gamma-Butyrolactone (oxolan-2-one; dihydrofuran-2(3H)-one; GBL)

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Reactions (367)

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Substances (27)

Citations (530)

Conditions

References A

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A: 77.2% B: 6.7% C: 5.3%

With ZnCuO2; hydrogen

T=260°C; P=750.075 Torr;

Ding, Guoqiang; Zhu, Yulei; Zheng, Hongyan; Zhang, Wei; Li, Yongwang

Catalysis Communications, 2010 , vol. 11, # 14 p. 1120 - 1124 Title/Abstract

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Ding, Guoqiang; Zhu, Yulei; Zheng, Hongyan; Zhang, Wei; Li, Yongwang

Catalysis Communications, 2010 , vol. 11, # 14 p. 1120 - 1124 Title/Abstract

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With ZnCuO2; hydrogen

T=260°C; P=30003 Torr;

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102

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With hydrogen; DRD 92/89 D T=190 - 194°C; P=46528.9 Torr; Product distribution / selectivity; Hide Experimental Procedure

DAVY PROCESS TECHNOLOGY LIMITED

Patent: US2011/92721 A1, 2011 ; Location in patent: Page/Page column 5 ; Title/Abstract

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Catalyst DRD 92/89 D obtained from Davy Process Technology Ltd and activated as detailed above was used in a process for the production of tetrahydrofuran from a feed comprising maleic anhydride. The reaction conditions are detailed in Table 1 and the results in Table 2. TABLE 1 Example 2 Example 3 Example 4 Example 5 Inlet Temperature ° C. 194 194 204 217 Exit Temperature ° C. 190 189 198 210 Pressure psig 885 900 900 900 Hydrogen:ester 352 246 246 246True LHSV, hr-1 0.344 0.344 0.344 0.344 TABLE 2 Selectivities, mole percent Example 2 Example 3 Example 4 Example 5 Tetrahydrofuran 83.21 82.69 92.78 97.43 n-butanol 0.15 0.15 0.25 0.52 γ-butyrolactone 11.79 13.38 4.07 0.13 1,4-butanediol 1.63 1.85 0.70 0.00 Conversion, mole percent 67.72 67.48 91.59 99.28 With hydrogen

T=220 - 600°C; P=760.051 Torr; 1 h; Reagent/catalystTimeTemperature; Hide Experimental Procedure

Yu, Yang; Guo, Yanglong; Zhan, Wangcheng; Guo, Yun; Wang, Yunsong; Lu, Guanzhong

Journal of Molecular Catalysis A: Chemical, 2014 , vol. 392, p. 1 - 7 Title/Abstract

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Gas-phase hydrogenation of MA to GBL was carried outin a tubular quartz fixed-bed reactor (inside diameter = 13 mm,length = 650 mm) at atmospheric pressure. 6 mL of catalyst (height = 45 mm) was packed in the constant temperature part of the reactor, and then 15 mL of quartz sand pre treated at 600 °C inair was loaded above the catalyst for the complete gasification ofthe raw material (20 wt.percent MA dissolved in GBL). Prior to the test, the as-prepared catalyst was activated by 60 mL min−1of 5 vol.percent H2/N2at 300 °C for 6 h (designated as the fresh catalyst). Then the temperature was lowered to 220 °C, and 27.5 N mL min−1 of pure H2 and 0.2 h−1 (liquid hourly space velocity, LHSV) of raw material, were fed into the reactor. The products

were sampled using the conical beakers cooled by an ice-bath at intervals of 1 h and analyzed by Perkin-Elmer Clarus 500 gas chromatograph equipped with a FID detector and a SE-54 capillary column (25 m × 0.32 mm × 1.0 m). The temperatures of the injector and detector were 220 °C, and the temperature of the column oven was kept at 100 °C for 1 min and then increased programmedly to 120 °C at the rate of 5C min−1.

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With hydrogenchloride; methanol

T=23°C; 12 h; Hide Experimental Procedure

La Clair, James J.; Rodriguez, Abimael D.

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 22 p. 6645 - 6653 Title/Abstract

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4.8.6. Room temperature acid hydrolysis

Compound 4 (600 μg) dissolved in 300 μL of 1 M HCl in 95percent MeOH was incubated for 12 h at rt. The reaction mixture was dried under N2 flow and the resulting material was partitioned between CHCl3 (2 mL) and 20percent MeOH (2 mL). The CHCl3 fraction was evaluated by GC/MS indicating the presence of γ-butyrolactone, tR = 4.5 min with M+ at m/z 86.

104

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With lithium boron tetrafluoride; N-ethyl-N,N-diisopropylamine in hexadeuterioacetone

T=23°C; 0.583333 h; Inert atmosphereIrradiation;

Zlotorzynska, Maria; Sammis, Glenn M.

Organic Letters, 2011 , vol. 13, # 23 p. 6264 - 6267 Title/Abstract

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105

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With hydrogen in water

T=220°C; P=760.051 Torr; Product distribution / selectivity; Hide Experimental Procedure

BASF SE; PINKOS, Rolf; OSETSKA, Olga; KOeNIGSMANN, Lucia; BASF JAPAN LTD.

Patent: WO2012/95777 A1, 2012 ; Location in patent: Page/Page column 10-11 ; Title/Abstract

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4:

Examples 1 -6 below were carried out using pure 1 ,4-butynediol as 40percent strength by weight aqueous solution at atmospheric pressure. The butynediol solution was pumped continuously into an externally heated tube (diameter 2.7 cm). The tube was charged with glass rings (30 ml) in the upper region. This zone served as vaporization section in which 1 ,4-butynediol/water and hydrogen (300 liter/h) were heated and passed in gaseous form into a second zone in the reactor tube in which the catalyst was located (20 ml). After the reactor tube, the gaseous reactor output was cooled to about 20°C and product which condensed out was collected. The offgas was passed through a cold trap at -78°C and further product was condensed out in this way. The two condensates were combined for the purposes of analysis. The catalysts were activated in a stream of hydrogen before the reaction. The results are shown in table 1

With hydrogen; Co/Cu/Mnx/MoOy in water

T=220 - 225°C; P=3750.38 Torr; Product distribution / selectivity; Hide Experimental Procedure

BASF SE; PINKOS, Rolf; OSETSKA, Olga; KOeNIGSMANN, Lucia; BASF JAPAN LTD.

Patent: WO2012/95777 A1, 2012 ; Location in patent: Page/Page column 12-13 ; Title/Abstract

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In these examples, aqueous pure or technical-grade butynediol (denoted by *) was vaporized in a stream of hydrogen under superatmospheric pressure in a vaporizer which comprised metal packing rings and was externally heated by means of oil (about 240°C) and hydrogenated in a reactor tube filled with catalyst or catalyst mixture (100 ml unless indicated otherwise). The reactor tube was configured as a double-walled tube which was heated or cooled externally by means of oil. The reaction output was cooled and the product which condensed out was depressurized to atmospheric pressure through a valve, while the gas phase was recirculated via the vaporizer by means of a recycle gas blower. A small part of the gas was discharged as offgas. Hydrogen was introduced into the reaction in an amount corresponding to hydrogen consumed by reaction and offgas via a fresh gas supply. The reaction pressure was kept constant in this way. The experimental results are shown in table 2. The conversion of butynediol was quantitative in each case. To calculate the selectivity, products such as 1 ,4-butenediol and 4-hydroxybutanal and acetals thereof, gamma-butyrolactone (GBL) and butanediol (BDO) were included in the calculation as compounds still to be hydrogenated or reacted to form THF. The results are shown in table 3.

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With hydrogen in 1,4-dioxane

T=200°C; P=18751.9 Torr; Product distribution / selectivity; Hide Experimental Procedure

Korea Research Institute Of Chemical Technology

Patent: EP2476674 A2, 2012 ; Location in patent: Page/Page column 7 ; Title/Abstract

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Example 8] Production of butyrolactone from the fumaric acid through the hydrogenation reaction [catalyst: CuO (80) SiO2 (20)]The catalyst was produced by using the same method as Example 1. The reaction temperature was fixed to 200°C, the reaction was performed by using the same method as Example 1, and the reaction results over time are described in the following Table 8. It could be observed that the present catalyst exhibited very high selectivity of butyrolactone after a predetermined period of time.

With carbon monoxide; hydrogen in water

T=180°C; P=30003 Torr; 8 h;

Yu, Lei; Du, Xian-Long; Yuan, Jing; Liu, Yong-Mei; Cao, Yong; He, He-Yong; Fan, Kang-Nian

ChemSusChem, 2013 , vol. 6, # 1 p. 42 - 46 Title/Abstract

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With C40H38NP3; hydrogen; [Ru(acac)3] in 2-methyltetrahydrofuran

T=170°C; P=52505.3 Torr; 48 h;

Deng, Li; Kang, Bin; Englert, Ulli; Klankermayer, Jürgen; Palkovits, Regina

ChemSusChem, 2016 , vol. 9, # 2 p. 177 - 180 Title/Abstract

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107

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A: 7.2 %Chromat.

B: 62.2 %Chromat.

With hydrogen in 1,4-dioxane

T=240°C; P=60006 Torr; 8 h; Autoclave;

Hong, Ung Gi; Park, Hai Woong; Lee, Joongwon; Hwang, Sunhwan; Yi, Jongheop; Song, In Kyu

Applied Catalysis A: General, 2012 , vol. 415-416, p. 141 - 148 Title/Abstract

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A: 38.3 %Chromat.

B: 26.8 %Chromat.

With hydrogen in 1,4-dioxane

T=240°C; P=60006 Torr; 8 h; Autoclave;

Hong, Ung Gi; Park, Hai Woong; Lee, Joongwon; Hwang, Sunhwan; Yi, Jongheop; Song, In Kyu

Applied Catalysis A: General, 2012 , vol. 415-416, p. 141 - 148 Title/Abstract

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With hydrogen in 1,4-dioxane

P=75867.6 Torr; 10 h; Reagent/catalyst; Hide Experimental Procedure

Lee, Han Won; Yang, Young Lyeol; Kim, So Young; Shin, Yong Uk; Chang, Jin Sook; Um, Hye Won; Goh, Young Hyoung; Jhon, Sung Hoo

Patent: US2014/296466 A1, 2014 ; Location in patent: Paragraph 0259; 0260 ; Title/Abstract

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15.2:15-2) Production of Gamma-Butyrolactone and Tetrahydrofuran

In a batch reactor, 5 g of the succinic acid produced in Example 3-2) and to 3 g of the catalyst prepared in Example 15-1) were added to 50 ml of 1,4-dioxane solvent to produce gamma-butyrolactone and tetrahydrofuran. Specifically, hydrogen was added to the reactor until a reaction pressure reached to 1467 psi, followed by a reaction for 10 hours, thereby producing gammabutyrolactone and tetrahydrofuran. The results of the reaction are shown in Table 6 below.

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With hydrogen

T=400°C; P=37503.8 Torr; 10 h; Autoclave;

Liu, Xiaoran; Wang, Xicheng; Xu, Guoqiang; Liu, Qiang; Mu, Xindong; Liu, Haichao

Journal of Materials Chemistry A, 2015 , vol. 3, # 46 p. 23560 - 23569 Title/Abstract

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With hydrogen in 1,4-dioxane

T=240°C; P=60006 Torr; 4 h; Autoclave; Hide Experimental Procedure

Hong, Ung Gi; Kang, Ki Hyuk; Song, Ji Hwan; Kim, Tae Hyeop; Song, In Kyu

Journal of Nanoscience and Nanotechnology, 2016 , vol. 16, # 10 p. 10841 - 10845 Title/Abstract

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2.3. Hydrogenation of Succinic Acid

Liquid-phase hydrogenation of succinic acid (SA) to THFwas carried out over Ru–C-X (X = 3, 5, 7, 9, 11, and 15)catalysts in a batch reactor at 240 C and 80 bar (H2. Succinicacid (0.5 g) and a reduced Ru–C-X catalyst (0.2 g)were charged into an autoclave (150 ml). 1,4-Dioxane(50 ml) was used as a solvent for the reaction. The reactorwas purged with nitrogen to remove air, and then itwas pressurized up to 40 bar using hydrogen. After heatingthe reactor to reaction temperature (240 C), hydrogenpressure was raised up to 80 bar. The catalytic reactionwas carried out for 4 h. During the reaction, reaction mixturewas stirred at 500 rpm in order to avoid mass transferlimitation. Reaction products were analyzed using a gaschromatograph (Younglin, ACME-6100) equipped with aFID (flame ionization detector).

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Korea Research Institute of Chemical Technology

Patent: US2012/197029 A1, 2012 ; Location in patent: Page/Page column 4-5 ;

With hydrogen; CuO(80)SiO2(20) in 1,4-dioxane

T=200°C; P=18751.9 Torr; 4 h; Inert atmosphere; Product distribution / selectivity; Hide Experimental Procedure

Title/Abstract

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8:

The catalyst was produced by using the same method as Example 1. The reaction temperature was fixed to 200° C., the reaction was performed by using the same method as Example 1, and the reaction results over time are described in the following Table 8. It could be observed that the present catalyst exhibited very high selectivity of butyrolactone after a predetermined period of time.

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109

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A: 78.0 %Chromat.

B: 24.0 %Chromat.

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With hydrogen in ethylene glycol dimethyl ether

T=200°C; P=51716.2 Torr; SolventReagent/catalystTimeTemperaturePressure; Hide Experimental Procedure

MYRIANT CORPORATION; TOSUKHOWONG, Thidarat; ROFFI, Kirk; MORE, Santosh, Raghu; AUGUSTINE, Robert, L.; TANIELYAN, Setrak

Patent: WO2013/33649 A1, 2013 ; Location in patent: Paragraph 096 ; Title/Abstract

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5:Example 5 Hydrogenation reaction with diglyme or glyme as the reaction solvent

(096) Succinimide was obtained from TCI (Tokyo Chemical Industry Co. Ltd., Japan) with 98percent purity. Five gram of succinimide (49.4 mmol) was dissolved in 45 gram of diglyme or glyme. The hydrogenation reaction was carried out with a number of different catalysts in a Parr Reactor under hydrogen environment (1000 psi) at 200°C as described above. For carbon supported catalysts, catalysts were used at amount necessary to provide 0.47 mmol metal. Raney Nickel catalyst was used at 1 gram. Samples were collected at different time points and analyzed for the concentration of pyrrolidine, gammabutyrolactone, pyrrolidone and succinamic acid and the results are shown in Tables 7, 8 and 9. Table 7 shows the results of the hydrogenation reaction with diglyme as the reaction solvent. Table 8 shows the results of the hydrogenation reaction with glyme as the reaction solvent. Table 9 shows the results of catalyst optimization study where diglyme was used as the reaction solvent with 5percent Rh/Carbon catalyst. As the result in the Tables 7, 8 and 9 indicate, under the solvent environment, there was a significant reduction in the hydrolysis of succinimide into succinamic acid as compared to the similar reaction under aqueous environment. Furthermore, the reaction time required to achieve maximum conversion was reduced significantly compared to that in the aqueous environment.

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A: 9.9% B: 26.8% C: 33.3%

With hydrogen; platinum

T=240°C; P=760.051 Torr; 0.166667 h;

Regenhardt; Trasarti; Meyer; Garetto; Marchi

Catalysis Communications, 2013 , vol. 35, p. 59 - 63 Title/Abstract

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Zhang, Qian; Zhang, Yin; Li, Haitao; Gao, Chunguang; Zhao, Yongxiang

Applied Catalysis A: General, 2013 , vol. 466, p. 233 - 239 Title/Abstract

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T=350°C; Flow reactorInert atmosphere; Reagent/catalyst; Hide Experimental Procedure

Catalytic reaction

The dehydration of BDO was carried out in a fixed-bed flow reac-tor. Before the reaction, 2.0 g catalyst (20–40 mesh) was preheatedin the N2flow at 350C for 1 h. At this temperature, the BDO gaswas fed into the reactor at a flow rate of 2.0 mL h−1together witha N2(carrier gas) flow of 30 mL min−1. In the poisoning experi-ment, CO2or 10percentNH3–N2were used as carrier gas.

