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Comparison of Reactivity in the Cross Metathesis of Allyl Acetate-Derivatives with Oleochemical Compounds

Journal of the American Oil Chemists' Society volume 92, pages 603–611 (2015)Cite this article

Abstract

The metathesis of unsaturated oleochemicals is an excellent tool for generating α,ω-difunctional substrates, which are useful intermediates for polymer synthesis. This article describes the cross metathesis of allyl acetate and cis-1,4-diacetoxy-2-butene with methyl 10-undecenoate and methyl oleate, which are oleochemical key substrates. Detailed optimizations led to high conversion rates and yields of the desired products under mild reaction conditions by using a low concentration of commercially available homogeneous ruthenium catalysts.

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Acknowledgments

This work was supported financially by the German Federal Ministry of Food, Agriculture and Consumer Protection (represented by the Fachagentur Nachwachsende Rohstoffe) and the Emery Oleochemicals GmbH. The authors would like to thank Umicore AG & Co. KG and Evonik Industries for their donations of ruthenium metathesis catalysts.

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Authors and Affiliations

  1. Department of Biochemical und Chemical Engineering, Chair of Technical Chemistry, Technical University Dortmund, Emil-Figge Str. 66, 44227, Dortmund, Germany

    Arno Behr & Stephanie Toepell

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  1. Arno Behr
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  2. Stephanie Toepell
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Correspondence to Arno Behr.

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Behr, A., Toepell, S. Comparison of Reactivity in the Cross Metathesis of Allyl Acetate-Derivatives with Oleochemical Compounds. J Am Oil Chem Soc 92, 603–611 (2015). https://doi.org/10.1007/s11746-015-2614-7

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  • DOI: https://doi.org/10.1007/s11746-015-2614-7

Keywords

  • Oleochemistry
  • Metathesis
  • Homogeneous catalysis
  • Allyl acetate
  • cis-1,4-Diacetoxy-2-butene
  • Methyl oleate
  • Methyl 10-undecenoate