Ultra-stable Cu-based catalyst for dimethyl oxalate hydrogenation to ethylene glycol

doi:10.1016/j.cjche.2023.06.008

Chinese Journal of Chemical Engineering ›› 2023, Vol. 60 ›› Issue (8): 186-193.DOI: 10.1016/j.cjche.2023.06.008

Previous Articles Next Articles

Ultra-stable Cu-based catalyst for dimethyl oxalate hydrogenation to ethylene glycol

Peipei Ai¹, Huiqing Jin¹, Jie Li², Xiaodong Wang¹, Wei Huang¹

1. State Key Laboratory of Clean and Efficient Coal Utilization, College of Chemical Engineering and Technology, Taiyuan University of Technology, Taiyuan 030024, China;
2. CAS Key Laboratory of Nanophotonic Materials and Devices & Key Laboratory of Nanodevices and Applications, i-Lab, Suzhou Institute of Nano-Tech and Nano-Bionics (SINANO), Chinese Academy of Sciences, Suzhou 215123, China

Received:2023-02-07 Revised:2023-06-04 Online:2023-10-28 Published:2023-08-28
Contact: Xiaodong Wang,E-mail:wangxiaodong@tyut.edu.cn;Wei Huang,E-mail:huangwei@tyut.edu.cn
Supported by:
This work was financially supported by 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).

Ultra-stable Cu-based catalyst for dimethyl oxalate hydrogenation to ethylene glycol

Peipei Ai¹, Huiqing Jin¹, Jie Li², Xiaodong Wang¹, Wei Huang¹

1. State Key Laboratory of Clean and Efficient Coal Utilization, College of Chemical Engineering and Technology, Taiyuan University of Technology, Taiyuan 030024, China;
2. CAS Key Laboratory of Nanophotonic Materials and Devices & Key Laboratory of Nanodevices and Applications, i-Lab, Suzhou Institute of Nano-Tech and Nano-Bionics (SINANO), Chinese Academy of Sciences, Suzhou 215123, China

通讯作者: Xiaodong Wang,E-mail:wangxiaodong@tyut.edu.cn;Wei Huang,E-mail:huangwei@tyut.edu.cn
基金资助:
This work was financially supported by 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).

Abstract

Abstract: Dimethyl oxalate (DMO) hydrogenation is a crucial step in the coal to ethylene glycol (CTEG) process. Herein, Cu catalyst supported on fibrous mesoporous silica (Cu/FMS) was synthesized via liquid phase deposition technique and applied for the DMO hydrogenation to EG. The catalyst exhibited a remarkable EG selectivity of 96.95% and maintained its activity without deactivation for 1000 h. Fibers of FMS support and liquid phase deposition technology cooperated to give high dispersion of Cu species in the Cu/FMS catalyst, resulting in a high Cu surface area. The formation of Si—O—Cu during catalyst preparation process increased the Cu⁺/(Cu⁰ + Cu⁺) ratio and enhanced the thermal and valence stability of Cu species. The high Cu⁺ surface area and Cu stability (thermal and valence stability) of the Cu/FMS catalyst were key factors for achieving superior EG selectivity and ultra-high stability.

Key words: Stability, Cu⁺ surface area, Fibrous mesoporous silica, Catalyst, Hydrogenation

摘要： Dimethyl oxalate (DMO) hydrogenation is a crucial step in the coal to ethylene glycol (CTEG) process. Herein, Cu catalyst supported on fibrous mesoporous silica (Cu/FMS) was synthesized via liquid phase deposition technique and applied for the DMO hydrogenation to EG. The catalyst exhibited a remarkable EG selectivity of 96.95% and maintained its activity without deactivation for 1000 h. Fibers of FMS support and liquid phase deposition technology cooperated to give high dispersion of Cu species in the Cu/FMS catalyst, resulting in a high Cu surface area. The formation of Si—O—Cu during catalyst preparation process increased the Cu⁺/(Cu⁰ + Cu⁺) ratio and enhanced the thermal and valence stability of Cu species. The high Cu⁺ surface area and Cu stability (thermal and valence stability) of the Cu/FMS catalyst were key factors for achieving superior EG selectivity and ultra-high stability.

关键词: Stability, Cu⁺ surface area, Fibrous mesoporous silica, Catalyst, Hydrogenation

Peipei Ai, Huiqing Jin, Jie Li, Xiaodong Wang, Wei Huang. Ultra-stable Cu-based catalyst for dimethyl oxalate hydrogenation to ethylene glycol[J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 186-193.