A flow rate wasalso 30 mL min−1. Liquid effluent was collected periodically andanalyzed by gas chromatography (Agilent-7890A) using a 30 m cap-illary column (AT.OV-1701) and a flame ionization detector (FID). The catalytic performance was evaluated using average of the initial 2–9 h

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With Oxonereg;; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; [C4mim][DCA]

T=40°C; Baeyer-Villiger Ketone Oxidation; 5 h; Sonication;

Matuszek, Karolina; Zawadzki, Przemyslaw; Czardybon, Wojciech; Chrobok, Anna

New Journal of Chemistry, 2014 , vol. 38, # 1 p. 237 - 241 Title/Abstract

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With 2,6-bis-(1-[toluene-4-sulfonyl]-[4R,5R]-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-pyridine; iron(II) triflate; oxygen

T=60°C; P=760.051 Torr; 24 h; Green chemistry; Catalytic behavior; chemoselective reaction;

Gonzalez-De-Castro, Angela; Robertson, Craig M.; Xiao, Jianliang

Journal of the American Chemical Society, 2014 , vol. 136, # 23 p. 8350 - 8360 Title/Abstract

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With hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor in water

pH=5.5; 15 h; Enzymatic reaction; chemoselective reaction;

Díaz-Rodríguez, Alba; Martínez-Montero, Lía; Lavandera, Iván; Gotor, Vicente; Gotor-Fernández, Vicente

Advanced Synthesis and Catalysis, 2014 , vol. 356, # 10 p. 2321 - 2329 Title/Abstract

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115

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With hydrogen

T=100 - 500°C; P=7500.75 - 75007.5 Torr; Hide Experimental Procedure

Lee, Han Won; Yang, Young Lyeol; Kim, So Young; Shin, Yong Uk; Chang, Jin Sook; Um, Hye Won; Goh, Young Hyoung; Jhon, Sung Hoo

Patent: US2014/296466 A1, 2014 ; Location in patent: Paragraph 0206 ; Title/Abstract

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4:Synthesis of Gamma-Butyrolactone from Homoserine Lactone

The homoserine lactone hydrochloride obtained in Example 3 was loaded in a reactor and hydrodenitrified with hydrogen gas under a pressure of 10-100 bar at 100500° C. in the presence of a catalyst which supported on Pd, Pt, Ni or Co on C or silica, to produce gamma-butyrolactone.

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With hydrogen in methanol

T=220°C; P=22502.3 Torr; Inert atmosphere;

Hu, Qi; Fan, Guoli; Yang, Lan; Li, Feng

ChemCatChem, 2014 , vol. 6, # 12 p. 3501 - 3510 Title/Abstract

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With benzyl alcohol

T=150°C; 10 h; Inert atmosphereAutoclaveGreen chemistry;

Gao, Zhi; Yang, Lan; Fan, Guoli; Li, Feng

ChemCatChem, 2016 , vol. 8, # 24 p. 3769 - 3779 Title/Abstract

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100%

With 5 active carbon-supported ruthenium; isopropyl alcohol

T=160°C; 0.416667 h; Microwave irradiation; Reagent/catalystTemperature;

Al-Shaal, Mohammad Ghith; Calin, Marc; Delidovich, Irina; Palkovits, Regina

Catalysis Communications, 2016 , vol. 75, p. 65 - 68 Title/Abstract

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With hydrogen in 1,4-dioxane

T=180°C; P=37503.8 Torr; 3 h; Autoclave; Reagent/catalystSolvent;

Long, Xiangdong; Sun, Peng; Li, Zelong; Lang, Rui; Xia, Chungu; Li, Fuwei

Chinese Journal of Catalysis, 2015 , vol. 36, # 9 p. 1512 - 1518 Title/Abstract

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With quinuclidine; Ir(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)2(4,4’-di-tert-butyl-2,2’-bipyridine)PF6; TBAH2PO4 in acetonitrile

T=27°C; Irradiation;

Jeffrey, Jenna L.; Terrett, Jack A.; MacMillant, David W.C.

Science, 2015 , vol. 349, # 6255 p. 1532 - 1536 Title/Abstract

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6%

With 5 active carbon-supported ruthenium; isopropyl alcohol

T=140°C; 0.5 h; Microwave irradiation;

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Al-Shaal, Mohammad Ghith; Calin, Marc; Delidovich, Irina; Palkovits, Regina

Catalysis Communications, 2016 , vol. 75, p. 65 - 68 Title/Abstract

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120

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34%

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With 5 active carbon-supported ruthenium; isopropyl alcohol

T=140°C; 0.5 h; Microwave irradiation;

Al-Shaal, Mohammad Ghith; Calin, Marc; Delidovich, Irina; Palkovits, Regina

Catalysis Communications, 2016 , vol. 75, p. 65 - 68 Title/Abstract

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With hydrogen

T=500°C; P=37503.8 Torr; 10 h; Autoclave;

Liu, Xiaoran; Wang, Xicheng; Xu, Guoqiang; Liu, Qiang; Mu, Xindong; Liu, Haichao

Journal of Materials Chemistry A, 2015 , vol. 3, # 46 p. 23560 - 23569 Title/Abstract

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11%

With copper(II) oxide; zinc

T=250°C; 2 h; Hide Experimental Procedure

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Fu, Jun; Ren, Dezhang; Li, Lu; Liu, Yunjie; Jin, Fangming; Huo, Zhibao

Catalysis Today, 2016 , vol. 263, p. 123 - 127 Title/Abstract

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2.2. Experimental procedure

General procedure: All experiments were carried out in a Tefion-lined stainless steelbatch reactor with an internal volume of 30 mL. 0.5 mmol DMP wasused in all experiments. The typical procedure for the synthesisof PHT was as follows. First, desired DMP, reductant, catalyst andultrapure water were loaded into the reactor. Then, the nitrogenwas charged into the reactor in order to exclude the effect of air andthen the sealed reactor was put into a drying oven, it will take about20 min to be preheated to the desired temperature. After a desiredreaction time, the reactor was quickly moved out from the dry-ing oven to cool down. Liquid sample was collected and extractedby 10 mL ethyl acetate, then filtered with 0.45 m Syringe Filter.Solid sample was collected and washed with deionized water andethanol several times to remove impurities and dried in the ovenat 50C for 24 h.

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With C40H38NP3; hydrogen; [Ru(acac)3] in 2-methyltetrahydrofuran

T=170°C; P=52505.3 Torr; 48 h;

Deng, Li; Kang, Bin; Englert, Ulli; Klankermayer, Jürgen; Palkovits, Regina

ChemSusChem, 2016 , vol. 9, # 2 p. 177 - 180 Title/Abstract

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97.98%

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Rx-ID: 44196196 Find similar reactions

With palladium on activated carbon; hydrogen

T=200°C; P=760.051 Torr; 149 h; TemperatureReagent/catalyst; Hide Experimental Procedure

CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0154; 0159-0164 ; Title/Abstract

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6-2:Dechlorination of chloro-gamma butyrolactone

Cl-GBL and H2 were fed to the reactor under the following feed conditions and Pd (5) / Ac was used as the catalyst.- Feed: H2 / Cl-GBL = 43/1 m / m, WHSV = 1.0 h-1The reaction conditions were 200 ° C. and atmospheric pressure (1 atm). The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 12 below.

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With palladium on activated carbon in diethylene glycol dimethyl ether

T=130°C; P=760.051 Torr; 4 h; SolventTemperatureReagent/catalyst; Overall yield = 98.85 percent; Hide Experimental Procedure

CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ;

Location in patent: Paragraph 0154-0158; 0188 ;

Title/Abstract

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6-1:Dechlorination of chloro-gamma butyrolactone

3 g of Cl-GBL and the solvent of Table 11 (30 g) and the catalyst were charged into the reactor, respectively, and the reaction was allowed to proceed to evaluate the degree of dechlorination of Cl-GBL. The reaction was allowed to proceed at atmospheric pressure (1 atm), and the product was partially recovered to analyze the components. The results are shown in Table 11 below.

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With Re/Ac; hydrogen in 1,4-dioxane

T=250°C; P=3800.26 Torr; 6 h; Reagent/catalyst; Hide Experimental Procedure

CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223-0229 ; Title/Abstract

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7-1:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below.

A

B

C

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127

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With hydrogen in 1,4-dioxane

T=250°C; P=3800.26 Torr; 14.5 h; Hide Experimental Procedure

CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223-0228 ; Title/Abstract

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7-1:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below.

A

B

C

D

128

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With hydrogen in 1,4-dioxane

T=250°C; P=3800.26 Torr; 5 h; Reagent/catalyst; Hide Experimental Procedure

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CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223-0229 ; Title/Abstract

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7-1:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below.

A

B

C

D

E

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129

Synthesize Find similar Rx-ID: 44196216 Find similar reactions

With hydrogen in 1,4-dioxane

T=250°C; P=11400.8 Torr; 90 h; Hide Experimental Procedure

CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223; 0227-0227; 0238-0241 ; Title/Abstract

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7-4:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

General procedure: The reaction was carried out in the same manner as in Example 7-1 except that Rh (5) Re (5) / Ac was used as the catalyst, and the reaction temperature and the reaction pressure were changed as shown in Table 26, and the reaction was carried out for 90 hours. The results are shown in Table 26 below. Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below.

A

130

B

C

Synthesize Find similar Rx-ID: 44196221 Find similar reactions

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With hydrogen in 1,4-dioxane

T=250°C; P=3800.26 Torr; 5 h; Reagent/catalyst; Hide Experimental Procedure

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CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223; 0224-0227; 0230-0232 ; Title/Abstract

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7-2:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

General procedure: The procedure of Example 7-1 was repeated except that Rh (2.5) Re (5) / Ac was used as the catalyst. The results are shown in Table 24 below. Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below.

A

B

C

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131

Synthesize Find similar Rx-ID: 44196224 Find similar reactions

With hydrogen in 1,4-dioxane

T=250°C; P=3800.26 Torr; 5 h; Hide Experimental Procedure

CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223-0229 ; Title/Abstract

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7-1:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below.

A

132

B

C

Synthesize Find similar Rx-ID: 44196226 Find similar reactions

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With hydrogen in 1,4-dioxane

T=250°C; P=3800.26 Torr; 7 h; Hide Experimental Procedure

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CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223; 0242-0247 ; Title/Abstract

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7-5:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and 2 g of Rh (5) Re (5) / SiO2 (HISIL233) was used as the catalyst.- feed: 50/50 vol percent HO-GBL / 1,4-dioxane, H2 / HO-GBL = 50/1, WHSV: 0.3h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 27 below.

A

B

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133

Synthesize Find similar Rx-ID: 44196228 Find similar reactions

With hydrogen in 1,4-dioxane

T=250°C; P=3800.26 Torr; 4 h; Hide Experimental Procedure

CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223; 0242-0247 ; Title/Abstract

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7-5:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and 2 g of Rh (5) Re (5) / SiO2 (HISIL233) was used as the catalyst.- feed: 50/50 vol percent HO-GBL / 1,4-dioxane, H2 / HO-GBL = 50/1, WHSV: 0.3h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 27 below.

A

134

B

C

D

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A: 0.7% B: 0.1% C: 60% D: 22%

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With hydrogen in 1,4-dioxane

T=139.84°C; P=60006 Torr; 96 h; Autoclave; Catalytic behavior; Reagent/catalystTime; Overall yield = 100 percent;

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Takeda, Yasuyuki; Tamura, Masazumi; Nakagawa, Yoshinao; Okumura, Kazu; Tomishige, Keiichi

Catalysis Science and Technology, 2016 , vol. 6, # 14 p. 5668 - 5683 Title/Abstract

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135

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Rx-ID: 10247295 Find similar reactions

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane

cooling;

Naeser, Ulrike; Pierik, Antonio J.; Scott, Richard; Cinkaya, Irfan; Buckel, Wolfgang; Golding, Bernard T.

Bioorganic Chemistry, 2005 , vol. 33, # 1 p. 53 - 66 Title/Abstract

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136

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With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane

cooling;

Rx-ID: 10247296 Find similar reactions

Naeser, Ulrike; Pierik, Antonio J.; Scott, Richard; Cinkaya, Irfan; Buckel, Wolfgang; Golding, Bernard T.

Bioorganic Chemistry, 2005 , vol. 33, # 1 p. 53 - 66 Title/Abstract

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137

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Rx-ID: 10247297 Find similar reactions

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane

cooling;

Naeser, Ulrike; Pierik, Antonio J.; Scott, Richard; Cinkaya, Irfan; Buckel, Wolfgang; Golding, Bernard T.

Bioorganic Chemistry, 2005 , vol. 33, # 1 p. 53 - 66 Title/Abstract

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138

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With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane

cooling;

Rx-ID: 10247298 Find similar reactions

Naeser, Ulrike; Pierik, Antonio J.; Scott, Richard; Cinkaya, Irfan; Buckel, Wolfgang; Golding, Bernard T.

Bioorganic Chemistry, 2005 , vol. 33, # 1 p. 53 - 66 Title/Abstract

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139

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Rx-ID: 6814027 Find similar reactions

γ-Butyrolacton, 1) Li-diisopropylamid, 2) D2O;

Poosner; Loomis

Journal of the Chemical Society, Chemical Communications, 1972 , p. 892 Full Text View citing articles Show Details

140

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Rx-ID: 9745639 Find similar reactions

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane

T=0°C;

Scott, Richard; Naeser, Ulrike; Friedrich, Peter; Selmer, Thorsten; Buckel, Wolfgang; Golding, Bernard T

Chemical communications (Cambridge, England), 2004 , # 10 p. 1210 - 1211 Title/Abstract

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141

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Rx-ID: 9745640 Find similar reactions

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane

T=0°C; 3 h;

Scott, Richard; Naeser, Ulrike; Friedrich, Peter; Selmer, Thorsten; Buckel, Wolfgang; Golding, Bernard T

Chemical communications (Cambridge, England), 2004 , # 10 p. 1210 - 1211 Title/Abstract

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142

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100%

With hydrogenchloride in dichloromethane

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Rx-ID: 27996680 Find similar reactions

Friedrich, Peter; Darley, Daniel J.; Golding, Bernard T.; Buckel, Wolfgang

Angewandte Chemie - International Edition, 2008 , vol. 47, # 17 p. 3254 - 3257 Title/Abstract

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143

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100%

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Rx-ID: 27996681 Find similar reactions

With hydrogenchloride in dichloromethane

Friedrich, Peter; Darley, Daniel J.; Golding, Bernard T.; Buckel, Wolfgang

Angewandte Chemie - International Edition, 2008 , vol. 47, # 17 p. 3254 - 3257 Title/Abstract

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144

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Rx-ID: 27996705 Find similar reactions

Friedrich, Peter; Darley, Daniel J.; Golding, Bernard T.; Buckel, Wolfgang

Angewandte Chemie - International Edition, 2008 , vol. 47, # 17 p. 3254 - 3257 Title/Abstract

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With formate dehydrogenase; potassium phosphate; β-NADP+

T=20°C; pH=7.4; 1 h;

A

B

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145

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Okumura et al.

Yuki Gosei Kagaku Kyokaishi, 1959 , vol. 17, p. 419,421 Chem.Abstr., 1959 , p. 17958 Full Text Show Details

146

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99%

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Rx-ID: 2430332 Find similar reactions

With pyridinium chromate in dichloromethane

2 h;

Malon, Petr; Mickley, Loretta J.; Sluis, Kathleen M.; Tam, Cheok N.; Keiderling, Timothy A.; et al.

