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

Reiko Kondo, Kazunobu Toshima, Shuichi Matsumura

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)267-271
Number of pages5
JournalMacromolecular Chemistry and Physics
Volume203
Issue number12
Publication statusPublished - 2002 Aug 30

Fingerprint

polymer chemistry
Polycaprolactone
Lipases
Dione
Antarctic regions
Lipase
Carbon Dioxide
carbon dioxide
molecular weight
Carbon dioxide
fluids
water
Candida
Polymers
Compaction
Molecular weight
Fluids
polycaprolactone
1,8-dioxacyclotetradecane-2,9-dione
Water

Keywords

  • Biodegradable
  • Chemical recycling
  • Enzymes
  • Polyesters
  • Supercritical carbon dioxide

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Polymers and Plastics

Cite this

Lipase-catalyzed selective transformation of polycaprolactone into cyclic dicaprolactone and its repolymerization in supercritical carbon dioxide. / Kondo, Reiko; Toshima, Kazunobu; Matsumura, Shuichi.

In: Macromolecular Chemistry and Physics, Vol. 203, No. 12, 30.08.2002, p. 267-271.

Research output: Contribution to journalArticle

@article{23c0af3be9cb424f9375ac91e532d4d6,
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",
year = "2002",
month = "8",
day = "30",
language = "English",
volume = "203",
pages = "267--271",
journal = "Macromolecular Chemistry and Physics",
issn = "1022-1352",
publisher = "Wiley-VCH Verlag",
number = "12",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=0037200501&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037200501&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0037200501

VL - 203

SP - 267

EP - 271

JO - Macromolecular Chemistry and Physics

JF - Macromolecular Chemistry and Physics

SN - 1022-1352

IS - 12

ER -