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Nitration of chlorobenzene by ultrasonic-assisted synthesized sulfated ZrO2 catalyst with NO2

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Abstract

Different solid superacid sulfated zirconium dioxide (SO42−/ZrO2) samples were successfully prepared by conventional and ultrasonic-assisted chemical precipitation process, and then, they were characterized by X-ray diffraction, Fourier transform infrared, thermal gravimetric analyzer (TGA), nitrogen adsorption–desorption, ammonia temperature programmed desorption (NH3-TPD) and pyridine adsorbs Fourier transform infrared. The results of characterizations indicate that the sulfonic acid group is successfully introduced, and the acidity and surface area of sulfated sample can be increased by using ultrasonic method. Furthermore, this ultrasonic-assisted catalyst was used for the chlorobenzene nitration using nitrogen dioxide (NO2) as nitrating agent. The catalyst shows excellent catalytic activity and reusability for the nitration of chlorobenzene giving high para-selectivity. In the optimal reaction conditions, the conversion of chlorobenzene can reach 85.2% with 88.5% selectivity to para-nitrochlorobenzene (p-NCB). Furthermore, the reaction mechanism was proposed by combination of experimental results and theoretical calculations. The present work provides an easy-to-implement, mild and environmentally friendly approach for the efficient preparation of valuable p-NCB, which has extensive industrial application prospects.

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Acknowledgements

We are grateful for the Natural Science Foundation for Young Scholars in Hunan Province (2020JJ5099, 2021JJ50103), Scientific Research Fund of Hunan Provincial Education Department (19C0485), Science and Technology Innovation Talents Program of Hunan Province, China (2021RC1011), National Innovation Training Program for College Students (202211342012), Hunan Innovation Training Program for College Students (202211342043).

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Author notes

  1. Renjie Deng and Haishuai Cui contributed equally to this work and should be considered co-first authors.

Authors and Affiliations

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

    Renjie Deng, Haishuai Cui, Meilin Liu, Yao Tian & Huajie Liu

  2. Hunan Province Key Laboratory of Environmental Catalysis and Waste Rechemistry, Hunan Institute of Engineering, Xiangtan, 411104, People’s Republic of China

    Renjie Deng, Haishuai Cui & Huajie Liu

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

    Wenjin Ni

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  1. Renjie Deng
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  3. Meilin Liu
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Contributions

RD and HC were involved in experimental operation, data curation, and manuscript preparation. ML and WN helped in supervision and writing—review and editing. YT and HL contributed to writing—review and editing.

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Correspondence to Renjie Deng or Huajie Liu.

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Deng, R., Cui, H., Liu, M. et al. Nitration of chlorobenzene by ultrasonic-assisted synthesized sulfated ZrO2 catalyst with NO2. Res Chem Intermed 49, 3029–3044 (2023). https://doi.org/10.1007/s11164-023-05020-8

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