Conversion of N‐Acetylglucosamine to 3‐Acetamido‐5‐Acetylfuran over Al‐Exchanged Montmorillonite

Abstract

Abstract 3‐Acetamido‐5‐acetylfuran (3A5AF) is a potential platform compound for the production of nitrogen‐containing pharmaceuticals and chemicals. 3A5AF can be obtained by dehydration of chitin or its monomer, N‐acetylglucosamine (NAG). Here, we examined the use of solid catalysts for the dehydration of NAG to 3A5AF to achieve a more economical process that uses a recyclable catalyst. NAG was dehydrated using various solid catalysts in the presence of NaCl and N,N‐dimethyl acetamide as solvent at 433 K. The yield of 3A5AF with the solid catalysts decreased in the following order: Al‐exchanged montmorillonite>H‐ZSM‐5 (SiO2/Al2O3=40)>H‐montmorillonite (K‐10)>Amberlyst15>H‐ZSM‐5 (SiO2/Al2O3=300)>TiO2>γ‐Al2O3>ZrO2>SiO2 ⋅ MgO>Na‐montmorillonite. The highest yield of 3A5AF (14 %) was obtained with the Al‐exchanged montmorillonite. The montmorillonite catalysts were characterized by using inductively coupled plasma optical emission spectroscopy, energy‐dispersive X‐ray spectroscopy, N2 adsorption, Fourier‐transformed infrared spectroscopy, X‐ray diffraction, and 27Al magic‐angle spinning nuclear magnetic resonance spectroscopy (MAS‐NMR). In addition, a combined catalyst of Al‐exchanged montmorillonite and Cl− from synthetic hydrotalcite was found to be an active and recyclable solid catalyst for NAG dehydration to 3A5AF.

Keywords

• biomass
• clays
• nitrogen-containing compounds
• recyclable solid catalyst
• shell biorefinery