Lipase-catalyzed synthesis of poly(1,4-butyl sebacate) from sebacic acid or its derivatives with 1,4-butanediol

Linko, Yu‐Yen; Wang, Zhuolin; Seppälä, Jukka

doi:10.1016/0168-1656(95)00039-s

Cited by 68 publications

(47 citation statements)

References 16 publications

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“…[234] The other breakthrough in this methodw as the use of immobilized enzymes. Molar mass could be thus quadrupled simply by modifying the pressure in the reaction mixture.…”

Section: Proteasesmentioning

confidence: 98%

“…[232] However,s ome lipases,s uch as CALB or those from R. miehei and P. cepacia,e xhibitedi nteresting results, with M n > 10 000 gmol À1 for divinyl dicarboxylate substrates. [234] This halogenation methodwas widely used in early studies during which processes weren ot optimized. Compared with water,m ethanol, or ethanol leaving groups, the halogenated moiety increasedthe electrophilicity of the acyl carbonyl to avoid significant alcoholysis of the products by decreasing the nucleophilicity of the leaving alkoxyg roups.…”

Section: Proteasesmentioning

confidence: 99%

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Biotic and Abiotic Synthesis of Renewable Aliphatic Polyesters from Short Building Blocks Obtained from Biotechnology

2018

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Biobased polymers have seen their attractiveness increase in recent decades thanks to the significant development of biorefineries to allow access to a wide variety of biobased building blocks. Polyesters are one of the best examples of the development of biobased polymers because most of them now have their monomers produced from renewable resources and are biodegradable. Currently, these polyesters are mainly produced by using traditional chemical catalysts and harsh conditions, but recently greener pathways with nontoxic enzymes as biocatalysts and mild conditions have shown great potential. Bacterial polyesters, such as poly(hydroxyalkanoate)s (PHA), are the best example of the biotic production of high molar mass polymers. PHAs display a wide variety of macromolecular architectures, which allow a large range of applications. The present contribution aims to provide an overview of recent progress in studies on biobased polyesters, especially those made from short building blocks, synthesized through step-growth polymerization. In addition, some important technical aspects of their syntheses through biotic or abiotic pathways have been detailed.

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“…[234] The other breakthrough in this methodw as the use of immobilized enzymes. Molar mass could be thus quadrupled simply by modifying the pressure in the reaction mixture.…”

Section: Proteasesmentioning

confidence: 98%

Section: Proteasesmentioning

confidence: 99%

Biotic and Abiotic Synthesis of Renewable Aliphatic Polyesters from Short Building Blocks Obtained from Biotechnology

2018

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“…High-molecular-weight polyesters were enzymatically obtained by the polymerization of sebacic acid and 1,4-butanediol under vacuum [30,31]. In lipase MM-catalyzed polymerization in hydrophobic solvents of high boiling points such as diphenyl ether and veratrole using a programmed vacuum profile, the molecular weight reached higher than 4 × 10 4 .…”

Section: Dicarboxylic Acidsmentioning

confidence: 99%

Enzymatic Synthesis of Polyesters via Polycondensation

Uyama

Kobayashi

Advances in Polymer Science

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“…[22] Previous studies of lipase-catalyzed polycondensation have limited to the esterification at the primary hydroxyl group for the formation of linear aliphatic polyesters containing pendant secondary hydroxyl groups, which might be due to the regioselectivity of lipases. [32][33][34][35][36][37] It would be, however, one of the approaches for synthesizing aliphatic polyesters that contains structural complexity to utilize the esterification at secondary hydroxyl groups of diols. In this study, we report lipase B-catalyzed polycondensation reaction between a diacid (sebacic acid) and the diols bearing both primary and secondary hydroxyl groups (glycerol, 1,2-propanediol, 1,3-butanediol, 2,3-butanediol, and 2,4-pentanediol) (Fig.…”

Section: Introductionmentioning

confidence: 99%

Polycondensation of Sebacic Acid with Primary and Secondary Hydroxyl Groups Containing Diols Catalyzed by Candida antarctica Lipase B

Yoon

Hong

Kong

et al. 2012

Synthetic Communications

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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 C for 72 h. The resulting polymers were characterized by 1 H and 13 C NMR spectroscopy, Fourier transform-infrared spectroscopy, thermogravimetric analysis, and gel permeation chromatography.

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Lipase-catalyzed synthesis of poly(1,4-butyl sebacate) from sebacic acid or its derivatives with 1,4-butanediol

Cited by 68 publications

References 16 publications

Biotic and Abiotic Synthesis of Renewable Aliphatic Polyesters from Short Building Blocks Obtained from Biotechnology

Biotic and Abiotic Synthesis of Renewable Aliphatic Polyesters from Short Building Blocks Obtained from Biotechnology

Enzymatic Synthesis of Polyesters via Polycondensation

Polycondensation of Sebacic Acid with Primary and Secondary Hydroxyl Groups Containing Diols Catalyzed by Candida antarctica Lipase B

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