Preparation of 9,15-octadecadienoate isomers1

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 purecis,cis-9,15-octadecadienoate and the equimixture ofcis,cis-9,12- and 12,15-octadecadienoates. Following isomerization of thecis,cis-9,15-octadecadienoate with selenium, the geometric isomers were fractionated by CCD with methanolic silver nitrate and hexane. Puretrans,trans and purecis,cis isomers were isolated, as well as an unresolved mixture ofcis,trans andtrans,cis isomers. The characteristics of these isomers and related compounds are compared as determined by CCD, IR absorption, and capillary gas-liquid chromatography (GLC). Presented at the AOCS meeting in Minneapolis, 1963. A laboratory of the No. Utiliz. Res. and Dev. Div., ARS, USDA.