高級脂肪酸およびその誘導体のエポキシ化合物に関する研究 (第3報) : 過酢酸による不飽和脂肪酸のエポキシ化の速度

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The specific reaction rates of epoxidations of various unsaturated fatty acids with per-acetic acid in acetic acid solution were calculated by measuring the concentration decrease of per-acetic acid in reaction solution. The specific reaction rate of epoxidation of cis-acid was higher than that of trans-acid. It was not affected by carboxyl group at the θ-position to ethylenic double bond, but it was affected a little by that of β-position to ethylenic double bond. The specific reaction rate of epoxidation of dienoic acid to monoepoxy acid may be similiar to that of monoenoic acid, but that of monoepoxy acid to diepoxy acid was very slow. It was not affected by sulfuric acid in reaction solution, but it was increased by the presence of water in the solution. The specific reaction rates, K×103 (l·mol·-1 min-1) at 30°C were as follows; oleic acid 180, elaidic acid 149, ricinoleic acid 133, monoepoxy octadecenoic acid 91.1, linoleic acid 230 and erucic acid 207. The activation energy of oleic acid and elaidic acid were 7970 cal and 8660 cal respectively. They were calculated with Arrhenius equation from value of the specific reaction rates at 22.5, 25, 27.5 and 30°C.