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The aromatization of linoleic acid with palladium catalyst

  • Published:
Journal of the American Oil Chemists Society

Summary

Hydrogen transfer catalysts are known to promote the elaidinization and conjugation of unsaturated fatty acid derivatives. More extensive reactions were indicated when palladium was tried as a polymerization catalyst. A subsequent study showed that methyl linoleate could be readily cyclized and aromatized in the presence of palladium.

Methyl linoleate was heated in an evacuated ampule for 6 hrs. at 270°C. with 5% of a 10% palladium on charcoal. The iodine value was lowered to 43.9 and the apparent linoleate content to less than 2%. The products were separated by urea segregation and distillation. They consisted of approximately 7% polymer, 18% methyl stearate, 40% monoolefins, and 30% of a methyl ester of an aromatic fatty acid (handling loss 5%). The aromatic material was readily oxidized to orthophthalic acid.

The mechanism by which aromatics, mono-olefins, and saturates are produced through cyclization and hydrogen transfer is not known, but possible routes are suggested.

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Author information

Authors and Affiliations

  1. General Mills Inc., Minneapolis, Minnesota

    Don E. Floyd, R. F. Paschke, D. H. Wheeler & W. S. Baldwin

Authors
  1. Don E. Floyd
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  2. R. F. Paschke
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  3. D. H. Wheeler
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  4. W. S. Baldwin
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Additional information

Paper No. 199, Journal Series, Research Laboratory, General Mills Inc.

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Floyd, D.E., Paschke, R.F., Wheeler, D.H. et al. The aromatization of linoleic acid with palladium catalyst. J Am Oil Chem Soc 33, 609–614 (1956). https://doi.org/10.1007/BF02633247

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  • DOI: https://doi.org/10.1007/BF02633247

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