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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....

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Detalles Bibliográficos
Autores principales: Wu, Yongmeng, Zhao, Jinghui, Wang, Changhong, Li, Tieliang, Zhao, Bo-Hang, Song, Ziyang, Liu, Cuibo, Zhang, Bin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
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
Descripción
Sumario: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.