Lipase-catalyzed transformation of poly(lactic acid) into cyclic oligomers

Yosuke Takahashi, Sachiko Okajima, Kazunobu Toshima, Shuichi Matsumura

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

Enzymatic transformations into cyclic oligomers were carried out with the objective of developing chemical recycling of poly(lactic acid)s, such as poly(D),L-lactic acid) (PDLLA), poly(D-lactic acid) (PDLA) and poly(L-lactic acid) (PLLA), which are typical biodegradable polymers. They were degraded by lipase in an organic solvent to produce the corresponding cyclic oligomer with a molecular weight of several hundreds. PDLLA (with a M̄W of 84 000) was quantitatively transformed into cyclic oligomers by lipase RM (Lipozyme RM IM) in chloroform/hexane at 60 °C. PLLA (with a M̄R of 120 000) was transformed into cyclic oligomer by lipase CA (Novozym 435) at a higher temperature of 100 °C in o-xylene. The oligomer structure was identified by 1H and 13C NMR spectroscopy and MALDI-TOF (matrix assisted laser desorption/ionization-time-of-flight) mass spectrometry.

Original languageEnglish
Pages (from-to)346-353
Number of pages8
JournalMacromolecular Bioscience
Volume4
Issue number3
DOIs
Publication statusPublished - 2004 Mar 15

Fingerprint

Lipases
Lactic acid
Lipase
Oligomers
Lactic Acid
Biodegradable polymers
Hexanes
Chloroform
Organic solvents
Nuclear magnetic resonance spectroscopy
Recycling
Ionization
Mass spectrometry
Xylene
Chlorine compounds
Hexane
Desorption
Molecular weight
poly(lactic acid)
Mass Spectrometry

Keywords

  • Degradation
  • Enzymes
  • Oligomers
  • Poly(lactic acid)
  • Recycling

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biomaterials
  • Polymers and Plastics
  • Materials Chemistry
  • Bioengineering

Cite this

Lipase-catalyzed transformation of poly(lactic acid) into cyclic oligomers. / Takahashi, Yosuke; Okajima, Sachiko; Toshima, Kazunobu; Matsumura, Shuichi.

In: Macromolecular Bioscience, Vol. 4, No. 3, 15.03.2004, p. 346-353.

Research output: Contribution to journalArticle

Takahashi, Yosuke ; Okajima, Sachiko ; Toshima, Kazunobu ; Matsumura, Shuichi. / Lipase-catalyzed transformation of poly(lactic acid) into cyclic oligomers. In: Macromolecular Bioscience. 2004 ; Vol. 4, No. 3. pp. 346-353.
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