Yield

Conditions & References in der Kaelte Nagel; Chemische Berichte; vol. 60; (1927); p. 609 View in Reaxys

HO

E

E

HO

(v4)

OH

HO

O

O

O

O

O

O

O

Rx-ID: 6959678 View in Reaxys 295/353 Yield

Conditions & References Boeesken; Smit; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 623 View in Reaxys

O

H

H

HO

Ag2O

OH HO

OH

OH O

O

HO O

Rx-ID: 6959679 View in Reaxys 296/353 Yield

Conditions & References Nagel; Mertens; Chemische Berichte; vol. 74; (1941); p. 981 View in Reaxys

O

O

E

OH

potassium permanganate

O

HO

OH O

O

HO O

Rx-ID: 6959681 View in Reaxys 297/353 Yield

Conditions & References Armstrong; Hilditch; Journal of the Society of Chemical Industry, London; vol. 44; (1925); p. 182 T; Chem. Zentralbl.; vol. 96; nb. II; (1925); p. 576 View in Reaxys

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O

HO

OH

potassium permanganate O

HO

OH O

HO O

O

Rx-ID: 6959682 View in Reaxys 298/353 Yield

Conditions & References der Methylester Armstrong; Hilditch; Journal of the Society of Chemical Industry, London; vol. 44; (1925); p. 182 T; Chem. Zentralbl.; vol. 96; nb. II; (1925); p. 576 View in Reaxys

O OH H

HO HO

KMnO4

H

alkali

racemate O

HO

OH

HO

HO OH

O

O

O

O

Rx-ID: 6961511 View in Reaxys 299/353 Yield

Conditions & References Spiridonow; Journal fuer Praktische Chemie (Leipzig); vol. <2>40; (1889); p. 249 View in Reaxys

O OH

HO HO

O

HO

OH O

S OO

KMnO4

OH

HO O

O

Rx-ID: 6965209 View in Reaxys 300/353 Yield

Conditions & References Oxidation bei Siedetemperatur.

King; Journal of the Chemical Society; (1936); p. 1788,1791; Journal of the Chemical Society; (1938); p. 1826 View in Reaxys

OH OH

HO HO

O

HO

OH O

S OO

KMnO4

O

O

HO O

Rx-ID: 6965210 View in Reaxys 301/353 Yield

Conditions & References Siedetemperatur King; Journal of the Chemical Society; (1936); p. 1788,1791; Journal of the Chemical Society; (1938); p. 1826 View in Reaxys

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86/102

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O

KMnO4

O O

HO

OH O

HO O

O

Rx-ID: 6965212 View in Reaxys 302/353 Yield

Conditions & References Maruyama; Suzuki; Proceedings of the Imperial Academy (Tokyo); vol. 7; (1931); p. 267,382; Chem. Zentralbl.; vol. 102; nb. II; (1931); p. 2594 View in Reaxys

O

O N O

HO

petroleum ether

N O

Z O

HO

OH O

HO O

O

Rx-ID: 6965218 View in Reaxys 303/353 Yield

Conditions & References und Erhitzen das rohe Reaktionsprodukt mit konz.Salzsaeure auf 120grad Jegorow; Journal fuer Praktische Chemie (Leipzig); vol. <2>86; (1912); p. 539 View in Reaxys

O

potassium permanganate O

Z O

HO

OH O

HO O

O

Rx-ID: 6965219 View in Reaxys 304/353 Yield

Conditions & References Behandeln des Reaktionsprodukts mit siedender Natronlauge Armstrong; Hilditch; Journal of the Society of Chemical Industry, London; vol. 44; (1925); p. 45 T; Chem. Zentralbl.; vol. 96; nb. I; (1925); p. 1586 View in Reaxys

O

O

permanganate O

HO

OH O

O

HO O

Rx-ID: 6969754 View in Reaxys 305/353 Yield

Conditions & References Toyama; ; vol. 30; p. 154 B; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 2744 View in Reaxys

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87/102

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HO

O O

OH O

O

HO

11-oxo-undecanoic acid (1)

