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Keywords:

  • Cross-metathesis;
  • Methyl 10-undecenoate;
  • Monomer;
  • Polyester;
  • Polymer;
  • Renewable resources

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.