3-Oxopentanedioic acid (1,3-Acetonedicarboxylic acid)

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Reactions (29)

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Substances (2)

Citations (56)

Conditions

References

1

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With potassium bromate; hydrogenchloride; water

kobs vs. substrate concentration at 35 deg C and vs. HCl concentration at 40 deg C; ΔH(excit), ΔS(excit) (temp.-range 30-45 deg C); Rate constantThermodynamic data;

Gupta, Kalyan Kali Sen; Banerjee, Amalendu; Chatterjee, Hrishikesh

Tetrahedron, 1992 , vol. 48, # 25 p. 5323 - 5330 Title/Abstract

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With potassium bromate; cerium (IV) sulfate in water

T=26°C; oscillatory reaction, effect of the storing time;

Mishra, H. C.; Ojha, A. N.; Bhathena, K.

Journal of the Indian Chemical Society, 1987 , vol. 64, p. 510 - 511 Title/Abstract

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With sulfuric acid

Reaktion ueber mehrere Stufen;

v. Pechmann Justus Liebigs Annalen der Chemie, 1891 , vol. 261, p. 158,164 Full Text View citing articles Show Details Jerdan Journal of the Chemical Society, 1899 , vol. 75, p. 809 Anm. Full Text View citing articles Show Details

With sulfuric acid

Cappuyns

Bulletin des Societes Chimiques Belges, 1945 , vol. 54, p. 80 Full Text View citing articles Show Details

Deffner; Franke

Justus Liebigs Annalen der Chemie, 1939 , vol. 541, p. 94 Full Text View citing articles Show Details

Mueller

Biochemische Zeitschrift, 1935 , vol. 275, p. 347 Full Text View citing articles Show Details

Langecker

Biochemische Zeitschrift, 1934 , vol. 273, p. 47 Full Text View citing articles Show Details

With sulfuric acid

Willstaetter; Pfannenstiel

Justus Liebigs Annalen der Chemie, 1921 , vol. 422, p. 11 Full Text View citing articles Show Details

Ingold; Nickolls

Journal of the Chemical Society, 1922 , vol. 121, p. 1644 Full Text View citing articles Show Details

With manganese(III) oxide

Boeeseken; Verkade

Chemisches Zentralblatt, 1917 , p. I, 851 Full Text View citing articles Show Details

With potassium permanganate

Deniges

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1900 , vol. 130, p. 32 Full Text View citing articles Show Details

With sulfuric acid

Koessler; Hanke

Journal of the American Chemical Society, 1918 , vol. 40, p. 1722 Full Text View citing articles Show Details

Willstaetter; Pfannenstiel

Justus Liebigs Annalen der Chemie, 1921 , vol. 422, p. 11 Full Text View citing articles Show Details

Ingold; Nickolls

Journal of the Chemical Society, 1922 , vol. 121, p. 1644 Full Text View citing articles Show Details

Organic Syntheses 5 <New York 1925>, S. 5 Full Text Show Details

Schroeter

Chemische Berichte, 1916 , vol. 49, p. 2704 Chemische Berichte, 1920 , vol. 53, p. 1917 Full Text Show Details

With sulfuric acid

T=70 - 75°C; 0.5 h;

Ranade, V. R.; Deodhar, K. D.; Kulkarni, R. A.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981 , vol. 20, # 6 p. 500 - 502 Title/Abstract

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With sulfuric acid

Patel

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004 , vol. 43, # 8 p. 1774 - 1778 Title/Abstract

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With sulfuric acid

T=60 - 65°C;

Mashelkar; Audi

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006 , vol. 45, # 4 p. 967 - 971 Title/Abstract

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Multi-step reaction with 2 steps 1: concentrated sulfuric acid 2: sulfuric acid monohydrate View Scheme

Schroeter

Chemische Berichte, 1905 , vol. 38, p. 3199 Full Text View citing articles Show Details

With sulfuric acid

T=10°C;

Manvar, Atul; Malde, Alpeshkumar; Verma, Jitender; Virsodia, Vijay; Mishra, Arun; Upadhyay, Kuldip; Acharya, Hrishikesh; Coutinho, Evans; Shah, Anamik

European Journal of Medicinal Chemistry, 2008 , vol. 43, # 11 p. 2395 - 2403 Title/Abstract

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With sulfuric acid

T=70°C; 0.5 h;

Sanap, Kailas K.; Samant, Shriniwas D.