O O

Rx-ID: 6969759 View in Reaxys 306/353 Yield

Conditions & References Ozonisierung Toyama; ; vol. 30; p. 154 B; Chem. Zentralbl.; vol. 98; nb. II; (1927); p. 2744 View in Reaxys

O

HO N

HO

OH

OH

O

O

O

O

O

N

O

HO

ψ.ι-diketo-stearic acid

O N O

O

Rx-ID: 6983415 View in Reaxys 307/353 Yield

Conditions & References Limpach; Justus Liebigs Annalen der Chemie; vol. 190; (1878); p. 297 View in Reaxys Overbeck; Justus Liebigs Annalen der Chemie; vol. 140; (1866); p. 62 View in Reaxys

O OH H

HO HO

KMnO4

H

alkali

racemate

HO

OH O

O

HO

HO

O

O

O OH

Rx-ID: 7054677 View in Reaxys 308/353 Yield

Conditions & References Edmed; Journal of the Chemical Society; vol. 73; (1898); p. 630 View in Reaxys O

HO

HO H

H OH

permanganate

alkali

racemate

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HO

OH O

HO

HO

O

O

O

O OH

Rx-ID: 7054678 View in Reaxys 309/353 Yield

Conditions & References Edmed; Journal of the Chemical Society; vol. 73; (1898); p. 630 View in Reaxys

O OH H

HO HO

KOH-solution

H

permanganate

racemate

HO

OH O

HO

HO

O

O

O

O OH

Rx-ID: 7054679 View in Reaxys 310/353 Yield

Conditions & References Edmed; Journal of the Chemical Society; vol. 73; (1898); p. 630 View in Reaxys

HO

E

chromic acid

O

HO

OH O

HO

HO

ψ.ι-dioxy-stearic acid O

O

O

O OH

Rx-ID: 7054682 View in Reaxys 311/353 Yield

Conditions & References Edmed; Journal of the Chemical Society; vol. 73; (1898); p. 630 View in Reaxys

O

O

HO

N O

O

HO

OH

O

OH

N O

O

O

Rx-ID: 7058235 View in Reaxys 312/353 Yield

Conditions & References Addition und Spaltung des Additionsproduktes mit HCl Jegorow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 46; (1914); p. 982; Chem. Zentralbl.; vol. 86; nb. I; (1915); p. 934 View in Reaxys

OH

O

O

aqueous KOH

O OH

HO

OH

O

O

OH

O

OH

HO OH

O

O

H

O

Rx-ID: 7058370 View in Reaxys 313/353 Yield

Conditions & References bei der Ozonolyse und folgenden Verseifung Schmid; Helvetica Chimica Acta; vol. 28; (1945); p. 1187,1192, 1196 View in Reaxys

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O

E

E

E

E

alkaline KMnO4

OH

HO

HO

OH O

O

O

O

HO

OH

O

Rx-ID: 7058932 View in Reaxys 314/353 Yield

Conditions & References α-parinaric acid Farmer; Sunderland; Journal of the Chemical Society; (1935); p. 760 View in Reaxys

HO

E

E

(v4)

O

O

O

HO

OH O

O

HO

HO

H 2N 2 O

O

O

OH

Rx-ID: 7059995 View in Reaxys 315/353 Yield

Conditions & References Boeesken; Smit; Gaster; Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences; vol. 32; p. 379; Chem. Zentralbl.; vol. 100; nb. II; (1929); p. 716 View in Reaxys Smit; Recueil des Travaux Chimiques des Pays-Bas; vol. 49; (1930); p. 545 View in Reaxys

OH

OH

O

alkaline permanganate

OH OH

OH O

HO

OH

HO

O

HO

HO

OH

O

O

O

O

OH

O

Rx-ID: 7067084 View in Reaxys 316/353 Yield

Conditions & References Produkt 5: n-Capronsaeure, β-sativic acid of Nicolet, Cox Haworth; Journal of the Chemical Society; (1929); p. 1460 View in Reaxys Reinger; Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 32; p. 127; Chem. Zentralbl.; vol. 93; nb. III; (1922); p. 127 View in Reaxys