Journal of Physical Chemistry, 1992 , vol. 96, # 25 p. 10139 - 10149 Title/Abstract

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147

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With lithium aluminium tetrahydride; pyridinium chlorochromate

1) THF, reflux, 4 h, 2) CH2Cl2, 2 h; Yield given. Multistep reaction;

Rx-ID: 3229222 Find similar reactions

Malon, Petr; Mickley, Loretta J.; Sluis, Kathleen M.; Tam, Cheok N.; Keiderling, Timothy A.; et al.

Journal of Physical Chemistry, 1992 , vol. 96, # 25 p. 10139 - 10149 Title/Abstract

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148

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81%

Rx-ID: 6520257 Find similar reactions

CONCERT PHARMACEUTICALS INC.; TUNG, Roger, D.; MORGAN, Adam; SILVERMAN, I., Robert

Patent: WO2012/112492 A1, 2012 ; Location in patent: Page/Page column 41 ; Title/Abstract

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81%

Stage #1: With methanol-d1; sodium

15 h; Reflux; Stage #2: With water-d2; DCl

T=110°C; 1 h; Hide Experimental Procedure

CONCERT PHARMACEUTICALS, INC.; TUNG, Roger D.; SILVERMAN, I. Robert

Patent: WO2014/31840 A1, 2014 ; Location in patent: Paragraph 182; 194 ; Title/Abstract

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1.1:Step 2. 3,3,5,5 -dihvdrofuran-2(3H)-one (4):

General procedure: Several small pieces of sodium metal (253 mg, 1 1 .0 mmol, washed in heptane) were added slowly to CH3OD (20 mL) at 40 'C and allowed to stir until fully dissolved. 5,5-Dideuterodihydrofuran-2(3H)-one (3) (1 .75 g, 20.0 mmol) was then added as a solution in CH3OD (20 mL) and the reaction stirred at reflux for 15 hours. Upon cooling to room temperature the reaction was quenched with acetic acid-OD (1 .00 mL, Aldrich, 99 atom percentD) and 12N DCI (2 drops) and subsequently concentrated under reduced pressure. The resulting residue was diluted with CH2CI2, filtered through Celite®, and concentrated under reduced pressure. The resulting residue was then dissolved in D20 (35 mL) and 12N DCI (3 mL) was added. After stirring at 1 10 °C for 1 hour, the reaction was cooled to room temperature, diluted with brine and extracted with CH2CI2 (3 x 100 mL). The organic layers were combined, dried (MgS04), filtered and concentrated uder reduced pressure. The resulting oil was purified via Kugelrohr distillation to afford 3,3,5,5-tetradeuterodihydrofuran-2(3H)-one (4) as a clear oil (536 mg, 30percent). H NMR (CDCI3, 400 MHz) δ 2.23 (s, 2H).

Lambert et al.

Journal of the American Chemical Society, 1974 , vol. 96, p. 6112,6114, 6115, 6118 Full Text View citing articles Show Details

aus γ-Butyrolacton, Na/MeOD;

Hide Details

Drury,R.F.; Kaplan,L.

Journal of the American Chemical Society, 1972 , vol. 94, p. 3982 - 3986 Full Text View citing articles Show Details

Malonsaeurediethylester, 1) Na-Ethanolat, 2) Ethylenoxid, 3) D2O / Δ, 4) Thionylchlorid / Δ;

149

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Rx-ID: 6652062 Find similar reactions

Succinic anhydrid, LiAlD4, -6grad;

Mazzocchi et al.

Journal of Organic Chemistry, 1979 , vol. 44, p. 50,53 Full Text Show Details

Bernsteinsaeuremonomethylester, 1) NaBD4, 2) BF3*Et2O;

Drury,R.F.; Kaplan,L.

Journal of the American Chemical Society, 1972 , vol. 94, p. 3982 - 3986 Full Text View citing articles Show Details

150

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Rx-ID: 9179024 Find similar reactions

50.2%

With lithium aluminium deuteride in tetrahydrofuran

T=-55 - 20°C; 1.5 h;

Wheatley, Bronwen M. M.; Keay, Brian A.

Journal of Organic Chemistry, 2007 , vol. 72, # 19 p. 7253 - 7259 Title/Abstract

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35%

Stage #1: With lithium aluminium deuteride in tetrahydrofuran

T=-78 - 20°C; 1.5 h; Stage #2: With hydrogenchloride in water

T=-20 - 20°C; 15 h; Hide Experimental Procedure

CONCERT PHARMACEUTICALS INC.; TUNG, Roger, D.; MORGAN, Adam; SILVERMAN, I., Robert

Patent: WO2012/112492 A1, 2012 ; Location in patent: Page/Page column 44 ; Title/Abstract

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4.1:

Example 4. Synthesis of Sodium 2,2,4,4 -4-hvdroxybutanoate (IVb sodium salt)t[168] Step 1 . 5,5-dp-dihvdrofuran-2(3H)-one (3): A suspension of LiAID4 (1 .27 g, 30.0 mmol, Cambridge Isotope Laboratories, 98 atom percentD) in THF (100 mL) was stirred at reflux for 1 hour then cooled to -78 °C. Succinic anhydride (5.00 g, 50.0 mmol) was then added dropwise as a solution in THF (80 mL) and the reaction was allowed to warm to room temperature over 1 .5 hours. The reaction was then cooled to -20 'C and was quenched with 6M HCI (20 mL). The reaction then stirred at room temperature for 15 hours then was subsequently diluted with brine. The resulting solution was extracted with MTBE (5 x 50 mL), dried (Na2S04), filtered and concentrated under reduced pressure. The resulting oil was purified via Kugelrohr distillation to afford 5,5- dideuterodihydrofuran-2(3H)-one (3) as a clear oil (1 .75 g, 35percent). H NMR (CDCI3, 400 MHz) δ 2.48 (t, J= 7.8 Hz, 2H), 2.24 (t, J = 8.3 Hz, 2H).

35%

Stage #1: With lithium aluminium deuteride in tetrahydrofuran

T=-78 - 20°C; Stage #2: With hydrogenchloride in tetrahydrofuran

CONCERT PHARMACEUTICALS, INC.; TUNG, Roger D.; SILVERMAN, I. Robert

Patent: WO2014/31840 A1, 2014 ; Location in patent: Paragraph 193 ;

Hide Experimental Procedure

Title/Abstract

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4.1:Step 1 . 5.5-dp-dihvdrofuran-2(3H)-one (3):

A suspension of LiAID4 (1 .27 g, 30.0 mmol, Cambridge Isotope Laboratories, 98 atom percentD) in THF (100 mL) was stirred at reflux for 1 hour then cooled to -78 °C. Succinic anhydride (5.00 g, 50.0 mmol) was then added dropwise as a solution in THF (80 mL) and the reaction was allowed to warm to room temperature over 1 .5 hours. The reaction was then cooled to -20 'C and was quenched with 6M HCI (20 mL). The reaction then stirred at room temperature for 15 hours then was subsequently diluted with brine. The resulting solution was extracted with MTBE (5 x 50 mL), dried (Na2S04), filtered and concentrated under reduced pressure. The resulting oil was purified via Kugelrohr distillation to afford 5,5-dideuterodihydrofuran- 2(3H)-one (3) as a clear oil (1 .75 g, 35percent). H NMR (CDCI3, 400 MHz) δ 2.48 (t, J= 7.8 Hz, 2H), 2.24 (t, J = 8.3 Hz, 2H).

Hide Details

With lithium aluminium deuteride in diethyl ether

Turecek, Frantisek; Vivekananda, Shetty; Sadilek, Martin; Polasek, Miroslav

Journal of Mass Spectrometry, 2002 , vol. 37, # 8 p. 829 - 839 Title/Abstract

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151

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100%

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Rx-ID: 11091212 Find similar reactions

With deuterium; Ru4H4(CO)8(PBu3)4 in tetrahydrofuran

T=180°C; 48 h;

Frediani, Piero; Rosi, Luca; Frediani, Marco; Bartolucci, Gianluca; Bambagiotti-Alberti, Massimo

Journal of Agricultural and Food Chemistry, 2007 , vol. 55, # 10 p. 3877 - 3883 Title/Abstract

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152

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2.30 g

With hydrogenchloride

T=110°C; 1 h;

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Rx-ID: 11161078 Find similar reactions

Wheatley, Bronwen M. M.; Keay, Brian A.

Journal of Organic Chemistry, 2007 , vol. 72, # 19 p. 7253 - 7259 Title/Abstract

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153

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83.3%

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Rx-ID: 11161089 Find similar reactions

Stage #1: With methanol-d1; sodium

19 h; Heating; Stage #2: With hydrogenchloride

T=110°C; 1 h; Further stages.;

Wheatley, Bronwen M. M.; Keay, Brian A.

Journal of Organic Chemistry, 2007 , vol. 72, # 19 p. 7253 - 7259 Title/Abstract

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154

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24%

Stage #1: With sodium tetrahydroborate; water

T=20°C; 15 h; Stage #2: With hydrogenchloride in water

T=110°C; 1 h; Hide Experimental Procedure

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Rx-ID: 29871490 Find similar reactions

CONCERT PHARMACEUTICALS INC.; TUNG, Roger, D.; MORGAN, Adam; SILVERMAN, I., Robert

Patent: WO2012/112492 A1, 2012 ; Location in patent: Page/Page column 42-43 ; Title/Abstract

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2.2:

Step 2. 4.4-dp-dihvdrofuran-2(3H)-one (2): To a solution of 1 (4.21 g, 31 .4 mmol) in water (50 mL) was slowly added NaBH4 (10.09 g, 267 mmol). Additional water (15 mL) was then added and the reaction stirred at room temperature for 15 hours. Upon cooling to 0 ', the reaction was quenched via slow addition of 12N HCI (29 mL). Additional 12N HCI (6 mL) was then added and the reaction was stirred at 1 10 °C for 1 hour. The reaction was then cooled to room temperature, diluted with brine and extracted with DCM (3 x 100 mL). The organic layers were combined, dried (MgS04), filtered and concentrated uder reduced pressure. The resulting oil was purified via Kugelrohr distillation to afford 4,4-dideuterodihydrofuran-2(3H)-one (2) as a clear oil (654 mg, 24percent). H NMR (CDCI3, 400 MHz) δ 4.33 (s, 2H), 2.47 (s, 2H).

24%

Stage #1: With sodium tetrahydroborate in water

T=20°C; 15 h; Stage #2: With hydrogenchloride; water

T=0 - 110°C; Hide Experimental Procedure

CONCERT PHARMACEUTICALS, INC.; TUNG, Roger D.; SILVERMAN, I. Robert

Patent: WO2014/31840 A1, 2014 ; Location in patent: Paragraph 186 ; Title/Abstract

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2.2:Step 2. 4.4-dp-dihvdrofuran-2(3H)-one (2):

To a solution of 1 (4.21 g, 31 .4 mmol) in water (50 mL) was slowly added NaBH4 (10.09 g, 267 mmol). Additional water (15 mL) was then added and the reaction stirred at room temperature for 15 hours. Upon cooling to 0 °C, the reaction was quenched via slow addition of 12N HCI (29 mL). Additional 12N HCI (6 mL) was then added and the reaction was stirred at 1 10 ^ for 1 hour. The reaction was then cooled to room temperature, diluted with brine and extracted with DCM (3 x 100 ml_). The organic layers were combined, dried (MgS04), filtered and concentrated uder reduced pressure. The resulting oil was purified via Kugelrohr distillation to afford 4,4-dideuterodihydrofuran-2(3H)-one (2) as a clear oil (654 mg, 24percent). H NMR (CDCI3, 400 MHz) δ 4.33 (s, 2H), 2.47 (s, 2H).

With sodium tetrahydroborate in water

Hide Experimental Procedure

CONCERT PHARMACEUTICALS, INC.; TUNG, Roger, D.

Patent: WO2010/124046 A1, 2010 ; Location in patent: Page/Page column 28-29 ; Title/Abstract

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2:

Example 2. Sodium 3,3-d2-4-hydroxybutyrateSodium 3,3-d2-4-hydroxybutyrate is prepared in the following manner: treatment of mono-methylsuccinate with sodium methoxide in dl -methanol in a manner analogous to the procedure of Keay, B. A., et al, J. Org. Chem. 2007, 72, 7253-7259 affords the butanedioic-2,2-d2 acid, 1 -methyl ester. Treatment of the d2 ester in a manner analogous to Keay et al. with sodium borohydride in water affords the 4,4-dideutero- dihydrofuran-2(3H)-one. Finally, saponification of the dideutro-butyrolactone with sodium hydroxide in dl-methanol in a manner analogous to the procedure of Goto, G., et al, Chem. Pharm. Bull. 1985, 33, 4422-4431 affords the desired sodium 3,3-d2-4- hydroxybutyrate .

155

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Rx-ID: 9214950 Find similar reactions

Stage #1: With sodium hydroxide in ethanol; water

13 h; Heating; Stage #2: With hydrogenchloride in water

T=20°C; 1 h;

Seidel, Dietrich

Journal of Labelled Compounds and Radiopharmaceuticals, 2002 , vol. 45, # 13 p. 1177 - 1177 Title/Abstract

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156

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Rx-ID: 9177779 Find similar reactions

Turecek, Frantisek; Vivekananda, Shetty; Sadilek, Martin; Polasek, Miroslav

Journal of Mass Spectrometry, 2002 , vol. 37, # 8 p. 829 - 839 Title/Abstract

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With sulfuric acid; H218O

A

B

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157

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A: 9% B: 30%

With cobalt(III) acetylacetonate; oxygen in ethyl acetate

T=70°C; 24 h; various cyclic ethers; Product distribution;

Reetz, Manfred T.; Toellner, Karl

Tetrahedron Letters, 1995 , vol. 36, # 52 p. 9461 - 9464 Title/Abstract

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A: 21% B: 7%

With tert.-butylhydroperoxide; water; copper(II) bis(trifluoromethanesulfonate)

T=90°C; 20 h; Inert atmosphere;

Kawade, Rahul Kisan; Huple, Deepak B.; Lin, Rong-Jing; Liu, Rai-Shung

Chemical Communications, 2015 , vol. 51, # 30 p. 6625 - 6628 Title/Abstract

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With 1,1,1-trifluoro-2-propanone; methyltrifluoromethyldioxirane in dichloromethane

T=0°C; 0.166667 h; Yield given. Yields of byproduct given;

Curci; D'Accolti; Fiorentino; Fusco; Adam; Gonzalez-Nunez; Mello

Tetrahedron Letters, 1992 , vol. 33, # 29 p. 4225 - 4228 Title/Abstract

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Hide Details

A: 5 % Chromat.

B: 20 % Chromat.

With lt;Fe(μ-O2)(μ-PXDK)(O2CPhCy)2(Bu-Im)2gt;

T=-80 - 20°C; 0.0833333 h; Product distribution;

LeCloux, Daniel D.; Barrios, Amy M.; Lippard, Stephen J.

Bioorganic and Medicinal Chemistry, 1999 , vol. 7, # 5 p. 763 - 772 Title/Abstract

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With dihydrogen peroxide in water

T=69.84°C; 12 h;

Sasidharan, Manickam; Bhaumik, Asim

Journal of Molecular Catalysis A: Chemical, 2011 , vol. 338, # 1-2 p. 105 - 110 Title/Abstract

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A: 1.6 %Chromat.

B: 1.4 %Chromat.

