<i>Candida antarctica</i> Lipase B Catalyzed Synthesis of Poly(butylene succinate): Shorter Chain Building Blocks Also Work

Azim, Himanshu; Dekhterman, Alex; Jiang, Zhaozhong; Gross, Richard A.

doi:10.1021/bk-2008-0999.ch019

Cited by 18 publications

(29 citation statements)

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“…Novozym Ò 435 (specific activity 10000 PLU/g) was purchased from NOVO Nordisk A/S (Bagsvaerd, Denmark) and consists of Candida antarctica lipase B (triacylglycerol hydrolase, EC 3.1.1.3) physically adsorbed within the macroporous acrylic resin (poly[methyl methacrylateco-butyl methacrylate]) [3]. Succinic acid and oleyl alcohol (cis-9-octadecen-1-ol) were purchased from Merck Co. (Darmstadt, Germany).…”

Section: Methodsmentioning

confidence: 99%

“…The extent of esterification decreased with an increase in temperature from 40.2 to 65.0°C. Considering the fact that Novozym 435 [3], this result can be related to the decrease in equilibrium constants at higher reaction temperatures. By increasing the time, at any given temperature, a decrease in ester formation was observed.…”

Section: Effect Of Parameters and Optimum Conditionmentioning

confidence: 99%

“…Application of enzymes to produce these high value-added esters may overcome such limitations. Candida antarctica lipase B was employed as a catalyst for copolymerization of succinic acid and 1,4-butanediol to produce low molecular weight oligomers [3]. Jiang [8] also reported immobilized Candida antarctica lipase B-catalyzed production of di(n-hexadecyl) succinate and its use as a substrate in the synthesis of aliphatic copolyesters.…”

Section: Introductionmentioning

confidence: 99%

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Modeling and optimization of lipase-catalyzed production of succinic acid ester using central composite design analysis

Rahman

Jarmi

Chaibakhsh

et al. 2010

J Ind Microbiol Biotechnol

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Esterification of succinic acid with oleyl alcohol catalyzed by immobilized Candida antarctica lipase B (Novozym 435) was investigated in this study. Response surface methodology (RSM) based on a five-level, four-variable central composite design (CCD) was used to model and analyze the reaction. A total of 21 experiments representing different combinations of the four parameters including temperature (35-65°C), time (30-450 min), enzyme amount (20-400 mg), and alcohol:acid molar ratio (1:1-8:1) were generated. A partial cubic equation could accurately model the response surface with a R(2) of 0.9853. The effect and interactions of the variables on the ester synthesis were also studied. Temperature was found to be the most significant parameter that influenced the succinate ester synthesis. At the optimal conditions of 41.1°C, 272.8 min, 20 mg enzyme amount and 7.8:1 alcohol:acid molar ratio, the esterification percentage was 85.0%. The model can present a rapid means for estimating the conversion yield of succinate ester within the selected ranges.

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Section: Methodsmentioning

confidence: 99%

Section: Effect Of Parameters and Optimum Conditionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Modeling and optimization of lipase-catalyzed production of succinic acid ester using central composite design analysis

Rahman

Jarmi

Chaibakhsh

et al. 2010

J Ind Microbiol Biotechnol

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“…This is an excellent result for the enzymatic synthesis of this polyester that proves the suitability of the applied procedure. In fact, the highest molecular weight reported for enzymatically prepared PBS is about 3,000 g·mol -1 [32]. The PBS x G I y copolyesters were obtained with M n in the ~13,000-5,000 range and viscosities ranging from ~0.4 to ~0.6 dL·g −1…”

Section: Synthesis Of Polyesters and Copolyestersmentioning

confidence: 98%

“…In fact, lipase-catalyzed polymerization in the melt is a recently developed method that allows producing aliphatic polyesters under mild conditions and avoiding residual metals [30,31]. Thus Azim et al [32] reported the CAL-B mediated synthesis of PBS with a M w close to 40,000. In this paper…”

Section: Introductionmentioning

confidence: 99%

Cationic poly(butylene succinate) copolyesters

Bautista

Ilarduya

Alla

et al. 2016

European Polymer Journal

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 A series of cationic copolyesters of PBS containing ammonium side groups was synthesized by enzymatic polycondensation. A series of cationic copolyesters of PBS containing phosphonium side groups was synthesized by organometallically catalyzed melt polycondensation. Both ammonium and phosphonium containing PBS copolyesters are thermally stable, semicrystalline and able to crystallize from the melt for moderate contents in ionic units. Both ammonium and phosphonium containing PBS copolyesters show high antimicrobial activity against both gram-positive and gram-negative bacteria. Abstract: The synthesis, characterization and comparative evaluation of properties of two series of cationic PBS copolyesters bearing respectively ammonium and tributylphosphonium side groups, are reported. The copolyesters with contents in ionic units up to 50 mole-% as well as the fully ionic homopolyesters were prepared by polycondensation in the melt catalyzed by CALB or TBT. Their M n ranged between 20,000 and 5,000 g·mol -1 depending of composition and the type of ionic group that is involved. All the copolyesters were non-water soluble and showed good thermal stability. They were semicrystalline with melting temperatures and enthalpies decreasing with the ionic contents. The interactions interplayed by the ionic groups restricted largely the molecular mobility and caused a significant increase in the melt viscosity and glass transition temperature of PBS and a decrease in crystallization rate.Both ammonium and phosphonium containing PBS copolyesters were able to be coupled with sulfonated PBS to generate ionic polymer blends with modified crystallizability. The presence of both ammoniums and phosphoniums provided PBS with remarkable antimicrobial activity against gram-positive and gram-negative bacteria.

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Biocatalyzed approach for the surface functionalization of poly(L‐lactic acid) films using hydrolytic enzymes

Pellis

Acero

Weber

et al. 2015

Biotechnology Journal

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Poly(lactic acid) as a biodegradable thermoplastic polyester has received increasing attention. This renewable polyester has found applications in a wide range of products such as food packaging, textiles and biomedical devices. Its major drawbacks are poor toughness, slow degradation rate and lack of reactive side-chain groups. An enzymatic process for the grafting of carboxylic acids onto the surface of poly(L-lactic acid) (PLLA) films was developed using Candida antarctica lipase B as a catalyst. Enzymatic hydrolysis of the PLLA film using Humicola insolens cutinase in order to increase the number of hydroxyl and carboxylic groups on the outer polymer chains for grafting was also assessed and showed a change of water contact angle from 74.6 to 33.1° while the roughness and waviness were an order of magnitude higher in comparison to the blank. Surface functionalization was demonstrated using two different techniques, (14) C-radiochemical analysis and X-ray photoelectron spectroscopy (XPS) using (14) C-butyric acid sodium salt and 4,4,4-trifluorobutyric acid as model molecules, respectively. XPS analysis showed that 4,4,4-trifluorobutyric acid was enzymatically coupled based on an increase of the fluor content from 0.19 to 0.40%. The presented (14) C-radiochemical analyses are consistent with the XPS data indicating the potential of enzymatic functionalization in different reaction conditions.

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Candida antarctica Lipase B Catalyzed Synthesis of Poly(butylene succinate): Shorter Chain Building Blocks Also Work

Cited by 18 publications

References 0 publications

Modeling and optimization of lipase-catalyzed production of succinic acid ester using central composite design analysis

Modeling and optimization of lipase-catalyzed production of succinic acid ester using central composite design analysis

Cationic poly(butylene succinate) copolyesters

Biocatalyzed approach for the surface functionalization of poly(L‐lactic acid) films using hydrolytic enzymes

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