Synlett, 2012 , vol. 23, # 15 p. 2189 - 2194 Title/Abstract

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With iron(III); PMS

pH=3; 6 h; Heating; Kinetics; Reagent/catalystpH-value; Hide Experimental Procedure

Ragukumar; Andal; Murugavelu; Lavanya; Ramachandran

Journal of Molecular Catalysis A: Chemical, 2014 , vol. 390, p. 22 - 28 Title/Abstract

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Materials and methods

The stoichiometry of the reaction was determined at pH 4.8.A large excess of PMS (0.05 M) over citric acid (0.01 M) and the metal ion (0.002–0.0002 M) were allowed to stand for 6–8 h and the unreacted PMS was estimated. The unreacted oxidant concentration was very small in Ni(II) and Co(II) ions and this may be due tothe self decomposition of PMS catalyzed by the metal ions. Therefore the stoichiometry was determined with equal concentration(0.01 M) of PMS and citric acid. The evolution of carbon dioxidefrom this mixture was confirmed with freshly prepared lime water.The oxidation product from citric acid gave 2,4-dinitro phenylhydrazone derivative which decomposed on heating. The formation of acetone dicarboxylic acid (3-ketoglutaric acid) was confirmedby the color test with sodium nitroprusside [44]. Acetone dicarboxylicacid was converted into acetone by the addition of aniline[45] and acetone was estimated as 2,4-dinitro phenylhydrazone (m.pt 126–127 C, lit. 128 C [46]). The quantitative estimation indicated that∼95–97percent of the keto compound is produced per mole of PMS. Therefore, the oxidation of citric acid can be represented as inEq. (1).

With chlorosulfonic acid in chloroform

T=10 - 30°C;

Jiang; Wang

Asian Journal of Chemistry, 2014 , vol. 26, # 22 p. 7867 - 7868 Title/Abstract

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With sulfuric acid

0.5 h;

Velikorodov; Ionova; Melent'eva; Stepkina; Starikova

Russian Journal of Organic Chemistry, 2014 , vol. 50, # 8 p. 1112 - 1116 Zh. Org. Khim., 2014 , vol. 50, # 8 p. 1112 - 1116,5 Title/Abstract

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With sulfuric acid

Khatri, Adil I.; Samant, Shriniwas D.

RSC Advances, 2015 , vol. 5, # 3 p. 2009 - 2012 Title/Abstract

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With sulfuric acid

T=70°C; 0.5 h;

Sanap, Kailas K.; Samant, Shriniwas D.

RSC Advances, 2015 , vol. 5, # 46 p. 36696 - 36706 Title/Abstract

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With sulfuric acid

T=20 - 70°C; Hide Experimental Procedure

Sanap, Anita K.; Sanap, Kailas K.; Shankarling, Ganapati S.

Dyes and Pigments, 2015 , vol. 120, p. 190 - 199 Title/Abstract

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2.2.1 Synthesis of 6,7,8-substituted coumarin-4-acetic acid (4)

All coumarin-4-acetic acids (4) were synthesized using reported methods [23]. A mixture of anhydrous citric acid (1) (192 g, 1 mol) and conc. H2SO4 (280 mL) was stirred at room temperature for 1 h and then slowly heated (rate of heating governed by foaming) to 70 °C. After 30–35 min at this temperature, with stirring throughout, the evolution of carbon monoxide slackened. The clear solution was rapidly cooled to 0 °C. To the cooled solution, m-cresol (3a) (86.4 g, 0.8 mol) and conc. H2SO4 (112 mL) were added with stirring, each in three equal portions, at such a rate that the internal temperature did not exceed 10 °C. The resulting mixture was stirred at room temperature for 16 h, poured into ice and the resulting precipitate was filtered and washed thoroughly with water. The precipitate was stirred with saturated NaHCO3 solution (1000 mL) for 15 min at 65 °C. The solution was filtered and the insoluble material was washed with water. Acidification with conc. HCl of the combined filtrate gave 110 g, 63percent of solid 4a which was used further without purification.

Khan, Zaheer; Al-Thabaiti, Shaeel Ahmad; Malik, Maqsood Ahmad

RSC Advances, 2016 , vol. 6, # 51 p. 45993 - 46001 Title/Abstract

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With potassium permanganate

T=20°C; pH=3.2; Kinetics; Reagent/catalyst;

2

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With aluminum oxide; phenyl hypochlorite; sodium chloride in 5,5-dimethyl-1,3-cyclohexadiene

T=6 - 55°C; 4.5 h; Temperature; Hide Experimental Procedure

Rx-ID: 43696409 Find similar reactions

Chengdu Chiba Longhua Petroleum Engineering Consulting Co., Ltd; Guan, Genan

Patent: CN105503603 A, 2016 ; Location in patent: Paragraph 0014; 0015 ;

Title/Abstract

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3:Example 3

A reaction vessel equipped with a stirrer, a thermometer and a dropping funnel was charged with 2.8 mol of a 55percent phenyl hypochlorite solution (3), 600 mlSodium chloride solution,3-amino-3-amide-glutaric acid (2) was slowly added in portions, at a stirring rate of 160 rpm,3.6mol, alumina 1.6mol, mass fraction of 35percent xylene 300ml, adding the process time control in 120min, slowly raise the solution temperature to55 , reaction 150min, reduce the solution temperature to 5 , put it aside for 5h, in the stirring state by adding 1200ml mass fraction of 20percent potassium bromide dissolvedLiquid, precipitation of white solid, filtration, ammonium sulfate solution washing, the mass fraction of 75percent cyclohexanone washing, anhydrous calcium sulfate dehydration, the mass fractionWas recrystallized from 95percent N-methylformamide to obtain 372.01 g of acetone dicarboxylic acid in a yield of 91percent.

