4.5 Article

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

Journal

RESEARCH ON CHEMICAL INTERMEDIATES
Volume 47, Issue 9, Pages 3569-3582

Publisher

SPRINGER
DOI: 10.1007/s11164-021-04502-x

Keywords

SO42-; ZrO2; NO2; 1; 5-dinitronaphthalene; Molecular oxygen; Acetic anhydride

Funding

  1. National Natural Science Foundation of China [21676226]
  2. Key Research and Development Program in Hunan Province [2019GK2041]
  3. Postgraduate Scientific Research Innovation Project of Hunan Province [CX20200637]
  4. Innovation and Entrepreneurship Training Program for College Students in Hunan Province [S201910530024]
  5. Hunan Key Laboratory of Environment Friendly Chemical Process Integrated Technology

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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 using sulfated zirconia (SO42-/ZrO2) as solid superacid catalyst, achieving high conversion rate and selectivity. Physicochemical properties of SO42-/ZrO2 were determined, and a nitration reaction mechanism was proposed. This work provides an eco-friendly approach for the efficient preparation of valuable 1,5-dinitronaphthalene with extensive industrial application prospects.
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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