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Reductive Amination of Biomass-Derived 2-Hydroxytetrahydropyran into 5-Amino-1-Pentanol Over Hydroxylapatite Nanorod Supported Ni Catalysts

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Abstract

Valuable 5-amino-1-pentanol (5-AP) was efficiently synthesized from biomass-derived dihydropyran over hydroxylapatite nanorod supported Ni catalysts (Ni-HAP), by coupling the in situ generation of 5-hydroxypentanal (5-HP, via the ring-opening tautomerization of 2-hydroxytetrahydropyran (2-HTHP)) and its subsequent reductive amination. The Ni-HAP catalyst with 10 wt% Ni loading exhibited the highest 5-AP yield than the other Ni-HAP catalysts with different Ni loadings and several commercial hydrogenation catalysts, including Ru/C, Pt/C and Pd/C, as well as Raney Ni. High Ni particles dispersion, high reducibility and acidic intensity were found to account for the superior catalytic performance of 10Ni-HAP. The effect of reaction parameters on the catalytic performance was investigated, and an excellent 5-AP yield of 92% was achieved under mild reaction conditions of 80 °C and 2 MPa H2. The stability of the Ni-HAP catalyst was studied using a continuous flow reactor, and the sintering of Ni nanoparticles was considered as the major reason for the decline in hydrogenation activity.

Graphical Abstract

The Ni-HAP catalyst exhibited high catalytic performance to synthesis 5-AP due to the high Ni particles dispersion, reducibility and acidic intensity.

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Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (Grant Nos. 21872155, 21902164, 22102198), the Strategic Pilot Science and Technology Project of the Chinese Academy of Sciences (XDA21010700), the Lanzhou Chengguan District Science and Technology Plan Project (2020JSCX0051) and the Western Young Scholar Program of Chinese Academy of Sciences.

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Authors and Affiliations

  1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, China

    Jian Yang, Xuemei Li, Jia Zhang, Junying Tian, Xiaolan Yao, Hailong Liu, Chungu Xia & Zhiwei Huang

  2. School of Petrochemical Engineering, Lanzhou University of Technology, Lanzhou, 730050, China

    Junying Tian

  3. University of Chinese Academy of Sciences, Beijing, 100049, China

    Jia Zhang

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  1. Jian Yang
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Yang, J., Li, X., Zhang, J. et al. Reductive Amination of Biomass-Derived 2-Hydroxytetrahydropyran into 5-Amino-1-Pentanol Over Hydroxylapatite Nanorod Supported Ni Catalysts. Catal Lett 153, 2813–2823 (2023). https://doi.org/10.1007/s10562-022-04201-1

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