HO O

HO

HO

OH

O

adipaldehydic acid

O

O

O

O

OH

Rx-ID: 7068458 View in Reaxys 317/353 Yield

Conditions & References bei der Ozonspaltung Seher; Justus Liebigs Annalen der Chemie; vol. 589; (1954); p. 222,235 View in Reaxys

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H

OH

Z

Cl

Cl (v4)

O

O

Cl

O

O OH

HO

OH O

azelaaldehydic acid

O

Rx-ID: 7069325 View in Reaxys 318/353 Yield

Conditions & References Noorduyn; Recueil des Travaux Chimiques des Pays-Bas; vol. 38; (1919); p. 327 View in Reaxys

H

OH

Z

(v4)

O

O

O

O OH

O

HO

OH

OH O

H

O

O

OH

azelaaldehydic acid OH

Rx-ID: 7069338 View in Reaxys 319/353 Yield

Conditions & References Matthes; Kuerschner; Archiv der Pharmazie (Weinheim, Germany); (1931); p. 92,104 View in Reaxys

O

OH

H

H

potassium salt of suberic acid monoethyl ester

O

O

O

O

HO

OH

HO OH

O

O

dodecane-dicarboxylic acid-(1.12)

O

Rx-ID: 7075162 View in Reaxys 320/353 Yield

Conditions & References an Platinelektroden und folgendes Verseifen mit Kalilauge.Electrolysis Carmichael; Journal of the Chemical Society; vol. 121; (1922); p. 2549 View in Reaxys

H

H O

HO

oxygen

Z O

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HO

OH O

O

OH

nonyloic acid

H

O

ψ.ι-dioxy-stearic acid Rx-ID: 7083046 View in Reaxys 321/353

Yield

Conditions & References im Sonnenlicht Ciamician; Silber; Chemische Berichte; vol. 47; (1914); p. 642; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 23 I; (1914); p. 116 View in Reaxys

O

E

O

permanganate

O

O

HO

OH O

O

OH H

O

O

HO

HO

O

Rx-ID: 8255749 View in Reaxys 322/353 Yield

Conditions & References Produkt 5:Korksaeure Jones; ; vol. 45; p. 38; ; vol. 29; (1935); p. 4341; Chem. Zentralbl.; vol. 105; nb. II; (1934); p. 3259 View in Reaxys Jones; Smith; Journal of the Chemical Society; (1928); p. 69 View in Reaxys

E

E

OH O

HO

OH

HO

O

O

caproic acid (?)

O O

O

O

OH

Rx-ID: 8270739 View in Reaxys 323/353 Yield

Conditions & References bei der Ozonspaltung van Romburgh; van Veen; Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences; vol. 32; p. 694; Chem. Zentralbl.; vol. 100; nb. II; (1929); p. 2785 View in Reaxys

HO O O

HO

OH O

O

O

HO

O

HO OH O

O

OH

Rx-ID: 185456 View in Reaxys 324/353 Yield

Conditions & References bei der Ozonspaltung Steger; van Loon; Recueil des Travaux Chimiques des Pays-Bas; vol. 59; (1940); p. 1156 - 1164 View in Reaxys

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Z E HO

Z O

HO

HO

OH

O

HO

O O

O

O

O

OH

O

Rx-ID: 206159 View in Reaxys 325/353 Yield

Conditions & References bei der Ozonspaltung Toyama; Tsuchiya; ; vol. 38; (1935); p. 183; Chem. Zentralbl.; vol. 107; nb. II; (1936); p. 392 View in Reaxys

O

O

HO

N

OH

OH

O

O

O

HO

OH

HO

OH

HO OH

O

O

O

O

O

adipic acid and glutaric acid and succinic acid and acetic acid

Rx-ID: 6726032 View in Reaxys 326/353 Yield

Conditions & References unter Druck Kobayashi; ; vol. 5; (1956); p. 85,88; ; (1960); p. 2787 View in Reaxys -1

OH OH

(v1)

O

HO

H+ O

O

O

HO

OH O

I OO

O

O

Rx-ID: 6801024 View in Reaxys 327/353 Yield

Conditions & References King; Journal of the Chemical Society; (1936); p. 1788,1791; Journal of the Chemical Society; (1938); p. 1826 View in Reaxys

