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The reaction of nonconjugated unsaturated fatty acid esters with maleic anhydride

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Oil & Soap

Summary

1. The non-conjugated unsaturated fatty acid esters react with maleic anhydride at 200° C. or above.

2. At 200° C., methyl oleate reacts with almost 1 mole, methyl linoleate with 2 moles, and methyl linolenate with 2.5 moles of maleic anhydride, when an excess of anhydride is present. Methyl stearate reacts negligibly.

3. Methyl oleate reacts without affecting unsaturation.

4. The first molecule of anhydride reacting with methyl linoleate reacts mostly to saturate one double bond, while the second one adds on without affecting unsaturation.

5. The first two molecules of anhydride reacting with methyl linolenate react mostly to saturate one double bond each, while the third molecule adds on without affecting unsaturation.

6. The possible structures of the reaction products have been discussed.

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Authors and Affiliations

  1. U. S. Regional Soybean Industrial Products Laboratory, Urbana, Illinois

    W. G. Bickford, P. Krauczunas & D. H. Wheeler

Authors
  1. W. G. Bickford
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  2. P. Krauczunas
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  3. D. H. Wheeler
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Additional information

Now associated with the Southern Regional Research Laboratory, New Orleans, Louisiana.

A cooperative organization participated in by the Bureaus of Agricultural Chemistry and Engineering and Plant Industry of the U. S. Department of Agriculture, and the Agricultural Experiment Stations of the North Central States of Illinois, Indiana, Iowa, Kansas, Michigan, Minnesota, Missouri, Nebraska, North Dakota, Ohio, South Dakota, and Wisconsin.

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Bickford, W.G., Krauczunas, P. & Wheeler, D.H. The reaction of nonconjugated unsaturated fatty acid esters with maleic anhydride. Oil Soap 19, 23–27 (1942). https://doi.org/10.1007/BF02547718

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  • DOI: https://doi.org/10.1007/BF02547718

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