油化学
Online ISSN : 1884-2003
ISSN-L : 0513-398X
高級脂肪酸エステルと金属ナトリウムとの反応 (第9報)
α-エレオステアリン酸メチルのBouveault et Blanc還元
福島 正敏
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ジャーナル フリー

1961 年 10 巻 11 号 p. 701-707

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The fatty alcohol was prepared from methyl α-eleostearate by Bouveault et Blanc reduction which is quite different from the case of nonconjugated fatty acid esters. The yield of the fatty alcohol was only 83% of theory. The fatty alcohol was separated by liquid chromatography into dienoic (D-part) and trienoic (T-part) alcohols. The infrared absorbtion curves of these two parts showed cis, trans cojugated diene and isolated trans ethylene, not corresponding to that of original methyl α-eleostearate. The ultraviolet absorbtion curves of these two samples, entirely independent from that of the original ester, showed that D-part is mainly composed of conjugated diene and T-part contains less conjugation than D-part. The paper chromatography of oxidation products by potassium permanganate in acetone was studied for the purpose of determining the double bond position of fatty alcohols.
It came to conclusion that D-part is a mixture of 10, 12-octadecadiene-1-ol and 11-octadecene-1-ol, and trienoic component of T-part is a mixture of some positional isomers, namely 9, 12, 15-, 9, 12, 14-, 9, 11, 13-octadecatriene-1-ol which were consequently formed by the shift of double bonds.
The mechanism of double bonds shift and isomer formation was discussed.

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