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Reactions of fatty materials with oxygen. XVIII. Catalytic hydrogenation of autoxidized methyl oleate and oleic acid. Preparation of monohydroxystearic acids

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Journal of the American Oil Chemists Society

Summary

Autoxidation of methyl oleate and oleic acid beyond the peak peroxide values followed by catalytic hydrogenation gave mixed monohydroxystearic acids in high yield. The complicated autoxidation mixture which contains peroxides, hydroxy, carbonyl, and oxirane compounds was simplified considerably in composition by this procedure.

For complete reduction of the double bond, and the carbonyl and oxirane groups, hydrogenation was conducted at about 150° and 150 lbs.. Peroxides were reduced at room temperature. Catalysts used were palladium on carbon and Raney nickel.

The selective reduction of peroxides in autoxidation mixtures has been studied by chemical and catalytic means. Peroxides were converted largely to carbonyl compounds rather than to the anticipated hydroxy compounds. Palladium-lead on calcium carbonate is an excellent catalyst for reducing peroxides with hydrogen.

tert-Butyl hydroperoxide, 12- ketostearic acid, stearone,cis-9,10-epoxystearic acid and methyl oleate peroxide concentrate were employed as model substances in determining hydrogenation conditions.

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Authors and Affiliations

  1. Eastern Regional Research Laboratory, Philadelphia, Pennsylvania

    Joseph E. Coleman & Daniel Swern

Authors
  1. Joseph E. Coleman
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  2. Daniel Swern
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Additional information

Paper XVII. is reference 5.

A laboratory of the Eastern Utilization Research Branch, Agricultural Research Service, U. S. Department of Agriculture.

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Coleman, J.E., Swern, D. Reactions of fatty materials with oxygen. XVIII. Catalytic hydrogenation of autoxidized methyl oleate and oleic acid. Preparation of monohydroxystearic acids. J Am Oil Chem Soc 32, 221–224 (1955). https://doi.org/10.1007/BF02649017

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  • DOI: https://doi.org/10.1007/BF02649017

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