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Isolation of pure linolenate as its mercuric acetate adduct
Author(s) -
White H. B.,
Quackenbush F. W.
Publication year - 1962
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02672541
Subject(s) - linolenate , linseed oil , chemistry , organic chemistry , extraction (chemistry) , fractionation , solubility , methanol , chloroform , yield (engineering) , petroleum ether , aqueous solution , adduct , iodine value , chromatography , ethyl acetate , fatty acid , materials science , metallurgy
After addition of mercuric acetate to the unsaturated methyl esters obtained from the methanolysis of linseed oil, linolenate of 99% minimum purity was isolated by means of a liquid‐liquid continuous extraction technique and subsequent decomposition of the mercurial adduet. The methyl linolenate‐mercuric acetate addition compound was extracted with 10% methanol in water from an ether solution of the reaction mixture. Infrared analysis of the regenerated methyl linolenate showed the complete absence of trans ‐linkages. The yield, at least 60% of the linolenic acid present in linseed oil, was considerably higher than that obtained by bromination‐debromination procedures. The solubility in aqueous solutions of fatty acid derivatives having 3 or more acetoxymer‐euri‐groups/molecule provides an approach to the fractionation of highly unsaturated oils. For example, a fraction having an iodine value of 395 was isolated readily from the methyl esters of pilchard oil by this technique.