Lipase-catalyzed enantioselective synthesis of (R,R)-lactide from alkyl lactate to produce PDLA (poly D-lactic acid) and stereocomplex PLA (poly lactic acid)

Byoung Wook Jeon, Jumin Lee, Hyun Sook Kim, Dae Haeng Cho, Hyuk Lee, Rakwoo Chang, Yong Hwan Kim

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

R-lactide, a pivotal monomer for the production of poly (D-lactic acid) (PDLA) or stereocomplex poly (lactic acid) (PLA) was synthesized from alkyl (R)-lactate through a lipase-catalyzed reaction without racemization. From among several types of lipase, only lipase B from Candida antarctica (Novozym 435; CAL-B) was effective in the reaction that synthesized (R,. R)-lactide. Enantiopure (R,. R)-lactide, which consisted of over 99% enantiomeric excess, was synthesized from methyl (R)-lactate through CAL-B catalysis. Removal of the methanol by-product was critical to obtain a high level of lactide conversion. The (R,. R)-lactide yield was 56% in a reaction containing 100. mg of Novozym 435, 10. mM methyl (R)-lactate and 1500. mg of molecular sieve 5. A in methyl tert-butyl ether (MTBE). The important monomer (R,. R)-lactide that is required for the production of the widely recognized bio-plastic PDLA and the PLA stereocomplex can be obtained using this novel synthetic method.

Original languageEnglish
Pages (from-to)201-207
Number of pages7
JournalJournal of Biotechnology
Volume168
Issue number2
DOIs
StatePublished - Oct 2013

Keywords

  • (R,R)-lactide
  • Alkyl (R)-lactate
  • Lipase
  • Molecular sieve
  • Novozym 435

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