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Enzymatic Synthesis and Polymerization of Cyclic Trimethylene Carbonate Monomer with/without Methyl Substituent
Author(s) -
Tasaki Hiroaki,
Toshima Kazunobu,
Matsumura Shuichi
Publication year - 2003
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/mabi.200350013
Subject(s) - chemistry , trimethylene carbonate , lipase , dimethyl carbonate , candida antarctica , substituent , diethyl carbonate , monomer , diol , organic chemistry , triacylglycerol lipase , transesterification , yield (engineering) , polymerization , carbonate , polymer chemistry , ethylene carbonate , catalysis , polymer , enzyme , materials science , electrode , electrolyte , metallurgy
The direct enzymatic synthesis of a cyclic trimethylene carbonate (1,3‐dioxane‐2‐one) monomer with/without a methyl substituent was carried out using dimethyl or diethyl carbonate and 1,3‐diol with the objective of producing aliphatic poly(trimethylene carbonate), a typical biodegradable synthetic plastic. The lipase‐catalyzed condensation of dimethyl or diethyl carbonate with aliphatic 1,3‐diols using immobilized Candida antarctica lipase (lipase CA) in an organic solvent at 70 °C afforded the corresponding methyl‐substituted and unsubstituted cyclic trimethylene carbonates. The cyclic trimethylene carbonates obtained by the reaction of dimethyl or diethyl carbonates with 1,3‐propanediol and 2‐methyl‐1,3‐propanediol were polymerized by lipase to produce the corresponding polycarbonates.Total TMC yield as a function of the reaction time.