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Issue 6, 2014
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Olefin cross-metathesis as a valuable tool for the preparation of renewable polyesters and polyamides from unsaturated fatty acid esters and carbamates

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Abstract

Olefin cross-metathesis of unsaturated fatty acid methyl ester (FAME) derived benzyl carbamates with methyl acrylate is described. The obtained by-product, an α,β-unsaturated ester, was further modified via thia-Michael addition reactions in order to synthesize branched AA-type or AB-type monomers for the preparation of polyesters, which are tuneable by oxidation. Cross-metathesis of fatty acid derived carbamates was used as a novel approach to prepare linear AB-type monomers, which can be used for the preparation of renewable polyamides PA11, PA12 and PA15. The necessary fatty acid carbamates were prepared by applying a catalytic Lossen rearrangement procedure. The presented synthesis strategy has potential for the bio-sourced preparation of monomers for the production of polyamides. All prepared polymers were fully characterized by NMR, SEC, and DSC analyses. Additionally, the Young's modulus of the prepared long-chain polyamide PA15 was determined.

Graphical abstract: Olefin cross-metathesis as a valuable tool for the preparation of renewable polyesters and polyamides from unsaturated fatty acid esters and carbamates

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Publication details

The article was received on 17 Feb 2014, accepted on 18 Apr 2014 and first published on 22 Apr 2014


Article type: Paper
DOI: 10.1039/C4GC00273C
Citation: Green Chem., 2014,16, 3335-3340
  • Open access: Creative Commons BY license
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    Olefin cross-metathesis as a valuable tool for the preparation of renewable polyesters and polyamides from unsaturated fatty acid esters and carbamates

    M. Winkler and M. A. R. Meier, Green Chem., 2014, 16, 3335
    DOI: 10.1039/C4GC00273C

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