Preparation of aliphatic poly(thioester) by the lipase-catalyzed direct polycondensation of 11-mercaptoundecanoic acid

Makoto Kato, Kazunobu Toshima, Shuichi Matsumura

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40 Citations (Scopus)

Abstract

An aliphatic polythioester was enzymatically prepared by the direct polycondensation of mercaptoalkanoic acid using immobilized lipase of Candida antarctica (lipase CA) in bulk. The commercially available 11-mercaptoundecanoic acid was polymerized by lipase CA in bulk in the presence of molecular sieves 4A as a water absorbent at 110 °C for 48 h to produce poly(11-mercaptoundecanoate) with an Mw of 34 000 in high yield. The 104.5 °C melting temperature (Tm) of poly(11-mercaptoundecanoate) was about 20 °C higher than that of the corresponding polyoxyester, poly(11-hydroxyundecanoate). The polythioester was readily transformed by lipase into the corresponding cyclic oligomers mainly consisting of the dimer, which were readily repolymerized by the ring-opening polymerization using lipase as a sustainable chemical recycling.

Original languageEnglish
Pages (from-to)2275-2280
Number of pages6
JournalBiomacromolecules
Volume6
Issue number4
DOIs
Publication statusPublished - 2005 Jul 1

ASJC Scopus subject areas

  • Bioengineering
  • Biomaterials
  • Polymers and Plastics
  • Materials Chemistry

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