Lipase-catalyzed selective transformation of polycaprolactone into cyclic dicaprolactone and its repolymerization in supercritical carbon dioxide

Kondo, Reiko; Toshima, Kazunobu; Matsumura, Shuichi

doi:10.1002/1616-5195(200208)2:6<267::aid-mabi267>3.0.co;2-f

Cited by 31 publications

(22 citation statements)

References 11 publications

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“…In this report, the degradation of P(3HB‐ co ‐3HHx) and P(3HB‐ co ‐3HV), which showed a practical significance, was analyzed using immobilized lipase GCA with respect to the reaction conditions and compared with the degradation by PHBDP. In our previous reports, lipase CA was used instead of lipase GCA for the degradation of polyesters 5,10–15. Both lipase GCA immobilized on hydrophilic silica and lipase CA immobilized on acrylic resin showed the same degradation and repolymerization profiles towards microbial PHAs.…”

Section: Resultsmentioning

confidence: 99%

“…It was previously reported that the typical chemically synthesized biodegradable plastics, such as poly( ε ‐caprolactone), poly(alkylene alkanedioate), and poly( L ‐lactic acid), were readily transformed into the corresponding cyclic oligomers by lipase in diluted organic solvents and supercritical carbon dioxide. The oligomers were readily repolymerized to produce the corresponding polymers 10–15. Kobayashi et al also reported the enzymatic hydrolytic degradation of aliphatic polyesters as a polymer recycling 16–18.…”

Section: Introductionmentioning

confidence: 99%

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Enzymatic Transformation of Bacterial Polyhydroxyalkanoates into Repolymerizable Oligomers Directed towards Chemical Recycling

Kaihara

Osanai

Nishikawa

et al. 2005

Macromolecular Bioscience

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The enzymatic transformation into an oligomer was carried out with the objective of developing the chemical recycling of bacterial polyesters. Poly(R-3-hydroxyalkanoate)s (PHAs), such as poly[(R-3-hydroxybutyrate)-co-12%(R-3-hydroxyhexanoate)] and poly[(R-3-hydroxybutyrate)-co-12%(R-3-hydroxyvalerate)], were degraded by granulated Candida antarctica lipase B immobilized on hydrophilic silica (lipase GCA) in a diluted organic solvent at 70 degrees C. The degradation products were cyclic oligomers having a molecular weight of a few hundreds. The obtained cyclic oligomer was readily repolymerized by the same lipase (lipase GCA) to produce the corresponding polyester in a concentrated solution. The cyclic oligomer was copolymerized with epsilon-caprolactone using lipase to produce the corresponding terpolymers having an Mw of 21,000. This is the first example of the enzymatic chemical recycling of bacterial PHAs using lipase. Poly(R-3-hydroxybutyrate) [P(3HB)] was also degraded into the linear-type R-3HB monomer to trimer by P(3HB)-depolymerase (PHBDP) in phosphate buffer at 37 degrees C. The degradation using PHBDP required a longer reaction time compared with the lipase-catalyzed degradation in organic solvent. The monomer composition of the oligomer depended on the origin of the PHBDP. The R-3HB monomer was predominately produced by PHBDP from Pseudomonas stutzeri, while the R-3HB dimer was produced by PHBDP from Alcaligenes faecalis T1. Repolymerization of these oligomers by lipase in concentrated organic solvent produced a relatively low-molecular-weight P(3HB) (e.g., Mw=2,000). Degradation of P(3HB) by lipase in organic solvent into repolymerizable cyclic oligomer and degradation of P(3HB) by PHBDP in buffer into hydroxy acid type R-3HB dimer.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enzymatic Transformation of Bacterial Polyhydroxyalkanoates into Repolymerizable Oligomers Directed towards Chemical Recycling

Kaihara

Osanai

Nishikawa

et al. 2005

Macromolecular Bioscience

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“…Furthermore, poly(e-CL) was selectively transformed into cyclic dicaprolactone in scCO 2 , which was polymerized with lipase CA to produce high-molecularweight poly(e-CL). [188] Besides poly(e-CL), various polyesters were subjected to lipase-catalyzed hydrolytic degradation. Poly[(R,S)-3-hydroxybutyrate] was transformed into cyclic oligomers with molecular weights of 500 using lipase CA as a catalyst.…”

Section: In-vitro Enzymatic Synthesis Of Aliphatic Polyestersmentioning

confidence: 41%

Biomacromolecules and Bio‐Related Macromolecules

Kobayashi

Uyama

2003

Macro Chemistry & Physics

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The present article briefly reviews research developments in the area of biomacromolecules and bio‐related macromolecules, whose research papers have been published for several decades preferably in the Macromolecular Journals. The area covers the important classes of macromolecules, polysaccharides (cellulose, amylose, chitin, etc.), polyesters (poly(lactic acid), poly(hydroxyalkanoate)s, etc.), and phenolic polymers (lignin, urushi, etc.). These polymers and their derivatives are very important for scientific interests as well as for industrial applications. Their synthesis, structure, reactions, and properties are mainly mentioned, and important topics of the target polymers are selected and mostly chronologically reviewed.

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“…Beckman and co-workers have reported the inverse emulsion polymerization of acrylamide in scCO 2 [68]. Much work has been performed on precipitation polymerization, such as the polymerization of vinyl ethers and oxetanes [63], the continuous polymerization of vinylidene fluoride as well as of acrylic acid [71,72], MMA polymerization initiated by ultrasound [73], the catalytic polymerization of olefins [74,75] and the enzymatic polymerization to polycaprolactone [76]. Macroporous beads of trimethylolpropane trimethacrylate (TRIM) can be synthesized by means of suspension polymerization [70].…”

Section: Polymerization Processes In Supercritical Carbon Dioxidementioning

confidence: 99%

Recent Developments in Polymer Processes

Kemmere¹

2005

Handbook of Polymer Reaction Engineering

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Lipase-catalyzed selective transformation of polycaprolactone into cyclic dicaprolactone and its repolymerization in supercritical carbon dioxide

Cited by 31 publications

References 11 publications

Enzymatic Transformation of Bacterial Polyhydroxyalkanoates into Repolymerizable Oligomers Directed towards Chemical Recycling

Enzymatic Transformation of Bacterial Polyhydroxyalkanoates into Repolymerizable Oligomers Directed towards Chemical Recycling

Biomacromolecules and Bio‐Related Macromolecules

Recent Developments in Polymer Processes

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