Boron-doped lamellar porous carbon supported copper catalyst for dimethyl oxalate hydrogenation

doi:10.1016/j.cjche.2022.06.020

中国化学工程学报 ›› 2023, Vol. 55 ›› Issue (3): 222-229.DOI: 10.1016/j.cjche.2022.06.020

• Full Length Article • 上一篇下一篇

Boron-doped lamellar porous carbon supported copper catalyst for dimethyl oxalate hydrogenation

Peipei Ai, Li Zhang, Jinchi Niu, Huiqing Jin, Wei Huang

State Key Laboratory of Clean and Efficient Coal Utilization, Taiyuan University of Technology, Taiyuan 030024, China

收稿日期:2022-04-13 修回日期:2022-05-30 出版日期:2023-03-28 发布日期:2023-06-03
通讯作者: Peipei Ai,E-mail:aipeipei@tyut.edu.cn;Wei Huang,E-mail:huangwei@tyut.edu.cn
基金资助:
This work is financially supported by the National Natural Science Foundation of China (22008166), Natural Science Foundation of Shanxi (201901D211047), and Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi (2019L0185).

Boron-doped lamellar porous carbon supported copper catalyst for dimethyl oxalate hydrogenation

Peipei Ai, Li Zhang, Jinchi Niu, Huiqing Jin, Wei Huang

State Key Laboratory of Clean and Efficient Coal Utilization, Taiyuan University of Technology, Taiyuan 030024, China

Received:2022-04-13 Revised:2022-05-30 Online:2023-03-28 Published:2023-06-03
Contact: Peipei Ai,E-mail:aipeipei@tyut.edu.cn;Wei Huang,E-mail:huangwei@tyut.edu.cn
Supported by:
This work is financially supported by the National Natural Science Foundation of China (22008166), Natural Science Foundation of Shanxi (201901D211047), and Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi (2019L0185).

摘要/Abstract

摘要： Doping heteroatoms on carbon materials could bring some special advantages for using as catalyst support. In this work, a boron doped lamellar porous carbon (B-LPC) was prepared facilely and utilized as carbon-based support to construct Cu/B-LPC catalyst for dimethyl oxalate (DMO) hydrogenation. Doping boron could make the B-LPC own more defects on surface and bigger pore size than B-free LPC, which were beneficial to disperse and anchor Cu nanoparticles. Moreover, the interaction between Cu species and B-LPC could be strengthened by the doped B, which not only stabilized the Cu nanoparticles, but also tuned the valence of Cu species to maintain more Cu⁺. Therefore, the B-doped Cu/B-LPC catalyst exhibited stronger hydrogenation ability and obtained higher alcohols selectivity than Cu/LPC, as well as high stability without decrease of DMO conversion and ethylene glycol selectivity even after 300 h of reaction at 240 ℃.

关键词: Hydrogenation, Cu-based catalyst, Boron doping, Porous carbon, Catalyst support, Alcohol

Abstract: Doping heteroatoms on carbon materials could bring some special advantages for using as catalyst support. In this work, a boron doped lamellar porous carbon (B-LPC) was prepared facilely and utilized as carbon-based support to construct Cu/B-LPC catalyst for dimethyl oxalate (DMO) hydrogenation. Doping boron could make the B-LPC own more defects on surface and bigger pore size than B-free LPC, which were beneficial to disperse and anchor Cu nanoparticles. Moreover, the interaction between Cu species and B-LPC could be strengthened by the doped B, which not only stabilized the Cu nanoparticles, but also tuned the valence of Cu species to maintain more Cu⁺. Therefore, the B-doped Cu/B-LPC catalyst exhibited stronger hydrogenation ability and obtained higher alcohols selectivity than Cu/LPC, as well as high stability without decrease of DMO conversion and ethylene glycol selectivity even after 300 h of reaction at 240 ℃.