KMnO4 HO O O

HO

OH

HO

HO

HO OH

O

O

O

O

O

Rx-ID: 6965228 View in Reaxys 328/353 Yield

Conditions & References in alkal.Loesung Arnaud; Hasenfratz; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 152; (1911); p. 1604 View in Reaxys

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O

O N O

HO

petroleum ether

N O

Z O

HO

OH

O

HO

N O

O

O

O

ψ-nitro-pelargonic acid Rx-ID: 6969946 View in Reaxys 329/353 Yield

Conditions & References und Erhitzen das rohe Reaktionsprodukt mit Wasser auf 160-170grad Jegorow; Journal fuer Praktische Chemie (Leipzig); vol. <2>86; (1912); p. 539 View in Reaxys

O

E

E

(v4)

O

HO

OH O

O

O

O O

HO

OH

O

O

Rx-ID: 7058342 View in Reaxys 330/353 Yield

Conditions & References und anschliessend mit KMnO4 Baudart; Bulletin de la Societe Chimique de France; vol. <5>9; (1942); p. 923; ; (1946); p. 5584 View in Reaxys

O

E

O

E

KMnO4

O

HO

OH O

O

HO

OH

O

O

Rx-ID: 7058343 View in Reaxys 331/353 Yield

Conditions & References Baudart; Bulletin de la Societe Chimique de France; vol. <5>9; (1942); p. 923; ; (1946); p. 5584 View in Reaxys

alkaline potassium permanga‐ nate

O O

HO

OH O

HO

O

OH O

O

HO O

O

HO

OH

O

Rx-ID: 7064810 View in Reaxys 332/353 Yield

Conditions & References linolic acid methyl ester Haworth; Journal of the Chemical Society; (1929); p. 1460 View in Reaxys

O

O

KMnO4

O

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HO

O

OH O

OH

HO O

O

Rx-ID: 7064819 View in Reaxys 333/353 Yield

Conditions & References bei der Ozonspaltung entstehen auch die entsprechenden Aldehyde, methyl ester of/the/ natural 11.14-eicosadienoic acid Baudart; Bulletin de la Societe Chimique de France; vol. <5>9; (1942); p. 923; ; (1946); p. 5584 View in Reaxys

OH OH

OH

chromic acid

O O

HO

OH

O

HO

HO

OH

O

O

O

O

O

Rx-ID: 7066085 View in Reaxys 334/353 Yield

Conditions & References Asahina; Shimidzu; Yakugaku Zasshi; nb. 479; (1922); p. 2; Chem. Zentralbl.; vol. 93; nb. I; (1922); p. 976 View in Reaxys

Cl

Cl

O

(v4)

O

Cl

O

O

HO

O

OH O

O

OH

azelaaldehydic acid

H

O

Rx-ID: 7069327 View in Reaxys 335/353 Yield

Conditions & References Zersetzung des Ozonids mit Wasser Gruen; Wirth; Chemische Berichte; vol. 55; (1922); p. 2218 View in Reaxys

OH E N

O

OH HO

S OO

HO

HO

OH

HO NH 2

NH 2

O

n-nonyloic acid

O

O

Rx-ID: 7082950 View in Reaxys 336/353 Yield

Conditions & References Erhitzen mit konz. Salzsaeure auf 180grad.Hydrolysis Le Sueur; Withers; Journal of the Chemical Society; vol. 105; (1914); p. 2813 View in Reaxys

O O Cl

Cl

Cl

Cl

HO

O O

E O

N

N

N

N

O

O O

HO

OH O

O

O

O

O

HO

HO O

O

O

Rx-ID: 60853 View in Reaxys 337/353 Yield

Conditions & References Kaufmann; Chemische Berichte; vol. 75; (1942); p. 1201,1212 View in Reaxys

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O

O

O

O

OH

HO

O

Z O

HO

chromium (VI)-oxide

OH O

HO

O

HO

lauric acid and myristic acid O

O

Rx-ID: 7079659 View in Reaxys 338/353 Yield

Conditions & References Verb.5: Benzol Watanabe; Nippon Kagaku Zasshi; vol. 80; (1959); p. 1187; ; (1961); p. 4359 View in Reaxys

O

Cl

Cl (v4)