With Cu3(tBuNHC(S)NP(S)(OiPr)2-S,S')3

T=20°C; 72 h; IrradiationInert atmosphere;

Luckay, Robert C.; Sheng, Xia; Strasser, Christoph E.; Raubenheimer, Helgard G.; Safin, Damir A.; Babashkina, Maria G.; Klein, Axel

New Journal of Chemistry, 2010 , vol. 34, # 12 p. 2835 - 2840 Title/Abstract

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With C100H102Cr2Li2O18Si8; oxygen

72 h; Darkness; Catalytic behavior; Reagent/catalyst;

Schax, Fabian; Bill, Eckhard; Herwig, Christian; Limberg, Christian

Angewandte Chemie - International Edition, 2014 , vol. 53, # 47 p. 12741 - 12745 Angew. Chem., 2014 , vol. 126, # 47 p. 12955 - 12959,5 Title/Abstract

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A

B

C

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158

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Rx-ID: 3951007 Find similar reactions

A: 48 % Chromat.

B: 18 % Chromat.

C: 5 % Chromat.

With hydrogen; anhydrous cobalt diacetate

T=180°C; P=150012 Torr; 5 h;

Bitsi, Gustave; Kheradmand, Houchang; Jenner, Gerard

Journal of Organometallic Chemistry, 1986 , vol. 310, p. 115 - 120 Title/Abstract

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A

159

B

C

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Rx-ID: 5082902 Find similar reactions

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With bis(triphenylphosphine)carbonylrhodium(I) chloride; air

48 h; Ambient temperatureother transition metal complexes; Product distribution;

Shi, Min

Journal of Chemical Research - Part S, 1998 , # 9 p. 592 - 593 Title/Abstract

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A: 6.7 % Chromat.

B: 88.4 % Chromat.

C: 4.9 % Chromat.

With dihydrogen peroxide; macrocyclic polyamine copper

8 h; Heating; Product distribution; Further Variations:Catalysts;

Salavati-Niasari; Najafian

Journal of Chemical Research - Part S, 2003 , # 9 p. 538 - 539 Title/Abstract

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With iron(II) perchlorate monohydrate; ozone in acetonitrile

Overall yield = 75 percentSpectr.;

Bataineh, Hajem; Pestovsky, Oleg; Bakac, Andreja

ACS Catalysis, 2015 , vol. 5, # 3 p. 1629 - 1637 Title/Abstract

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A

B

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160

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Rx-ID: 5588927 Find similar reactions

Clutterbuck et al.

Biochemical Journal, 1935 , vol. 29, p. 871,881 Full Text View citing articles Show Details

A

B

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161

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T=230 - 300°C;

Balandin et al.

Doklady Akademii Nauk SSSR, 1958 , vol. 122, p. 227,229 Doklady Chemistry, 118-123<1958>661,663 Full Text Show Details

A

B

C

D

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162

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A: 54%

With hydrogen in 1,4-dioxane

T=260°C; P=45004.5 Torr; 4 h; Inert atmosphere;

Hong, Ung Gi; Hwang, Sunhwan; Seo, Jeong Gil; Yi, Jongheop; Song, In Kyu

Catalysis Letters, 2010 , vol. 138, # 1-2 p. 28 - 33 Title/Abstract

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A

B

C

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163

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A: 25.2 %Chromat.

B: 7.4 %Chromat.

C: 2.6 %Chromat.

Luckay, Robert C.; Sheng, Xia; Strasser, Christoph E.; Raubenheimer, Helgard G.; Safin, Damir A.; Babashkina, Maria G.; Klein, Axel

New Journal of Chemistry, 2010 , vol. 34, # 12 p. 2835 - 2840 Title/Abstract

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With Cu3(tBuNHC(S)NP(S)(OiPr)2-S,S')3; oxygen

T=20°C; 72 h; IrradiationInert atmosphere;

A

B

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164

Synthesize Find similar Rx-ID: 36979220 Find similar reactions

With platinum on carbon; oxygen; acetic acid in water

T=69.84°C; P=7500.75 Torr; pH=2.5; Catalytic behavior;

Ide, Matthew S.; Davis, Robert J.

Journal of Catalysis, 2013 , vol. 308, p. 50 - 59

Hide Experimental Procedure

Title/Abstract

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2.3 Alcohol oxidation

General procedure: The semi-batch aqueous alcohol oxidation reactions were performed in a 50 cm3 Parr Instrument Company 4592 batch reactor with a 30 cm3 glass liner. The appropriate amounts of substrate, acid (to control pH), and catalyst were added to approximately 10 cm3 of distilled, deionized water in the glass liner. The glass liner was inserted into the reactor, sealed, purged with He, and heated to 343 K. The reaction was initiated by pressurizing the reactor with 10 bar absolute O2 (GT&S, 99.993percent). The pressure was maintained at a constant value by continually feeding O2. No conversion was observed after 240 min when N2 was substituted for O2. Samples were periodically removed and the catalyst was filtered using 0.2 μm PTFE filters before analysis with a Waters e2695 high pressure liquid chromatograph (HPLC). The HPLC was equipped with refractive index and UV/Vis detectors. Product separation in the HPLC was carried out with a Aminex HPX-87H column (Bio-Rad) operating at 318 K with 5 mM H2SO4 in water flowing at 5 cm3min−1. Carbon balances were always greater than 90percent except when specifically mentioned in the text. The retention times and calibration curves were determined by injecting known concentrations of standards. The pH of the samples was determined by a Orien 3-Star Plus pH Portable Meter with a Thermo Orion 9810BN Micro-pH Electrode after the sample had cooled to room temperature.

A

B

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165

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With palladium on activated carbon; hydrogen in 1,4-dioxane

T=250°C; P=3800.26 Torr; 4 h; Reagent/catalystPressure; Hide Experimental Procedure

CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223-0229 ; Title/Abstract

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7-1:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below.

A

B

C

D

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166

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With Re/Ac; hydrogen in 1,4-dioxane

T=250°C; P=3800.26 Torr; 25 h; Hide Experimental Procedure

CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223-0229 ; Title/Abstract

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7-1:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below.

A

B

C

D

167

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With hydrogen in 1,4-dioxane

T=250°C; P=3800.26 Torr; 5 h; Hide Experimental Procedure

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CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223; 0224-0227; 0234-0237 ; Title/Abstract

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7-3:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

General procedure: The procedure of Example 7-1 was repeated except that Rh (5) Re (5) / SiO2 was used as the catalyst, and the results are shown in Table 25 below. Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below.

A

B

C

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168

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With hydrogen in 1,4-dioxane

T=250°C; P=3800.26 Torr; 9.5 h; Time; Hide Experimental Procedure

CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223; 0224-0227; 0234-0237 ; Title/Abstract

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7-3:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

General procedure: The procedure of Example 7-1 was repeated except that Rh (5) Re (5) / SiO2 was used as the catalyst, and the results are shown in Table 25 below. Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below.

A

169

B

C

D

E

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With hydrogen in 1,4-dioxane

T=250°C; P=3800.26 Torr; 15 h; Hide Experimental Procedure

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CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223; 0242-0247 ; Title/Abstract

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7-5:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and 2 g of Rh (5) Re (5) / SiO2 (HISIL233) was used as the catalyst.- feed: 50/50 vol percent HO-GBL / 1,4-dioxane, H2 / HO-GBL = 50/1, WHSV: 0.3h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 27 below.

A

B

C

D

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170

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With hydrogen in 1,4-dioxane

T=250°C; P=3800.26 Torr; 25 h; Hide Experimental Procedure

CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223; 0242-0246 ; Title/Abstract

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7-5:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and 2 g of Rh (5) Re (5) / SiO2 (HISIL233) was used as the catalyst.- feed: 50/50 vol percent HO-GBL / 1,4-dioxane, H2 / HO-GBL = 50/1, WHSV: 0.3h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 27 below.

A

171

B

C

D

E

F

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With hydrogen in 1,4-dioxane

T=250°C; P=19001.3 Torr; 90 h; Time; Hide Experimental Procedure

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CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO

Patent: KR2015/118287 A, 2015 ; Location in patent: Paragraph 0223; 0227-0227; 0238-0241 ; Title/Abstract

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7-4:Hydrolytic Dehydration of Hydroxy-gamma Butyrolactone

General procedure: The reaction was carried out in the same manner as in Example 7-1 except that Rh (5) Re (5) / Ac was used as the catalyst, and the reaction temperature and the reaction pressure were changed as shown in Table 26, and the reaction was carried out for 90 hours. The results are shown in Table 26 below. Hydrogen dehydration of HO-GBL was carried out as follows. Specifically, HO-GBL and 1,4-dioxane were fed to the reactor under the following feed conditions and the catalysts were Pd (5) / Ac, Re (5) / Ac, Pd (5) Ac, Pd (5) Re (5) / Ac, Pt (5) Re (5) / Ac and Rh (5) Re (5) / Ac.HO-GBL / dioxane, H2 / HO-GBL = 110/1 m / m, WHSV = 0.15 h-1The reaction conditions were 250 ° C. and 5 atm. The product was partially recovered according to the elapsed time of the reaction, and the components were analyzed. The results are shown in Table 23 below.

172

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Rx-ID: 27996696 Find similar reactions

Friedrich, Peter; Darley, Daniel J.; Golding, Bernard T.; Buckel, Wolfgang

Angewandte Chemie - International Edition, 2008 , vol. 47, # 17 p. 3254 - 3257 Title/Abstract

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With formate dehydrogenase; potassium phosphate; β-NADP+

T=20°C; pH=7.4; 1 h;

173

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With formate dehydrogenase; potassium phosphate; β-NADP+

T=20°C; pH=7.4; 1 h;

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Rx-ID: 27996697 Find similar reactions

Friedrich, Peter; Darley, Daniel J.; Golding, Bernard T.; Buckel, Wolfgang

Angewandte Chemie - International Edition, 2008 , vol. 47, # 17 p. 3254 - 3257 Title/Abstract

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174

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Rx-ID: 10250617 Find similar reactions

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane

cooling;

Naeser, Ulrike; Pierik, Antonio J.; Scott, Richard; Cinkaya, Irfan; Buckel, Wolfgang; Golding, Bernard T.

Bioorganic Chemistry, 2005 , vol. 33, # 1 p. 53 - 66 Title/Abstract

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175

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100%

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Rx-ID: 11091213 Find similar reactions

With deuterium; Ru4H4(CO)8(PBu3)4 in tetrahydrofuran

T=180°C; 48 h;

Frediani, Piero; Rosi, Luca; Frediani, Marco; Bartolucci, Gianluca; Bambagiotti-Alberti, Massimo

Journal of Agricultural and Food Chemistry, 2007 , vol. 55, # 10 p. 3877 - 3883 Title/Abstract

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176

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100%

With deuterium; Ru4H4(CO)8(PBu3)4 in tetrahydrofuran

T=180°C; 48 h;

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Rx-ID: 11091214 Find similar reactions

Frediani, Piero; Rosi, Luca; Frediani, Marco; Bartolucci, Gianluca; Bambagiotti-Alberti, Massimo

Journal of Agricultural and Food Chemistry, 2007 , vol. 55, # 10 p. 3877 - 3883 Title/Abstract

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177

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94%

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Rx-ID: 29483515 Find similar reactions

Stage #1: With sodium in methanol

32 h; Reflux; Stage #2: With hydrogenchloride; acetic acid in methanol; water

T=20°C; Hide Experimental Procedure

CONCERT PHARMACEUTICALS, INC.; HARBESON, Scott, L.; MASSE, Craig, E.

Patent: WO2010/47819 A1, 2010 ; Location in patent: Page/Page column 53-54 ; Title/Abstract

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9.1:

Sodium metal (2.1 g, 90.6 mmol, 0.56 eq) was dissolved in MeOH (180 mL). To this was added γ- butyrolactone-ck (38-rfβ) (15.0 g, 163 mmol, 1 eq; Aldrich, 98 atom percent D) as a solution in MeOH (180 mL). The resulting solution was heated at reflux for 16 hours. The reaction was cooled to room temperature and concentrated under reduced pressure. A fresh portion of MeOH (360 mL) was added to the residue and the reaction was heated at reflux for an additional 16 hours. The reaction was cooled to room temperature and quenched by the addition of acetic acid (5.3 mL, 90.0 mmol) and several drops of concentrated HCl. The solvent was evaporated under reduced pressure and CH2Cl2 (100 mL) was added. The resulting suspension was filtered and the filtrate was evaporated under reduced pressure leaving a slightly yellow oil (γ- hydroxy-methylbutyrate-d*). This material was dissolved in H2O (100 mL) and concentrated HCl (9 mL) was added. The reaction was heated at reflux for 1 hour and then cooled to room temperature. The solution was saturated with NaCl and the product extracted with CH2Cl2 (3 x 500 mL). The combined organics were dried over Na2SO4, filtered, and evaporated to give 15.1 g of a yellow oil. The crude product was purified by Kugelrohr distillation yielding 13.9 g (94percent) of 38-</4 as a colorless liquid.

94%

Stage #1: With methanol; sodium

32 h; Reflux; Stage #2: With acetic acid; hydrogenchloride in methanol

CONCERT PHARMACEUTICALS, INC.; HARBESON, Scott, L.; TUNG, Roger, D.; LIU, Julie, F.; MASSE, Craig, E.

Patent: WO2010/127272 A2, 2010 ; Location in patent: Page/Page column 92; 93 ;

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Title/Abstract

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4B.2:

Sodium metal (2.10 g, 90.6 mmol) was dissolved in MeOH (180 mL). To this was added γ- butyrolactone-c4(15.0 g, 163 mmol; Aldrich, 98 atom percentD) as a solution in MeOH (180 mL). The resulting solution was heated at reflux for 16 hours. The reaction was cooled to room temperature and concentrated under reduced pressure. A fresh portion of MeOH (360 mL) was added to the residue and the reaction was heated at reflux for an additional 16 hours. The reaction was cooled to room temperature and quenched by the addition of acetic acid (5.30 mL, 90.0 mmol) and several drops of concentrated HCl. The solvent was evaporated under reduced pressure and CH2Cl2 (100 mL) was added. The resulting suspension was filtered and the filtrate was evaporated under reduced pressure leaving a slightly yellow oil (γ-hydroxy-methylbutyrate-<;i^). This material was dissolved in H2O (100 mL) and concentrated HCl (9 niL) was added. The reaction was heated at reflux for 1 hour and then cooled to room temperature. The solution was saturated with NaCl and the product extracted with CH2Cl2 (3 x 500 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated under reduced pressure to afford 15.1 g of a yellow oil. The crude product was purified by Kugelrohr distillation to afford γ-butyrolactone-c/^ (13.9 g, 94percent) as a colorless liquid.

178

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With Ca(OCl)2 in acetonitrile

Hide Experimental Procedure

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Rx-ID: 29871492 Find similar reactions

CONCERT PHARMACEUTICALS, INC.; TUNG, Roger, D.

Patent: WO2010/124046 A1, 2010 ; Location in patent: Page/Page column 29 ; Title/Abstract

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3:

Sodium 2.2.3.3-d4-4-hvdroxybutyrateSodium 2,2,3,3-d4-4-hydroxybutyrate is prepared in the following manner: treatment of 3,3,4,4-d4-tetrahydrofuran with calcium hypochlorite in acetonitrile according to the procedure of de Meijere, A. et al., Chem. Eur. J. 2007, 13, 167-177 affords the 3,3,4,4- tetradeutero-dihydrofuran-2(3H)-one. Saponification of the tetradeutero-butyrolactone with sodium hydroxide in dl-methanol in a manner analogous to the procedure of Goto, G., et al, Chem. Pharm. Bull. 1985, 33, 4422-4431 affords the desired sodium 2,2,3,3- d4-4-hydroxybutyrate .

