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 Samples were withdrawn at intervals and the oxidation products were analyzed and then separated into high-melting 9,10-dihydroxystearic acid, cleavage products, unoxidized and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 oftrans-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.
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Paper XIV is reference 10.
One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Service, U. S. Department of Agriculture.
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Knight, H.B., Jordan, E.F., Koos, R.E. et al. 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. J Am Oil Chem Soc 31, 93–96 (1954). https://doi.org/10.1007/BF02612490
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DOI: https://doi.org/10.1007/BF02612490