O

O

Cl

O

O

HO

OH

HO

HO

O

O O

O

O

O

OH

Rx-ID: 7916134 View in Reaxys 339/353 Yield

Conditions & References Kochen des Reaktionsprodukts mit Wasser Furukawa; Scientific Papers of the Institute of Physical and Chemical Research (Japan); vol. 24; (1934); p. 314,318; Chem. Zentralbl.; vol. 106; nb. I; (1935); p. 1070 View in Reaxys

Cl

Cl (v4)

O

Cl

O

Z

HO

O

O

OH

HO

HO

O

O O

O

O

O

OH

Rx-ID: 8236182 View in Reaxys 340/353 Yield

Conditions & References Erhitzen des entstandenen Ozonids mit Wasser Furukawa; Scientific Papers of the Institute of Physical and Chemical Research (Japan); vol. 24; (1934); p. 314,318; Chem. Zentralbl.; vol. 106; nb. I; (1935); p. 1070 View in Reaxys

HO

OH O

O

Rx-ID: 6331663 View in Reaxys 341/353 Yield 86%

Conditions & References 4 : EXAMPLE 4 EXAMPLE 4

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2.2 g of 30percent H2 O2 in the presence of 0.2 ml of 75percent H2 SO4 are added to 5.7 g of cyclohexanonepropionitrile.

The reaction is allowed to proceed for 10 minutes under stirring, and the mixture is then poured into 10 ml of acetonitrile containing 3 g of cupric acetate.

11 g of FeSO4.7H 2 O are added to this solution over a period of 15 minutes.

The temperature rises spontaneously to 38° C., and stirring is continued for a further 30 minutes.

After this period the solution is cooled and extracted with 50 ml of ethyl acetate.

The solvent is evaporated, and 3 g of cyclohexanonepropionitrile and 2.7 g of an unsaturated acid product are obtained by fractional distillation.

The conversion of the cyclohexanonepropionitrile is thus 47percent.

The distilled acid product is dissolved in 10percent NaOH and heated under reflux for 2 hours.

The solution is acidified, and the precipitated acid product is dissolved in ethyl alcohol.

0.1 g of Pd on carbon is added, and the mixture then subjected to hydrogenation at ordinary pressure and temperature until hydrogen absorption ceases.

3.2 g of azelaic acid are obtained, equal to a yield of 86percent with respect to the converted product.

Patent; Brichima S.p.A.; US4322547; (1982); (A1) English View in Reaxys 70.2%

2 : EXAMPLE 2 EXAMPLE 2 The same conditions as used for example 1 are used with the exception that 0.5 g of cobalt acetate is used instead of 1.2 g in the oxidation phase of the diol mixture.

Proceeding as described in example 1 a yield of 70.2percent of azelaic acid and 71percent of pelargonic acid is obtained.

Patent; Novaol S.r.l.; US5714623; (1998); (A1) English View in Reaxys Ueber Bildung bei der katalytischen Oxydation von synthetischem Paraffin mit Luft Appel et al.; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 282; (1947); p. 225 View in Reaxys Prelog,V. et al.; Helvetica Chimica Acta; vol. 45; (1962); p. 1658 - 1671 View in Reaxys Huisgen,R.; Pawellek,D.; Justus Liebigs Annalen der Chemie; vol. 641; (1961); p. 71 - 75 View in Reaxys Gunstone,F.D. et al.; Chemical Communications (London); (1967); p. 295 - 296 View in Reaxys Gensler,W.J.; Abrahams,C.B.; Journal of Organic Chemistry; vol. 26; (1961); p. 249 - 250 View in Reaxys Smith,C.R. et al.; Journal of Organic Chemistry; vol. 26; (1961); p. 2903 - 2905 View in Reaxys Mikolajczak,K.L. et al.; Journal of Organic Chemistry; vol. 29; (1964); p. 318 - 322 View in Reaxys Applewhite,T.H. et al.; Journal of Organic Chemistry; vol. 31; (1966); p. 3407 - 3409 View in Reaxys Minisci,F.; Pallini,U.; Gazzetta Chimica Italiana; vol. 91; (1961); p. 1030 - 1036 View in Reaxys Narula; Dev; Tetrahedron Letters; (1969); p. 1733 View in Reaxys Kircher; Journal of Organic Chemistry; vol. 29; (1964); p. 3658,3660 View in Reaxys Kobayashi; Nishino; Kagaku to Kogyo (Osaka, Japan); vol. 35; (1961); p. 91,92-93; ; nb. 25749; (1961) View in Reaxys Abbot et al.; Chemistry and Physics of Lipids; vol. 4; (1970); p. 351,354, 361, 362 View in Reaxys Ackman et al.; Canadian Journal of Chemistry; vol. 39; (1961); p. 1730 View in Reaxys Grimmer; Jacob; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie; vol. 24; (1969); p. 1004 View in Reaxys Moldawskii; Rudakowa; J. Appl. Chem. USSR (Engl. Transl.); vol. 33; (1960); p. 417,412; ; nb. 11985; (1960)