179

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61%

Rx-ID: 33820572 Find similar reactions

CONCERT PHARMACEUTICALS INC.; TUNG, Roger, D.; MORGAN, Adam; SILVERMAN, I., Robert

Patent: WO2012/112492 A1, 2012 ; Location in patent: Page/Page column 43 ;

Title/Abstract

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61%

Stage #1: With methanol-d1; sodium

15 h; Reflux; Stage #2: With water-d2; DCl

T=110°C; 1 h; Hide Experimental Procedure

CONCERT PHARMACEUTICALS, INC.; TUNG, Roger D.; SILVERMAN, I. Robert

Patent: WO2014/31840 A1, 2014 ; Location in patent: Paragraph 190; 194 ; Title/Abstract

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3.2:Step 2. 3,3,5,5 -dihvdrofuran-2(3H)-one (4):

General procedure: Several small pieces of sodium metal (253 mg, 1 1 .0 mmol, washed in heptane) were added slowly to CH3OD (20 mL) at 40 'C and allowed to stir until fully dissolved. 5,5-Dideuterodihydrofuran-2(3H)-one (3) (1 .75 g, 20.0 mmol) was then added as a solution in CH3OD (20 mL) and the reaction stirred at reflux for 15 hours. Upon cooling to room temperature the reaction was quenched with acetic acid-OD (1 .00 mL, Aldrich, 99 atom percentD) and 12N DCI (2 drops) and subsequently concentrated under reduced pressure. The resulting residue was diluted with CH2CI2, filtered through Celite®, and concentrated under reduced pressure. The resulting residue was then dissolved in D20 (35 mL) and 12N DCI (3 mL) was added. After stirring at 1 10 °C for 1 hour, the reaction was cooled to room temperature, diluted with brine and extracted with CH2CI2 (3 x 100 mL). The organic layers were combined, dried (MgS04), filtered and concentrated uder reduced pressure. The resulting oil was purified via Kugelrohr distillation to afford 3,3,5,5-tetradeuterodihydrofuran-2(3H)-one (4) as a clear oil (536 mg, 30percent). H NMR (CDCI3, 400 MHz) δ 2.23 (s, 2H).

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30%

Stage #1: With methanol-d1; sodium

T=40°C; 15 h; Reflux; Stage #2: With acetic acid-d1; DCl in water-d2

T=20°C; Stage #3: With DCl in water-d2

T=110°C; 1 h; Hide Experimental Procedure

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CONCERT PHARMACEUTICALS INC.; TUNG, Roger, D.; MORGAN, Adam; SILVERMAN, I., Robert

Patent: WO2012/112492 A1, 2012 ; Location in patent: Page/Page column 44-45 ; Title/Abstract

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4.2:

Step 2. 3,3,5,5 -dihvdrofuran-2(3H)-one (4): Several small pieces of sodium metal (253 mg, 1 1 .0 mmol, washed in heptane) were added slowly to CH3OD (20 mL) at 40 'C and allowed to stir until fully dissolved. 5,5-Dideuterodihydrofuran-2(3H)-one (3) (1 .75 g, 20.0 mmol) was then added as a solution in CH3OD (20 mL) and the reaction stirred at reflux for 15 hours. Upon cooling to room temperature the reaction was quenched with acetic acid-OD (1 .00 mL, Aldrich, 99 atom percentD) and 12N DCI (2 drops) and subsequently concentrated under reduced pressure. The resulting residue was diluted with CH2CI2, filtered through Celite.(R)., and concentrated under reduced pressure. The resulting residue was then dissolved in D20 (35 mL) and 12N DCI (3 mL) was added. After stirring at 1 10 ^ for 1 hour, the reaction was cooled to room temperature, diluted with brine and extracted with CH2CI2 (3 x 100 mL). The organic layers were combined, dried (MgS04), filtered and concentrated uder reduced pressure. The resulting oil was purified via Kugelrohr distillation to afford 3,3,5,5- tetradeuterodihydrofuran-2(3H)-one (4) as a clear oil (536 mg, 30percent). H NMR (CDCI3, 400 MHz) δ 2.23 (s, 2H).

30%

Stage #1: With methanol-d1; sodium

15 h; Reflux; Stage #2: With water-d2; DCl

T=110°C; 1 h; Hide Experimental Procedure

CONCERT PHARMACEUTICALS, INC.; TUNG, Roger D.; SILVERMAN, I. Robert

Patent: WO2014/31840 A1, 2014 ; Location in patent: Paragraph 194 ; Title/Abstract

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4.2:Step 2. 3,3,5,5 -dihvdrofuran-2(3H)-one (4):

Several small pieces of sodium metal (253 mg, 1 1 .0 mmol, washed in heptane) were added slowly to CH3OD (20 mL) at 40 'C and allowed to stir until fully dissolved. 5,5-Dideuterodihydrofuran-2(3H)-one (3) (1 .75 g, 20.0 mmol) was then added as a solution in CH3OD (20 mL) and the reaction stirred at reflux for 15 hours. Upon cooling to room temperature the reaction was quenched with acetic acid-OD (1 .00 mL, Aldrich, 99 atom percentD) and 12N DCI (2 drops) and subsequently concentrated under reduced pressure. The resulting residue was diluted with CH2CI2, filtered through Celite®, and concentrated under reduced pressure. The resulting residue was then dissolved in D20 (35 mL) and 12N DCI (3 mL) was added. After stirring at 1 10 °C for 1 hour, the reaction was cooled to room temperature, diluted with brine and extracted with CH2CI2 (3 x 100 mL). The organic layers were combined, dried (MgS04), filtered and concentrated uder reduced pressure. The resulting oil was purified via Kugelrohr distillation to afford 3,3,5,5-tetradeuterodihydrofuran-2(3H)-one (4) as a clear oil (536 mg, 30percent). H NMR (CDCI3, 400 MHz) δ 2.23 (s, 2H).

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181

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A: 78 % Chromat.

B: 6 % Chromat.

C: 3 % Chromat.

D: 13 % Chromat.

With hydrogen; rhenium

T=199.9°C; P=172514 Torr; 18 h; further catalyst: Tc "black"; Title compound not separated from byproducts;

Bayerl, Bernd; Wahren, Manfred

Zeitschrift fuer Chemie (Stuttgart, Germany), 1981 , vol. 21, # 4 p. 149 Title/Abstract

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A: 21 % Chromat.

B: 66 % Chromat.

C: 5 % Chromat.

D: 8 % Chromat.

With hydrogen; Tc "black"

T=199.9°C; P=172514 Torr; 24 h; further catalyst: Re "black"; Title compound not separated from byproducts;

Bayerl, Bernd; Wahren, Manfred

Zeitschrift fuer Chemie (Stuttgart, Germany), 1981 , vol. 21, # 4 p. 149 Title/Abstract

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A: 21 % Chromat.

B: 66 % Chromat.

C: 5 % Chromat.

D: 8 % Chromat.

With hydrogen; Tc "black"

T=199.9°C; P=172514 Torr; 24 h; Product distribution;

Bayerl, Bernd; Wahren, Manfred

Zeitschrift fuer Chemie (Stuttgart, Germany), 1981 , vol. 21, # 4 p. 149 Title/Abstract

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A: 78 % Chromat.

B: 6 % Chromat.

C: 3 % Chromat.

D: 13 % Chromat.

With hydrogen; rhenium

T=199.9°C; P=172514 Torr; 18 h; Product distribution;

Bayerl, Bernd; Wahren, Manfred

Zeitschrift fuer Chemie (Stuttgart, Germany), 1981 , vol. 21, # 4 p. 149 Title/Abstract

Full Text Show Details

A: 78 % Chromat.

B: 6 % Chromat.

C: 3 % Chromat.

D: 13 %

With hydrogen; rhenium

T=199.9°C; P=172514 Torr; 18 h; further catalyst: Tc "black"; Title compound not separated from byproducts;

Bayerl, Bernd; Wahren, Manfred

Zeitschrift fuer Chemie (Stuttgart, Germany), 1981 , vol. 21, # 4 p. 149 Title/Abstract

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Chromat.

A: 21 % Chromat.

B: 66 % Chromat.

C: 5 % Chromat.

D: 8 % Chromat.

With hydrogen; Tc "black"

T=199.9°C; P=172514 Torr; 24 h; further catalyst: Re "black"; Title compound not separated from byproducts;

Bayerl, Bernd; Wahren, Manfred

Zeitschrift fuer Chemie (Stuttgart, Germany), 1981 , vol. 21, # 4 p. 149 Title/Abstract

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182

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Rx-ID: 3323186 Find similar reactions

A: 68% B: 11% C: 21%

With 2-ethoxy-ethanol; 4-(N,N-dimethlyamino)pyridine; Rh6(CO)12 in water

T=50°C; P=7600 Torr; 48 h;

Kaneda, Kiyotomi; Imanaka, Toshinobu; Teranishi, Shiichiro

Chemistry Letters, 1983 , p. 1465 - 1466 Title/Abstract

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A: 10 %Chromat.

B: 20 %Chromat.

C: 31 %Chromat.

With {[2,3,4,5-Ph4(η5-C4CO)]2H}Ru2(CO)4(μ-H); [Rh(acac)2(CO)2]; hydrogen; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene in N,Ndimethyl acetamide

T=120°C; P=15001.5 Torr; 12.5 h;

Takahashi, Kohei; Yamashita, Makoto; Nozaki, Kyoko

Journal of the American Chemical Society, 2012 , vol. 134, # 45 p. 18746 - 18757 Title/Abstract

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183

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Rx-ID: 3323188 Find similar reactions

A: 8% B: 19% C: 72% D: 1%

With 2-ethoxy-ethanol; N,N'-methyl-(3-dimethylaminopropyl)-amine; Rh6(CO)12 in water

T=60°C; P=7600 Torr; 5 h; further amine additives, variation of reaction conditions; Product distribution;

Kaneda, Kiyotomi; Imanaka, Toshinobu; Teranishi, Shiichiro

Chemistry Letters, 1983 , p. 1465 - 1466 Title/Abstract

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A: 8% B: 19% C: 72% D: 1%

With 2-ethoxy-ethanol; N,N'-methyl-(3-dimethylaminopropyl)-amine; Rh6(CO)12 in water

T=60°C; P=7600 Torr; 5 h;

Kaneda, Kiyotomi; Imanaka, Toshinobu; Teranishi, Shiichiro

Chemistry Letters, 1983 , p. 1465 - 1466 Title/Abstract

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184

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Rx-ID: 6868534 Find similar reactions

Broadbent et al.

Journal of Organic Chemistry, 1959 , vol. 24, p. 1847,1852 Full Text Show Details

T=205°C; P=132391 Torr; Hydrogenation;

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185

Synthesize Find similar Rx-ID: 22891353 Find similar reactions

With hydrogen

T=180°C; P=60006 Torr; 48 h; Hide Experimental Procedure

BASF AKTIENGESELLSCHAFT

Patent: WO2003/104176 A1, 2003 ; Location in patent: Page 26 ; Title/Abstract

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2.c:2 c) Hydrierapparatur

Der in Beispiel 2a beschriebene Katalysator wird nach der Aktivierung in einer 300 mL- Autoklaven gefuellt und mit dem Reaktionsaustrag der MSA-Hydrierung in Beispiel 1 versetzt. Nach einer Reaktionsdauer von 48 h bei 180 °C und 80 bar konnten im Austrag 89 percent BDO, 2 percent GBL, 6 percent THF nachweisen.

With hydrogen

T=180°C; P=45004.5 Torr; Hide Experimental Procedure

BASF AKTIENGESELLSCHAFT

Patent: WO2003/104214 A2, 2003 ; Location in patent: Page 26 ; Title/Abstract

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2.c:2 c) Hydrierapparatur

Der Reaktor der in Beispiel Ic beschriebenen Hydrierapparatur wird mit 220 ml des nach Beispiel 2 a hergestellten Katalysators und 130 ml Glasringen gefuellt. Die Aktivierung erfolgte wie in Beispiel 1 b beschrieben. Als Edukt wird der Reaktionsaustrag der MSA-Hydrierung aus Beispiel 1 eingesetzt, aus dem mehr als 50 percent des BSA-Gehaltes durch partielle Kondensation entfernt wurden. Bei einer Reaktortemperatur von [180 °C,] einem Druck von 60 bar und Katalysatorbelastung von 0.15 kg/LKath (Wasserstoff : [GBL-MOLVERHaeLTNIS] 200 : 1) erhaelt man einen Reaktionsaustrag der Zusammensetzung : 87 percent BDO, 7 percent GBL, 5 percent THF.

With hydrogen

T=180°C; P=45004.5 Torr; Hide Experimental Procedure

BASF AKTIENGESELLSCHAFT

Patent: WO2003/104175 A1, 2003 ; Location in patent: Page 28, 29 ; Title/Abstract

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2.c:2 c) Hydrierapparatur

Der Reaktor der in Beispiel Ic beschriebenen Hydrierapparatur wird mit 220 ml des nach Beispiel 2 a hergestellten Katalysators und 130 ml Glasringen gefuellt. Die Aktivierung erfolgte wie in Beispiel 1 b beschrieben. Als Edukt wird der Reaktionsaustrag der MSA-Hydrierung aus Beispiel 1 eingesetzt, aus dem mehr als 50 percent des BSA-Gehaltes durch partielle Kondensation entfernt wurden. Bei einer Reaktortemperatur von [180 °C,] einem Druck von 60 bar und Katalysatorbelastung von 0.15 kg/LKath (Wasserstoff : [GBL-MOLVERHaeLTNIS] 200 : 1) erhaelt man einen Reaktionsaustrag der Zusammensetzung : 87 percent BDO, 7 percent GBL, 5 percent THF. A

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186

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A: 0.1 0.9 %Chromat.

B: 0.0 14.4 %Chromat.

C: 58.6 72.5 %Chromat.

D: 6.3 17.9 %Chromat.

With hydrogen

T=160°C; P=60006 Torr; Product distribution / selectivity; Hide Experimental Procedure

BASF AKTIENGESELLSCHAFT

Patent: WO2004/43890 A2, 2004 ; Location in patent: Page 7 ; Title/Abstract

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1; 2; 3:Beispiele 2 und 3, Vergleichsbeispiel 1

25 ml des Katalysators A wurden in einen kontinuierlichen Rohrreaktor eingebaut. Der Feed (Eduktgemisch) bestand aus einer Maleinsaeureloesung (10 GEW.-percent Maleinsaeure) und 50 NI/h Wasserstoff. Die Hydrierung wurde bei 160°C und 80 bar durchgefuehrt. Der Fluessigaustrag wurde mittels Gaschromatographie analysiert. Die Werte in Tabelle 1 sind jeweils als Ausbeuten in [percent] pro mol Maleinsaeure angegeben.

A: 1.1 %Chromat.

B: 0.1 %Chromat.

C: 60.1 %Chromat.

D: 19.8 %Chromat.

With hydrogen

T=160°C; P=56255.6 Torr; 1 h; Product distribution / selectivity; Hide Experimental Procedure

BASF AKTIENGESELLSCHAFT

Patent: WO2004/43890 A2, 2004 ; Location in patent: Page 11 ; Title/Abstract

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10:Beispiel 10

12 ml des Katalysators E wurden mit 80 mi waessriger Maleinsaeureloesung (5 Gew.-percent Maleinsaeure) in einen Autoklaven eingebaut. Es wurden bei Raumtemperatur 75 bar Wasserstoff aufgepresst. Die Temperatur wurde auf 160°C angehoben. Nach 1 h WUR- de die Reaktion abgebrochen. Der FLueSSIGAUSTRAG wurde mittels Gaschromatographie analysiert. Die Werte in Tabelle 7 sind jeweils als Ausbeuten in [percent] pro mol Maleinsaeure angegeben

A: 0.5 1.0 %Chromat.

