POLYCONDENSATION OF SEBACIC ACID WITH PRIMARY AND SECONDARY HYDROXYL GROUPS CONTAINING DIOLS CATALYZED BY CANDIDA ANTARCTICA LIPASE B

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The aliphatic polyesters are normally synthesized by ester interchange reactions or direct esterification of hydroxyacids or diacid/diol combinations. Biotransformation, utilizing the enzymes as catalysts, was accepted as an alternative route for the synthesis of aliphatic polyesters and offers various advantages compared with the conventional, metal-catalyzed polymerization reactions. Previous studies indicated that lipase-catalyzed polycondensation reactions between diols and diacids occurred preferentially at primary hydroxyl groups of diols, when diols contained both primary and secondary hydroxyl groups. In this work, we investigated lipase-catalyzed polycondensation of diacids and secondary hydroxyl group-containing diols, and successfully synthesized polyesters by polycondensation with secondary hydroxyl groups as well as primary hydroxyl groups. Various diols, glycerol, 1,2-propanediol, 1,3-butanediol, 2,3-butanediol, and 2,4-pentanediol were tested for the polycondensation. The polymerization was achieved by heating a mixture of lipase B, sebacic acid, and the diols in anhydrous toluene at 100 degrees C for 72 h. The resulting polymers were characterized by H-1 and C-13 NMR spectroscopy, Fourier transform-infrared spectroscopy, thermogravimetric analysis, and gel permeation chromatography.
Publisher
TAYLOR & FRANCIS INC
Issue Date
2012
Language
English
Article Type
Article
Keywords

VITRO ENZYME CATALYSIS; ORGANIC-SOLVENTS; BIODEGRADABLE POLYMERS; REGIOSELECTIVE POLYMERIZATION; BIOCATALYTIC SYNTHESIS; DIVINYL SEBACATE; POLYESTERS; ACYLATION; TRANSESTERIFICATION; DEGRADATION

Citation

SYNTHETIC COMMUNICATIONS, v.42, no.23, pp.3504 - 3512

ISSN
0039-7911
DOI
10.1080/00397911.2011.585267
URI
http://hdl.handle.net/10203/104052
Appears in Collection
CH-Journal Papers(저널논문)
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