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View in Reaxys Ackman et al.; Canadian Journal of Chemistry; vol. 39; (1961); p. 1956 View in Reaxys Passero; Naudet; Revue Francaise des Corps Gras; vol. 7; (1960); p. 189; ; nb. 14727; (1960) View in Reaxys Ogino et al.; Agricultural and Biological Chemistry; vol. 29; (1965); p. 1009,1011 View in Reaxys Seshadri et al.; Indian Journal of Chemistry; vol. 9; (1971); p. 524 View in Reaxys Huenig; Lendle; Chemische Berichte; vol. 93; (1960); p. 913,919 View in Reaxys Izumi; Kogyo Kagaku Zasshi; vol. 61; (1958); p. 1475,1476-1477; ; nb. 1333; (1962) View in Reaxys Korschak et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 30; (1960); p. 907,922 View in Reaxys Patent; Baschkirow et al.; SU165444; (1963); ; vol. 62; nb. 6397; (1965) View in Reaxys Patent; DEGUSSA; DE2052815; (1970); ; vol. 77; nb. 33963 View in Reaxys Patent; Degussa; DE2106913; (1971); ; vol. 77; nb. 151493 View in Reaxys Babel; Proskuryakov; J. Appl. Chem. USSR (Engl. Transl.); vol. 38; (1965); p. 1085,1064,1067 View in Reaxys Proskuryakov et al.; J. Appl. Chem. USSR (Engl. Transl.); vol. 39; (1966); p. 144,122 View in Reaxys Sacharkin; Shigarewa; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); (1965); p. 1465; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1965); p. 1497 View in Reaxys Zwierzykowski et al.; Przemysl Chemiczny; vol. 51; (1972); p. 146,147,148; ; vol. 77; nb. 39032; (1972) View in Reaxys Patent; Degussa; DE2035558; (1970); ; vol. 76; nb. 72034; (1972) View in Reaxys Patent; Yur'ev et al.; SU330154; (1972); Ref. Zh., Khim.; vol. 23; nb. N46P; (1972) View in Reaxys Bu'lock; Smith; Journal of the Chemical Society [Section] C: Organic; (1967); p. 332 View in Reaxys Typical polycarboxylic acids may include: adipic acid azelaic acid sebacic acid dodecanedioic acid Patent; Texaco Inc.; US4973732; (1990); (A1) English View in Reaxys Patent; Texaco Inc.; US4973733; (1990); (A1) English View in Reaxys Examples of suitable dicarboxylic acids are: Oxalic acid, malonic acid, ... itaconic acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, 1,12-dodecanedioic acid, terephthalic acid and ...

Patent; Bayer Aktiengesellschaft; US5074884; (1991); (A1) English

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View in Reaxys 1 : EXAMPLE 1 The acid product thus prepared is dissolved in 20 ml of methanol, and 0.1 g of Pd on carbon are added.

Hydrogen is introduced at ambient temperature until 0.026 g have been absorbed.

The methanol is evaporated to dryness, and the separated product is dissolved in 15 g of 10percent aqueous NaOH. The mixture is left under reflux for 2 hours, and is then cooled and acidified with 10percent sulphuric acid.

2.4 g of azelaic acid are obtained on crystallising the product from water.

