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Novel S2O82−/Fe-ZrO2 solid superacid catalyst combined with O2-Ac2O for highly efficient catalytic nitration of 1-nitronaphthalene with NO2 to 1,5-dinitronaphthalene

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Abstract

A mild, efficient, and green approach for highly selective synthesis of 1,5-dinitronaphthalene (1,5-DNN) has been devolved from catalytic nitration of 1-nitronaphthalene (1-NN) with NO2 combined with O2-Ac2O over solid superacid S2O82−/Fe-ZrO2. The prepared S2O82−/Fe-ZrO2 catalyst presents better catalytic performance than most of the reported catalysts for this purpose, with 96.8% conversion of 1-NN and 62.6% selectivity of 1,5-DNN under the optimized reaction conditions. The excellent catalytic activity of S2O82−/Fe-ZrO2 can be attributed to its remarkable Lewis acid sites and strong acidity. A possible catalytic nitration reaction pathway of 1-NN with NO2 over S2O82−/Fe-ZrO2 in the O2-Ac2O system was proposed. This work provides a practical strategy for the cost-effective, environmentally friendly, and efficient synthesis of 1,5-DNN with significant industrial application prospects.

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Funding

This work was supported by the National Natural Science Foundation of China (22208271), Science and Technology Innovation Program of Hunan Province (2021RC2089), Guangdong Basic and Applied Basic Research Foundation (2021A1515110136), Research fund of Hunan Provincial Education Department (20B550).

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Authors and Affiliations

  1. Furong College, Hunan University of Arts and Science, Changde, 415000, People’s Republic of China

    Jiaqi Yan

  2. School of Chemical Engineering, Xiangtan University, Xiangtan, 411105, People’s Republic of China

    Xiaowen Zhang, Jiahong Yin, Fangfang Zhao, Kuiyi You & He’an Luo

  3. National & Local United Engineering Research Center for Chemical Process Simulation and Intensification, Xiangtan University, Xiangtan, 411105, People’s Republic of China

    Kuiyi You & He’an Luo

  4. Foshan Green Intelligent Manufacturing Research Institute of Xiangtan University, Foshan, 528311, People’s Republic of China

    Xiaowen Zhang

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  1. Jiaqi Yan
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  2. Xiaowen Zhang
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  3. Jiahong Yin
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  4. Fangfang Zhao
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Contributions

Jiaqi Yan: Data curation, Validation, Formal analysis, Writing-original draft. Xiaowen Zhang: Supervision, Formal analysis, Writing-original draft, Funding acquisition. Jiahong Yin: Data curation, Validation, Formal analysis. Fangfan Zhao: Formal analysis, Funding acquisition. Kuiyi You: Conceptualization, Supervision, Revision, Data curation. He'an Luo: Conceptualization, Supervision.

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Correspondence to Xiaowen Zhang or Kuiyi You.

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Yan, J., Zhang, X., Yin, J. et al. Novel S2O82−/Fe-ZrO2 solid superacid catalyst combined with O2-Ac2O for highly efficient catalytic nitration of 1-nitronaphthalene with NO2 to 1,5-dinitronaphthalene. Res Chem Intermed 49, 3065–3078 (2023). https://doi.org/10.1007/s11164-023-05029-z

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