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3

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With ruthenium trichloride; perchloric acid; bromate salt; sulfuric acid; mercury(II) diacetate in water

T=19.9 - 39.9°C; Rate constant;

Reddy, Ch. Sanjeeva; Kumar, T. Vijaya

Indian Journal of Chemistry, Section A: Inorganic, Bio-inorganic, Physical, Theoretical & Analytical Chemistry, 1995 , vol. 34, # 11 p. 871 - 877 Title/Abstract

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With KBrO3; perchloric acid; mercury(II) diacetate in acetic acid

T=29.84°C; Kinetics; Further Variations:Reagents;

Reddy, Cherkupally Sanjeeva

Journal of the Indian Chemical Society, 2007 , vol. 84, # 2 p. 165 - 170 Title/Abstract

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4

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83%

With sodium hydrogencarbonate in water

T=20°C; 24 h; Hide Experimental Procedure

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ISAGRO S.P.A.

Patent: WO2004/103074 A1, 2004 ; Location in patent: Page 34-35 ; Title/Abstract

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3:Example 3; Preparation of the copper salt of 3-ketoglutaric acid (Compound Nr. 132).

Example 3; Preparation of the copper salt of 3-ketoglutaric acid (Compound Nr. 132). 11.5 g of sodium bicarbonate are added in portions, on an ice bath, to a suspension of 10 g of 3-ketoglutaric acid in 45 CM3 of HO. 9. 1 g of copper (II) chloride are then added, again on an ice bath. The reaction mixture is left under stirring for 24 hours at room temperature. The solid precipitated is filtered and washed with water, ob- taining, after drying in the air, 12.0 g of compound Nr. 129 (yield 83percent). Elemental analysis [percent found (theoretical)] = C 28.2 (28.9) ; H 2.0 (1.9) ; Cu 30.7 (30.6).

5

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With N-bromosuccinmide; perchloric acid; mercury(II) diacetate; palladium dichloride

T=35°C; ΔE(a), ΔH(excit.), ΔS(excit.), ΔG(excit.); Rate constantKineticsThermodynamic data;

Saxena, Rashmi; Upadhyay, S. K.

Indian Journal of Chemistry, Section A: Inorganic, Bio-inorganic, Physical, Theoretical and Analytical Chemistry, 1993 , vol. 32, # 12 p. 1060 - 1063 Title/Abstract

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6

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With sulfuric acid

1 h 20 deg C, then 3 h 50 deg C;

Zefirov, N. S.; Sadovaya, N. K.; Kombarova, S. V.

Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, p. 101 - 104 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 1 p. 116 - 119 Title/Abstract

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7

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With KBrO3; sulfuric acid; Ce(NO3)3

T=25 - 35°C; activation energy, dual frequency oscillating reaction; Thermodynamic data;

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Tsukada, Masao

Chemistry Letters, 1987 , p. 1537 - 1540 Title/Abstract

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8

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Ito et al.

Yakugaku Zasshi, 1966 , vol. 86, p. 300,304 Chem.Abstr., 1966 , vol. 65, # 3852 Full Text Show Details

Chas. Pfizer and Co.

Patent: DE1092900 , 1958 ; Chem.Abstr., 1962 , vol. 56, # 9974f Full Text Show Details

Bottaccio et al.

Gazzetta Chimica Italiana, 1977 , vol. 107, p. 499 Full Text Show Details

Toyo Jozo Company, Ltd.

Patent: US4609640 A1, 1986 ;

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Title/Abstract

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Aliphatic keto-polycarboxylic acid compounds: oxaloacetic acid, α-ketoglutaric acid, β-ketoglutaric acid, α-ketomalonic acid; glucuronic acid, galacturonic acid, mannuronic acid; A

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9

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With cerium (IV) sulfate; phosphoric acid in water

T=25°C; CH3COOH, other neutral salts and temperatures, ΔE(activ.); KineticsMechanismThermodynamic data;

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Tripathy, S. N.; Prasad, R. K.

Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1980 , vol. 19, # 3 p. 214 - 217 Title/Abstract

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10

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Montedison S.p.A.

