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

• Published in: Synthetic Communications
• Main Authors: Yoon, KR Yoon, Kuk Ro, Hong, SP Hong, Suk-Pyo, Kong, B Kong, Bokyung, Choi, IS Choi, Insung
• Format: Article in Journal/Newspaper
• Language: English
• Published: TAYLOR & FRANCIS INC 2012
• Subjects: Antarc*; Antarctica
• Online Access: http://hdl.handle.net/10203/104052; https://doi.org/10.1080/00397911.2011.585267

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. 화학과