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Displacement of the double bonds during hydrogenation of unsaturated fatty acid methyl esters
Author(s) -
Boelhouwer C.,
Gerckens J.,
Lie Ong Tian,
Waterman H. I.
Publication year - 1953
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/bf02634998
Subject(s) - double bond , elaidic acid , chemistry , oleic acid , acetic acid , catalysis , methyl oleate , organic chemistry , fatty acid , linoleic acid , cis–trans isomerism , catalytic hydrogenation , biochemistry
Summary The displacement of the double bond of several unsaturated fatty acid methyl esters during hydrogenation with a nickel‐kieselguhr catalyst at 180°C. was investigated. The analysis of the dicarboxylic acids (obtained by oxidation of the reaction products with KMnO 4 in acetic acid solution) by means of partition chromatography enabled a reliable semiquantitative determination of the position isomers formed. During hydrogenation of methyl esters of oleic, elaidic, petroselinic, and linoleic acid formation of large amounts of position isomers was proved to occur. Migration of the double bonds in both directions took place but was in all cases strongly pronounced in a direction opposite the ester group. The place and configuration (cis or trans) of the double bonds in the starting material apparently were of little importance in this respect. It follows that hydrogenation of fatty acid esters leads to products which are far more complicated, as is generally known. This is especially of importance with respect to the application of hydrogenated fatty oils in the food industries.