A simple one-pot dehydration process to convert N-acetyl-D-glucosamine into a nitrogen-containing compound, 3-acetamido-5-acetylfuran

Abstract

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. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.