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Transfer Hydrogenation of Cinnamaldehyde Catalyzed by Al2O3 Using Ethanol as a Solvent and Hydrogen Donor

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    Research Article

    Transfer Hydrogenation of Cinnamaldehyde Catalyzed by Al2O3 Using Ethanol as a Solvent and Hydrogen Donor
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    • Huanjun Wang
      Huanjun Wang
      Beijing Key Laboratory of Green Reaction Engineering and Technology, Department of Chemical Engineering, Tsinghua University, Shuangqing Road No. 30, Haidian District, Beijing 100084, China
      More by Huanjun Wang
    • Boyang Liu
      Boyang Liu
      Beijing Key Laboratory of Green Reaction Engineering and Technology, Department of Chemical Engineering, Tsinghua University, Shuangqing Road No. 30, Haidian District, Beijing 100084, China
      More by Boyang Liu
    • Fang Liu
      Fang Liu
      Beijing Key Laboratory of Green Reaction Engineering and Technology, Department of Chemical Engineering, Tsinghua University, Shuangqing Road No. 30, Haidian District, Beijing 100084, China
      More by Fang Liu
    • Yaning Wang
      Yaning Wang
      Beijing Key Laboratory of Green Reaction Engineering and Technology, Department of Chemical Engineering, Tsinghua University, Shuangqing Road No. 30, Haidian District, Beijing 100084, China
      More by Yaning Wang
    • Xiaocheng Lan
      Xiaocheng Lan
      Beijing Key Laboratory of Green Reaction Engineering and Technology, Department of Chemical Engineering, Tsinghua University, Shuangqing Road No. 30, Haidian District, Beijing 100084, China
      More by Xiaocheng Lan
    • Shiqing Wang
      Shiqing Wang
      Beijing Key Laboratory of Green Reaction Engineering and Technology, Department of Chemical Engineering, Tsinghua University, Shuangqing Road No. 30, Haidian District, Beijing 100084, China
      More by Shiqing Wang
    • Babar Ali
      Babar Ali
      Beijing Key Laboratory of Green Reaction Engineering and Technology, Department of Chemical Engineering, Tsinghua University, Shuangqing Road No. 30, Haidian District, Beijing 100084, China
      More by Babar Ali
    • Tiefeng Wang*
      Tiefeng Wang
      Beijing Key Laboratory of Green Reaction Engineering and Technology, Department of Chemical Engineering, Tsinghua University, Shuangqing Road No. 30, Haidian District, Beijing 100084, China
      *E-mail: [email protected]
      More by Tiefeng Wang
      Orcidhttp://orcid.org/0000-0002-4607-8650
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    ACS Sustainable Chemistry & Engineering

    Cite this: ACS Sustainable Chem. Eng. 2020, 8, 22, 8195–8205
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    https://doi.org/10.1021/acssuschemeng.0c00942
    Published May 11, 2020
    Copyright © 2020 American Chemical Society
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    Abstract

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    Allylic alcohols produced from α,β-unsaturated aldehydes by selective hydrogenation are useful intermediates and additives in the fine chemicals industry. An efficient process for the catalytic transfer hydrogenation (CTH) of cinnamaldehyde (CMA) to cinnamyl alcohol (CMO) was developed by using ethanol as a solvent and hydrogen donor over Al2O3. Under optimized reaction conditions (120 °C, 12 h), 97.8% conversion of CMA and 96.8% selectivity to CMO were obtained. The solvent effect on catalytic performance was investigated with different primary alcohols, and the results showed that the activity decreased with decreasing polarity of the C2–C5 alcohols, which was ascribed to decreased alcohol–CMA and alcohol–catalyst interaction. In addition, on the basis of the results of poisoning experiments and catalyst characterizations, a reaction mechanism involving a six-membered ring intermediate on acid–base pair active sites of Al2O3 was proposed for the CTH of CMA in ethanol, which was further confirmed by density functional theory calculations. Furthermore, this catalytic system demonstrated good stability and wide compatibility for a range of α,β-unsaturated aldehydes.

    Copyright © 2020 American Chemical Society

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acssuschemeng.0c00942.

    • Powder XRD patterns, N2 adsorption–desorption isotherms and pore size distributions, effect of polarity on reaction, NH3-TPD profiles, CO2-TPD profiles, substrate scope results, DFT calculation results, effect of Al2O3 calcination temperature on reactions, summary of different heterogeneous catalysts for the CTH of CMA in recent published works (PDF)

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    ACS Sustainable Chemistry & Engineering

    Cite this: ACS Sustainable Chem. Eng. 2020, 8, 22, 8195–8205
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acssuschemeng.0c00942
    Published May 11, 2020
    Copyright © 2020 American Chemical Society
    Request reuse permissions

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