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Imine-bridged periodic mesoporous organosilica as stable high-activity catalytic for Knoevenagel reaction in aqueous medium

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Abstract

An imine-functionalized mesoporous solid base catalyst (BA@BE-PMO) was prepared by template agent-directed self-assembly condensation of bis[3-(triethoxysilyl)propyl]amine and 1,2-bis(triethoxysilyl)ethane in acid solution. The imine groups with catalytic activity were integrally embedded into mesopore walls of as-made BA@BE-PMO. In Knoevenagel reactions in aqueous medium, the BA@BE-PMO catalyst exhibited better catalytic activity than imine-functionalized SBA-15 catalyst synthesized using the traditional co-condensation method, which can be attributed to the pore surface with strong hydrophobicity originating from –CH2CH2– group fragments incorporated into pore walls. The strong hydrophobicity of the surface facilitates adsorption and diffusion of organic compounds on the catalyst surface in reactions in aqueous medium. Moreover, it exhibited comparable catalytic activity to dipropylamine homogeneous base catalyst because of the uniform dispersion of imine group active sites. The BA@BE-PMO catalyst could also be recovered and reused in up to five runs without significant loss in activity without any negative environmental impact.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (51872109, 21677099, 21876112), Natural Science Foundation of Jiangsu Provincial Department of Education (17KJA150002, 15KJA150003), and College Students’ Practical Innovation Project of Jiangsu Province (201810323009Z).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai’an, 223300, China

    Zechun Sun, Zhiruo Zhang, Fengxia Zhu, Pusu Zhao & Jiahui Rui

  2. School of Basic Medical Sciences, Fudan University, Shanghai, 200032, China

    Yiran Wang

  3. Education Ministry Key and International Joint Lab of Resource Chemistry, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, Shanghai, 200234, People’s Republic of China

    Fengxia Zhu, Guisheng Li & Fengfeng Shao

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  1. Zechun Sun
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Correspondence to Fengxia Zhu, Pusu Zhao or Guisheng Li.

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Sun, Z., Wang, Y., Zhang, Z. et al. Imine-bridged periodic mesoporous organosilica as stable high-activity catalytic for Knoevenagel reaction in aqueous medium. Res Chem Intermed 45, 3107–3121 (2019). https://doi.org/10.1007/s11164-019-03781-9

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