Peipei Ai, Huiqing Jin, Jie Li, Xiaodong Wang, Wei Huang. Ultra-stable Cu-based catalyst for dimethyl oxalate hydrogenation to ethylene glycol[J]. 中国化学工程学报, 2023, 60(8): 186-193.

References

[1] H.J. Huang, B. Wang, Y. Wang, Y.J. Zhao, S.P. Wang, X.B. Ma, Partial hydrogenation of dimethyl oxalate on Cu/SiO₂ catalyst modified by sodium silicate, Catal. Today 358 (2020) 68-73.
[2] M.L. Wang, D.W. Yao, A.T. Li, Y.W. Yang, J. Lv, S.Y. Huang, Y.E. 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.
[3] 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.
[4] X.P. Wang, M. Chen, X.K. Chen, R.H. Lin, H.J. Zhu, C.Q. Huang, W.S. Yang, Y.A. Tan, S.S. Wang, Z.N. Du, Y.J. Ding, Constructing copper-zinc interface for selective hydrogenation of dimethyl oxalate, J. Catal. 383 (2020) 254-263.
[5] X.B. Yu, T.A. Vest, N. Gleason-Boure, S.G. Karakalos, G.L. Tate, M. Burkholder, J.R. Monnier, C.T. Williams, Enhanced hydrogenation of dimethyl oxalate to ethylene glycol over indium promoted Cu/SiO₂, J. Catal. 380 (2019) 289-296.
[6] L. Zhang, P.P. Ai, Z.H. Gao, W. Huang, Enhanced catalytic stability of Cu-based catalyst for dimethyl oxalate hydrogenation, Fuel 324 (2022) 124536.
[7] X.B. Yu, M. Burkholder, S.G. Karakalos, G.L. Tate, J.R. Monnier, B.F. Gupton, C.T. Williams, Hydrogenation of dimethyl oxalate to ethylene glycol over Cu/KIT-6 catalysts, Catal. Sci. Technol. 11 (7) (2021) 2403-2413.
[8] 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.
[9] Y.Y. Zhu, S.R. Wang, L.J. Zhu, X.L. Ge, X.B. Li, Z.Y. Luo, The influence of copper particle dispersion in Cu/SiO₂ catalysts on the hydrogenation synthesis of ethylene glycol, Catal. Lett. 135 (3) (2010) 275-281.
[10] Y.B. Song, J.A. Zhang, J. Lv, Y.J. Zhao, X.B. Ma, Hydrogenation of dimethyl oxalate over copper-based catalysts: Acid-base properties and reaction paths, Ind. Eng. Chem. Res. 54 (40) (2015) 9699-9707.
[11] Y.J. Zhao, S. Zhao, Y.C. Geng, Y.L. Shen, H.R. Yue, J. Lv, S.P. Wang, X.B. Ma, Ni-containing Cu/SiO₂ catalyst for the chemoselective synthesis of ethanol via hydrogenation of dimethyl oxalate, Catal. Today 276 (2016) 28-35.
[12] 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.
[13] C.C. Chen, L. Lin, R.P. Ye, M.L. Sun, J.X. Yang, F. Li, Y.G. Yao, Mannitol as a novel dopant for Cu/SiO₂: A low-cost, environmental and highly stable catalyst for dimethyl oxalate hydrogenation without hydrogen prereduction, J. Catal. 389 (2020) 421-431.
[14] Q. Wang, L. Qiu, D. Ding, Y.Z. Chen, C.W. Shi, P. Cui, Y. Wang, Q.H. Zhang, R. Liu, H. Shen, Performance enhancement of Cu/SiO₂ catalyst for hydrogenation of dimethyl oxalate to ethylene glycol through zinc incorporation, Catal. Commun. 108 (2018) 68-72.
[15] Y.E. Wang, Y.J. Zhao, J. Lv, X.B. Ma, Facile synthesis of Cu@CeO₂ and its catalytic behavior for the hydrogenation of methyl acetate to ethanol, ChemCatChem 9 (12) (2017) 2085-2090.
[16] 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.
[17] X.B. Ma, H.W. Chi, H.R. Yue, Y.J. Zhao, Y. Xu, J. Lv, S.P. Wang, J.L. Gong, Hydrogenation of dimethyl oxalate to ethylene glycol over mesoporous Cu-MCM-41 catalysts, AIChE J. 59 (7) (2013) 2530-2539.
