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

Authors

  • Khaled W. Omari,

    1. Centre for Green Chemistry and Catalysis, Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland and Labrador, A1B 3X7 (Canada), Fax: (+1) 709-8643702
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  • Linda Dodot,

    1. Centre for Green Chemistry and Catalysis, Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland and Labrador, A1B 3X7 (Canada), Fax: (+1) 709-8643702
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  • Prof. Francesca M. Kerton

    Corresponding author
    1. Centre for Green Chemistry and Catalysis, Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland and Labrador, A1B 3X7 (Canada), Fax: (+1) 709-8643702
    • Centre for Green Chemistry and Catalysis, Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland and Labrador, A1B 3X7 (Canada), Fax: (+1) 709-8643702
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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.

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