Summary
Low temperature fractional crystallization from acetone has been applied to the separation of methyl hydroperoxido oleate in 85 to 90 percent purity from partially oxidized methyl oleate. The hydroperoxido ester was subjected to hydrogenation, oxidative fission, and reduction with hydrogen iodide. Certain characteristics of the original hydroperoxide and its reaction products have been described. The results obtained lend definite support to the view that the first oxidation product of methyl oleate is a mixture of 8- and 11-hydroperoxido octadecenoic acids, at least under the conditions employed,i.e., oxidation under the influence of ultraviolet light or reaction temperatures up to 60° C.
The spectral absorption of methyl hydroperoxido oleate and some derived products was determined. The hydroperoxide group was shown to have no characteristic absorption in the ultraviolet region.
The reactions of the peroxide with alkali, hydroxylamine, lead tetraacetate, and α-tocopherol have been described and discussed.
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One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture.
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Swift, C.E., Dollear, F.G. & O'Connor, R.T. The oxidation of methyl oleate I. The preparation, properties and reactions of methyl hydroperoxido oleate. Oil Soap 23, 355–359 (1946). https://doi.org/10.1007/BF02641663
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DOI: https://doi.org/10.1007/BF02641663