Synthesis of metal-free poly(1,4-dioxan-2-one) by enzyme-catalyzed ring-opening polymerization

Nishida, Haruo; Yokota, Mitsuhiro; Nagashima, Masumi; Endō, Takeshi; Tokiwa, Yutaka

doi:10.1002/(sici)1099-0518(20000501)38:9<1560::aid-pola20>3.0.co;2-f

Cited by 82 publications

(54 citation statements)

References 26 publications

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“…Various substituted lactones were used for enzymatic polyester synthesis via ROP: [104] , α -methyl -ε -caprolactone [96] , α -methyl -δ -valerolactone [96] , 1,4 -dioxane -2 -one [91] , and others (see also Table 4.2 ).…”

Section: Substituted Lactonesmentioning

confidence: 99%

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Enzymatic Polymerization of Polyester

Miletić¹,

Loos²,

Gross³

2010

Biocatalysis in Polymer Chemistry

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Section: Substituted Lactonesmentioning

confidence: 99%

“…Similarly, Nishida et al . [91] carried out enzymatic ROP of 1,4 -dioxan -2 -one at 60 ° C catalyzed by Novozym 435 that resulted in a polymer with M w = 41000 in 77% yield.…”

Section: Cyclic Ester Related Monomersmentioning

confidence: 99%

Enzymatic Polymerization of Polyester

Miletić¹,

Loos²,

Gross³

2010

Biocatalysis in Polymer Chemistry

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“…[92] Also, the 6-membered 1,4-dioxan-2-one polymerized at 60 8C by lipase CA produced the metal-free poly(1,4-dioxan-2-one) with the highest molecular weight, M -w , of 41 000 (Scheme 19). [93] Among these lactones, CL has been the most extensively studied with respect to the lipase-catalyzed poly- merization. [94 -98] Kumar and Gross reported that toluene appeared to help stabilize lipase CA so that the lipase-catalyzed polymerization could be effectively conducted at 90 8C.…”

Section: Condensation Polymerizationmentioning

confidence: 99%

Enzyme-Catalyzed Synthesis and Chemical Recycling of Polyesters

Matsumura¹

2002

Macromol. Biosci.

113

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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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“…For ROP, various catalysts have been employed including metal catalyst such as Sn(Oct) 2 , AlEt 3 , and derivatives of Ti, Zr, and Hg [23][24][25]. To minimize harmful effects of metallic residues in medically applied PPDO, some nontoxic catalysts have also been investigated, including diethyl zinc, zinc lactate, and recently enzymatic catalysis [9,26,27]. Enzymatic polymerization in vitro has become an area of increasing research activity as a new environment-friendly methodology for material synthesis.…”

Section: Introductionmentioning

confidence: 99%

Graft polymerization of p-dioxanone onto polyhydroxyethylaspartamide through ring-opening polymerization using organometallic and enzyme catalysts

Park

Ramaraj

Yoon

2012

Designed Monomers and Polymers

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The grafting of poly(p-dioxanaone) (PPDO) onto β-poly(N-2-hydroxyethyl)-DL-aspartamide (PHEA) was achieved, first, by synthesis of polysuccinimide (PSI) from DL-aspartic acid through thermal condensation polymerization, and then, followed by aminolysis of PSI to form PHEA with hydroxyl end groups, and finally the PPDO was grafted onto PHEA through these hydroxyl end groups by ring-opening polymerization (ROP) of PDO in the presence of tin octoate [Sn (Oct) 2 ] and Candida Antarctica Lipase B (Novozyme 435) catalysts. Evidence of grafting was obtained by comparing Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), X-ray diffraction (XRD) analysis, polarized optical microscopy (POM), proton nuclear magnetic resonance ( 1 H-NMR) spectroscopy, and solubility characteristics of PHEA with PPDO-grafted copolymers (PHEA-g-PPDO). The FT-IR spectroscopic analysis reveals the formation of ester linkage between PPDO and hydroxyl end groups of PHEA. TGA analysis shows a quite different thermal profile for grafted polymers. DSC and XRD results reveal the existence of graft copolymer in two different crystalline forms. POM shows banded spherulitic morphology for the graft copolymers. The grafting of PPDO was further confirmed by 1 H-NMR. Eventhough, graft copolymer was obtained by both these methods, the graft copolymer obtained by enzyme catalyzed ROP shows higher crystalline order, better spherulitic morphology, and solubility characteristics than that of the graft polymer obtained by organometal catalyzed ROP.

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Synthesis of metal-free poly(1,4-dioxan-2-one) by enzyme-catalyzed ring-opening polymerization

Cited by 82 publications

References 26 publications

Enzymatic Polymerization of Polyester

Enzymatic Polymerization of Polyester

Enzyme-Catalyzed Synthesis and Chemical Recycling of Polyesters

Graft polymerization of p-dioxanone onto polyhydroxyethylaspartamide through ring-opening polymerization using organometallic and enzyme catalysts

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