Research Paper

Catalytic cleavage of methyl oleate or oleic acid

  1. Angela Köckritz1,*,
  2. Michael Blumenstein2,
  3. Andreas Martin1

Article first published online: 30 SEP 2009

DOI: 10.1002/ejlt.200900103

Issue

European Journal of Lipid Science and Technology

European Journal of Lipid Science and Technology

Special Issue: Oil and fats as renewable resources for the chemical industry

Volume 112, Issue 1, pages 58–63, No. 1 January 2010

Additional Information

How to Cite

Köckritz, A., Blumenstein, M. and Martin, A. (2010), Catalytic cleavage of methyl oleate or oleic acid. Eur. J. Lipid Sci. Technol., 112: 58–63. doi: 10.1002/ejlt.200900103

Author Information

  1. 1

    Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Rostock, Germany

  2. 2

    Hobum Oleochemicals GmbH, Hamburg, Germany

*Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany. Fax: +49 381 128151289

Publication History

  1. Issue published online: 25 JAN 2010
  2. Article first published online: 30 SEP 2009
  3. Manuscript Accepted: 25 JUN 2009
  4. Manuscript Received: 4 MAY 2009

Funded by

  • Federal Ministry of Food, Agriculture and Consumer Protection. Grant Number: FKZ 22003704

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Keywords:

  • Co-oxidant;
  • Double bond cleavage;
  • Methyl oleate;
  • Molecular oxygen;
  • Oleic acid;
  • Osmium catalyst

Abstract

Different reaction pathways are discussed for the Os-catalyzed oxidation of methyl oleate and oleic acid using O2/aldehyde as oxidation system. Monomethyl azelate and pelargonic acid were the main products obtained in yields of approximately 50–70% starting from methyl oleate. Besides, varying amounts of methyl 9,10-epoxystearate and methyl 9,10-dihydroxystearate were found as by-products. Azelaic acid and pelargonic acid were obtained exclusively from oleic acid used as reactant. Some mechanistic considerations led to the conclusion that the observed products are formed in parallel reaction paths. The effective oxidant for the scission of the C=C double bond seems to be very likely an in situ formed peracid generated by Os-catalysis from O2/aldehyde. Additional investigations concerning the cleavage of oleic acid and methyl oleate with in situ formed performic acid from H2O2/formic acid corroborate this assumption.

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