Enzymatic Ring-Opening Polymerization of ε-Caprolactone by Yarrowia lipolytica Lipase in Ionic Liquids

被引:29
作者
Barrera-Rivera, Karla A. [1 ]
Marcos-Fernandez, Angel [2 ]
Vera-Graziano, Ricardo [3 ]
Martinez-Richa, Antonio [1 ]
机构
[1] Univ Guanajuato, Dept Quim, Guanajuato 36050, Gto, Mexico
[2] CSIC, Inst Ciencia & Tecnol Polimeros, Dept Quim & Tecnol Elastomeros, E-28006 Madrid, Spain
[3] Univ Nacl Autonoma Mexico, Inst Invest Mat, Mexico City 04510, DF, Mexico
关键词
ionic liquids; lipase; ROP (ring-opening polymerization); Yarrowia lipolytica; CATALYZED POLYMERIZATION; POLYESTER SYNTHESIS; BIOCATALYSIS; KINETICS; MONOMERS;
D O I
10.1002/pola.23623
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Yarrowia lipolytica (YLL), Candida rugosa (CRL), and porcine pancreatic lipase (PPL) were employed successfully as catalysts in the enzymatic ring-opening polymerization (ROP) of epsilon-caprolactone in the presence of 1-ethyl-3-methylimidazolium tetrafluoroborate ([EMIM][BF4]), 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM][BF4]), 1-butylpyridinium tetrafluoroborate ([BuPy][BF4]), 1-butylpyridinium trifluoroacetate ([BuPy][CF3COO]), 1-ethyl-3-methylimidazolium nitrate ([EMIM][NO3]) ionic liquids. Poly(epsilon-caprolactone)s (PCLs) with molecular weights (M-n) in the range of 300-9000 Da were obtained. H-1- and C-13-NMR analyses on PCLs formed by YLL, CRL, and PPL showed asymmetric telechelic alpha-hydroxy-omega-carboxylic acid end groups. Differences between CP-MAS and MAS spectra are observed and discussed in terms of morphology. MALDI-TOF spectra show the formation of at least seven species. Differential scanning calorimetry (DSC) and Wide Angle X-Ray Scattering (WAXS) results demonstrate the high degree of crystallinity present in all the polyesters. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 5792-5805, 2009
引用
收藏
页码:5792 / 5805
页数:14
相关论文
共 32 条
[1]   Synthesis and characterization of poly (ε-caprolactone) and copolyesters by catalysis with molybdenum compounds:: polymers with acid-functional asymmetric telechelic architecture [J].
Báez, JE ;
Martínez-Richa, A .
POLYMER, 2005, 46 (26) :12118-12129
[2]   Enzymatic ring-opening polymerization of ε-caprolactone by a new lipase from Yarrowia lipolytica [J].
Barrera-Rivera, Karla A. ;
Flores-Carreon, Arturo ;
Martinez-Richa, Antonio .
JOURNAL OF APPLIED POLYMER SCIENCE, 2008, 109 (02) :708-719
[3]   Chain transfer to ionic liquid in an anionic polymerization of methyl methacrylate [J].
Biedron, Tadeusz ;
Kubisa, Przemyslaw .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2007, 45 (17) :4168-4172
[4]   Lipase-catalysed formation of macrocycles by ring-opening polymerisation of ε-caprolactone [J].
Cordova, A ;
Iversen, T ;
Martinelle, M .
POLYMER, 1998, 39 (25) :6519-6524
[5]   Understanding structure -: Stability relationships of Candida antartica lipase B in ionic liquids [J].
De Diego, T ;
Lozano, P ;
Gmouh, S ;
Vaultier, M ;
Iborra, JL .
BIOMACROMOLECULES, 2005, 6 (03) :1457-1464
[6]   Protic pyridinium ionic liquids: Synthesis, acidity determination and their performances for acid catalysis [J].
Duan, ZY ;
Gu, YL ;
Zhang, J ;
Zhu, LY ;
Deng, YQ .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 250 (1-2) :163-168
[7]   Decolorization of ionic liquids for spectroscopy [J].
Earle, Martyn J. ;
Gordon, Charles M. ;
Plechkova, Natalia V. ;
Seddon, Kenneth R. ;
Welton, Thomas .
ANALYTICAL CHEMISTRY, 2007, 79 (02) :758-764
[8]   Syntheses of high molecular weight aliphatic polyesters in 1-alkyl-3-methylimidazolium ionic liquids [J].
Fu, Chengjie ;
Liu, Zhengping .
POLYMER, 2008, 49 (02) :461-466
[9]   Ring-opening metathesis polymerization of functionalized cyclooctene by a ruthenium-based catalyst in ionic liquid [J].
Han, Huijing ;
Chen, Fengxiang ;
Yu, Jiahui ;
Dang, Jingya ;
Ma, Zhuo ;
Zhang, Yiqun ;
Xie, Meiran .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2007, 45 (17) :3986-3993
[10]   Reverse ATRP process of acrylonitrile in the presence of ionic liquids [J].
Hou, Chen ;
Qu, Rongjun ;
Ji, Chunnuan ;
Sun, Changmei ;
Wang, Chunhua .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (08) :2701-2707