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

Reiko Kondo; Kazunobu Toshima; Shuichi Matsumura

doi:10.1002/1616-5195(200208)2:6<267::AID-MABI267>3.0.CO;2-F

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

Reiko Kondo, Kazunobu Toshima, Shuichi Matsumura

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

26 Citations (Scopus)

Abstract

The lipase-catalyzed selective transformation of poly(ε-caprolactone) (pcl) into dicaprolactone (dcl: 1,8-dioxacyclotetradecane-2,9-dione) and the repolymerization of dcl in supercritical carbon dioxide (scco₂) were carried out for the establishment of a sustainable green polymer chemistry for pcl. Pcl with a number-average molecular weight of m̄_n = 110 000 was selectively transformed into repolymerizable cyclic dcl in 90% yield using immobilized candida antarctica lipase (lipase ca) in scco₂ fluid by compression to 18 mpa in the presence of a small amount of water at 40 °c. The dcl obtained such was readily polymerized by lipase ca in scco₂ to produce a pcl with an m̄_n of 33 000 after 6 h.

Original language	English
Pages (from-to)	267-271
Number of pages	5
Journal	Macromolecular Bioscience
Volume	2
Issue number	6
DOIs	https://doi.org/10.1002/1616-5195(200208)2:6<267::AID-MABI267>3.0.CO;2-F
Publication status	Published - 2002 Dec 1

Keywords

Biodegradable
Chemical recycling
Enzymes
Polyesters
Supercritical carbon dioxide

ASJC Scopus subject areas

Biotechnology
Bioengineering
Biomaterials
Polymers and Plastics
Materials Chemistry

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

abstract = "The lipase-catalyzed selective transformation of poly(ε-caprolactone) (pcl) into dicaprolactone (dcl: 1,8-dioxacyclotetradecane-2,9-dione) and the repolymerization of dcl in supercritical carbon dioxide (scco2) were carried out for the establishment of a sustainable green polymer chemistry for pcl. Pcl with a number-average molecular weight of {\=m}n = 110 000 was selectively transformed into repolymerizable cyclic dcl in 90% yield using immobilized candida antarctica lipase (lipase ca) in scco2 fluid by compression to 18 mpa in the presence of a small amount of water at 40 °c. The dcl obtained such was readily polymerized by lipase ca in scco2 to produce a pcl with an {\=m}n of 33 000 after 6 h.",

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author = "Reiko Kondo and Kazunobu Toshima and Shuichi Matsumura",

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AU - Kondo, Reiko

AU - Toshima, Kazunobu

AU - Matsumura, Shuichi

PY - 2002/12/1

Y1 - 2002/12/1

N2 - The lipase-catalyzed selective transformation of poly(ε-caprolactone) (pcl) into dicaprolactone (dcl: 1,8-dioxacyclotetradecane-2,9-dione) and the repolymerization of dcl in supercritical carbon dioxide (scco2) were carried out for the establishment of a sustainable green polymer chemistry for pcl. Pcl with a number-average molecular weight of m̄n = 110 000 was selectively transformed into repolymerizable cyclic dcl in 90% yield using immobilized candida antarctica lipase (lipase ca) in scco2 fluid by compression to 18 mpa in the presence of a small amount of water at 40 °c. The dcl obtained such was readily polymerized by lipase ca in scco2 to produce a pcl with an m̄n of 33 000 after 6 h.

AB - The lipase-catalyzed selective transformation of poly(ε-caprolactone) (pcl) into dicaprolactone (dcl: 1,8-dioxacyclotetradecane-2,9-dione) and the repolymerization of dcl in supercritical carbon dioxide (scco2) were carried out for the establishment of a sustainable green polymer chemistry for pcl. Pcl with a number-average molecular weight of m̄n = 110 000 was selectively transformed into repolymerizable cyclic dcl in 90% yield using immobilized candida antarctica lipase (lipase ca) in scco2 fluid by compression to 18 mpa in the presence of a small amount of water at 40 °c. The dcl obtained such was readily polymerized by lipase ca in scco2 to produce a pcl with an m̄n of 33 000 after 6 h.

KW - Biodegradable

KW - Chemical recycling

KW - Enzymes

KW - Polyesters

KW - Supercritical carbon dioxide

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

Abstract

Keywords

ASJC Scopus subject areas

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