[18] J.Z. Shi, Y. He, K. Ma, S.Y. Tang, C.J. Liu, H.R. Yue, B. Liang, Cu active sites confined in MgAl layered double hydroxide for hydrogenation of dimethyl oxalate to ethanol, Catal. Today 365 (2021) 318-326.
[19] H.B. Sheng, H.T. Zhang, H.F. Ma, W.X. Qian, W.Y. Ying, An effective Cu-Ag/HMS bimetallic catalyst for hydrogenation of methyl acetate to ethanol, Catal. Today 358 (2020) 122-128.
[20] 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 539 (2017) 59-69.
[21] A. Abdul Jalil, A.S. Zolkifli, S. Triwahyono, A.F. Abdul Rahman, N.N. Mohd Ghani, M.Y. Shahul Hamid, F.H. Mustapha, S.M. Izan, B. Nabgan, A. Ripin, Altering dendrimer structure of fibrous-silica-HZSM5 for enhanced product selectivity of benzene methylation, Ind. Eng. Chem. Res. 58 (2) (2019) 553-562.
[22] M.Y. Ouyang, Y. Wang, J. Zhang, Y.J. Zhao, S.P. Wang, X.B. Ma, Three dimensional Ag/KCC-1 catalyst with a hierarchical fibrous framework for the hydrogenation of dimethyl oxalate, RSC Adv. 6 (16) (2016) 12788-12791.
[23] N. Bayal, B. Singh, R. Singh, V. Polshettiwar, Size and fiber density controlled synthesis of fibrous nanosilica spheres (KCC-1), Sci. Rep. 6 (2016) 24888.
[24] I. Munaweera, J. Hong, A. D’Souza, K.J. Balkus Jr, Novel wrinkled periodic mesoporous organosilica nanoparticles for hydrophobic anticancer drug delivery, J. Porous Mater. 22 (1) (2015) 1-10.
[25] Z.S. Qureshi, P.B. Sarawade, M. Albert, V. D'Elia, M.N. Hedhili, K. Köhler, J.M. Basset, Palladium nanoparticles supported on fibrous-structured silica nanospheres (KCC-1): An efficient and selective catalyst for the transfer hydrogenation of alkenes, ChemCatChem 7 (4) (2015) 635-642.
[26] T.J. Siang, A.A. Jalil, M.Y.S. Hamid, Bifunctional metal-free KAUST Catalysis Center 1 (KCC-1) as highly active catalyst for syngas production via methane partial oxidation, Mater. Today Chem. 23 (2022) 100684.
[27] V. Polshettiwar, D. Cha, X. Zhang, J.M. Basset, High-surface-area silica nanospheres (KCC-1) with a fibrous morphology, Angew. Chem. Int. Ed Engl. 49 (50) (2010) 9652-9656.
[28] M.Z. Sun, A. Hanif, T.Q. Wang, C. Yang, D.C.W. Tsang, J. Shang, Chrysanthemum flower like silica with highly dispersed Cu nanoparticles as a high-performance NO₂ adsorbent, J. Hazard. Mater. 418 (2021) 126400.
[29] P.P. Ai, H.Q. Jin, J.C. Niu, W. Huang, M.H. Tan, Synergistic effect of urchin-like spherical Cu-based catalyst for enhanced dimethyl oxalate hydrogenation capacity, Fuel 333 (2023) 126330.
[30] R. Soltani, A. Marjani, M.R.S. Moguei, B. Rostami, S. Shirazian, Novel diamino-functionalized fibrous silica submicro-spheres with a bimodal-micro-mesoporous network: Ultrasonic-assisted fabrication, characterization, and their application for superior uptake of Congo red, J. Mol. Liq. 294 (2019) 111617.
[31] J.W. Zheng, L.L. Huang, C.H. Cui, Z.C. Chen, X.F. Liu, X.P. Duan, X.Y. Cao, T.Z. Yang, H.P. Zhu, K. Shi, P. Du, S.W. Ying, C.F. Zhu, Y.G. Yao, G.C. Guo, Y.Z. Yuan, S.Y. Xie, L.S. Zheng, Ambient-pressure synthesis of ethylene glycol catalyzed by C60-buffered Cu/SiO₂, Science 376 (6590) (2022) 288-292.
[32] R.P. Ye, L. Lin, L.C. Wang, D. Ding, Z.F. Zhou, P.B. Pan, Z.H. Xu, J.A. 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.

