Enzyme-Catalyzed Ring-Opening Polymerization of Four-Membered Lactones: Preparation of Poly(β-propiolactone) and Poly(β-malic acid)

Shuichi Matsumura, Hideki Beppu, Kazunobu Toshima

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Lipase-catalyzed ring-opening polymerization of β-propiolactone (PL) and benzyl β-malolactonate (BM) was studied with respect to the influence of reaction conditions on molecular weight of the polymers and the monomer conversion. PL and BM were polymerized in bulk using lipase as a catalyst to yield the corresponding polyesters having molecular weights of greater than 50,000 and 7,000, respectively. It was found that the molecular weight of poly(β-propiolactone) produced by the lipase-catalyzed polymerization of PL was inversely dependent on the concentration of lipase. Both molecular weight and polymerization speed were increased with increasing reaction temperature from 40 to 60°C. BM was readily polymerized by porcine pancreatic lipase or Novozym 435 lipase at 60°C to yield poly(benzyl β-malate), which was readily debenzylated by catalytic hydrogenolysis to form poly(β-malic acid). This polyester was readily biodegraded both by the aerobic and anaerobic microbes.

Original languageEnglish
Pages (from-to)74-89
Number of pages16
JournalACS Symposium Series
Volume684
Publication statusPublished - 1998

Fingerprint

Propiolactone
Ring opening polymerization
Lipases
Lactones
Lipase
Enzymes
Acids
Molecular weight
Polyesters
Polymerization
Hydrogenolysis
poly(malic acid)
Polymers
Monomers
Catalysts

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Enzyme-Catalyzed Ring-Opening Polymerization of Four-Membered Lactones : Preparation of Poly(β-propiolactone) and Poly(β-malic acid). / Matsumura, Shuichi; Beppu, Hideki; Toshima, Kazunobu.

In: ACS Symposium Series, Vol. 684, 1998, p. 74-89.

Research output: Contribution to journalArticle

@article{6c862a499d8c4732a8406af8e5269d9f,
title = "Enzyme-Catalyzed Ring-Opening Polymerization of Four-Membered Lactones: Preparation of Poly(β-propiolactone) and Poly(β-malic acid)",
abstract = "Lipase-catalyzed ring-opening polymerization of β-propiolactone (PL) and benzyl β-malolactonate (BM) was studied with respect to the influence of reaction conditions on molecular weight of the polymers and the monomer conversion. PL and BM were polymerized in bulk using lipase as a catalyst to yield the corresponding polyesters having molecular weights of greater than 50,000 and 7,000, respectively. It was found that the molecular weight of poly(β-propiolactone) produced by the lipase-catalyzed polymerization of PL was inversely dependent on the concentration of lipase. Both molecular weight and polymerization speed were increased with increasing reaction temperature from 40 to 60°C. BM was readily polymerized by porcine pancreatic lipase or Novozym 435 lipase at 60°C to yield poly(benzyl β-malate), which was readily debenzylated by catalytic hydrogenolysis to form poly(β-malic acid). This polyester was readily biodegraded both by the aerobic and anaerobic microbes.",
author = "Shuichi Matsumura and Hideki Beppu and Kazunobu Toshima",
year = "1998",
language = "English",
volume = "684",
pages = "74--89",
journal = "ACS Symposium Series",
issn = "0097-6156",
publisher = "American Chemical Society",

}

TY - JOUR

T1 - Enzyme-Catalyzed Ring-Opening Polymerization of Four-Membered Lactones

T2 - Preparation of Poly(β-propiolactone) and Poly(β-malic acid)

AU - Matsumura, Shuichi

AU - Beppu, Hideki

AU - Toshima, Kazunobu

PY - 1998

Y1 - 1998

N2 - Lipase-catalyzed ring-opening polymerization of β-propiolactone (PL) and benzyl β-malolactonate (BM) was studied with respect to the influence of reaction conditions on molecular weight of the polymers and the monomer conversion. PL and BM were polymerized in bulk using lipase as a catalyst to yield the corresponding polyesters having molecular weights of greater than 50,000 and 7,000, respectively. It was found that the molecular weight of poly(β-propiolactone) produced by the lipase-catalyzed polymerization of PL was inversely dependent on the concentration of lipase. Both molecular weight and polymerization speed were increased with increasing reaction temperature from 40 to 60°C. BM was readily polymerized by porcine pancreatic lipase or Novozym 435 lipase at 60°C to yield poly(benzyl β-malate), which was readily debenzylated by catalytic hydrogenolysis to form poly(β-malic acid). This polyester was readily biodegraded both by the aerobic and anaerobic microbes.

AB - Lipase-catalyzed ring-opening polymerization of β-propiolactone (PL) and benzyl β-malolactonate (BM) was studied with respect to the influence of reaction conditions on molecular weight of the polymers and the monomer conversion. PL and BM were polymerized in bulk using lipase as a catalyst to yield the corresponding polyesters having molecular weights of greater than 50,000 and 7,000, respectively. It was found that the molecular weight of poly(β-propiolactone) produced by the lipase-catalyzed polymerization of PL was inversely dependent on the concentration of lipase. Both molecular weight and polymerization speed were increased with increasing reaction temperature from 40 to 60°C. BM was readily polymerized by porcine pancreatic lipase or Novozym 435 lipase at 60°C to yield poly(benzyl β-malate), which was readily debenzylated by catalytic hydrogenolysis to form poly(β-malic acid). This polyester was readily biodegraded both by the aerobic and anaerobic microbes.

UR - http://www.scopus.com/inward/record.url?scp=0008857004&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0008857004&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0008857004

VL - 684

SP - 74

EP - 89

JO - ACS Symposium Series

JF - ACS Symposium Series

SN - 0097-6156

ER -