Catalytic Depolymerization of Chitin with Retention of N-Acetyl Group

Mizuho Yabushita, Hirokazu Kobayashi, Kyoichi Kuroki, Shogo Ito, Atsushi Fukuoka

Research output: Contribution to journalArticlepeer-review

41 Citations (Scopus)

Abstract

Chitin, a polymer of N-acetylglucosamine units with β-1,4-glycosidic linkages, is the most abundant marine biomass. Chitin monomers containing N-acetyl groups are useful precursors to various fine chemicals and medicines. However, the selective conversion of robust chitin to N-acetylated monomers currently requires a large excess of acid or a long reaction time, which limits its application. We demonstrate a fast catalytic transformation of chitin to monomers with retention of N-acetyl groups by combining mechanochemistry and homogeneous catalysis. Mechanical-force-assisted depolymerization of chitin with a catalytic amount of H2SO4 gave soluble short-chain oligomers. Subsequent hydrolysis of the ball-milled sample provided N-acetylglucosamine in 53 % yield, and methanolysis afforded 1-O-methyl-N-acetylglucosamine in yields of up to 70 %. Our process can greatly reduce the use of acid compared to the conventional process.

Original languageEnglish
Pages (from-to)3760-3763
Number of pages4
JournalChemSusChem
Volume8
Issue number22
DOIs
Publication statusPublished - 2015 Nov 23
Externally publishedYes

Keywords

  • biomass
  • catalysis
  • chitin
  • hydrolysis
  • mechanochemistry

ASJC Scopus subject areas

  • Environmental Chemistry
  • Chemical Engineering(all)
  • Materials Science(all)
  • Energy(all)

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