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Ternary SO42−–ZrO2–TiO2 Solid Super Acid Catalyst for One-Step Synthesis of Adipicdihydrazide

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Abstract

An efficient SO42−–ZrO2–TiO2 super acid catalyst was fabricated via simple impregnation precipitation strategy and applied in one-step synthesis of adipicdihydrazide (ADH). The purity and yield of ADH reached up to 97.5 and 96.7% respectively without separation treatment. After five recycling of the catalyst, the ADH yield still remained 82%, revealing the excellent stability performance of SO42−–ZrO2–TiO2 catalyst. Further, the excellent catalytic performance could be attributed to (1) solid super acid existed in SO42−–ZrO2–TiO2; (2) robust SO42− maintained in ZrO2–TiO2; (3) the accelerated cleavage of C =O and improved nucleophilic attack reaction rate of hydrazine hydrate by vast proton produced. DFT calculation was employed to further analyze the electron cloud change of ZrO2–TiO2 with the SO42− introduction and calculate the adsorption energy barrier of SO42−–ZrO2–TiO2 for AA (− 2.08 eV).

Graphical Abstract

An efficient SO42−-ZrO2-TiO2 super acid catalyst was fabricated via simple impregnation precipitation strategy and applied in one-step synthesie of adipic dihydrazide. The resulting acidic centers of SO42−-ZrO2-TiO2 attracted electrons from surrounding water molecules to restore neutrality. Meanwhile, a large amount of H+ floated around in the reaction system, which could break the C=O double bond and improve the adipic acid conversion rate. The extreme catalytic activity was based on the fact that the electronic effects of SO42− and ZrO2-TiO2 facilitated the interaction with H+ in adipic acid and reduced hydrazine hydrate nucleophilic attack difficulty.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (NSFC21978141) and of Shandong province (ZR2019BB010), the China Postdoctoral Science Foundation (2020M672015), the Open Project of Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education (KFJJ2021009), the Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education &Hubei Key Laboratory of Catalysis and Materials Science (CHCL20004), the special fund of Bei**g Key Laboratory of Clean Fuels and Efficient Catalytic Emission Reduction Technology, and Qingdao Postdoctoral Applied Research Program.

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Authors and Affiliations

  1. State Key Laboratory Base for Eco-Chemical Engineering, Key Laboratory of Multiphase Flow Reaction and Separation Engineering of Shandong Province, School of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China

    **angxue Liu, Ke Wang, Baoquan Liu, Zhenmei Guo, Chao Zhang & Zhiguo Lv

  2. Center for Testing and Standardization, Shenyang Rubber Research and Design Institute Co. LTD, Shenyang, 110021, China

    **angxue Liu

  3. Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou, 311121, China

    Chao Zhang

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  1. **angxue Liu
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Correspondence to Chao Zhang or Zhiguo Lv.

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Liu, X., Wang, K., Liu, B. et al. Ternary SO42−–ZrO2–TiO2 Solid Super Acid Catalyst for One-Step Synthesis of Adipicdihydrazide. Catal Lett 152, 2756–2766 (2022). https://doi.org/10.1007/s10562-021-03837-9

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