Summary
Methyl oleate, irradiated with ultraviolet, has been autoxidized at 35°, 70°, and 100°C. for 2,000, 264, and 168 hours, respectively. Samples were withdrawn at intervals and total oxygen introduced was determined by chemical analysis for peroxide, carbonyl, hydroxyl, oxirane, ester, and carboxyl oxygen.
Total oxygen introduced was also determined by difference from carbon and hydrogen analyses. In the autoxidation at 35° good agreement was obtained between the two methods for determining total oxygen introduced, over the entire time period studied. At 70° and 100° however good agreement was noted only during the early stages, after which the combustion values were higher and the spread between them became progressively larger. This difference is accounted for by formation of ethers, which could not be determined chemically. At all three temperatures about 2.5 to 3.0 atoms of oxygen were introduced per molecule of methyl oleate.
Even with such a comparatively simple substrate as methyl oleate the autoxidation reaction is exceedingly complex.
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References
Hamilton, L. A., and Olcott, H. S., Ind. Eng. Chem.,29, 217 (1937).
Knight, H. B., Eddy, C. R., and Swern, D., J. Am. Oil Chem. Soc.,28, 188 (1951).
Knight, H. B., and Swern, D., J. Am. Oil Chem. Soc.,26, 366 (1949).
Swern, D., Knight, H. B., Scanlan, J. T., and Ault, W. C., J. Am. Chem. Soc.,67, 1132 (1945).
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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., Coleman, J.E. & Swern, D. Reactions of fatty materials with oxygen. IX. Analytical study of the autoxidation of methyl oleate. J Am Oil Chem Soc 28, 498–501 (1951). https://doi.org/10.1007/BF02645825
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DOI: https://doi.org/10.1007/BF02645825