高級脂肪酸エステルと金属ナトリウムの反応 (第6報) : 金属ナトリウムによる高級脂肪酸メチルエステルの還元縮合

概要

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The reductive condensation reaction of C6C18 saturated fatty acid methyl esters by means of metallic sodium was studied for the purpose of analysis in reaction systems. The yields of reduction and Claisen condensation products, such as acyloins, α-diketones, α-glycols, fatty alcohols, and β-ketoesters could be determined. From the fairly high yields of acyloins, principal reaction of this system is to form acyloins when used esters of more than six carbon atoms. The yields of reductive condensation products were obtained in maximum at some chain length. The formation of fatty alcohols as well as the generation of hydrogen was found to increase with chain length, while those of fatty acids and β-ketoesters decreased. From these results about the action of metallic sodium in tolueme, the reactions stated above in the presence of the bases were classitied into two initial mechanisms, namely base addition to the carboyl group and proton removal from the α-carbon aton. The mechanism of the reaction system was discussed.
社団法人日本油化学会の論文