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Enzyme‐Catalyzed Preparation of Aliphatic Polythioester by Direct Polycondensation of Diacid Diester and Dithiol
Author(s) -
Kato Makoto,
Toshima Kazunobu,
Matsumura Shuichi
Publication year - 2006
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.200500836
Subject(s) - dithiol , condensation polymer , polymerization , polymer chemistry , lipase , hexane , chemistry , yield (engineering) , catalysis , melting point , crystallization , organic chemistry , materials science , enzyme , polymer , metallurgy
Summary: Aliphatic dithiol‐diacid type polythioesters were first enzymatically prepared by the direct polycondensation of hexane‐1,6‐dithiol and diacid diesters using the immobilized lipase from Candida antarctica (lipase CA). As a typical example, diethyl sebacate and hexane‐1,6‐dithiol were polymerized using lipase CA in bulk in the presence of molecular sieves 4A to produce the corresponding polythioester with an $\overline M _{\rm w}$ of 10 200 in 90% yield. Both the melting and crystallization temperatures of the produced polythioesters were higher when compared to those of the corresponding polyoxyesters. A higher molecular weight polythioester was produced using lipase in a two‐step procedure, i.e., cyclization with subsequent ring‐opening polymerization.Preparation of polythioester and melting temperature of various polythioesters and polyoxyesters.