Lipase-catalyzed ring-opening polymerization and copolymerization of cyclic dicarbonates

Namekawa, Shuhei; Uyama, Hiroshi; Kobayashi, Shiro; Kricheldorf, Hans R.

doi:10.1002/(sici)1521-3935(20000201)201:2<261::aid-macp261>3.0.co;2-q

Cited by 44 publications

(39 citation statements)

References 17 publications

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“…[21] The formation of random copolymers, in spite of the different enzymatic polymerizability of these lactones, suggests the frequent occurrence of transesterification during the copolymerization. The lipase-catalyzed synthesis of random ester/carbonate copolymers has been achieved from a combination of lactone and cyclic dicarbonate [22] and of lactide and trimethylene carbonate. [23] Demonstrated recently was the copolymerization of lactones, dicarboxylic acid divinyl esters and glycols using Pseudomonas family lipases and Candida antarctica lipase (lipase CA) to give the corresponding ester copolymers, in which two different types of polymerization, ring-opening polymerization and polycondensation, as well as transesterification, simultaneously occurred via the same reaction intermediate ("acyl-lipase intermediate") [17] to give the copolymer with a relatively high degree of randomness.…”

Section: Introductionmentioning

confidence: 62%

Lipase-Catalyzed Transesterification of Polyesters to Ester Copolymers

et al. 2001

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Section: Introductionmentioning

confidence: 62%

Lipase-Catalyzed Transesterification of Polyesters to Ester Copolymers

et al. 2001

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“…[152] The lipase-catalyzed ring-opening polymerization and copolymerization of novel cyclic dicarbonates were reported by Namekawa et al as shown in Scheme 32. [153] That is, the ring-opening polymerization of cyclic dicarbonate, cyclobis(hexamethylene carbonate) and cyclobis(diethylene glycol carbonate), and the enzymatic copolymerization with lactones, such as 12-dodecanolide, have been carried out using lipase CA.…”

Section: Ring-opening Polymerization Andmentioning

confidence: 99%

Enzyme-Catalyzed Synthesis and Chemical Recycling of Polyesters

Matsumura¹

2002

Macromol. Biosci.

112

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This article summarizes the enzyme‐catalyzed synthesis and chemical recycling of biodegradable aliphatic polyesters and poly(carbonate ester)s directed towards establishing green polymer chemistry. Lipase catalyzes the condensation polymerization of a hydroxy acid, diacid with diol, diacid anhydride with oxirane, and polyanhydride with diol, or the ring‐opening polymerization of lactones of small to large rings, and a cyclic diester to produce the corresponding polyesters. Also, lipase catalyzes the condensation polymerization of a dialkyl carbonate with diol, and the ring‐opening polymerization of a cyclic carbonate to produce the corresponding polycarbonates. These polyesters and polycarbonates were selectively degraded by lipase to produce repolymerizable oligomers. These chemical recycling systems using an enzyme will establish a novel methodology for sustainable polymer recycling. Finally, current trends in green polymer production using enzymes are discussed.

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“…In order to create the sustainable polymer production and recycling system as shown in Scheme , a direct production method for TMC, using dimethyl carbonate and 1,3‐propanediol, is needed. The enzyme‐catalyzed ring‐opening homopolymerization of TMC11–13 and related compounds, 5‐methyl‐5‐benzyloxycarbonyl‐1,3‐dioxan‐2‐one14 and cyclic dicarbonates,15 and the ring‐opening copolymerization of TMC with lactide,16 ε ‐caprolactone,17 5‐methyl‐5‐benzyloxycarbonyl‐1,3‐dioxan‐2‐one,18 and ω ‐pentadecalactone19 have already been reported.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic Synthesis and Polymerization of Cyclic Trimethylene Carbonate Monomer with/without Methyl Substituent

Tasaki

Toshima

Matsumura

2003

Macromolecular Bioscience

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The direct enzymatic synthesis of a cyclic trimethylene carbonate (1,3‐dioxane‐2‐one) monomer with/without a methyl substituent was carried out using dimethyl or diethyl carbonate and 1,3‐diol with the objective of producing aliphatic poly(trimethylene carbonate), a typical biodegradable synthetic plastic. The lipase‐catalyzed condensation of dimethyl or diethyl carbonate with aliphatic 1,3‐diols using immobilized Candida antarctica lipase (lipase CA) in an organic solvent at 70 °C afforded the corresponding methyl‐substituted and unsubstituted cyclic trimethylene carbonates. The cyclic trimethylene carbonates obtained by the reaction of dimethyl or diethyl carbonates with 1,3‐propanediol and 2‐methyl‐1,3‐propanediol were polymerized by lipase to produce the corresponding polycarbonates.Total TMC yield as a function of the reaction time.magnified imageTotal TMC yield as a function of the reaction time.

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Lipase-catalyzed ring-opening polymerization and copolymerization of cyclic dicarbonates

Cited by 44 publications

References 17 publications

Lipase-Catalyzed Transesterification of Polyesters to Ester Copolymers

Lipase-Catalyzed Transesterification of Polyesters to Ester Copolymers

Enzyme-Catalyzed Synthesis and Chemical Recycling of Polyesters

Enzymatic Synthesis and Polymerization of Cyclic Trimethylene Carbonate Monomer with/without Methyl Substituent

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