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Alkali isomerization of linoleate isomers: Characterization of products
Author(s) -
Koritala Sambasivarao
Publication year - 1972
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/bf02628899
Subject(s) - cis–trans isomerism , double bond , isomerization , conjugated system , chemistry , ozonolysis , structural isomer , stereochemistry , diene , conjugated diene , organic chemistry , catalysis , polymer , monomer , natural rubber
Geometrical isomers of methyl linoleate were reacted with alakli, and the resulting conjugated isomers were separated into trans,trans;cis,trans ; and cis,cis fractions. The position of double bonds in the various fractions was determined by reductive ozonolysis. trans ‐9, trans ‐12‐Isomer of linoleate formed trans,trans ‐ and cis,trans ‐conjugated dienes, whereas cis ‐9, trans ‐12‐ and trans ‐9, cis ‐12‐isomers in addition formed cis,cis ‐conjugated dienes. The formation of the products is in accordance with the theoretical predictions. During conjugation trans double bonds shifted to form a trans bond preferentially. During conjugation of cis ‐9, trans ‐12‐ and trans ‐9, cis ‐12‐linoleate isomers, the cis double bond shifted preferentially over the trans double bond. A small amount of diene not conjugated was probably a geometrical and positional isomer of the starting material.