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Highly selective catalytic nitration of 1-nitronaphthalene with NO2 to 1,5-dinitronaphthalene over solid superacid SO42−/ZrO2 promoted by molecular oxygen and acetic anhydride under mild conditions

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Abstract

A simple and efficient method for liquid-phase catalytic nitration of 1-nitronaphthalene with NO2 to 1,5-dinitronaphthalene under mild conditions has been developed. The results indicated that the sulfated zirconia (SO42−/ZrO2) as solid superacid catalyst exhibits superior catalytic performance with dioxygen and acetic anhydride. 93.8% conversion of 1-nitronaphthalene and 52.8% 1,5-dinitronaphthalene selectivity were achieved. Furthermore, the physicochemical properties of SO42−/ZrO2 were determined by XRD, Py-FT-IR, BET, FT-IR, Raman spectroscopy and ICP-OES technologies. The possible nitration reaction mechanism over SO42−/ZrO2 catalyst was proposed. The present work provides an easy-to-implement, mild and eco-friendly approach for the efficient preparation of valuable 1,5-dinitronaphthalene, which has extensive industrial application prospects.

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Acknowledgements

The authors are grateful for the financial support of the National Natural Science Foundation of China (21676226), Key Research and Development Program in Hunan Province (2019GK2041), the Postgraduate Scientific Research Innovation Project of Hunan Province (CX20200637), Innovation and Entrepreneurship Training Program for College Students in Hunan Province (S201910530024) and Hunan Key Laboratory of Environment Friendly Chemical Process Integrated Technology.

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Author notes

  1. Jiaqi Yan and Wenjin Ni have contributed to the work equally.

Authors and Affiliations

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

    Jiaqi Yan, Wenjin Ni, Kuiyi You, Yi Chen, Fangfang Zhao, Pingle Liu & He’an Luo

  2. School of Educational Science, Hunan Normal University, Changsha, 410081, People’s Republic of China

    Ting Duan, Pingle Liu & He’an Luo

  3. College of Material and Chemical Engineering, Hunan Institute of Engineering, Xiangtan, 411104, People’s Republic of China

    Renjie Deng

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  1. Jiaqi Yan
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Correspondence to Kuiyi You or He’an Luo.

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Yan, J., Ni, W., You, K. et al. Highly selective catalytic nitration of 1-nitronaphthalene with NO2 to 1,5-dinitronaphthalene over solid superacid SO42−/ZrO2 promoted by molecular oxygen and acetic anhydride under mild conditions. Res Chem Intermed 47, 3569–3582 (2021). https://doi.org/10.1007/s11164-021-04502-x

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