Key words: Hydrogenation, Cu-based catalyst, Boron doping, Porous carbon, Catalyst support, Alcohol

Peipei Ai, Li Zhang, Jinchi Niu, Huiqing Jin, Wei Huang. Boron-doped lamellar porous carbon supported copper catalyst for dimethyl oxalate hydrogenation[J]. 中国化学工程学报, 2023, 55(3): 222-229.

Peipei Ai, Li Zhang, Jinchi Niu, Huiqing Jin, Wei Huang. Boron-doped lamellar porous carbon supported copper catalyst for dimethyl oxalate hydrogenation[J]. Chinese Journal of Chemical Engineering, 2023, 55(3): 222-229.

参考文献

[1] H.R. Yue, Y.J. Zhao, X.B. Ma, J.L. Gong, Ethylene glycol: properties, synthesis, and applications, Chem. Soc. Rev. 41 (11) (2012) 4218–4244.
[2] A. Corma, S. Iborra, A. Velty, Chemical routes for the transformation of biomass into chemicals, Chem. Rev. 107 (6) (2007) 2411–2502.
[3] R.A. Kerr, R.F. Service, What can replace cheap oil: and when? Science 309 (5731) (2005) 101.https://doi.org/10.1126/science.309.5731.101
[4] Y.N. Sun, Q.X. Ma, Q.J. Ge, J. Sun, Tunable synthesis of ethanol or methyl acetate via dimethyl oxalate hydrogenation on confined iron catalysts, ACS Catal. 11 (8) (2021) 4908–4919.
[5] J.L. Gong, H.R. Yue, Y.J. Zhao, S. Zhao, L. Zhao, J. Lv, S.P. Wang, X.B. Ma, Synthesis of ethanol via syngas on Cu/SiO₂ catalysts with balanced Cu⁰-Cu⁺ sites, J. Am. Chem. Soc. 134 (34) (2012) 13922–13925.
[6] L. Zhang, L.P. Han, G.F. Zhao, R.J. Chai, Q.F. Zhang, Y. Liu, Y. Lu, Structured Pd–Au/Cu-fiber catalyst for gas-phase hydrogenolysis of dimethyl oxalate to ethylene glycol, Chem. Commun. 51 (52) (2015) 10547–10550.https://doi.org/10.1039/c5cc03009a
[7] J. Goldemberg, Ethanol for a sustainable energy future, Science 315 (5813) (2007) 808–810.https://pubmed.ncbi.nlm.nih.gov/17289989/
[8] M.L. Wang, D.W. Yao, A.T. Li, Y.W. Yang, J. Lv, S.Y. Huang, Y. Wang, X.B. Ma, Enhanced selectivity and stability of Cu/SiO₂ catalysts for dimethyl oxalate hydrogenation to ethylene glycol by using silane coupling agents for surface modification, Ind. Eng. Chem. Res. 59 (20) (2020) 9414–9422.
[9] Y.J. Zhao, H.H. Zhang, Y.X. Xu, S.N. Wang, Y. Xu, S.P. Wang, X.B. Ma, Interface tuning of cu⁺/Cu⁰ by zirconia for dimethyl oxalate hydrogenation to ethylene glycol over Cu/SiO₂ catalyst, J. Energy Chem. 49 (2020) 248–256.
[10] G. Giorgianni, C. Mebrahtu, S. Perathoner, G. Centi, S. Abate, Hydrogenation of dimethyl oxalate to ethylene glycol on Cu/SiO₂ catalysts prepared by a deposition-decomposition method: Optimization of the operating conditions and pre-reduction procedure, Catal. Today 390-391 (2022) 343–353.
[11] Y.X. Xu, L.X. Kong, H.J. Huang, H. Wang, X.F. Wang, S.P. Wang, Y.J. Zhao, X.B. Ma, Promotional effect of indium on Cu/SiO₂ catalysts for the hydrogenation of dimethyl oxalate to ethylene glycol, Catal. Sci. Technol. 11 (20) (2021) 6854–6865.
