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Electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions

Author

Listed:
  • Yongmeng Wu

    (Tianjin University)

  • Jinghui Zhao

    (Tianjin University)

  • Changhong Wang

    (Hebei Normal University)

  • Tieliang Li

    (Tianjin University)

  • Bo-Hang Zhao

    (Tianjin University)

  • Ziyang Song

    (Tianjin University)

  • Cuibo Liu

    (Tianjin University)

  • Bin Zhang

    (Tianjin University
    Tianjin University)

Abstract

Cyclohexanone oxime, an important nylon-6 precursor, is conventionally synthesized through cyclohexanone-hydroxylamine (NH2OH) and cyclohexanone ammoxidation methodologies. These strategies require complicated procedures, high temperatures, noble metal catalysts, and toxic SO2 or H2O2 usage. Here, we report a one-step electrochemical strategy to synthesize cyclohexanone oxime from nitrite (NO2−) and cyclohexanone under ambient conditions using a low-cost Cu-S catalyst, avoiding complex procedures, noble metal catalysts and H2SO4/H2O2 usage. This strategy produces 92% yield and 99% selectivity of cyclohexanone oxime, comparable to the industrial route. The reaction undergoes a NO2− → NH2OH→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.

Suggested Citation

  • Yongmeng Wu & Jinghui Zhao & Changhong Wang & Tieliang Li & Bo-Hang Zhao & Ziyang Song & Cuibo Liu & Bin Zhang, 2023. "Electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions," Nature Communications, Nature, vol. 14(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-38888-6
    DOI: 10.1038/s41467-023-38888-6
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    References listed on IDEAS

    as
    1. Yongmeng Wu & Cuibo Liu & Changhong Wang & Yifu Yu & Yanmei Shi & Bin Zhang, 2021. "Converting copper sulfide to copper with surface sulfur for electrocatalytic alkyne semi-hydrogenation with water," Nature Communications, Nature, vol. 12(1), pages 1-11, December.
    2. Yueshen Wu & Zhan Jiang & Zhichao Lin & Yongye Liang & Hailiang Wang, 2021. "Direct electrosynthesis of methylamine from carbon dioxide and nitrate," Nature Sustainability, Nature, vol. 4(8), pages 725-730, August.
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    Cited by:

    1. Meng He & Yongmeng Wu & Rui Li & Yuting Wang & Cuibo Liu & Bin Zhang, 2023. "Aqueous pulsed electrochemistry promotes C−N bond formation via a one-pot cascade approach," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    2. Yirong Tang & Zhan Jiang & Yubo Yuan & Li Xu & Chuyao Jin & Bulin Chen & Zhichao Lin & Jie Zao & Jianwei Du & Xiao Zhang & Xiang Gao & Yongye Liang, 2024. "Selective electrosynthesis of hydroxylamine from aqueous nitrate/nitrite by suppressing further reduction," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    3. Shunhan Jia & Libing Zhang & Hanle Liu & Ruhan Wang & Xiangyuan Jin & Limin Wu & Xinning Song & Xingxing Tan & Xiaodong Ma & Jiaqi Feng & Qinggong Zhu & Xinchen Kang & Qingli Qian & Xiaofu Sun & Buxin, 2024. "Upgrading of nitrate to hydrazine through cascading electrocatalytic ammonia production with controllable N-N coupling," Nature Communications, Nature, vol. 15(1), pages 1-11, December.

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