Journal
JOURNAL OF OLEO SCIENCE
Volume 58, Issue 1, Pages 37-42Publisher
JAPAN OIL CHEMISTS SOC
DOI: 10.5650/jos.58.37
Keywords
polycarboxylic acid; cyclic olefin; oxidative cleavage; hydrogen peroxide; heteropolyacid; 12-tungstophospholic acid
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Oxidative cleavage of carbon-carbon double bonds of cyclic olefins with hydrogen peroxide in the presence of heteropolyacids has been investigated as a clean and environmentally friendly preparation or polycarboxylic acids. In the presence of 12-tungstophospholic acid (H3PW12O40), adipic acid was obtained in 95% yield from cyclohexene in lipophilic phase and hydrogen peroxide in aqueous phase. In addition, 1,2,3,4-butanetetracarboxylic acid was also obtained in 87% yield from 1,2,3,6-tetrahydrophtharic acid anhydride, while endic acid anhydride did not afford corresponding 2,3,6-cyclopentanetetracarboxylic acid but only lactone compound was obtained. In this oxidation process, oxidative cleavage of carbon-carbon double bonds would proceed as the sequential reactions in which the rate determining step is oxidative cleavage of vicinal-diol compounds.
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