B: 1.1 6.0 %Chromat.

C: 73.3 93.1 %Chromat.

D: 3.4 4.0 %Chromat.

With hydrogen

T=160 - 180°C; P=60006 Torr; Product distribution / selectivity; Hide Experimental Procedure

BASF AKTIENGESELLSCHAFT

Patent: WO2004/43890 A2, 2004 ; Location in patent: Page 13 ; Title/Abstract

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12; 13:Beispiele 12 und 13

Jeweils 25 mi Katalysator wurden in einen kontinuierlichen Rohrreaktor eingebaut. Der Feed bestand aus einer waessrigen Maleinsaeureloesung (10 Gew.-percent Maleinsaeure). 50 NI/h Wasserstoff wurden zugegeben. Der Fluessigaustrag wurde mittels Gaschromatographie analysiert. Die Werte in Tabelle 8 sind jeweils als Ausbeuten in [percent] pro mol Maleinsaeure angegeben.

Hide Details

A: 0.1 0.3

With hydrogen

T=160°C; P=60006 Torr; Product distribution / selectivity;

BASF AKTIENGESELLSCHAFT

Patent: WO2004/43890 A2, 2004 ;

%Chromat.

B: 0.7 1.8 %Chromat.

C: 91.1 91.4 %Chromat.

D: 4.4 6.6 %Chromat.

Location in patent: Page 8 ;

Hide Experimental Procedure

Title/Abstract

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5; 6:Beispiele 5 und 6

25 ml des Katalysators B wurden in einen kontinuierlichen Rohrreaktor eingebaut. Der Feed bestand aus einer Maleinsaeureloesung (10 Gew.-percent Maleinsaeure) und wurde mit 25 g/h dosiert. Es wurde bei 160°C und 80 bar hydriert. Der FLueSSIGAUSTRAG wurde mit- tels Gaschromatographie analysiert. Die Werte in Tabelle 2 sind jeweils als Ausbeuten in [percent] pro mol Maleinsaeure angegeben.

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187

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With hydrogen; Ru(acac)3; 1,1,1-tris (diphenylphosphinomethyl)ethane in water

T=250°C; P=36201.3 - 51716.2 Torr; Product distribution / selectivity; Hide Experimental Procedure

DAVY PROCESS TECHNOLOGY LIMITED

Patent: WO2005/51875 A1, 2005 ; Location in patent: Page/Page column 12 ; Title/Abstract

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1:

Example 1 illustrates that maleic acid may be successfully hydrogenated in the presence of water; Ruthenium (III) acetylacetonate (0.46 mmols, 0. 181g) and 1, 1, 1 tris (diphenyl- phosphinomethyl) ethane (triphos) (6. 1mmols, 0. 38g), water (71g) and maleic acid (ex Fluka, 20.2g) were transferred into a 300ml Hastelloy Parr autoclave. This was sealed and purged with hydrogen before being pressurised to 700 psig with hydrogen and heated to 250°C. Once 250°C had been achieved, the reactor was topped up with hydrogen to 1000 psig and this pressure was maintained throughout the reaction via a mass flow meter, which recorded the amount of hydrogen added. At the end of the reaction the hydrogen supply was isolated and the reactor cooled. At room temperature the headspace gas was analysed using a Pye-Unicam refinery gas analyser, before being vented. The product was removed from the reactor and weighed (91. 42g). The maleic conversion was determined by titration of the liquid product against 0.1 M sodium hydroxide (>99. 9percent). The water and organic analysis was determined using an HP gas chromatograph equipped with a micro TCD (wtpercent): water (86. 52), propanol (0.84), tetrahydrofuran (7.02) propionic acid (0.14), y- butyrolactone (2.47) butanediol (2.83) ; giving an overall molar selectivity to tetrahydrofuran of 5 1. 1 percent, to y-butyrolactone of 15. 1percent and to butanediol of 16.5percent.

With hydrogen in 1-methyl-pyrrolidin-2-one; water

T=250°C; P=36201.3 - 51716.2 Torr; Product distribution / selectivity; Hide Experimental Procedure

DAVY PROCESS TECHNOLOGY LIMITED

Patent: WO2005/51875 A1, 2005 ; Location in patent: Page/Page column 13 ; Title/Abstract

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3:

Example 3 illustrates the use of other tridentate facially co-ordinated phosphines. Ru (acac) 3, (2.541g) tris-1, 1, l- (diethylphosphinomethyl) ethane (2. 00g) N- methylpyrrolidone (153g) were loaded under argon into a 300 ml Hastelloy C autoclave, then heated at 200°C for 30 minutes to preform the catalyst. The method of Example 1 was then repeated except that 15.89 Nmethylpyrrolidone were added instead of the ruthenium acetylacetonate and triphos. At the end of the reaction the products were analysed and found to be (wtpercent) water (61.43), propanol (0.14) tetrahydrofuran (3.69), propionic acid (0.15), y-butyrolactone (3.87), butanediol (5.22) ; giving an overall selectivity to tetrahydrofuran (30.49) to y-butyrolactone (26.81) and to butanediol of (34.57) and a conversion of>99percent

A: 7.02 %Chromat.

B: 0.14 %Chromat.

C: 0.84 %Chromat.

D: 2.83 %Chromat.

E: 0.14 %Chromat.

With water; hydrogen; Ru(acac)3; 1,1,1-tris (diphenylphosphinomethyl)ethane

T=241°C; P=36961.4 - 52476.2 Torr; Product distribution / selectivity; Hide Experimental Procedure

DAVY PROCESS TECHNOLOGY LIMITED

Patent: WO2003/93208 A1, 2003 ; Location in patent: Page/Page column 8-9 ; Title/Abstract

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1:

Ruthenium (III) acetylacetonate (0.46 mmols, 0. 181g) and 1,1, 1 tris (diphenyl- phosphinomethyl) ethane (triphos) (6. 1mmols, 0.38g), water (71g) and maleic acid (ex Fluka, 20.2g) were transferred into a 300ml Hastelloy Parr autoclave. This was sealed and purged with hydrogen before being pressurised to 700 psig with hydrogen and heated to 241°C. Once 241°C had been achieved, the reactor was topped up with hydrogen to 1000 psig and this pressure was maintained throughout the reaction via a mass flow meter, which recorded the amount of hydrogen added. At the end of the reaction the hydrogen supply was isolated and the reactor cooled. At room temperature the headspace gas was analysed using a Pye-Unicam refinery gas analyser, before being vented. The product was removed from the reactor and weighed (91.42g). The maleic conversion was determined by titration of the liquid product against 0. 1M sodium hydroxide. (>99.9percent). The water and organic analysis was determined using an HP gas chromatograph equipped with a micro TCD (wtpercent): water (86.52), propanol (0.84), tetrahydrofuran (7.02) propionic acid (0.14), y- butyrolactone (2.47) butanediol (2.83) ; giving an overall molar selectivity to tetrahydrofuran of 51. 1percent, to y-butylractone of 15. 1percent, and to butanediol of 16.5percent, others 17.3percent.

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188

Synthesize Find similar Rx-ID: 23491962 Find similar reactions

With hydrogen; Ru(acac)3; 1,1,1-tris (diphenylphosphinomethyl)ethane in 1-methyl-pyrrolidin-2-one; water

T=250°C; P=36201.3 - 51716.2 Torr; Product distribution / selectivity; Hide Experimental Procedure

DAVY PROCESS TECHNOLOGY LIMITED

Patent: WO2005/51875 A1, 2005 ; Location in patent: Page/Page column 13 ; Title/Abstract

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2:

Examples 2 illustrates the direct hydrogenation of succinic acid in the presence of a solvent. In Example 2, Example 1 was repeated using except that maleic acid was replaces with succinic acid (20.03g) 1-methyl-2-pyrrolidone (20.61g) was included as a solvent and the 49.86g water were used. At the end of the reaction the products were analysed and found to be (wtpercent) water (67.43), propanol (0.14) tetrahydrofuran (3.69), propionic acid (0.15) y-butyrolactone (3.87), butanediol (5.22) ; giving an overall selectivity to tetrahydrofuran (32. 55) y-butyrolactone (42.91) and to butanediol of (9.57) and a conversion of >88percent.

A: 3.69 %Chromat.

B: 3.87 %Chromat.

C: 0.14 %Chromat.

D: 5.22 %Chromat.

E: 0.15 %Chromat.

With water; hydrogen; Ru(acac)3; 1,1,1-tris (diphenylphosphinomethyl)ethane in 1-methyl-pyrrolidin-2-one

T=241°C; P=36961.4 - 52476.2 Torr; Product distribution / selectivity; Hide Experimental Procedure

DAVY PROCESS TECHNOLOGY LIMITED

Patent: WO2003/93208 A1, 2003 ; Location in patent: Page/Page column 12-13 ; Title/Abstract

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8:

The method of Example 1 was repeated except that maleic acid was replaced with succinic acid (20. 03g), 1-methyl-2-pyrrolidinine (20. 61g) was included as a solvent and the amount of water (49.86g) included, was reduced. At the end of the reaction the products were analysed and found to be (wtpercent): water (61.43), propanol (0.14), tetrahydrofuran (3.69), propionic acid (0.15), y-butyrolactone (3.87), butanediol (5. 22) ; giving an overall selectivity to tetrahydrofuran of 30.49percent, to y-butyrolactone of 26.81percent, and to butanediol of 34.57percent, and a conversion of >99percent.

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189

Synthesize Find similar Rx-ID: 23511696 Find similar reactions

A: 37.5 53.3 %Chromat.

B: 21.0 47.4 %Chromat.

C: 1.6 40.0

With hydrogen

T=180 - 260°C; P=7500.75 - 18751.9 Torr; Gas phase; Product distribution / selectivity;

BASF Aktiengesellschaft

Patent: WO2005/58853 A2, 2005 ; Location in patent: Page/Page column 21-22 ; Title/Abstract

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%Chromat.

D: 1.4 9.8 %Chromat.

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190

Synthesize Find similar Rx-ID: 23662962 Find similar reactions

A: 0.2% B: 3.1% C: 89% D: 7.6%

With hydrogen in 1,4-dioxane

T=139.84°C; P=60006 Torr; 96 h; Autoclave; Catalytic behavior; Reagent/catalystTimeTemperature; Overall yield = 100 percent;

Takeda, Yasuyuki; Tamura, Masazumi; Nakagawa, Yoshinao; Okumura, Kazu; Tomishige, Keiichi

Catalysis Science and Technology, 2016 , vol. 6, # 14 p. 5668 - 5683 Title/Abstract

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A: 2.95% B: 0% C: 81.5% D: 3.35%

With hydrogen; 1.0percent Pd/ 3.0percent Re on Rutile TiO2

T=164 - 185°C; 21 - 237 h; Product distribution / selectivity; Hide Experimental Procedure

Bhattacharyya, Alakananda; Manila, Maynard D.

Patent: US2006/4212 A1, 2006 ; Location in patent: Page/Page column 16 - 17 ; Title/Abstract

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7:

The catalyst of Example 7 is made by the same procedure as the catalyst of Example 1(a) except that the amounts of palladium and rhenium are adjusted to give a catalyst containing 1.0 wt percent palladium and 3.0 wt percent rhenium. Table 7 shows the results of the second stage hydrogenation of succinic acid to 1,4-Butanediol (BDO). In this reaction the first stage reaction wherein maleic acid was converted to succinic acid was conducted using a standard carbon catalyst, such as Carbon Catalyst B, and the second stage reaction was conducted using a catalyst comprising 1.0percent Pd and 3percent Re on a 1/16 rutile titanium dioxide support.

A: 3.38% B: 0% C: 64.14% D: 2.86%

With hydrogen; 0percent Pd/5.0percent Re on Rutile TiO2

T=170 - 185°C; 90 - 825 h; Product distribution / selectivity; Hide Experimental Procedure

Bhattacharyya, Alakananda; Manila, Maynard D.

Patent: US2006/4212 A1, 2006 ; Location in patent: Page/Page column 16 ; Title/Abstract

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6:

The catalyst of Example 6 is made by the same procedure as the catalyst of Example 1(a) except that palladium is not used and the amount of rhenium is adjusted to give a catalyst containing and 5.0 wt percent rhenium. Table 6 shows the results of the second stage hydrogenation of succinic acid to 1,4-Butanediol (BDO). In this reaction the first stage reaction wherein maleic acid was converted to succinic acid was conducted using a standard carbon catalyst, such as Carbon Catalyst B, and the second stage reaction was conducted using a catalyst comprising 0percent Pd and 5percent Re on a 1/16 rutile titanium dioxide support.

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A: 12.52% B: 4.72% C: 62.45% D: 4.14%

With hydrogen; 2.0percent Pd/ 5.0percent Re on Rutile TiO2

T=165°C; 68 - 281 h; Product distribution / selectivity; Hide Experimental Procedure

Bhattacharyya, Alakananda; Manila, Maynard D.

Patent: US2006/4212 A1, 2006 ; Location in patent: Page/Page column 17-18 ; Title/Abstract

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8:

(A) Rutile TiO2 Support (94percent Rutile, 6percent Anatase, 1/16) rutile titanium dioxide 93.0 g (dry) (B) Pd/HNO3 Impregnation Solution 9.48 g of Pd (NO3)2 Solution (21.1percent Pd) 10.07 g of concentrated nitric acid (70 wt percent) (C) Re/HNO3 Impregnation Solution 9.09 g HReO4 Solution (54.98percent Re) 10.46 g of concentrated nitric acid (70 wt percent) Preparation Procedure: Step 1: The rutile TiO2 support (A) is gradually impregnated with solution (B) and allowed to stand for 1 hour. The material is then dried in an oven at 130° C. for 2 hours. Step 2: The palladium-impregnated TiO2 rutile support (A) from Step 1 is gradually impregnated with solution (C) and allowed to stand for 1 hour. The material is then dried in an oven at 130° C. for 2 hours. The results for the stage 1 reaction converting maleic acid to succinic acid are shown in Table 8(a), in which a sample was taken at 139 hours. The results for the second stage reaction converting succinic acid to BDO, THF, and GBL or mixtures thereof over several hours is shown in Table 8(b). Table 8a shows the results of the first stage hydrogenation of maleic acid to succinic acid (SAC) using a catalyst comprising 2.0percent Pd and 5.0percent Re on a 1/16 rutile titanium dioxide support. Table 8b shows the results of the second stage hydrogenation of succinic acid to 1,4-Butanediol (BDO) using a catalyst comprising 2.0percent Pd and 5.0percent Re on a 1/16 rutile titanium dioxide support.

A: 1.84% B: 0.12% C: 18.8% D: 0.89%

With hydrogen; 0.5percent Pd/5.0percent Re on Rutile TiO2

T=165 - 185°C; 112 - 495 h; Product distribution / selectivity; Hide Experimental Procedure

Bhattacharyya, Alakananda; Manila, Maynard D.

Patent: US2006/4212 A1, 2006 ; Location in patent: Page/Page column 15 - 16 ; Title/Abstract

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5:0.5percent Pd/5.0percent Re on 1/16" Rutile Titanium Dioxide Support (94percent Rutile/6percent Anatase Crystalline Phase

The Example 5(a) is made by the same procedure as the catalyst of Example 1(a) except that the amounts of palladium and rhenium are adjusted to give a catalyst containing 0.5 wt percent palladium and 5.0 wt percent rhenium. Example 5(b) 0.5percent Pd/5.0percent Re on 1/16 Rutile Titanium Dioxide Support (98percent Rutile/2percent Anatase Crystalline Phase) The catalyst of Example 5(b) is made by the procedure of Example 5(a) except that a 1/16 diameter rutile TiO2 support (98percent Rutile/2percent Anatase Crystalline Phase) is used. Table 5 shows the results of the second stage hydrogenation of succinic acid to 1,4-Butanediol (BDO). The first stage reaction (not shown) wherein maleic acid was converted to succinic acid was conducted using a catalyst comprising 0.5percent palladium on a rutile TiO2 support, such as the catalyst of Example 2, and the second stage reaction was conducted using a catalyst made by the process of Example 5 comprising 0.5percent Pd and 5percent Re on a 1/16 rutile titanium dioxide support.