Patent: US3976677 A1, 1976 ;

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6:EXAMPLE 6

EXAMPLE 6 By operating under the conditions of Example 2, starting from 18 g of potassium 2,6-di-t-butyl-p-cresolate in 80 cc of toluene, and from 1 g of acetone (molar ratio = 4:1), 0.26 g of acetoacetic acid and 1.1 g of beta-keto-glutaric acid were obtained as sodium salts.

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11

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MacMahon; Srivastava

Journal of the Indian Chemical Society, 1946 , vol. 23, p. 262 Current Science, 1946 , vol. 15, p. 249 Chem.Abstr., 1947 , p. 1921 Full Text View citing articles Show Details

Reaktion des Trinatriumcitrats beim Belichten;

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MacMahon; Srivastava

Journal of the Indian Chemical Society, 1946 , vol. 23, p. 262 Current Science, 1946 , vol. 15, p. 249 Chem.Abstr., 1947 , p. 1921 Full Text View citing articles Show Details

Reaktion des Trinatriumcitrats beim Belichten;

13

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With sulfuric acid

T=-5°C;

Archer; Pratt

Journal of the American Chemical Society, 1944 , vol. 66, p. 1658 Full Text View citing articles Show Details

Adams; Chiles; Rassweiler

Organic Syntheses, Coll. Vol. I <2. Ausg. 1941> 10 Full Text View citing articles Show Details

14

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Quartaroli; Belfiori

Ann.Chim.applic., 1938 , vol. 28, p. 297 Chem. Zentralbl., 1939 , vol. 110, # I p. 1163 Full Text Show Details

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Kuyper

Journal of the American Chemical Society, 1933 , vol. 55, p. 1723 Full Text View citing articles Show Details

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With bacterium pyocyaneus

Butterworth; Walker

Biochemical Journal, 1929 , vol. 23, p. 929,934 Full Text View citing articles Show Details

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Dey; Row

Journal of the Indian Chemical Society, 1923 , vol. 1, p. 117 Chem. Zentralbl., 1925 , vol. 96, # I p. 521 Full Text View citing articles Show Details

Limaye

Journal of the Indian Chemical Society, 1927 , vol. 4, p. 159 Chem. Zentralbl., 1927 , vol. 98, # II p. 1701 Full Text View citing articles Show Details

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Walker; Subramaniam; Challenger

Journal of the Chemical Society, 1927 , p. 3047 Nature (London, United Kingdom), vol. 119, p. 674 Chem. Zentralbl., 1927 , vol. 98, # II p. 841 Full Text View citing articles Show Details

bei der Einw.von Aspergillus niger;

19

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With Aspergillus niger

Walker; Subramaniam; Challenger

Journal of the Chemical Society, 1927 , p. 3047 Nature (London, United Kingdom), vol. 119, p. 674 Chem. Zentralbl., 1927 , vol. 98, # II p. 841 Full Text View citing articles Show Details

20

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Boeeseken; Verkade

Chem. Zentralbl., 1917 , vol. 88, # I p. 851 Full Text Show Details

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21

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Hale

Journal of the American Chemical Society, 1911 , vol. 33, p. 1132 Full Text View citing articles Show Details

22

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With sulfuric acid

Schroeter

Chemische Berichte, 1905 , vol. 38, p. 3199 Full Text View citing articles Show Details

23

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Schroeter

Chemische Berichte, 1905 , vol. 38, p. 3199 Full Text View citing articles Show Details

24

Synthesize Find similar Multi-step reaction with 3 steps 1: concentrated sulfuric acid 2: concentrated sulfuric acid; sodium nitrite 3: sulfuric acid monohydrate View Scheme

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Schroeter

Chemische Berichte, 1905 , vol. 38, p. 3199 Full Text View citing articles Show Details

25

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Multi-step reaction with 2 steps 1: concentrated sulfuric acid; sodium nitrite 2: sulfuric acid monohydrate View Scheme

Schroeter

Chemische Berichte, 1905 , vol. 38, p. 3199 Full Text View citing articles Show Details

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26

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Deniges

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1900 , vol. 130, p. 32 Full Text View citing articles Show Details

27

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v. Lippmann

Chemische Berichte, 1893 , vol. 26, p. 3058 Chemische Berichte, 1908 , vol. 41, p. 3981 Full Text View citing articles Show Details

28

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With sulfuric acid

Rx-ID: 6726819 Find similar reactions

Hoechster Farbw.

Patent: DE32245 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 216 Full Text Show Details

v. Pechmann Chemische Berichte, 1884 , vol. 17, p. 2543 Full Text View citing articles Show Details

29

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wasserfreie Citronensaeure reagiert;

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v.Pechmann Chemische Berichte, 1884 , vol. 17, p. 2542 Justus Liebigs Annalen der Chemie, 1891 , vol. 261, p. 155 Full Text View citing articles Show Details