Premium
Catalytic Depolymerization of Chitin with Retention of N ‐Acetyl Group
Author(s) -
Yabushita Mizuho,
Kobayashi Hirokazu,
Kuroki Kyoichi,
Ito Shogo,
Fukuoka Atsushi
Publication year - 2015
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201501224
Subject(s) - depolymerization , chitin , chemistry , monomer , catalysis , hydrolysis , organic chemistry , glycosidic bond , yield (engineering) , polysaccharide , polymer , polymer chemistry , chitosan , materials science , enzyme , metallurgy
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 H 2 SO 4 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.