A: 12.98% B: 0% C: 14.44% D: 4.21%

With hydrogen; 2.0percent Pd/5.0percent Re on Rutile TiO2

T=165 - 188°C; 90 - 945 h; Product distribution / selectivity; Hide Experimental Procedure

Bhattacharyya, Alakananda; Manila, Maynard D.

Patent: US2006/4212 A1, 2006 ; Location in patent: Page/Page column 15 ; Title/Abstract

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4:2.0percent Pd/5.0percent Re on 1/16" Rutile Titanium Dioxide Support (94percent Rutile/6percent Anatase Crystalline Phase)

The catalyst of Example 4 is made by the same procedure as the catalyst of Example 1(a) except that the amounts of palladium and rhenium are adjusted to give a catalyst containing 2.0 wt percent palladium and 5.0 wt percent rhenium. Table 4 shows the results of the second stage hydrogenation of succinic acid to 1,4-Butanediol (BDO). The first stage reaction (not shown) wherein maleic acid was converted to succinic acid was conducted using a catalyst comprising 0.5percent palladium on a rutile TiO2 support, such as the catalyst of Example 2, and the second stage reaction was conducted using a catalyst made by the process of Example 4, comprising 2.0percent Pd and 5percent Re on a 1/16 rutile titanium dioxide support.

A

B

C

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191

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With hydrogen; 0.4percent Fe, 1.9percent Na, 2.66percent Ag, 2.66percent Pd, 10.0percent Re on carbon T=130 - 175°C; P=129290 - 206865 Torr; Product distribution / selectivity; Hide Experimental Procedure

Bhattacharyya, Alakananda; Manila, Maynard D.

Patent: US2006/4212 A1, 2006 ; Location in patent: Page/Page column 11-13 ; Title/Abstract

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The catalyst testing unit is comprised of a two-reactor system connected in series where maleic acid is first converted to succinic acid (SAC) in the first reactor at about 110° C. The effluent from the first stage reactor is delivered to the second stage reactor for the conversion of succinic acid to mainly BDO. Operating pressure is at 2500 to 4000 psi and internal reactor temperature is initially set at 165° C. Thereafter, temperature is adjusted closer to the temperature where a high conversion of SAC (about 99.7percent) is obtained. This temperature generally may vary from about 130° C. to about 175° C. At the lower end of the temperature range BDO selectivity is higher (80percent or higher) whereas THF is favored at higher temperatures (over 5percent). The results of the activity evaluation of a catalysts made according to the procedure of catalyst Example 1(a) is shown in Table 1a. Activity evaluation of a catalyst made according to the procedure of catalyst Example 2 is shown in Table 1(b). Catalyst results of the activity evaluation of a catalysts made according to the procedure of catalyst Example 3 is shown in Table 1(c). Tables 1a, 1b and 1c show that catalysts of Example 1(a), comprising Pd/Re on a rutile titanium dioxide support, and catalysts of Example 2 and Example 3, comprising Pd on a rutile titanium dioxide support, completely convert maleic acid to succinic acid with high selectivity to succinic acid and low amounts of other by-products. The Catalyst Testing Unit (CTU) results for Catalyst Example 1 and Catalyst Example 2 show that (a) Both 1/16 inch and inch Rutile extrudates can be used for hydrogenation. For carbon, inch was found to be less effective. (b) For maleic to succinic hydrogenation there is no need for other co-catalysts such as Ag, Fe, Na, etc., (c) 0.5percent Pd alone on a rutile TiO2 support gives good conversion of maleic acid to succinic acid.

With hydrogen; 0.5percent Pd/ 5percent Re on Rutile TiO2

T=130 - 175°C; P=129290 - 206865 Torr; Product distribution / selectivity; Hide Experimental Procedure

Bhattacharyya, Alakananda; Manila, Maynard D.

Patent: US2006/4212 A1, 2006 ; Location in patent: Page/Page column 11-13 ; Title/Abstract

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The catalyst testing unit is comprised of a two-reactor system connected in series where maleic acid is first converted to succinic acid (SAC) in the first reactor at about 110° C. The effluent from the first stage reactor is delivered to the second stage reactor for the conversion of succinic acid to mainly BDO. Operating pressure is at 2500 to 4000 psi and internal reactor temperature is initially set at 165° C. Thereafter, temperature is adjusted closer to the temperature where a high conversion of SAC (about 99.7percent) is obtained. This temperature generally may vary from about 130° C. to about 175° C. At the lower end of the temperature range BDO selectivity is higher (80percent or higher) whereas THF is favored at higher temperatures (over 5percent). The results of the activity evaluation of a catalysts made according to the procedure of catalyst Example 1(a) is shown in Table 1a. Activity evaluation of a catalyst made according to the procedure of catalyst Example 2 is shown in Table 1(b). Catalyst results of the activity evaluation of a catalysts made according to the procedure of catalyst Example 3 is shown in Table 1(c). Tables 1a, 1b and 1c show that catalysts of Example 1(a), comprising Pd/Re on a rutile titanium dioxide support, and catalysts of Example 2 and Example 3, comprising Pd on a rutile titanium dioxide support, completely convert maleic acid to succinic acid with high selectivity to succinic acid and low amounts of other by-products. The Catalyst Testing Unit (CTU) results for Catalyst Example 1 and Catalyst Example 2 show that (a) Both 1/16 inch and inch Rutile extrudates can be used for hydrogenation. For carbon, inch was found to be less effective. (b) For maleic to succinic hydrogenation there is no need for other co-catalysts such as Ag, Fe, Na, etc., (c) 0.5percent Pd alone on a rutile TiO2 support gives good conversion of maleic acid to succinic acid.

With hydrogen in ethanol; water

T=100°C; P=7500.75 Torr; 24 h;

Luque, Rafael; Clark, James H.; Yoshida, Kenta; Gai, Pratibha L.

Chemical Communications, 2009 , # 35 p. 5305 - 5307 Title/Abstract

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With hydrogen in water

T=160°C; P=112511 Torr; 48 h; Inert atmosphere; Reagent/catalyst; Hide Experimental Procedure

Tapin, Benoit; Epron, Florence; Especel, Catherine; Ly, Bao Khanh; Pinel, Catherine; Besson, Michele

Catalysis Today, 2014 , vol. 235, p. 127 - 133 Title/Abstract

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Succinic acid hydrogenation was performed in a Hastelloy Parr 4560 high pressure reactor of 300 mL equipped with an electrically heated jacket, a turbine agitator with a magnetic driver, and a liquid sample line. The reactor was loaded with 100 mL of a 5 wt.percent SUC aqueous solution (420 mmol L−1) and 1 g catalyst (molar ratio SUC/Pd = 225). After purging with Ar, the reactor was heated to 160 °C. At 160 °C, hydrogen is added at a pressure of 150 bar to start the reaction. The aqueous samples taken from the reactor at regular intervals were analyzed using both gas chromatography (HP-5 column, 30 m × 0.25 mm column, thickness 0.25 μm) and a high performance liquid chromatography instrument equipped with UV and RI detection (ICSep Coregel 107H column at 40 °C, 0.005 N H2SO4 as mobile phase at a flow rate of 0.5 mL min−1). The main reaction products consisted of GBL, THF and BDO. By-products analyzed in the liquid phase were n-butanol, n-propanol, butyric acid, and propionic acid (Scheme 1). The mass balance was checked by measuring Total Organic Carbon (TOC) in the liquid phase using a Shimadzu TOC-

VCSH analyzer.

With hydrogen in 1,4-dioxane

T=200°C; P=60006 Torr; 7 h; Inert atmosphereAutoclaveGlovebox; Reagent/catalyst; Hide Experimental Procedure

Kang, Ki Hyuk; Hong, Ung Gi; Bang, Yongju; Choi, Jung Ho; Kim, Jeong Kwon; Lee, Jong Kwon; Han, Seung Ju; Song, In Kyu

Applied Catalysis A: General, 2015 , vol. 490, p. 153 - 162 Title/Abstract

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Hydrogenation of succinic acid to BDO

Liquid-phase hydrogenation of succinic acid to BDO was con-ducted in a stainless steel autoclave reactor with a volume of200 ml. Prior to the reaction, the catalysts were reduced using anex situ reduction system at 500C for 4 h with a heating rate of5C/min under 5percent H2/N2flow (50 ml/min). In order to avoid airexposure, reduced catalyst (0.1 g), succinic acid (0.25 g), and 1,4dioxane (50 ml, an inert aprotic solvent) were charged into thereactor in an argon atmosphere glove box. The closed reactor filledwith argon was then mounted to the autoclave chamber as quicklyas possible. After purging the reactor with nitrogen, it was pressur-ized up to 50 bar using hydrogen. The sealed autoclave was heatedto the reaction temperature (200C), and then pressurized up to80 bar using hydrogen. Catalytic reaction was conducted with con-stant stirring (700 rpm) for 7 h. After the reaction, the reactor wascooled to room temperature and depressurized. Reaction productswere analyzed with a gas chromatograph (Younglin, ACME-6100)equipped with a flame ionization detector (FID). Conversion ofsuccinic acid, selectivity for product, and yield for product werecalculated according to the following equations.

With hydrogen in 1,4-dioxane

T=200°C; P=60006 Torr; 7 h; GloveboxInert atmosphereAutoclave; Catalytic behavior; Reagent/catalyst; Hide Experimental Procedure

Kang, Ki Hyuk; Hong, Ung Gi; Bang, Yongju; Choi, Jung Ho; Kim, Jeong Kwon; Lee, Jong Kwon; Han, Seung Ju; Song, In Kyu

Applied Catalysis A: General, 2015 , vol. 490, # 1 p. 153 - 162 Title/Abstract

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2.3. Hydrogenation of succinic acid to BDO

Liquid-phase hydrogenation of succinic acid to BDO was conducted in a stainless steel autoclave reactor with a volume of 200 ml. Prior to the reaction, the catalysts were reduced using an ex situ reduction system at 500 °C for 4 h with a heating rate of 5 °C/min under 5percent H2/N2 flow (50 ml/min). In order to avoid air exposure, reduced catalyst (0.1 g), succinic acid (0.25 g), and 1,4-dioxane (50 ml, an inert aprotic solvent) were charged into the reactor in an argon atmosphere glove box. The closed reactor filled with argon was then mounted to the autoclave chamber as quickly as possible. After purging the reactor with nitrogen, it was pressurized up to 50 bar using hydrogen. The sealed autoclave was heated to the reaction temperature (200 °C), and then pressurized up to 80 bar using hydrogen. Catalytic reaction was conducted with constant stirring (700 rpm) for 7 h. After the reaction, the reactor was cooled to room temperature and depressurized. Reaction products were analyzed with a gas chromatograph (Younglin, ACME-6100) equipped with a flame ionization detector (FID).

With water; hydrogen

T=160°C; P=112511 Torr; 48 h;

Ly, Bao Khanh; Tapin, Benot; Aouine, Mimoun; Delichere, Pierre; Epron, Florence; Pinel, Catherine; Especel, Catherine; Besson, Michle

ChemCatChem, 2015 , vol. 7, # 14 p. 2161 - 2178 Title/Abstract

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With hydrogen

T=300°C; P=37503.8 Torr; 10 h; Autoclave; Catalytic behavior; TemperaturePressure;

Liu, Xiaoran; Wang, Xicheng; Xu, Guoqiang; Liu, Qiang; Mu, Xindong; Liu, Haichao

Journal of Materials Chemistry A, 2015 , vol. 3, # 46 p. 23560 - 23569 Title/Abstract

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A

B

C

D

E

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192

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A: 6.00 %Chromat.

B: 2.19 %Chromat.

C: 0.13 %Chromat.

D: 8.35 %Chromat.

E: 0.04 %Chromat.

With water; hydrogen; Ru(acac)3; 1,1,1-tris (diphenylphosphinomethyl)ethane

T=241°C; P=36961.4 - 52476.2 Torr; 12 h; Product distribution / selectivity; Hide Experimental Procedure

DAVY PROCESS TECHNOLOGY LIMITED

Patent: WO2003/93208 A1, 2003 ; Location in patent: Page/Page column 12 ; Title/Abstract

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6:

The method of Example 1 was repeated except that the maleic acid was replaced with fumaric acid (20.3g, 98percent). After 12 hours at temperature, the reactor was cooled to room temperature The liquid product was recovered from the autoclave (90. 1g) and analysed (wtpercent), water (82.74), propanol (0.13), propionic acid (0.04), tetrahydrofuran (6.00), y-butylractone (2.19), butanediol (8.35) ; giving an overall molar selectivity to tetrahydrofuran of 40.0percent, y-butyrolactone of 12.2percent, and to butanediol of 44.53percent. Titration against 0. 01M sodium hydroxide gave >98percent conversion of the fumaric acid

A

B

C

D

E

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193

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A: 27.43 %Chromat.

B: 0.333 %Chromat.

C: 15.37 %Chromat.

D: 12.29 %Chromat.

E: 0.01 %Chromat.

With water; hydrogen; Ru(acac)3; 1,1,1-tris (diphenylphosphinomethyl)ethane

T=191°C; P=36961.4 - 52476.2 Torr; 53 h; Product distribution / selectivity; Hide Experimental Procedure

DAVY PROCESS TECHNOLOGY LIMITED

Patent: WO2003/93208 A1, 2003 ; Location in patent: Page/Page column 10 ; Title/Abstract

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2; 3:

In Example 2, Example 1 was repeated using 48.64g of water and 23.26g of dimethyl maleate as feed. The reaction was conducted at 191°C. After 53 hours the liquid and gaseous products were cooled and the liquid product analysed by gas chromatography and found to be off gas (molpercent) hydrogen (98.9), carbon monoxide (0.08), methane (0.01) and carbon dioxide (0.113) liquid (wtpercent) methanol (15.37) water (67.11) tetrahydrofuran (27.43), y-butyrolactone (0.333) and butanediol (12.29) giving a molar conversion of 99. 5molpercent and a selected activity to desired products of (molpercent) tetrahydrofuran (27.43) y-butylractone (1.88) butanediol of (66.24). In Example 3, Example 1 was again repeated using 48.4g of water and 20. 1 g of methyl propionate as feed. The reaction was conducted at 192°C. After 15 hours the reactor was cooled and the liquid product analysed by gas chromatography and found to be methanol (10.25) water (70.75) propanol (18.27) methyl propionate (<0. 1) propionic acid (<0. 1) propyl propionate (<0. 1), giving a molar selectivity and conversion of >99. 5percent A

B

C

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A: 4.2% B: 3.7% C: 8.6%

Bauduin, Christophe; Fischer, Wolfgang; Pinkos, Rolf; Scholten, Edzard

Patent: US2009/137825 A1, 2009 ; Location in patent: Page/Page column 7-8 ;

With hydrogen; [RuIII(2,4-pentanedionato)3]

T=150°C; P=112511 Torr; 24 h; Product distribution / selectivity; Hide Experimental Procedure

Title/Abstract

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1:

Reference Example 1Experiments on the Direct Catalytic Hydrogenation of Succinic Salts to THFFor comparative purposes, various salts of succinic acid were subjected to a homogeneous or heterogeneous hydrogenation. Either no reaction (disodium salt) or the formation of various hydrogenation products, such as BDO, GBL or pyrrolidone, is observed, but not the formation of the desired THF product.; Homogeneous hydrogenation conditions: Ru(acac)3/Triphos, 150° C., 150 bar H2, 24 h; (b)The monosodium salt can be regarded as a 50:50 mixture of diacid and disodium salt. Only the diacid could in butanediol BDO and GBL. No conversion of a sodium carboxylate was observed.

