Citation: Xuemei Li, Junying Tian, Hailong Liu, Congkui Tang, Chungu Xia, Jing Chen, Zhiwei Huang. Effective synthesis of 5-amino-1-pentanol by reductive amination of biomass-derived 2-hydroxytetrahydropyran over supported Ni catalysts[J]. Chinese Journal of Catalysis, ;2020, 41(4): 631-641. doi: S1872-2067(19)63471-6 shu

Effective synthesis of 5-amino-1-pentanol by reductive amination of biomass-derived 2-hydroxytetrahydropyran over supported Ni catalysts

State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, Gansu, China

Received Date: 1 September 2019
Revised Date: 10 October 2019

Fund Project: This work was supported by the National Natural Science Foundation of China (21872155, 21473224), Cooperation Foundation of Dalian National Laboratory for Clean Energy (DNL 180303),Key Research Project of Frontier Science of Chinese Academy of Sciences (QYZDJ-SSW-SLH051), the Youth Innovation Promotion Association, CAS (2016371), and the Suzhou Science and Technology Development Plan (SYG201626).

A highly efficient and green process was developed for the synthesis of useful 5-amino-1-pentanol (5-AP) from biomass-derived dihydropyran by coupling the in situ generation of 5-hydroxypentanal (5-HP, via the ring-opening tautomerization of 2-hydroxytetrahydropyran (2-HTHP)) and its reductive amination over supported Ni catalysts. The catalytic performances of the supported Ni catalysts on different oxides including SiO₂, TiO₂, ZrO₂, γ-Al₂O₃, and MgO as well as several commercial hydrogenation catalysts were investigated. The Ni/ZrO₂ catalyst presented the highest 5-AP yield. The characterization results of the oxide-supported Ni catalysts showed that the Ni/ZrO₂ catalyst possessed high reducibility and a high surface acid density, which lead to the enhanced activity and selectivity of the catalyst. The effect of reaction parameters on the catalytic performance of the Ni/ZrO₂ catalyst was studied, and a high 5-AP yield of 90.8% was achieved in the reductive amination of 2-HTHP aqueous solution under mild conditions of 80℃ and 2 MPa H₂. The stability of the Ni/ZrO₂ catalyst was studied using a continuous flow reactor, and only a slight decrease in the 5-AP yield was observed after a 90-h time-on-stream. Additionally, the reaction pathways for the reductive amination of 2-HTHP to synthesize 5-AP were proposed.
- Ni catalyst,
- Reductive amination,
- Dihydropyran,
- 5-Amino-1-pentanol,
- Structure-performance relationship
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