Patent; Brichima S.p.A.; US4322547; (1982); (A1) English View in Reaxys 1 : EXAMPLE 1 Conversion of the cyclohexanonepropionitrile 39percent.

Yield of azelaic acid with respect to the converted product 87percent.

The same example was repeated in an identical manner, but using 11 g of FeSO4.7H 2 O and 5 g of Fe2 (SO4)3 as catalyst.

Only traces of azelaic acid were obtained, which were difficult to separate from a mixture of saturated and unsaturated acids containing 9 and 18 carbon atoms.

Patent; Brichima S.p.A.; US4322547; (1982); (A1) English View in Reaxys 36 : EXAMPLE 36 This acid was mixed with water (400 parts by volume) and sodium hydroxide (20 parts by weight) and heated in an autoclave at 320°C for 1.5 hours.

The autoclave was cooled and the contents filtered, after addition of a small amount of charcoal, in order to remove inorganic materials.

The filtrate was acidified with concentrated hydrochloric acid and allowed to stand overnight, to give an aqueous suspension of azelaic acid.

The azelaic acid was recovered by filtration and the aqueous mother liquor was extracted with diethyl ether.

The ethereal solution was dried over sodium sulphate and the ether was evaporated off.

The solid residue was combined with the azelaic acid recovered by filtration, and the product was dried in a vacuum oven to give 38.6 parts by weight of crude azelaic acid.

Recrystallisation of the azelaic acid from toluene gave 31.0 parts by weight of crystals (melting point 107°-108°C), and a further 4.0 parts by weight (melting point 106°-107°C) were recovered from the toluene mother liquor.

The yield of azelaic acid was 85percent calculated on the basis of the ethyl cyclo-oct-4-ene-1-carboxylate and 78percent calculated on the basis of initial cyclo-octadiene.

Patent; Imperial Chemical Industries Limited; US3952034; (1976); (A1) English View in Reaxys B. By following the above procedure (A) and substituting for the sebacic acid an equivalent amount of: (a) pimelic acid (b) tetramethyl succinic acid (c) azelaic acid (d) thiodipropionic acid (e) suberic acid ...

Patent; Ciba-Geigy Corporation; US4116933; (1978); (A1) English View in Reaxys

HO

OH HO

O

O

OH OH

Rx-ID: 28028787 View in Reaxys 342/353 Yield

Conditions & References 2 :Example 2The triglycerides remaining in the boiler at the end of the distillation as per example 1 step (c) were subjected to a hydrolysis reaction by adding water in a ratio 1 : 1 at 1800C under pressure for 3h. This reaction released the mono- and dicarboxylic saturated fatty acids from glycerol. Azelaic acid and glycerol were separated from the mixture of fatty acids by means of successive extractions with water at 900C. By cooling of the aqueous solution, 370 g of azelaic acid were crystallised. The remaining water was passed through a basic ionic exchange resin and then

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evaporated to recover 100 g of glycerol.The quantity of azelaic acid obtained, cross-checked by a gas chromatographic analysis, corresponded to a cleavage yield of the oleic acid equal to approximately 70percent with respect to the quantity of azelaic acid theoretically obtainable.

With water, Time= 3h, T= 180 °C Patent; NOVAMONT S.P.A.; WO2008/138892; (2008); (A1) English View in Reaxys O N

HO

OH O

O

Rx-ID: 25060156 View in Reaxys 343/353 Yield

Conditions & References

70%

5 : EXAMPLE 5 The test was repeated in an identical manner, but using 2 g of cupric acetate and 4 g of cuprous acetate as catalyst.

A cyclohexanonepropionitrile conversion of 20percent was obtained, and an azelaic acid yield of 70percent with respect to the converted product.

Patent; Brichima S.p.A.; US4322547; (1982); (A1) English View in Reaxys

HO

OH O

O

O

Rx-ID: 24216915 View in Reaxys 344/353 Yield

Conditions & References

42%

B.7 : Example B7 Example B7 To 25 milliliters of acetic acid were added 1.26 grams (10 millimoles) of cyclononane, 0.13 gram (0.8 millimole) of Nhydroxyphthalimide and 0.015 gram (0.06 millimole) of Co(AA)2, and the resultant mixture was stirred in an oxygen atmosphere at a temperature of 100° C. for six hours.

