Unsaturated fatty acid esters metathesis catalyzed by silica supported WMe5

• Published in: Journal of molecular catalysis. A, Chemical Vol. 411; pp. 344 - 348
• Main Authors: Riache, Nassima, Callens, Emmanuel, Talbi, Karima, Basset, Jean-Marie
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01-01-2016
• Subjects: Metathesis; Silica supported WMe5 catalyst; Surface organometallic chemistry; Unsaturated fatty esters; Silica supported WMe5 catalyst; Surface organometallic chemistry; Unsaturated fatty esters; Metathesis
• ISSN: 1381-1169; 1873-314X
• DOI: 10.1016/j.molcata.2015.11.003

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•Metathesis of unsaturated fatty acid esters (FAEs) by W-based single catalytic system.•High selective olefin metathesis operating at high temperature.•Cross-metathesis of unfunctionalized α-olefins and FAEs studied.
Metathesis of unsaturated fatty acid esters (FAEs) by silica supported multifunctional W-based catalyst is disclosed. This transformation represents a novel route towards unsaturated di-esters. Especially, the self-metathesis of ethyl undecylenate results almost exclusively on the homo-coupling product whereas with such catalyst, 1-decene gives ISOMET (olefinisomerization and metathesis) products. The olefin metathesis in the presence of esters is very selective without any secondary cross-metathesis products demonstrating that a high selective olefin metathesis could operate at 150°C. Additionally, a cross-metathesis of unsaturated FAEs and α-olefins allowed the synthesis of the corresponding ester with longer hydrocarbon skeleton without isomerisation.