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Competitive hydrogenation rates of isomeric methyl octadecadienoates
Author(s) -
Snyder J. M.,
Scholfield C. R.,
Mounts T. L.,
Butterfield R. O.,
Dutton H. J.
Publication year - 1975
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/bf02639151
Subject(s) - chemistry , catalysis , cis–trans isomerism , catalytic hydrogenation , double bond , diene , methylene , medicinal chemistry , stereochemistry , organic chemistry , natural rubber
Determination of the relative reaction rates of isomeric methyl octadecadienoates is possible by competitive reduction of a mixture containing an inactive diene and a radioactively labeled isomer. The hydrogenation rate of methyl cis ‐9, cis ‐12‐octadecadienoate with platinum and nickel catalysts is compared to the hydrogenation rate of each of several isomers of methyl octadecadienoate, and the relative rate of the competitive hydrogenations is calculated by a digital computer. Methyl cis ‐9, cis ‐12 linoleate is reduced the most rapidly of all the dienes studied. The relative rates of the positional isomers tend to decrease with the increasing number of methylene groups between the double bonds, except when one of the double bonds is in the more reactive 15 position. Comparison of the geometric isomers shows that trans,trans diene is hydrogenated at a slower rate than cis,cis linoleate.