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Saturated keto esters from lesquerolic, dimorphecolic, and densipolic acids

  • Technical
  • Published:
Journal of the American Oil Chemists’ Society

Summary

The naturally occurring, unsaturated, hydroxy fatty esters, methyl lesquerolate (methyl 14-hydroxy-cis-11-eicosenoate), methyl dimorphecolate (methyl 9-hydroxy-trans, trans-10,12-octadecadienoate), and methyl densipolate (methyl 12-hydroxy-cis,cis-9,15-octadecadienoate) have been converted to the corresponding saturated keto esters by tow routes. The unsaturated esters were subjected to a hydrogenation-dehydrogenation reaction in the presence of Raney nickel or their saturated derivatives were dehydrogenated by copper chromite catalysis. Yields of the keto esters are 65–82% in the nickel-catalyzed reactions, and 71–94% by copper chromite-catalyzed dehydrogenation. In the hydrogenation-dehydrogenation system the order of reactivity is: methyl lesquerolate>methyl dimorphecolate>methyl densipolate. Relationships between structure and reactivity of these compounds, methyl 12-hydroxystearate, and methyl ricinoleate are discussed.

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Authors and Affiliations

  1. Western Regional Research Laboratory, Albany, California

    Bernard Freedman, R. G. Binder & T. H. Applewhite

Authors
  1. Bernard Freedman
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  2. R. G. Binder
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  3. T. H. Applewhite
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Additional information

W. Utiliz. Res. Dev. Div., ARS, USDA.

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Freedman, B., Binder, R.G. & Applewhite, T.H. Saturated keto esters from lesquerolic, dimorphecolic, and densipolic acids. J Am Oil Chem Soc 43, 458–460 (1966). https://doi.org/10.1007/BF02682415

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  • DOI: https://doi.org/10.1007/BF02682415

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