We thank Lars Bolk for DSC and GPC analysis and Marina Krumova for WAXS.
Linear Semicrystalline Polyesters from Fatty Acids by Complete Feedstock Molecule Utilization†
Article first published online: 7 MAY 2010
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 49, Issue 25, pages 4306–4308, June 7, 2010
How to Cite
Quinzler, D. and Mecking, S. (2010), Linear Semicrystalline Polyesters from Fatty Acids by Complete Feedstock Molecule Utilization. Angew. Chem. Int. Ed., 49: 4306–4308. doi: 10.1002/anie.201001510
- Issue published online: 1 JUN 2010
- Article first published online: 7 MAY 2010
- Manuscript Received: 12 MAR 2010
- 3Biopolymers, Vol. 3a,b,4, Wiley-VCH, Weinheim, 2002., ,
- 4Chem. Eng. News 2008, 86, 21–25.,
- 9Polyesters, Pergamon Press, Oxford, 1965., ,
- 10Physical Properties of Polymers Handbook (Ed.: J. E. Mark), Springer, New York, 2007, pp. 165–186., in
- 12This is underlined by the resulting necessity of incorporation of fossil-feedstock based aromatic diacid comonomers: Biopolymers, Vol. 4 (Eds. A. Steinbüchel, Y. Doi), Wiley-VCH, Weinheim, 2002, pp. 299–311., , , , in
- 13For enzymatic ω-oxidation of (saturated) fatty acids cf.;
- 18C. Jiménez-Rodriguez, Ph.D. thesis, University of St. Andrews, 2004.
- 19Remarkably, the multiple unsaturated linoleate and linolenate are also converted into the saturated, linear α,ω-diester, which is advantageous for the utilization of technical-grade fatty acid esters.
- 22Ullmann’s Encyclopedia of Industrial Chemistry, Vol. 28, 6th ed., Wiley-VCH, Weinheim, 2003, pp. 75–102., , , , in
- 23From ΔHm (determined by DSC) and χ (determined by WAXS), an enthalpy of fusion ΔHu of the crystalline portion of about 200 J g−1 (1) and 240 J g−1 (2) is estimated by comparison to ΔHu=293 J g−1 for linear polyethylene. Poly(decamethylene sebacate) as an example of a long-chain linear aliphatic polyester from currently accessible monomers melts with ΔHu 148 J g−1 (Tm=80 °C).
- 24In this work, reduction of diacid esters to diols was performed with inorganic hydrides, as this is convenient on a laboratory scale. Industrially, catalytic reduction of esters to alcohols with hydrogen as a reagent is an established reaction.