Issue 8, 2012

Polyamide precursors from renewable 10-undecenenitrile and methyl acrylateviaolefin cross-metathesis

Abstract

The ruthenium-catalyzed cross-metathesis of the unsaturated fatty acid derivative 10-undecenenitrile 1 arising from castor oil with methyl acrylate produces a C12 nitrile ester with high turnover number. This product has potential as a new bio-sourced intermediate for the production of polyamides. This route competes favourably with the reverse cross-metathesis of methyl 10-undecenoate with acrylonitrile leading to the same C12 α,ω-amino ester 7 after hydrogenation of the carbon–carbon double bond and the nitrile functionality.

Graphical abstract: Polyamide precursors from renewable 10-undecenenitrile and methyl acrylate via olefin cross-metathesis

Supplementary files

Article information

Article type
Paper
Submitted
27 Apr 2012
Accepted
25 May 2012
First published
14 Jun 2012

Green Chem., 2012,14, 2179-2183

Polyamide precursors from renewable 10-undecenenitrile and methyl acrylate via olefin cross-metathesis

X. Miao, C. Fischmeister, P. H. Dixneuf, C. Bruneau, J.-L. Dubois and J.-L. Couturier, Green Chem., 2012, 14, 2179 DOI: 10.1039/C2GC35648A

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