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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

Winkler, Matthias 1,2; Meier, Michael A. R. 1,2
1 Laboratorium für Applikationen der Synchrotronstrahlung (LAS), Karlsruher Institut für Technologie (KIT)
2 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)


Olefin cross-metathesis of unsaturated fatty acid methyl ester (FAME) derived benzyl carbamates with methyl acrylate is described. The obtained by-product{,} an [small alpha]{,}[small beta]-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.

Volltext §
DOI: 10.5445/IR/1000046418
DOI: 10.1039/C4GC00273C
Zitationen: 58
Web of Science
Zitationen: 52
Zitationen: 59
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2014
Sprache Englisch
Identifikator ISSN: 1463-9262
KITopen-ID: 1000046418
Erschienen in Green Chemistry
Verlag Royal Society of Chemistry (RSC)
Band 16
Heft 6
Seiten 3335-3340
Bemerkung zur Veröffentlichung RSC geförderter Open Access-Artikel
Nachgewiesen in Scopus
Web of Science
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