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Frontiers of Chemical Science and Engineering

ISSN 2095-0179

ISSN 2095-0187(Online)

CN 11-5981/TQ

Postal Subscription Code 80-969

2018 Impact Factor: 2.809

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Front. Chem. Sci. Eng.    2021, Vol. 15 Issue (4) : 998-1007    https://doi.org/10.1007/s11705-020-1994-x
RESEARCH ARTICLE
Highly uniform Ni particles with phosphorus and adjacent defects catalyze 1,5-dinitronaphthalene hydrogenation with excellent catalytic performance
Wei Xiong1,2, Susu Zhou1, Zeyong Zhao1, Fang Hao1(), Zhihui Cai1, Pingle Liu1(), Hailiang Zhang2, Hean Luo1
1. College of Chemical Engineering, National & Local United Engineering Research Centre for Chemical Process Simulation and Intensification, Xiangtan University, Xiangtan 411105, China
2. College of Chemistry, Xiangtan University, Xiangtan 411105, China
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Abstract

This work proposes a modified activated carbon support, with defects and heteroatoms (N,P-ACs) by nitrogen and phosphorus doping to load non-noble nickel to catalyze aromatic compound hydrogenation. The Ni/N,P-ACs-900 (prepared at 900 °C) showed promising catalytic activity in liquid-phase 1,5-dinitronaphthalene hydrogenation with a 1,5-diaminonaphthalene yield of 95.8% under the mild condition of 100 °C, which is comparable to the commercial Pd/C catalyst. The nitrogen species were burned off at 900 °C, causing more defects for nickel metal loading, facilitating the interaction between the supports and the nickel metal, and resulting in highly dispersed metal particles. The computational study of the nickel binding energy has been conducted using density functional theory. It exhibits that the defects formed by heteroatom doping are beneficial to nickel anchoring and deposition to form highly uniform nickel particles. The phosphorus species in combination with the defects are suitable for H2 adsorption and dissociation. These results reveal that the heteroatomic doping on the active carbon shows significant effects in the hydrogenation of the liquid-phase aromatic compounds. These findings could provide a promising route for the rational design of aromatic compound hydrogenation catalysts to significantly decrease the cost by instead using noble metal catalysts in the industry.
Keywords nitrogen and phosphorus doping      non-noble nickel catalyst      aromatic compounds hydrogenation     
Corresponding Author(s): Fang Hao,Pingle Liu   
Just Accepted Date: 27 October 2020   Online First Date: 18 January 2021    Issue Date: 04 June 2021
 Cite this article:   
Wei Xiong,Susu Zhou,Zeyong Zhao, et al. Highly uniform Ni particles with phosphorus and adjacent defects catalyze 1,5-dinitronaphthalene hydrogenation with excellent catalytic performance[J]. Front. Chem. Sci. Eng., 2021, 15(4): 998-1007.
 URL:  
https://academic.hep.com.cn/fcse/EN/10.1007/s11705-020-1994-x
https://academic.hep.com.cn/fcse/EN/Y2021/V15/I4/998
Fig.1  (A) N 1s and (B) P 2p XPS spectra of the N,P-ACs-T: (a) N,P-AC-800 and (b) N,P-AC-900.
Sample N
/At-%		 NP
/%		 NPyr
/%		 NQ
/%		 NOx
/%		 P
/At-%		 Ph3P
/%		 Ph3PO
/%		 (PhO)3PO
/%		 Phosphate/ phosphoric acid /
%		 P2O5 /% High oxidated state P
/%
N,P-AC-800 1.49 34.6 26.5 20.0 18.9 1.68 11.7 24.9 24.0 18.1 21.3 ?
N,P-AC-900 ? ? ? ? ? 1.47 ? 9.1 16.9 23.3 16.8 33.9
Tab.1  Nitrogen and phosphorus content and the composition on the N,P-ACs prepared at different temperatures a)
Fig.2  (A) Raman spectra of (a) AC, (b) N,P-AC-800, (c) N,P-AC-900, and (d) Ni/N,P-AC-900; (B) XRD spectra of the catalysts (a) Ni/AC, (b) Ni/N,P-AC-900, and (c) Ni/N,P-AC-800.
Fig.3  TEM pictures of the (a) Ni/AC, (b) Ni/N,P-AC-800, and (c) Ni/N,P-AC-900.
Catalysts Time/min Conv./% Select./%
5-Nitro-1-naphthalenamine 1,5-Diaminonaphthalene Others
Ni/AC 300 100 82.4 16.2 1.4
150 86.0 94.9 4.3 0.8
N,P-AC-900 300 − − − −
Ni/N-AC-900 300 100 80.4 15.9 3.7
Ni/P-AC-900 300 100 35.2 61.8 3.0
Ni/N,P-AC-800 300 100 38.3 59.2 2.5
150 99.5 88.8 9.6 1.9
Ni/N,P-AC-900 150 100 − 95.8 4.2
50 96.8 91.5 7.5 1.0
5% Pd/C 50 100 − 95.9 4.1
Tab.2  The catalytic performances of different samples in the liquid-phase hydrogenation of 1,5-dinitronaphthalene a)
Ni on different support modes Total E/eV Ebind (Ni)/eV
Original carbon support ?74203.2212 1.685837824
Graphite-N carbon ?74654.7350 2.033443912
Pyridine-N carbon ?73617.5047 5.704832528
Pyrrolic-N carbon ?73617.5049 5.704233864
Carbon with 12r-defect ?73164.0703 6.603644888
Carbon with 14r-defect ?72127.2686 6.872472236
2Ni on Carbon with 14r-defect ?113168.2959 5.025827819
3Ni on Carbon with 14r-defect ?154208.7550 4.220880532
4Ni on Carbon with 14r-defect ?195250.2349 4.073607147
5Ni on Carbon with 14r-defect ?236291.2345 3.889190199
6Ni on Carbon with 14r-defect ?277307.2994 ?0.389540234
Tab.3  The binding energies of Ni on the different modes of modified carbon supports
Different modes Total E/eV Eads (H2)/eV
H2 ?31.57349582 −
Ni on carbon support without P doping (1) ?72127.20158 −
Ni on carbon support with P doping (2) ?81413.59703 −
H2 adsorption on (1) ?72159.25703 0.48195717
H2 adsorption on (2) ?81445.92856 0.75803652
Tab.4  The adsorption energies of H2 on Ni loaded on the different carbon supports
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