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Preparation of 9,15‐octadecadienoate isomers
Author(s) -
Butterfield R. O.,
Scholfield C. R.,
Dutton H. J.
Publication year - 1964
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/bf02654866
Subject(s) - cis–trans isomerism , chemistry , silver nitrate , hexane , structural isomer , isomerization , acetonitrile , chromatography , organic chemistry , catalysis
Linolenic acid was reduced with hydrazine to produce a mixture containing a max of dienoic acids. After methylation this mixture was separated into trienoic, dienoic, monoenoic, and saturated esters by countercurrent distribution (CCD) with acetonitrile and hexane. The dienoic ester was further fractionated by CCD with methanolic silver nitrate and hexane to separate pure cis,cis ‐9,15‐octadecadienoate and the equimixture of cis,cis ‐9,12‐ and 12,15‐octadecadienoates. Following isomerization of the cis,cis ‐9,15‐octadecadienoate with selenium, the geometric isomers were fractionated by CCD with methanolic silver nitrate and hexane. Pure trans,trans and pure cis,cis isomers were isolated, as well as an unresolved mixture of cis,trans and trans,cis isomers. The characteristics of these isomers and related compounds are compared as determined by CCD, IR absorption, and capillary gas‐liquid chromatography (GLC).