[12] R.P. Ye, L. Lin, C.C. Chen, J.X. Yang, F. Li, X. Zhang, D.J. Li, Y.Y. Qin, Z.F. Zhou, Y.G. Yao, Synthesis of robust MOF-derived Cu/SiO₂ catalyst with low copper loading via Sol–gel method for the dimethyl oxalate hydrogenation reaction, ACS Catal. 8 (4) (2018) 3382–3394.
[13] P.P. Ai, M.H. Tan, P. Reubroycharoen, Y. Wang, X.B. Feng, G.G. Liu, G.H. Yang, N. Tsubaki, Probing the promotional roles of cerium in the structure and performance of Cu/SiO₂ catalysts for ethanol production, Catal. Sci. Technol. 8 (24) (2018) 6441–6451.
[14] R.P. Ye, L. Lin, L.C. Wang, D. Ding, Z.F. Zhou, P.B. Pan, Z.H. Xu, J. Liu, H. Adidharma, M. Radosz, M.H. Fan, Y.G. Yao, Perspectives on the active sites and catalyst design for the hydrogenation of dimethyl oxalate, ACS Catal. 10 (8) (2020) 4465–4490.
[15] W.Q. Yan, J.B. Zhang, R.J. Zhou, Y.Q. Cao, Y.A. Zhu, J.H. Zhou, Z.J. Sui, W. Li, D. Chen, X.G. Zhou, Identification of synergistic actions between Cu⁰ and cu⁺ sites in hydrogenation of dimethyl oxalate from microkinetic analysis, Ind. Eng. Chem. Res. 59 (52) (2020) 22451–22459.
[16] C.C. Chen, L. Lin, R.P. Ye, L. Huang, L.B. Zhu, Y.Y. Huang, Y.Y. Qin, Y.G. Yao, Construction of Cu-Ce composite oxides by simultaneous ammonia evaporation method to enhance catalytic performance of Ce-Cu/SiO₂ catalysts for dimethyl oxalate hydrogenation, Fuel 290 (2021) 120083.
[17] H.R. Yue, Y.J. Zhao, S. Zhao, B. Wang, X.B. Ma, J.L. Gong, A copper-phyllosilicate core-sheath nanoreactor for carbon-oxygen hydrogenolysis reactions, Nat. Commun. 4 (2013) 2339.
[18] R.P. Ye, L. Lin, Q.H. Li, Z.F. Zhou, T.T. Wang, C.K. Russell, H. Adidharma, Z.H. Xu, Y.G. Yao, M.H. Fan, Recent progress in improving the stability of copper-based catalysts for hydrogenation of carbon–oxygen bonds, Catal. Sci. Technol. 8 (14) (2018) 3428–3449.
[19] J.W. Zheng, J.F. Zhou, H.Q. Lin, X.P. Duan, C.T. Williams, Y.Z. Yuan, CO-mediated deactivation mechanism of SiO₂-supported copper catalysts during dimethyl oxalate hydrogenation to ethylene glycol, J. Phys. Chem. C 119 (24) (2015) 13758–13766.
[20] J. Ding, T. Popa, J.K. Tang, K.A.M. Gasem, M.H. Fan, Q. Zhong, Highly selective and stable Cu/SiO₂ catalysts prepared with a green method for hydrogenation of diethyl oxalate into ethylene glycol, Appl. Catal. B Environ. 209 (2017) 530–542.
[21] Y.J. Zhao, Y.Q. Zhang, Y. Wang, J. Zhang, Y. Xu, S.P. Wang, X.B. Ma, Structure evolution of mesoporous silica supported copper catalyst for dimethyl oxalate hydrogenation, Appl. Catal. A Gen. 539 (2017) 59–69.
[22] C. Wen, Y.Y. Cui, W.L. Dai, S.H. Xie, K.N. Fan, Solvent feedstock effect: the insights into the deactivation mechanism of Cu/SiO₂ catalysts for hydrogenation of dimethyl oxalate to ethylene glycol, Chem. Commun. (Camb) 49 (45) (2013) 5195–5197.
[23] P.P. Ai, M.H. Tan, Y. Ishikuro, Y. Hosoi, G.H. Yang, Y. Yoneyama, N. Tsubaki, Design of an autoreduced copper in carbon nanotube catalyst to realize the precisely selective hydrogenation of dimethyl oxalate, ChemCatChem 9 (6) (2017) 1067–1075.
