Oxidation of cyclohexanediol derivatives with 12-tungstophosphoric acid-hydrogen peroxide system

Journal of Oleo Science

Volumn 58, Issue 6, 2009, Pages 323-328

  Fujitani, Kango ^a   Mizutani, Toshihiro ^a   Oida, Tatsuo ^b   Kawase, Tokuzo ^b  

^a New Japan Chemical Co Ltd   (Japan)

^b KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

12 tungstophosphoric acid; Cyclohexanediol; Dicarboxylic acid; Hydrogen peroxide; Oxidative cleavage; Vicinal diol

Indexed keywords

EID: 66949129747     PISSN: 13458957     EISSN: 13473352     Source Type: Journal    
DOI: 10.5650/jos.58.323     Document Type: Article

References (11)

1. Fujitani, K.; Mizutani, T.; Oida, T.; Kawase, T. Oxidative cleavage with hydrogen peroxide: Preparation of polycarboxylic acids from cyclic olefins. J. Oleo Sci. 58(1), 37-42 (2009).
2. House, H.O. Modern Synthesis Reactions. 2nd edn. W.A. Benjamin, Inc. California. P.275 (1972).
3. Donald, S.N.; Donald, B.D. The direct chemical interrelation of the configuration of terpenes and hydroxyl acids. J. Am. Chem. Soc. 76, 768-771 (1954).
4. Olah, G.A; Fung, A.P.; Meidar, D. Synthetic methods and reactions; 68. Nafion-H-catalyzed hydration and methanolysis of epoxides. Synthesis 280-282 (1981).
5. Standard Methods for the Analysis of Fats, Oils and Related Materials (Japan Oil Chemists' Society ed.). 3.3.1 (1996).
6. Venturellro, C.; Ricci, M. Carboxylic acids from olefins or vicinal dihydroxy compounds. Eur. Pat. Appl. 122804 (1984).
7. Sakata, Y.; Ishii, Y.A Versatile transformation of vicdiols into α-hydroxy ketones with hydrogen peroxides catalyzed by peroxotungstophoshphate. J. Org. Chem. 56(21), 6233-6235 (1991).
8. Perkel A.L.; Fredin B.G. Possible role of 1,2-cyclohexanedione in cyclohexane oxidation. Zhurnal Prikladnoi Khimii. 52(8), 1829-1833 (1979).
9. Rieche, A. Peroxides of ether, carbonyl compounds, and the ozonides. Angew. Chem. 70, 251-266 (1958).
10. Kharasch, M.S.; Sosnovsky, G. Structure of peroxides from cyclohexanone and hydrogen peroxide, J. Org. Chem. 23, 1322-1326 (1958).
11. Katja, Z.; Marco, Z.; Stojan, S.; Jernej, I. Iodine as a catalyst for efficient conversion of ketones to gem-dihydroperoxides as aqueous hydrogen peroxide. Org. Lett. 8(12), 2491-2494 (2006).