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A Schiff Base Modified Pd Catalyst for Selective Hydrogenation of 2-Butyne-1,4-diol to 2-Butene-1,4-diol

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Abstract

Schiff-base modified Pd nanoparticles (NPs) supported on silica with an average size of ca. 2 nm have been synthesized via a one-pot aldimine condensation followed by impregnation-reduction of a palladium precursor, and the sample exhibits an excellent catalytic activity and selectivity in hydrogenation of 2-butyne-1,4-diol (BYD) to 2-butene-1,4-diol (BED). Under the mild reaction conditions (50 °C, 2 MPa H2, and 4 h) and additive-free, 95.2% BYD conversion has been achieved with ca. 100% BED selectivity over the Pd/SiO2–Schiff catalyst, and the Pd/SiO2–Schiff catalyst presents an excellent catalytic stability. The above results are much better than that of commercial Lindlar catalyst, and the improved catalytic performance is attributed to the strong metal–support interaction derived from the coordination of nitrogen sites (Schiff-base) to Pd NPs, based on catalyst characterization results.

Graphic Abstract

Featured by additive-free and high selectivity, hydrogenation of 2-butyne-1,4-diol to 2-butene-1,4-diol over the Pd/SiO2–Schiff catalyst has been developed, aiming for green production of fine chemicals.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant Nos. 21978032, 21676045, 21603198, 21377018, 21770643 and 21872135), the Science and Technology Innovation Fund in Dalian City (Grant No. 2019J12GX028), and the Fundamental Research Funds for the Central Universities (Grant No. DUT18LK34).

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Authors and Affiliations

  1. State Key Laboratory of Fine Chemicals, Department of Chemistry, Dalian University of Technology, Dalian, 116024, China

    Haomeng Li, Xinkui Wang, Xiao Chen, Chuang Li, Min Wang, Yanhui Yi, Min Ji, Huilong Wang & Changhai Liang

  2. Institute of Materials, China Academy of Engineering Physics, Mianyang, 621907, China

    Zhengfeng Shao

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  1. Haomeng Li
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  2. Xinkui Wang
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  3. Xiao Chen
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  4. Chuang Li
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  5. Min Wang
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  6. Yanhui Yi
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  7. Min Ji
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  8. Huilong Wang
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  9. Zhengfeng Shao
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  10. Changhai Liang
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Correspondence to Xinkui Wang.

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Li, H., Wang, X., Chen, X. et al. A Schiff Base Modified Pd Catalyst for Selective Hydrogenation of 2-Butyne-1,4-diol to 2-Butene-1,4-diol. Catal Lett 150, 2150–2157 (2020). https://doi.org/10.1007/s10562-020-03125-y

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