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Reactions of fatty materials with oxygen. VIII. Cis-trans isomerization during autoxidation of methyl oleate

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Journal of the American Oil Chemists Society

Summary

Methyl oleate irradiated with ultra-violet light has been autoxidized at 35° and the reaction has been followed by means of the infrared spectrophotometer. During the extremely early stages of autoxidation and continuing up to at least 700 hours, a cis-trans isomerization induced by oxygen is one of the reactions which occurs.

The data suggest that most, if not all, of the peroxides produced during the autoxidation of methyl oleate, at least up to 300 hours, are trans peroxides and not methyl oleate peroxides, as had been previously supposed. A mechanism for the formation of trans peroxides from allylic free radicals is proposed.

Mechanisms are also proposed for the formation of non-peroxidic trans materials during autoxidation. These could explain the formation of trans-9,10-epoxystearic acid and high melting 9,10-dihydroxystearic acid from autoxidizing oleic acid.

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Author information

Authors and Affiliations

  1. Eastern Regional Research Laboratory, 18, Philadelphia, Pennsylvania

    H. B. Knight, C. Roland Eddy & Daniel Swern

Authors
  1. H. B. Knight
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  2. C. Roland Eddy
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  3. Daniel Swern
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Additional information

The previous paper in this series is reference 30.

Report of a study in which certain phases were carried on under the Research and Marketing Act of 1946.

One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture.

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Knight, H.B., Roland Eddy, C. & Swern, D. Reactions of fatty materials with oxygen. VIII. Cis-trans isomerization during autoxidation of methyl oleate. J Am Oil Chem Soc 28, 188–192 (1951). https://doi.org/10.1007/BF02646545

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  • DOI: https://doi.org/10.1007/BF02646545

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