A simple one-pot dehydration process to convert N-acetyl-D-glucosamine into a nitrogen-containing compound, 3-acetamido-5-acetylfuran.
An efficient process for converting N-acetyglucosamine (NAG) into 3-acetamido-5-acetylfuran (3A5AF) is reported. 3A5AF is proposed as an N-containing platform chemical, which contains renewable nitrogen. In the reported method NAG, in the presence of boric acid (B(OH)₃) and sodium chloride (NaCl), produces 58 % yield 3A5AF in dimethylacetamide under microwave irradiation (220 °C, 15 min). A maximum yield of 62 % was obtained in the presence of 4 equivalent NaCl. Performing ICP-MS analysis on NAG from different chemical suppliers highlighted the importance of Cl and B levels in this process. Trace impurities are, therefore, important considerations in biomass transformations. This solution-phase process produces approximately 30 times more 3A5AF than a pyrolysis route reported previously.
Centre for Green Chemistry and Catalysis, Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland and Labrador, Canada.
Khaled W
KW
Omari
Linda
L
Dodot
Francesca M
FM
Kerton
D000081:Acetamides / Q000737:chemistry*; D000117:Acetylglucosamine / Q000737:chemistry*; D002384:Catalysis; D002713:Chlorine / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D007700:Kinetics; D012997:Solvents / Q000737:chemistry; D013696:Temperature; D014867:Water / Q000737:chemistry
D000081:Acetamides; D005663:Furans; D012997:Solvents; D014867:Water; D002713:Chlorine; D000117:Acetylglucosamine