Oxidation of Cyclohexanediol Derivatives with 12-Tungstophosphoric Acid-Hydrogen Peroxide System
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概要
- 論文の詳細を見る
Oxidation of cyclohexanediol derivatives with 12-tungstophospholic acid-hydrogen peroxide system was investigated focusing on a reaction mechanism in the preparation of dicarboxylic acids from olefin because oxidative cleavage of vicinal diols would be a rate-determining step in oxidative cleavage of carbon-carbon double bonds. trans-1,2-Cyclohexanediol (DHC) was converted to adipic acid almost quantatively, while 1-hydroxy-2-methoxycyclohexane (HMC) gave a mixture of adipic acid, glutaric acid and monomethyl adipate. In the case of 1,4-cyclohexanediol, 4-hydroxy-cyclohexanone and many hyperoxidated products were obtained. Based on results for HMC, it is concluded that following route would be also reasonable in oxidative cleavage of vicinal diol with 12-tungstophospholic acid-hydrogen peroxide system: (1) first oxidation of vicinal diol to α-hydroxyketone, (2) nucleophilic attack of hydrogen peroxide attacks to carbonyl carbon, (3) Baiyer-Villiger rearrangement of dihydroxy-hydroperoxide to a cyclic ester, (4) hydrolysis and final oxidation to dicarboxylic acid.
- 日本油化学会の論文
著者
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Kawase Tokuzo
Department of Chemistry and Materials Technology, Kyoto Institute of Technology
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Oida Tatsuo
Department of Chemistry and Materials Technology, Kyoto Institute of Technology
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Kawase Tokuzo
Department Of Chemistry And Materials Technology Kyoto Institute Of Technology
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Oida Tatsuo
Dep. Of Chemistry And Materials Technol. Kyoto Inst. Of Technol.
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Fujitani Kango
Environment Safety/Quality Assurance Department, New Japan Chemical Co., Ltd.
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Mizutani Toshihiro
Planning & Development Department, New Japan Chemical Co., Ltd.
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Oida Tatsuo
Department Of Chemistry And Materials Technology Kyoto Institute Of Technology
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Mizutani Toshihiro
Planning & Development Department, New Japan Chemical Co., Ltd.
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