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Ultrasound Assisted Lipase Catalyzed Synthesis of Poly-6-Hydroxyhexanoate

Ultrasound Assisted Lipase Catalyzed Synthesis of Poly-6-Hydroxyhexanoate

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Ultrasonic irradiation greatly improved the Candida antarctica lipase B mediated ring opening polymerization of -caprolactone to poly-6-hydroxyhexanoate in the ionic liquid 1-ethyl-3-methylimidazolium tetraflouroborate. Compared to the conventional nonsonicated reaction, sonication improved the monomer conversion by 63% and afforded a polymer product of a narrower molecular weight distribution and a higher degree of crystallinity. Under sonication, the polydispersity index of the product was 1.44 compared to a value of 2.55 for the product of the conventional reaction. With sonication, nearly 75% of the monomer was converted to product, but the conversion was only 16% for the reaction carried out conventionally. Compared to conventional operation, sonication enhanced the rate of polymer propagation by >2-fold and the turnover number of the lipase by >3-fold.
Ultrasonic irradiation greatly improved the Candida antarctica lipase B mediated ring opening polymerization of -caprolactone to poly-6-hydroxyhexanoate in the ionic liquid 1-ethyl-3-methylimidazolium tetraflouroborate. Compared to the conventional nonsonicated reaction, sonication improved the monomer conversion by 63% and afforded a polymer product of a narrower molecular weight distribution and a higher degree of crystallinity. Under sonication, the polydispersity index of the product was 1.44 compared to a value of 2.55 for the product of the conventional reaction. With sonication, nearly 75% of the monomer was converted to product, but the conversion was only 16% for the reaction carried out conventionally. Compared to conventional operation, sonication enhanced the rate of polymer propagation by >2-fold and the turnover number of the lipase by >3-fold.

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Categories:Types, Research, Science
Published by: Ahmad Mohammed Gumel on Sep 26, 2012
Copyright:Attribution Non-commercial

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Ultrasonics Sonochemistry 19 (2012) 659
667
1
Ultrasound assisted lipase catalyzed synthesis of poly-6-hydroxyhexanoate
 A. M. Gumel,
1
M. S. M. Annuar,
1*
Y. Chisti,
3
T. Heidelberg
2
 
1
Institute of Biological Sciences,
2
Department of Chemistry,Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
3
School of Engineering, PN 456, Massey University, Private Bag 11 222, PalmerstonNorth, New Zealand
*
Corresponding author:
Dr. M. Suffian M. Annuar Institute of Biological Sciences, Faculty of Science, University of Malaya, 50603 KualaLumpur, Malaysiae-mail: suffian_annuar@um.edu.myTel: +60379674003Fax: +60379674178
 
Ultrasonics Sonochemistry 19 (2012) 659
667
2
Abstract
Ultrasonic irradiation greatly improved the
Candida antarctica 
lipase B mediated ringopening polymerization of 
 
-caprolactone to poly-6-hydroxyhexanoate in the ionic liquid1-ethyl-3-methylimidazolium tetraflouroborate. Compared to the conventionalnonsonicated reaction, sonication improved the monomer conversion by 63% andafforded a polymer product of a narrower molecular weight distribution and a higher degree of crystallinity. Under sonication, the polydispersity index of the product was
1.44 compared to a value of 
2.55 for the product of the conventional reaction. Withsonication, nearly 75% of the monomer was converted to product, but the conversionwas only
16% for the reaction carried out conventionally. Compared to conventionaloperation, sonication enhanced the rate of polymer propagation by >2-fold and theturnover number of the lipase by >3-fold.
Keywords 
: lipase; polycaprolactone; polyhydroxyalkanoates; ultrasound; kinetics;biopolymers
 
Ultrasonics Sonochemistry 19 (2012) 659
667
3
1. Introduction
This work is concerned with enzyme-mediated sonication-enhanced production of thebiodegradable polymer poly-6-hydroxyhexanoate, a polyhydroxyalkanoates (PHA).Polymers such as PHA are important in many industrial and biomedical applicationsbecause of their biocompatibility, biodegradability and attractive mechanical properties[1, 2]. Temporary prostheses, controlled drug delivery devices, resorbable implants andtissue engineering scaffolds are some of the products made from biodegradablepolymers[3]. Poly-6-hydroxyhexanoate (poly-
 
-caprolactone) is a semi crystallinepolymer that can be inexpensively produced by ring-opening polymerization (ROP) of the monomer 
 
-caprolactone[4, 5].Ring-opening polymerization of lactones and lactides can be achieved withconventional chemical catalysis or by using biocatalysts[6]. Chemical catalysis relies onorganometallic compounds[7]
 
that can contaminate the product and are potentially toxicin biomedical applications. In contrast, the products of enzyme mediated biocatalyticring opening polymerization have little or no potential for an adverse health impact. Inaddition, enzymatic biocatalysis offers an excellent enantiomeric selectivity, specificityand catalytic activity under mild reaction conditions. Enzyme catalyzed ROP can makeuse of a wide range of substrates including cyclic lactones. The lipase B enzyme of 
Candida antarctica 
has proved to be a highly effective catalyst for ROP of cycliclactones[8-11].
 
Enzyme mediated synthesis of PHAs by ring opening polymerization isconventionally carried out in potentially hazardous volatile organic solvents such as

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