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Cross-metathesis of methyl 10-undecenoate with diethyl maleate: Formation of an α,ω-diester via a metathesis reaction network

Authors

  • Arno Behr,

    Corresponding author
    1. Department of Biochemical and Chemical Engineering, Technische Universität Dortmund, Dortmund, Germany
    • Department of Biochemical and Chemical Engineering, Technische Universität Dortmund, Emil-Figge-Str. 66, 44227 Dortmund, Germany Fax: +49-231-755-2311.
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  • Jessica Pérez Gomes,

    1. Department of Biochemical and Chemical Engineering, Technische Universität Dortmund, Dortmund, Germany
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  • Zeynep Bayrak

    1. Department of Biochemical and Chemical Engineering, Technische Universität Dortmund, Dortmund, Germany
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Abstract

The cross-metathesis of methyl 10-undecenoate 1 derived from castor oil as a renewable raw material with diethyl maleate 2 was investigated. These reactions were carried out with several phosphine and N-heterocyclic carbene ruthenium catalysts. The reaction conditions were optimised for high conversions in combination with high cross-metathesis selectivity. This single-step and atom-economic synthetic method illustrates an efficient and selective preparation procedure of linear α,ω-dicarboxylic acid esters starting from renewable resources and comparatively inexpensive base chemicals. Further by-products are hardly obtained due to their consumption in secondary metathesis reactions. Hence, a sustainable alternative for polyamide and polyester monomers is presented.

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