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Selective hydrogenation of soybean oil: IV. Fatty acid isomers formed with copper catalysts
Author(s) -
Koritala S.,
Dutton H. J.
Publication year - 1969
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/bf02544808
Subject(s) - isomerization , double bond , chemistry , ozonolysis , pentane , cis–trans isomerism , catalysis , diene , organic chemistry , methylene , natural rubber
Two samples of soybean oil hydrogenated with copper‐containing catalysts at 170 and 200 C were analyzed for their natural and isomeric fatty acids. Methyl esters of the hydrogenated oils were separated into saturates, monoenes, dienes and trienes by countercurrent distribution between acetonitrile and pentane‐hexane. Monoenes were further separated into cis‐ and trans ‐isomers on a silver‐saturated resin column. Double bond location in these fractions was determined by a microozonolysis‐pyrolysis technique. The diene fraction was separated with an argentation countercurrent distribution method, and linoleate was identified by infrared, ozonolysis and alkaliisomerization data. The double bonds in the cis ‐monoenes were located in the 9‐position almost exclusively. However, the double bonds in the trans ‐monoene were quite scattered with 10‐ and 11‐isomers predominating. About 86% to 92% of the dienes consisted of linoleate as measured by alkali isomerization. Other isomers identified as minor components include cis,trans and trans, trans conjugated dienes and dienes whose double bonds are separated by more than one methylene group.