Summary
The adduct of maleic anhydride and methyl oleate has been prepared and characterized. The physical and chemical properties of the adduct indicate that it is composed of one mole of each of the reactants and that the double bond of methyl oleate has not been saturated. Oxidative fission of the adduct showed that the adduct consisted of a mixture of four isomers which yielded octanoic, nonanoic, suberic, and azelaic acids on ozonolysis. Isolation of these four acids from the fission products indicates that the addition reaction probably proceeds by a mechanism analogous to that proposed by Farmer, Koch, and Sutton for autoxidation. In view of the similarity between the reactions of maleic anhydride and oxygen with unsaturated compounds, the foregoing observations appear to support the free radical chain mechanism for the autoxidation of fats.
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References
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One of the laboratories of the Bureau of the Agricultural and Industrial Chemistry Agricultural Research Administration, U. S. Department of Agriculture.
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Bickford, W.G., Fisher, G.S., Kyame, L. et al. Autoxidation of fats. II. Preparation and oxidation of methyl oleate-maleic anhydride adduct. J Am Oil Chem Soc 25, 254–257 (1948). https://doi.org/10.1007/BF02593478
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DOI: https://doi.org/10.1007/BF02593478