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Reactions of fatty materials with oxygen. XV. Formation of 9,10‐dihydroxystearic acid and cleavage products in the oxidation of oleic acid and methyl oleate in acetic acid
Author(s) -
Knight H. B.,
Jordan E. F.,
Koos R. E.,
Swern Daniel
Publication year - 1954
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/bf02612490
Subject(s) - oleic acid , acetic acid , autoxidation , chemistry , elaidic acid , catalysis , solvent , cleavage (geology) , organic chemistry , fatty acid , oxygen , polymer , linoleic acid , materials science , biochemistry , fracture (geology) , composite material
Summary The autoxidation of oleic acid and methyl oleate in acetic acid solution at 25–30°, 65°, and 115–120° with a cobalt salt as catalyst has been studied. Samples were withdrawn at intervals and the oxidation products were analyzed and then separated into high‐melting 9,10‐dihydroxystearic acid, cleavage products, unoxidized and hydroxy materials, and polymers. The best yields of desired oxidation products were obtained at 65°. Yields of pure 9,10‐dihydroxystearic acid, m.p. ≧128°, were 12–17% and cleavage products 64–68%, thus accounting for about 80% of the starting material. At 25–30° and 115–120°, yields of the above‐mentioned products were low. A mechanism is proposed which accounts for the formation of trans ‐9,10‐epoxystearic acid from both oleic and elaidic acid autoxidized in the absence of solvent, and the consequent isolation of high‐melting 9,10‐dihydroxystearic acid when acetic acid is the solvent.