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Cross‐metathesis of methyl 10‐undecenoate with diethyl maleate: Formation of an α,ω‐diester via a metathesis reaction network
Author(s) -
Behr Arno,
Gomes Jessica Pérez,
Bayrak Zeynep
Publication year - 2011
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201000299
Subject(s) - metathesis , salt metathesis reaction , chemistry , ruthenium , organic chemistry , phosphine , polyester , carbene , monomer , transesterification , catalysis , polymerization , polymer
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.