A

B

195

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A: 26.2% B: 10%

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With hydrogen; 3 Sn/7 Pt on C

T=120°C; P=150015 Torr; 24 h; Product distribution / selectivity; Hide Experimental Procedure

Bauduin, Christophe; Fischer, Wolfgang; Pinkos, Rolf; Scholten, Edzard

Patent: US2009/137825 A1, 2009 ; Location in patent: Page/Page column 7-8 ; Title/Abstract

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1:

Reference Example 1Experiments on the Direct Catalytic Hydrogenation of Succinic Salts to THFFor comparative purposes, various salts of succinic acid were subjected to a homogeneous or heterogeneous hydrogenation. Either no reaction (disodium salt) or the formation of various hydrogenation products, such as BDO, GBL or pyrrolidone, is observed, but not the formation of the desired THF product.; Heterogeneous hydrogenation conditions: 3percent Sn/7percent Pt on C, 120° C., 200 bar H2, 24 h.; (b)The monosodium salt can be regarded as a 50:50 mixture of diacid and disodium salt. Only the diacid could in butanediol BDO and GBL. No conversion of a sodium carboxylate was observed.

A: 3.3% B: 21.3%

Bauduin, Christophe; Fischer, Wolfgang; Pinkos, Rolf; Scholten, Edzard

Patent: US2009/137825 A1, 2009 ; Location in patent: Page/Page column 7-8 ;

With hydrogen; [RuIII(2,4-pentanedionato)3]

T=150°C; P=112511 Torr; 24 h; Product distribution / selectivity; Hide Experimental Procedure

Title/Abstract

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1:

Reference Example 1Experiments on the Direct Catalytic Hydrogenation of Succinic Salts to THFFor comparative purposes, various salts of succinic acid were subjected to a homogeneous or heterogeneous hydrogenation. Either no reaction (disodium salt) or the formation of various hydrogenation products, such as BDO, GBL or pyrrolidone, is observed, but not the formation of the desired THF product.; Homogeneous hydrogenation conditions: Ru(acac)3/Triphos, 150° C., 150 bar H2, 24 h; (b)The monosodium salt can be regarded as a 50:50 mixture of diacid and disodium salt. Only the diacid could in butanediol BDO and GBL. No conversion of a sodium carboxylate was observed.

A

B

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196

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A: 5% B: 95%

With C36H54IrN2P2(1+)*C24H20B(1-); hydrogen; sodium hydride in toluene

T=180°C; P=7500.75 - 45004.5 Torr; 18 h; AutoclaveSealed tube; Reagent/catalystTemperaturePressure; Hide Experimental Procedure

National University Corporation Nagoya University; Saito, Susumu; Noyori, Ryoji; Miura, Takashi; Naruto, Masayuki; Iida, Kazuki; Takada, Yuki; Toda, Katsuaki; Nimura, Sota; Agrawal, Santosh; Lee, Sunkook

Patent: US9463451 B2, 2016 ; Location in patent: Page/Page column 65 ; Title/Abstract

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F3:Reduction of Carboxylic Acid

A stirrer, an iridium(I)complex (Compound 2n) (10.9 mg, 0.01 mmol), sodium hydride (1.4 mg, 0.06 mmol), and succinic acid (118.1 mg, 1 mmol) were placed in a dried fluororesin tube (30 mL). The tube containing the mixture was rapidly inserted into an autoclave. Thereafter, dehydrated toluene (2 mL) was added to the mixture in the tube while introducing argon gas into the autoclave; then, the autoclave was rapidly hermetically sealed. Hydrogen gas was introduced into the autoclave from a hydrogen compressed gas cylinder connected via a stainless-steel pipe, thereby substituting the inside of the autoclave with hydrogen gas. More specifically, 1-MPa hydrogen gas pressure was applied inside the autoclave, and then the hydrogen gas pressure was removed through a leak valve. This operation was repeated three times. Finally, the hydrogen gas pressure inside the autoclave was set to 6 MPa, and the mixture was stirred for 18 hours using a constant-temperature bath at 180° C. (0362) After the reaction was completed, the autoclave was cooled to substantially room temperature by being immersed in an icy bath. Then, the leak valve of the autoclave was opened and the hydrogen gas inside the autoclave was released into the air. Subsequently, the tube was taken out of the autoclave, thereby obtaining a reaction product (solution). An internal standard substance (mesitylene) was added to the solution. Based on the integration value of the hydrogen atom amount of the internal standard substance, the yield of the reaction product was calculated. 1,4-butane diol and γ-butyrolactone were obtained at yields of 95percent and 5percent, respectively.

B: 64.7%

Kang, Ki Hyuk; Han, Seung Ju; Lee, Jong Won; Kim, Tae Hyeop; Song, In Kyu

Applied Catalysis A: General, 2016 , vol. 524, p. 206 - 213 Title/Abstract

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Stage #1: in 1,4-dioxane

T=500°C; 4 h; Stage #2: With hydrogen in 1,4-dioxane

T=200°C; P=60006 Torr; 5 h; Catalytic behavior; Reagent/catalyst; Hide Experimental Procedure

2.3. Hydrogenation of succinic acid to BDO

BDOHydrogenation of succinic acid was conducted in a high pressureautoclave reactor of 200 ml equipped with an electrically heatedjacket and an agitator with a magnetic driver. Before the experi-ment, the reactor was purged with N2gas to remove air. The reactorwas loaded with 50 ml of 1,4-dioxane (an inert aprotic solvent) and0.25 g of succinic acid. Then, 0.1 g of catalyst reduced at 500C for4 h was charged in the reaction vessel. After additional purging withN2gas, the reactor was heated to 200C and H2gas was injected to80 bar. The reaction was done at 700 rpm for 5 h. After the reaction,the aqueous samples taken from the reactor were analyzed witha gas chromatograph equipped with a capillary column (DB-624)and a flame ionization detector (FID). Catalytic performance wasevaluated by the following equations.

With hydrogen in ethanol; water

T=100°C; P=7500.75 Torr; 24 h;

Luque, Rafael; Clark, James H.; Yoshida, Kenta; Gai, Pratibha L.

Chemical Communications, 2009 , # 35 p. 5305 - 5307 Title/Abstract

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With hydrogen in ethanol; water

T=100°C; P=7500.75 Torr; 24 h;

Luque, Rafael; Clark, James H.

Catalysis Communications, 2010 , vol. 11, # 10 p. 928 - 931 Title/Abstract

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With hydrogen in water

T=160°C; P=112511 Torr; Reagent/catalyst;

Corbel-Demailly, Louis; Ly, Bao-Khanh; Minh, Doan-Pham; Tapin, Benoit; Especel, Catherine; Epron, Florence; Cabiac, Amandine; Guillon, Emmanuelle; Besson, Michele; Pinel, Catherine

ChemSusChem, 2013 , vol. 6, # 12 p. 2388 - 2395 Title/Abstract

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With hydrogen in 1,4-dioxane

T=200°C; P=60006 Torr; 7 h; Inert atmosphereAutoclaveGlovebox; Hide Experimental Procedure

Kang, Ki Hyuk; Hong, Ung Gi; Bang, Yongju; Choi, Jung Ho; Kim, Jeong Kwon; Lee, Jong Kwon; Han, Seung Ju; Song, In Kyu

Applied Catalysis A: General, 2015 , vol. 490, p. 153 - 162 Title/Abstract

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Hydrogenation of succinic acid to BDO

Liquid-phase hydrogenation of succinic acid to BDO was con-ducted in a stainless steel autoclave reactor with a volume of200 ml. Prior to the reaction, the catalysts were reduced using anex situ reduction system at 500C for 4 h with a heating rate of5C/min under 5percent H2/N2flow (50 ml/min). In order to avoid airexposure, reduced catalyst (0.1 g), succinic acid (0.25 g), and 1,4dioxane (50 ml, an inert aprotic solvent) were charged into thereactor in an argon atmosphere glove box. The closed reactor filledwith argon was then mounted to the autoclave chamber as quicklyas possible. After purging the reactor with nitrogen, it was pressur-ized up to 50 bar using hydrogen. The sealed autoclave was heatedto the reaction temperature (200C), and then pressurized up to80 bar using hydrogen. Catalytic reaction was conducted with con-stant stirring (700 rpm) for 7 h. After the reaction, the reactor wascooled to room temperature and depressurized. Reaction productswere analyzed with a gas chromatograph (Younglin, ACME-6100)equipped with a flame ionization detector (FID). Conversion ofsuccinic acid, selectivity for product, and yield for product werecalculated according to the following equations.

With hydrogen in 1,4-dioxane

T=240°C; P=22502.3 - 45004.5 Torr; 30 h; Autoclave;

You, Chenjia; Zhang, Chi; Chen, Lifang; Qi, Zhiwen

Applied Organometallic Chemistry, 2015 , vol. 29, # 10 p. 653 - 660 Title/Abstract

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A: 61 %Chromat.

B: 23 %Chromat.

With cobalt(II) tetrafluoroborate hexahydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3propanediyl]bis[diphenylphosphine] in tetrahydrofuran

T=100°C; P=60006 Torr; 22 h;

Korstanje, Ties J.; Van Der Vlugt, Jarl Ivar; Elsevier, Cornelis J.; De Bruin, Bas

Science, 2015 , vol. 350, # 6258 p. 298 - 302 Title/Abstract

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With hydrogen in 1,4-dioxane

T=200°C; P=60006 Torr; 7 h; GloveboxInert atmosphereAutoclave; Catalytic behavior; Hide Experimental Procedure

Kang, Ki Hyuk; Hong, Ung Gi; Bang, Yongju; Choi, Jung Ho; Kim, Jeong Kwon; Lee, Jong Kwon; Han, Seung Ju; Song, In Kyu

Applied Catalysis A: General, 2015 , vol. 490, # 1 p. 153 - 162 Title/Abstract

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2.3. Hydrogenation of succinic acid to BDO

Liquid-phase hydrogenation of succinic acid to BDO was conducted in a stainless steel autoclave reactor with a volume of 200 ml. Prior to the reaction, the catalysts were reduced using an ex situ reduction system at 500 °C for 4 h with a heating rate of 5 °C/min under 5percent H2/N2 flow (50 ml/min). In order to avoid air exposure, reduced catalyst (0.1 g), succinic acid (0.25 g), and 1,4-dioxane (50 ml, an inert aprotic solvent) were charged into the reactor in an argon atmosphere glove box. The closed reactor filled with argon was then mounted to the autoclave chamber as quickly as possible. After purging the reactor with nitrogen, it was pressurized up to 50 bar using hydrogen. The sealed autoclave was heated to the reaction temperature (200 °C), and then pressurized up to 80 bar using hydrogen. Catalytic reaction was conducted with constant stirring (700 rpm) for 7 h. After the reaction, the reactor was cooled to room temperature and depressurized. Reaction products were analyzed with a gas chromatograph (Younglin, ACME-6100) equipped with a flame ionization detector (FID).

Takeda, Yasuyuki; Tamura, Masazumi; Nakagawa, Yoshinao; Okumura, Kazu; Tomishige, Keiichi

Catalysis Science and Technology, 2016 , vol. 6, # 14 p. 5668 - 5683 Title/Abstract

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With hydrogen in 1,4-dioxane

T=99.84°C; P=60006 Torr; 4 h; Autoclave; Catalytic behavior; Overall yield = 2.0 percent;

A

B

197

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A: 11 %Chromat.

B: 81 %Chromat.

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With methanol; Ru(acac)3; hydrogen; zinc; 1,1,1-tris (diphenylphosphinomethyl)ethane

T=20 - 150°C; P=60006 Torr; Autoclave;

Rosi, Luca; Frediani, Marco; Frediani, Piero

Journal of Organometallic Chemistry, 2010 , vol. 695, # 9 p. 1314 - 1322 Title/Abstract

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A

B

C

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198

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With ZnCuO2; hydrogen

T=170°C; P=30003 Torr; 0.0005 h;

Ding, Guoqiang; Zhu, Yulei; Zheng, Hongyan; Zhang, Wei; Li, Yongwang

Catalysis Communications, 2010 , vol. 11, # 14 p. 1120 - 1124 Title/Abstract

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With hydrogen

T=231°C; Autoclave; Hide Experimental Procedure

ARCHER DANIELS MIDLAND COMPANY; STENSRUD, Kenneth; VENKITASUBRAMANIAN, Padmesh

Patent: WO2014/99431 A1, 2014 ; Location in patent: Page/Page column 22 ; Title/Abstract

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Example: Hydrogenolysis

The esters, resulting from the fermeatation extraction described above is then hydrogesoiyxed over a catalyst (e.g., reduced CnO/ZnO), which should obtain high conversions (>98percent) and sekeiicities (e.g., International Patent Application No. WO 82/03854). Alternatively, one can proceed according to a process such as described in U.S. Patent No. 4,584,419. A stainless steel with an oil jacket maintained at 231 °€ was used for this reaction. Hydrogen was introduced by w ay of a pressure regulator and Oow controller (not shown) through line to the bottom end of a vaporiser containing a number of steel bails. Ester w as metered as a liquid to vaporiser through a line. The resulting vaporous mixture of ester and hydrogen w as passed through preheating coil to reactor. This contained a layer of glass balls, on which rested the catalyst bed. The remainder of the reactor was filled with glass balls and the upper end of the reactor was fitted with as exit tube which led to a condenser (not downstream from the condenser usin a wet gas m er. A charge of 30 ml of a granulated copper chromlte catalyst: was placet in the reactor hich as then purged with nitrogen at 42 bar. The oil bath was raised to a temperature of 231. degree. C. A 2percent M.sul>,2 I N- ufcJ aseous mi ture at 42 bar was then passed over the catalyst for 8 hours* followed by 10percent H.suh.2 in .sah.2 (stiU at 42 bar) for a further 16 h urs, and then by pn e H,sfe,2 (also at 42 har) for an additional 12 hours. Diethyl succinate was then introduced into the vaporizer corresponding to a liquid ho rly space velocity of 0.2/hr. The hydrogen gastester molar ratio in the vaporous mixture was 313;. The temperature of the sand bat was maintained at 23i°C The condensate was analyzed by gas chromatography using a 1.82 meter long stainless steel column with an interna diameter of 3.18 mm containing 10percent dielhylene glycol succinate on Chromusorfe F 'W, a helium gas f ow rate of 3 ml/minute and a liaise iouisation detector. The n trumen was fitted with a chart recorder having a peak integrator and was calibrated asing a mixture of diethyl inaleafe, dialkyl succinate, bntyrelactsne, butane- 1, 4-dioi, teirahydrofuran and water of known composition. The exit gas was also sampled and analyzed by gas chromatography using the same tech usque. The identity of the peaks was confirmed by comparison of the retention times observed with those of authentic specimens of the materials in question and fey .mass spectroscopy. The following compounds were detected in the reaction mixture: diethyl succinate, hutyroiactone, butane- i,4~dkd, teirahydrofuran and water. Trace amounts of minor byproducts, including 2-eihoxytetrahydrofyran and 2~ethoxybutane-l ,4-dio were also detected n the reaction mixture, From the results obtained it appeared that diethyl succinate had been smoothly converted to products with a selectivity to teirahydrofuran of 52.2mol percent, a selectivity to o-butanol of l l.6 moi , a selectivity to gamma-butyrolactene of 2o.i snol percent, and a selectivity to feta.ne-l,4~d5ol of 10.1 snol percent, the balance being minor byproducts.