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Positional isomers formed during the hydrogenation of cottonseed oil
Author(s) -
Chahine M. H.,
Cousins E. R.,
Feuge R. O.
Publication year - 1958
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/bf02632554
Subject(s) - double bond , iodine , chemistry , iodine value , cottonseed oil , cottonseed , medicinal chemistry , organic chemistry , food science
Summary A commercial cottonseed oil was hydrogenated under nonselective, normal, and selective conditions. The operating variables used were within the ranges of those ordinarily found in large‐scale operations. For each run samples were withdrawn at iodine values of approximately 75, 62, and 48; and these samples were analyzed for the position of the donble bonds, content of trans isomers, and content of linoleins. Double bonds were found in the 6 through 14 positions of the monounsaturated fatty acid groups resulting from the hydrogenations. On the basis of the percentage distribution of the double bonds, there appeared to be no marked tendency for the linoleoyl group to form 9‐ or 12‐isomers of the oleoyl group. In the early stages of the selective hydrogenation the rate at which double bonds shifted from the 9‐position was greater than the rate at which double bonds were hydrogenated. The conditions of hydrogenation did not have a marked effect on the distribution of the double bonds at iodine values of about 62 and 48. The conditions of hydrogenation did have a marked effect on the percentage of trans bonds. At an iodine value of approximately 75 the content of trans bonds, expressed as weight percentage of trielaidin, was 9.4 for the nonselective hydrogenation and 27.3 for the selective hydrogenation while at an iodine value of approximately 48 these values increased to 21.6 and 37.7, respectively.