ヨウ素増感反応を利用したモノエン化合物の簡易精製法

概要

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Polyunsaturated fatty acids and their derivatives having the 1, 4-diene structure are conjugated easily at ordinary temperature in the presence of iodine by photoirradiation.<BR>The side reaction was investigated in detail in the present study. Addition of excess iodine to a mixture of monoenes and polyenes caused formation of petroleum ether-insoluble polymers from polyene compounds while monoene compounds remained unchanged under these conditions. Thus, polyene compounds can be selectively removed from a mixture of monoenes and polyenes by the iodine-sensitized method.<BR>An example of the purification of monoene compounds is presented below. Methyl esters of tsubaki fatty acids (C16 9.8%; C16 : 1 trace; C18 2.8%; C18 : 1 82.9%; C18 : 2 4.1%; C18 : 3 0.4%) were treated by the urea adducts method. The iodine-sensitized method was carried out on the mother liquor followed by rectification and methyl oleate with a purity of 99.6% was obtained in yields of 66%.<BR>Since this method can be also carried out in the sunlight, it is suited for conducting large scale reactions.