Products in the reaction mixture were analyzed by means of gas chromatography, which showed that cyclononane was transformed into cyclononanone (yield 46percent) and azelaic acid (yield 42percent) with a transformation rate of 92percent.

Patent; Daicel Chemical Industries, Ltd.; US5958821; (1999); (A1) English View in Reaxys

O

O OH

OH

O

O

HO

Rx-ID: 25167438 View in Reaxys 345/353 Yield

Conditions & References 4.a : (a) (a) 1,2-O-Dioctyl-rac-glycero-3-azelaic acid monoester Preparation analogous to Example 1(a) from 6.3 g. (20 mM) 1,2-O-dioctylglycerol, 80 ml. chloroform, 5 ml. pyridine and 5.2 g. (30 mM) azelaic acid anhydride.

Patent; Boehringer Mannheim GmbH; US4847376; (1989); (A1) English View in Reaxys

O

O OH

OH

O

O

HO

Rx-ID: 25167448 View in Reaxys 346/353

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Yield

Conditions & References 21.a : (a) (a) 1,2-O-Dilauryl-rac-glycero-3-azelaic acid monoester Preparation analogous to Example 1(a) from 6.7 g. (15.6 mM) 1,2-O-dilaurylglycerol, 100 ml. chloroform, 3.2 ml. pyridine and 4.0 g. (23 mM) azelaic acid anhydride.

TLC: Rf =0.22 (ethyl acetate/hexane 1:1 v/v).

IR (cm-1): (film) 1738, 1710.

Patent; Boehringer Mannheim GmbH; US4847376; (1989); (A1) English View in Reaxys

HO

OH O

succinic acid and dodecane-dicarboxylic acid-(1.12)

O

Rx-ID: 6731465 View in Reaxys 347/353 Yield

Conditions & References T= 15 °C , beim Elektrolysieren einer waessr. Loesung von 1 Mol des Kaliumsalzes des Korksaeuremonoaethylesters und 3 Mol des Kaliumsalzes des Malonsaeuremonoaethylesters an Platin-Elektroden Carmichael; Journal of the Chemical Society; vol. 121; (1922); p. 2549 View in Reaxys

O

O Ca 2+ O–

O– H

H O

Rx-ID: 8229515 View in Reaxys 348/353 Yield

Conditions & References With water, calcium chloride, diese Zusammensetzung kommt des Dikaliumsalzes bei Zimmertemperatur gefaellten Salz zu Kiliani; Chemische Berichte; vol. 54; (1921); p. 465; Chemische Berichte; vol. 61; (1928); p. 1163 View in Reaxys

N

HO

OH O

O

N H

Rx-ID: 8351125 View in Reaxys 349/353 Yield

Conditions & References Komponenten Duff et al.; Journal of Chemical Education; vol. 46; (1969); p. 388; ; vol. 71; nb. 61335a; (1969) View in Reaxys

HO

OH O

O

N

N H

Rx-ID: 8364718 View in Reaxys 350/353 Yield

Conditions & References Komponenten Duff et al.; Journal of Chemical Education; vol. 46; (1969); p. 388; ; vol. 71; nb. 61335a; (1969) View in Reaxys

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No structure RN: 11384728

Rx-ID: 22929556 View in Reaxys 351/353 Yield

Conditions & References C Patent; Pagilagan, Rolando U.; US2003/235551; (2003); (A1) English View in Reaxys

HO

OH O

O

H 2N

NH 2

Rx-ID: 8230441 View in Reaxys 352/353 Yield

Conditions & References 1,4-Bis-(2-aminoethyl)-benzol, Azelainsaeure Patent; Chemstrand Corp.; BE611607; (1962); ; vol. 57; nb. 15003g; (1962) View in Reaxys

O S O

O OH

OH

O H

N O

O

NH 2

OH

Rx-ID: 10602991 View in Reaxys 353/353 Yield

Conditions & References 3 Patent; NABRIVA THERAPEUTICS FORSCHUNGS GMBH; WO2007/1; (2007); (A2) English View in Reaxys

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