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Polyesters by lipase-catalyzed polycondensation of unsaturated and epoxidized long-chain α,ω-dicarboxylic acid methyl esters with diols

Authors

  • Siegfried Warwel,

    Corresponding author
    1. Institute for Biochemistry and Technology of Lipids, H. P. Kaufmann-Institute, Federal Centre for Cereal, Potato and Lipid Research, Piusallee 68, D-48147 Münster, Germany
    • Institute for Biochemistry and Technology of Lipids, H. P. Kaufmann-Institute, Federal Centre for Cereal, Potato and Lipid Research, Piusallee 68, D-48147 Münster, Germany
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  • Christoph Demes,

    1. Institute for Biochemistry and Technology of Lipids, H. P. Kaufmann-Institute, Federal Centre for Cereal, Potato and Lipid Research, Piusallee 68, D-48147 Münster, Germany
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  • Georg Steinke

    1. Institute for Biochemistry and Technology of Lipids, H. P. Kaufmann-Institute, Federal Centre for Cereal, Potato and Lipid Research, Piusallee 68, D-48147 Münster, Germany
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Abstract

Long-chain, symmetrically unsaturated α,ω-dicarboxylic acid methyl esters (C18, C20, C26) were obtained by the catalytic metathetical condensation of 9-decenoic, 10-undecenoic, and 13-tetradecenoic acid methyl esters, respectively, with the homogeneous Grubbs catalyst bis(tricyclohexyl phosphine) benzylidene ruthenium dichloride dissolved in methylene chloride. The dicarboxylic acid esters were epoxidized chemoenzymatically with H2O2/methyl acetate with Novozym 435®, an immobilized lipase B from Candida antarctica. Polyesters from symmetrically unsaturated or epoxidized α,ω-dicarboxylic acid methyl esters with 1,3-propanediol or 1,4-butanediol, respectively, were achieved by enzymatic polycondensation with the same biocatalyst applied. With 1,3-propanediol as a substrate, the linear unsaturated and epoxidized polyesters had molecular weights of 1950–3300 g/mol and melting points of 47–75 °C, whereas with 1,4-butanediol as a substrate, the resulting polyesters showed higher molecular weights, 7900–11,600 g/mol, with similar melting points of 55–74 °C. © 2001 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 1601–1609, 2001

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