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Highly efficient light-driven HNO3 nitration–oxidation of cyclohexane to co-product nitrocyclohexane and adipic acid in a biphasic system

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Abstract

Co-production of nitrocyclohexane and adipic acid by light-driven nitric acid (HNO3) nitration–oxidation of cyclohexane in an aqueous biphasic system was designed as a potential method for safe synthesis, because the reaction can be carried out at mild conditions (1 atmosphere, 298 K, and solvent-free media). In this process, we find that ultraviolet (UV) irradiation (λ = 365 nm) of a cyclohexane/HNO3 mixture in a N2 atmosphere efficiently produces nitrocyclohexane and adipic acid with total selectivity (ca. 87 %) at a 22 % conversion rate. Nitration–oxidation of cyclohexane is initiated by an ·OH from the direct photolysis of nitric acid. A reaction scheme has been proposed to explain the process and the different concentrations of nitric acid involved with the formation of the different reaction products.

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Authors and Affiliations

  1. National and Local United Engineering Laboratory for New Petrochemical Materials and Fine Utilization of Resources, Hunan Normal University, Changsha, 410081, People’s Republic of China

    Wenzhou Zhong, Liqiu Mao, Wenjun Yi, Gouqiang Zou, Yongqiang Li & Dulin Yin

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  1. Wenzhou Zhong
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  2. Liqiu Mao
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  3. Wenjun Yi
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  4. Gouqiang Zou
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  5. Yongqiang Li
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  6. Dulin Yin
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Correspondence to Wenzhou Zhong or Dulin Yin.

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Zhong, W., Mao, L., Yi, W. et al. Highly efficient light-driven HNO3 nitration–oxidation of cyclohexane to co-product nitrocyclohexane and adipic acid in a biphasic system. Res Chem Intermed 42, 461–470 (2016). https://doi.org/10.1007/s11164-015-2030-5

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  • DOI: https://doi.org/10.1007/s11164-015-2030-5

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