高級脂肪酸エステルと金属ナトリウムとの反応 (第1報)

高級脂肪酸メチルエステルのBouveault et Blanc還元

抄録

Bouveault et Blanc reduction of higher fatty acid methyl esters was studied for the purpose of making analysis in reaction system. The yields of reductive condensation products such as acyloins, β-ketoesters in addition to fatty alcohols were determined when C₆C₁₈ saturated fatty acid methyl esters were reduced by using ethanol and MIBC as the reducing alcohols. With increase of the length of acyl radicals, the yield of fatty alcohols increased. Inversely, yield of fatty acids and reductive condensation products decreased. The formation of β-ketoesters was trace when used MIBC, but the effect of the chain length was similar to the case of reductive condensation products when used ethanol.
Based on experimental results and reactivity investigation about following 4 items,
(1) esterketals as sodium ester intermediates, (2) alcoholates, (3) reducing alcohols, (4) generation of hydrogene, the mechanism of reaction system was analysed. It came to conclusion that several reactions in this system are extremely affected by the reducing alcohol.