[24] Z.Q. Jiang, Z.J. Jiang, T. Maiyalagan, A. Manthiram, Cobalt oxide-coated N- and B-doped graphene hollow spheres as bifunctional electrocatalysts for oxygen reduction and oxygen evolution reactions, J. Mater. Chem. A 4 (16) (2016) 5877–5889.
[25] H. Wang, Y. Shao, S.L. Mei, Y. Lu, M. Zhang, J.K. Sun, K. Matyjaszewski, M. Antonietti, J.Y. Yuan, Polymer-derived heteroatom-doped porous carbon materials, Chem. Rev. 120 (17) (2020) 9363–9419.
[26] Y.R. Sun, C.Y. Du, M.C. An, L. Du, Q. Tan, C.T. Liu, Y.Z. Gao, G.P. Yin, Boron-doped graphene as promising support for platinum catalyst with superior activity towards the methanol electrooxidation reaction, J. Power Sources 300 (2015) 245–253.
[27] P.P. Ai, M.H. Tan, N. Yamane, G.G. Liu, R.G. Fan, G.H. Yang, Y. Yoneyama, R.Q. Yang, N. Tsubaki, Synergistic effect of a boron-doped carbon-nanotube-supported Cu catalyst for selective hydrogenation of dimethyl oxalate to ethanol, Chem. Eur. J. 23 (34) (2017) 8252–8261.
[28] Y.S. Yun, H. Park, D. Yun, C.K. Song, T.Y. Kim, K.R. Lee, Y. Kim, J.W. Han, J. Yi, Tuning the electronic state of metal/graphene catalysts for the control of catalytic activity via N- and B-doping into graphene, Chem. Commun. 54 (52) (2018) 7147–7150.
[29] P. Joshi, H.H. Huang, R. Yadav, M. Hara, M. Yoshimura, Boron-doped graphene as electrocatalytic support for iridium oxide for oxygen evolution reaction, Catal. Sci. Technol. 10 (19) (2020) 6599–6610.
[30] A.Y. Yin, J.W. Qu, X.Y. Guo, W.L. Dai, K.N. Fan, The influence of B-doping on the catalytic performance of Cu/HMS catalyst for the hydrogenation of dimethyloxalate, Appl. Catal. A Gen. 400 (1–2) (2011) 39–47.
[31] Z. He, H.Q. Lin, P. He, Y.Z. Yuan, Effect of boric oxide doping on the stability and activity of a Cu-SiO₂ catalyst for vapor-phase hydrogenation of dimethyl oxalate to ethylene glycol, J. Catal. 277 (1) (2011) 54–63.
[32] S. Zhao, H.R. Yue, Y.J. Zhao, B. Wang, Y.C. Geng, J. Lv, S.P. Wang, J.L. Gong, X.B. Ma, Chemoselective synthesis of ethanol via hydrogenation of dimethyl oxalate on Cu/SiO₂: enhanced stability with boron dopant, J. Catal. 297 (2013) 142–150.
[33] G.A. Tiruye, D. Muñoz-Torrero, T. Berthold, J. Palma, M. Antonietti, N. Fechler, R. Marcilla, Functional porous carbon nanospheres from sustainable precursors for high performance supercapacitors, J. Mater. Chem. A 5 (31) (2017) 16263–16272.
[34] H.N. Yang, W.J. Kim, Effect of boron-doping levels in Pt-B-graphene on the electrochemical properties and cell performance of high temperature proton exchange membrane fuel cells, Electrochimica Acta 209 (2016) 430–439.

Boron-doped lamellar porous carbon supported copper catalyst for dimethyl oxalate hydrogenation

Boron-doped lamellar porous carbon supported copper catalyst for dimethyl oxalate hydrogenation

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