Polymer Synthesis by In Vitro Enzyme Catalysis

Gross, Richard A.; Kumar, and Ajay; Kalra, Bhanu

doi:10.1021/cr0002590

Cited by 678 publications

(536 citation statements)

References 153 publications

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“…Moreover, copolymeric polyoxoesters are commonly obtained by enzymatic polyesterification or polytransesterification of various alkanedioic acids or alkanedioates with alkanediols using immobilized lipases such as lipase B from C. antarctica (Gross et al 2001;Kazlauskas and Bornscheuer 1998), whereas , -end thiol-functionalized PE are formed by lipase-catalyzed ring-opening polymerization ofalkanelactones with various mercaptoalkanols (Takwa et al 2008). …”

Section: Resultsmentioning

confidence: 99%

“…miehei (Lipozyme RM IM) as biocatalysts (Fehling et al 2007;Weber et al 2006a;b). Similarly, 13 enzymatic preparation of thiol-functionalized polycondensates may be of advantage over chemical synthesis because expensive and toxic reagents are mostly applied to the latter one (Maignan 2002;Moad et al 2007;Watanabe et al 2000;Wilczewska et al 2002) whe reas no chemical activators are used in the polyesterification and polytransesterification reactions described here.…”

Section: Resultsmentioning

confidence: 99%

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Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol

et al. 2010

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Copolymeric polyoxoesters containing branched-chain methylenethiol functions, i.e.poly(1,12-dodecanedioic acid-co-1-thioglycerol) and poly(diethyl 1,12-dodecanedioate-co-1-thioglycerol), were formed by lipase-catalyzed polyesterification and polytransesterification of 1,12-dodecanedioic acid and diethyl 1,12-dodecanedioate, respectively, with 1-thioglycerol (3-mercaptopropane-1,2-diol) using immobilized lipase B from Candida antarctica (Novozym 435) in vacuo without drying agent in the reaction mixture. After 360 to 480 h, both polyoxoesters were purified by extraction from the reaction mixtures followed by solvent fractionation. The precipitate of poly(1,12-dodecanedioic acid-co-1-thioglycerol) demonstrated a M W of 170,000Da, whereas a M W of 7,100 Da only was found for poly(diethyl 1,12-dodecanedioate-co-1-thioglycerol). Both polycondensates were analyzed by GPC/SEC, alkali-catalyzed transmethylation, NMR-and FTIR-spectrometry.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol

et al. 2010

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“…13 Similar results have previously been described in the pseudo-living polymerization of e-caprolactone catalyzed by Sn(Oct) 2 , which would also catalyze both ROP and transesterification. 35 Meanwhile, the hydrolysis degradation may sometimes become prominent at a later stage in the ring-opening synthesis of polyester, 36 which was thought to be a main factor leading to deviation from living polymerization. In this study, we designed a 4-day experiment to explore the reaction process with respect to the changes in M n , M w /M n and monomer conversion.…”

Section: Resultsmentioning

confidence: 99%

Highly efficient enzymatic catalysis for cyclocarbonate polymerization

Luo

Feng

Wang

et al. 2010

Polym J

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In this study, we developed a metal-free biosynthetic strategy of enzymatic polymerization to fabricate aliphatic poly(pentamethylene carbonate) (PPMC). Novozym-435 lipase showed considerably high catalytic efficiency, and high molecular weights (M n ) of up to 6.0Â10 4 g mol À1 were readily achieved through the ring-opening polymerization of cyclobis(pentamethylene carbonate). The reaction parameters, including monomer concentration and lipase concentration, were examined. It seemed that little polymer degradation occurred during the polymerization, which would happen in the case of organometallic catalysis. In vitro enzymatic degradation tests indicate that the carbonate groups may not be sensitive to catalysis from the lipases of porcine pancreas and Candida rugosa (AYS). PPMC was found to possess higher flexibility and tenacity, relative to poly(trimethylene carbonate). Thermogravimetrical analyses suggest that the chemical structure of poly(alkylene carbonate)s exerts a significant influence on their thermal stability and decomposition mechanism.

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“…1, March 2011, 73Á79 remains largely unexplored. Enzymatic polymerizations offer unique advantages such as unique selectivity, avoidance of toxic metal catalyst, and the use of mild reaction conditions (18,19). However, due to the higher cost of the enzymes these processes are not commercially viable.…”

Section: Introductionmentioning

confidence: 99%

Microwave assisted lipase catalyzed solvent-free poly-ε-caprolactone synthesis

Matos

King

Simmons

et al. 2011

Green Chemistry Letters and Reviews

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Microwave (MW) assisted enzymatic polymerizations is an area that is largely unexplored. In the current study, the effect of MW reaction parameters on poly-o-caprolactone (PCL) properties has been investigated using a statistical design. A {3,5} modified mixture experimental design was used to identify the parameter values that gave the desired properties of PCL. The three process parameters that were tested are temperature, MW intensity, and the reaction time. Experimental results showed that in the range of values tested, temperature had the highest positive influence on the properties of PCL, whereas high MW irradiation is not desirable. A cubic regression model was developed and optimal process parameters were obtained using this model. Conducting the polymerization reaction under optimal conditions (908C, 240 min, 50 W), PCL with M n of 20,624 and polydispersity index of 1.2 were obtained. The regression model was validated by carrying out validation experiments and by 3D visualization.

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Polymer Synthesis by In Vitro Enzyme Catalysis

Cited by 678 publications

References 153 publications

Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol

Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol

Highly efficient enzymatic catalysis for cyclocarbonate polymerization

Microwave assisted lipase catalyzed solvent-free poly-ε-caprolactone synthesis

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