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Reactions of conjugated fatty acids. VI. Selenium catalysis, a method for preparing diels‐alder adducts from cis,trans‐octadecadienoic acid
Author(s) -
Teeter H. M.,
Bell E. W.,
O'Donnell J. L.,
Danzig M. J.,
Cowan J. C.
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/bf02639835
Subject(s) - chemistry , peracetic acid , catalysis , isomerization , yield (engineering) , adduct , conjugated linoleic acid , selenium , organic chemistry , conjugated system , linoleic acid , hydrogen peroxide , polyunsaturated fatty acid , fatty acid , medicinal chemistry , polymer , materials science , metallurgy
Summary Adducts of dienophiles and alkali‐conjugated safflower fatty acids containing conjugated linoleic acid in the cis,trans form were prepared by heating the reactants in the presence of selenium as a catalyst. The products appeared to be identical to those prepared from trans,trans conjugated linoleic acid so that isomerization of cis‐trans to trans,trans acids is eliminated as a separate step. Although yields of pure product were lower than desired because of difficulties in removing selenium, yields of crude adducts ranged from 64–82%. The adducts obtained could be epoxidized with hydrogen peroxide and an ion‐exchange resin as catalyst in 80–93% yield or with peracetic acid in 89–98% yield.