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Electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions
Cyclohexanone oxime, an important nylon-6 precursor, is conventionally synthesized through cyclohexanone-hydroxylamine (NH(2)OH) and cyclohexanone ammoxidation methodologies. These strategies require complicated procedures, high temperatures, noble metal catalysts, and toxic SO(2) or H(2)O(2) usage....
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10219941/ https://www.ncbi.nlm.nih.gov/pubmed/37236928 http://dx.doi.org/10.1038/s41467-023-38888-6 |
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author | Wu, Yongmeng Zhao, Jinghui Wang, Changhong Li, Tieliang Zhao, Bo-Hang Song, Ziyang Liu, Cuibo Zhang, Bin |
author_facet | Wu, Yongmeng Zhao, Jinghui Wang, Changhong Li, Tieliang Zhao, Bo-Hang Song, Ziyang Liu, Cuibo Zhang, Bin |
author_sort | Wu, Yongmeng |
collection | PubMed |
description | Cyclohexanone oxime, an important nylon-6 precursor, is conventionally synthesized through cyclohexanone-hydroxylamine (NH(2)OH) and cyclohexanone ammoxidation methodologies. These strategies require complicated procedures, high temperatures, noble metal catalysts, and toxic SO(2) or H(2)O(2) usage. Here, we report a one-step electrochemical strategy to synthesize cyclohexanone oxime from nitrite (NO(2)(−)) and cyclohexanone under ambient conditions using a low-cost Cu-S catalyst, avoiding complex procedures, noble metal catalysts and H(2)SO(4)/H(2)O(2) usage. This strategy produces 92% yield and 99% selectivity of cyclohexanone oxime, comparable to the industrial route. The reaction undergoes a NO(2)(−) → NH(2)OH→oxime reaction pathway. This electrocatalytic strategy is suitable for the production of other oximes, highlighting the methodology universality. The amplified electrolysis experiment and techno-economic analysis confirm its practical potential. This study opens a mild, economical, and sustainable way for the alternative production of cyclohexanone oxime. |
format | Online Article Text |
id | pubmed-10219941 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-102199412023-05-28 Electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions Wu, Yongmeng Zhao, Jinghui Wang, Changhong Li, Tieliang Zhao, Bo-Hang Song, Ziyang Liu, Cuibo Zhang, Bin Nat Commun Article Cyclohexanone oxime, an important nylon-6 precursor, is conventionally synthesized through cyclohexanone-hydroxylamine (NH(2)OH) and cyclohexanone ammoxidation methodologies. These strategies require complicated procedures, high temperatures, noble metal catalysts, and toxic SO(2) or H(2)O(2) usage. Here, we report a one-step electrochemical strategy to synthesize cyclohexanone oxime from nitrite (NO(2)(−)) and cyclohexanone under ambient conditions using a low-cost Cu-S catalyst, avoiding complex procedures, noble metal catalysts and H(2)SO(4)/H(2)O(2) usage. This strategy produces 92% yield and 99% selectivity of cyclohexanone oxime, comparable to the industrial route. The reaction undergoes a NO(2)(−) → NH(2)OH→oxime reaction pathway. This electrocatalytic strategy is suitable for the production of other oximes, highlighting the methodology universality. The amplified electrolysis experiment and techno-economic analysis confirm its practical potential. This study opens a mild, economical, and sustainable way for the alternative production of cyclohexanone oxime. Nature Publishing Group UK 2023-05-26 /pmc/articles/PMC10219941/ /pubmed/37236928 http://dx.doi.org/10.1038/s41467-023-38888-6 Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . |
spellingShingle | Article Wu, Yongmeng Zhao, Jinghui Wang, Changhong Li, Tieliang Zhao, Bo-Hang Song, Ziyang Liu, Cuibo Zhang, Bin Electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions |
title | Electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions |
title_full | Electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions |
title_fullStr | Electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions |
title_full_unstemmed | Electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions |
title_short | Electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions |
title_sort | electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10219941/ https://www.ncbi.nlm.nih.gov/pubmed/37236928 http://dx.doi.org/10.1038/s41467-023-38888-6 |
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