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Catalytic Depolymerization of Chitin with Retention of N-Acetyl Group

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Title: Catalytic Depolymerization of Chitin with Retention of N-Acetyl Group
Authors: Yabushita, Mizuho Browse this author
Kobayashi, Hirokazu Browse this author →KAKEN DB
Kuroki, Kyoichi Browse this author
Ito, Shogo Browse this author
Fukuoka, Atsushi Browse this author →KAKEN DB
Keywords: biomass
Issue Date: 23-Nov-2015
Publisher: Wiley-VCH
Journal Title: Chemsuschem
Volume: 8
Issue: 22
Start Page: 3760
End Page: 3763
Publisher DOI: 10.1002/cssc.201501224
PMID: 26538108
Abstract: Chitin, a polymer of N-acetylglucosamine units with -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.
Rights: This is the accepted version of the following article:, which has been published in final form at Chemsuschem, Vol.8(22), November 23, 2015. This article may be used for non-commercial purposes in accordance with the Wiley Self-Archiving Policy [].
Type: article (author version)
Appears in Collections:触媒科学研究所 (Institute for Catalysis) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 福岡 淳

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