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

Reiko Kondo; Kazunobu Toshima; Shuichi Matsumura

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

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.

Original language	English
Pages (from-to)	267-271
Number of pages	5
Journal	Macromolecular Chemistry and Physics
Volume	203
Issue number	12
Publication status	Published - 2002 Aug 30

Keywords

Biodegradable
Chemical recycling
Enzymes
Polyesters
Supercritical carbon dioxide

ASJC Scopus subject areas

Condensed Matter Physics
Physical and Theoretical Chemistry
Polymers and Plastics
Organic Chemistry
Materials Chemistry

Cite this

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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 Mn= 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 Mn of 33 000 after 6 h.",

keywords = "Biodegradable, Chemical recycling, Enzymes, Polyesters, Supercritical carbon dioxide",

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

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language = "English",

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T1 - Lipase-catalyzed selective transformation of polycaprolactone into cyclic dicaprolactone and its repolymerization in supercritical carbon dioxide

AU - Kondo, Reiko

AU - Toshima, Kazunobu

AU - Matsumura, Shuichi

PY - 2002/8/30

Y1 - 2002/8/30

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 Mn= 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 Mn 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 Mn= 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 Mn of 33 000 after 6 h.

KW - Biodegradable

KW - Chemical recycling

KW - Enzymes

KW - Polyesters

KW - Supercritical carbon dioxide

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SN - 1022-1352

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ER -

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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