A Simple One-Pot Dehydration Process to Convert N-acetyl-D-glucosamine into a Nitrogen-Containing Compound, 3-acetamido-5-acetylfuran

Kerton, Francesca M. and Omari, Khaled Walid Baker and Dodot, L. (2012) A Simple One-Pot Dehydration Process to Convert N-acetyl-D-glucosamine into a Nitrogen-Containing Compound, 3-acetamido-5-acetylfuran. ChemSusChem, 5 (9). pp. 1767-1772. ISSN 1864-564X

	[English] PDF (Migrated (PDF/A Conversion) from original format: (application/pdf)) - Accepted Version Available under License Creative Commons Attribution Non-commercial. Download (362kB) [English] PDF (Post-print) - Accepted Version Available under License Creative Commons Attribution Non-commercial. (Original Version)

Abstract

An efficient process for converting N-acetyglucosamine (NAG) into 3-acetamido-5-acetylfuran (3A5AF) is reported. 3A5AF is proposed as a 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 (DMA) under microwave irradiation (220 °C, 15 min). A maximum yield of 62% was obtained in the presence of 4 equiv 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 via a previously reported pyrolysis route.

Actions (login required)

View Item