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

Makoto Kato, Kazunobu Toshima, Shuichi Matsumura

Research output: Contribution to journalArticle

38 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

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Lipases
Polycondensation
Lipase
Acids
Candida
Ring opening polymerization
Molecular sieves
Recycling
Oligomers
Polymerization
Dimers
Freezing
Melting point
Temperature
11-mercaptoundecanoic acid
Water

ASJC Scopus subject areas

  • Organic Chemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Polymers and Plastics
  • Materials Chemistry

Cite this

Preparation of aliphatic poly(thioester) by the lipase-catalyzed direct polycondensation of 11-mercaptoundecanoic acid. / Kato, Makoto; Toshima, Kazunobu; Matsumura, Shuichi.

In: Biomacromolecules, Vol. 6, No. 4, 07.2005, p. 2275-2280.

Research output: Contribution to journalArticle

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