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

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 NA...

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Autores principales: Yamazaki, Kiyoyuki, Hiyoshi, Norihito, Yamaguchi, Aritomo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10695736/
https://www.ncbi.nlm.nih.gov/pubmed/37988701
http://dx.doi.org/10.1002/open.202300148
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author Yamazaki, Kiyoyuki
Hiyoshi, Norihito
Yamaguchi, Aritomo
author_facet Yamazaki, Kiyoyuki
Hiyoshi, Norihito
Yamaguchi, Aritomo
author_sort Yamazaki, Kiyoyuki
collection PubMed
description 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 (SiO(2)/Al(2)O(3)=40)>H‐montmorillonite (K‐10)>Amberlyst15>H‐ZSM‐5 (SiO(2)/Al(2)O(3)=300)>TiO(2)>γ‐Al(2)O(3)>ZrO(2)>SiO(2) ⋅ 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, N(2) adsorption, Fourier‐transformed infrared spectroscopy, X‐ray diffraction, and (27)Al 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.
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spelling pubmed-106957362023-12-06 Conversion of N‐Acetylglucosamine to 3‐Acetamido‐5‐Acetylfuran over Al‐Exchanged Montmorillonite Yamazaki, Kiyoyuki Hiyoshi, Norihito Yamaguchi, Aritomo ChemistryOpen Research Articles 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 (SiO(2)/Al(2)O(3)=40)>H‐montmorillonite (K‐10)>Amberlyst15>H‐ZSM‐5 (SiO(2)/Al(2)O(3)=300)>TiO(2)>γ‐Al(2)O(3)>ZrO(2)>SiO(2) ⋅ 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, N(2) adsorption, Fourier‐transformed infrared spectroscopy, X‐ray diffraction, and (27)Al 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. John Wiley and Sons Inc. 2023-11-21 /pmc/articles/PMC10695736/ /pubmed/37988701 http://dx.doi.org/10.1002/open.202300148 Text en © 2023 The Authors. ChemistryOpen published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Yamazaki, Kiyoyuki
Hiyoshi, Norihito
Yamaguchi, Aritomo
Conversion of N‐Acetylglucosamine to 3‐Acetamido‐5‐Acetylfuran over Al‐Exchanged Montmorillonite
title Conversion of N‐Acetylglucosamine to 3‐Acetamido‐5‐Acetylfuran over Al‐Exchanged Montmorillonite
title_full Conversion of N‐Acetylglucosamine to 3‐Acetamido‐5‐Acetylfuran over Al‐Exchanged Montmorillonite
title_fullStr Conversion of N‐Acetylglucosamine to 3‐Acetamido‐5‐Acetylfuran over Al‐Exchanged Montmorillonite
title_full_unstemmed Conversion of N‐Acetylglucosamine to 3‐Acetamido‐5‐Acetylfuran over Al‐Exchanged Montmorillonite
title_short Conversion of N‐Acetylglucosamine to 3‐Acetamido‐5‐Acetylfuran over Al‐Exchanged Montmorillonite
title_sort conversion of n‐acetylglucosamine to 3‐acetamido‐5‐acetylfuran over al‐exchanged montmorillonite
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10695736/
https://www.ncbi.nlm.nih.gov/pubmed/37988701
http://dx.doi.org/10.1002/open.202300148
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