Polyamide precursors from renewable 10-undecenenitrile and methyl acrylateviaolefin cross-metathesis†
J.-L. Dubois,J.-L. Couturier
Green Chemistry Pub Date : 06/14/2012 00:00:00 , DOI:10.1039/C2GC35648A
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