Ultra-stable Cu-based catalyst for dimethyl oxalate hydrogenation to ethylene glycol

Ultra-stable Cu-based catalyst for dimethyl oxalate hydrogenation to ethylene glycol

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jinlong Liu, Chenye Wang, Xingrui Wang, Chen Zhao, Huiquan Li, Ganyu Zhu, Jianbo Zhang. Reconstruction and recovery of anatase TiO₂ from spent selective catalytic reduction catalyst by NaOH hydrothermal method [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 53-60.
[2]	Yifan Jiang, Bingqi Xie, Jisong Zhang. Highly reactive and reusable heterogeneous activated carbons-based palladium catalysts for Suzuki-Miyaura reaction [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 165-172.
[3]	Yuehua Liu, Lili Chen, Shoujun Liu, Song Yang, Ju Shangguan. Role of iron-based catalysts in reducing NO_x emissions from coal combustion [J]. Chinese Journal of Chemical Engineering, 2023, 59(7): 1-8.
[4]	Fei Li, Xuemei Wang, Pengze Zhang, Qinqin Wang, Mingyuan Zhu, Bin Dai. Nitrogen and phosphorus co-doped activated carbon induces high density Cu⁺ active center for acetylene hydrochlorination [J]. Chinese Journal of Chemical Engineering, 2023, 59(7): 193-199.
[5]	Qunfeng Zhang, Bingcheng Li, Yuan Zhou, Deshuo Zhang, Chunshan Lu, Feng Feng, Jinghui Lv, Qingtao Wang, Xiaonian Li. Regulation of the selective hydrogenation performance of sulfur-doped carbon-supported palladium on chloronitrobenzene [J]. Chinese Journal of Chemical Engineering, 2023, 58(6): 69-75.
[6]	Jiajia Chen, Xinyu Lu, Dandan Wang, Pengcheng Xiu, Xiaoli Gu. Effective depolymerization of alkali lignin using an attapulgite-Ce_0.75Zr_0.25O₂(ATP-CZO)-supported cobalt catalyst in ethanol/isopropanol media [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 50-62.
[7]	Bin Gao, Junwen Chen, Qi Zuo, Hongyan Wang, Wenlin Li. The critical role of Zr in controlling the activity of Pd/Beta on the hydrogenation of phenol to cyclohexanone [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 79-87.
[8]	Linlin Su, Meijun Chen, Li Gong, Hua Yang, Chao Chen, Jun Wu, Ling Luo, Gang Yang, Lulu Long. Boost activation of peroxymonosulfate by iron doped K_2-xMn₈O₁₆: Mechanism and properties [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 88-97.
[9]	Qi Yang, Weikang Dai, Maoshuai Li, Jie Wei, Yi Feng, Cheng Yang, Wanxin Yang, Ying Zheng, Jie Ding, Mei-Yan Wang, Xinbin Ma. Enhanced selective hydrogenation of glycolaldehyde to ethylene glycol over Cu⁰-Cu⁺ sites [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 141-150.
[10]	Bingxiao Feng, Lining Hao, Chaoting Deng, Jiaqiang Wang, Hongbing Song, Meng Xiao, Tingting Huang, Quanhong Zhu, Hengjun Gai. A highly hydrothermal stable copper-based catalyst for catalytic wet air oxidation of m-cresol in coal chemical wastewater [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 338-348.
[11]	Shujun Peng, Song Lei, Sisi Wen, Jian Xue, Haihui Wang. A Ruddlesden–Popper oxide as a carbon dioxide tolerant cathode for solid oxide fuel cells that operate at intermediate temperatures [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 25-32.
[12]	Xia Xiong, Zuohua Liu, Changyuan Tao, Yundong Wang, Fangqin Cheng, Hong Li. Reduced power consumption in stirred vessel with high solid loading by equipping punched baffles [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 203-214.
[13]	Tinghao Jia, Yunbo Yu, Qing Liu, Yao Yang, Ji-Jun Zou, Xiangwen Zhang, Lun Pan. Theoretical and experimental study on the inhibition of jet fuel oxidation by diarylamine [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 225-232.
[14]	Zida Ma, Yuxia Li, Mengmeng Jin, Xiaoqin Liu, Linbing Sun. Fabrication of adsorbents with enhanced Cu^I stability: Creating a superhydrophobic microenvironment through grafting octadecylamine [J]. Chinese Journal of Chemical Engineering, 2023, 55(3): 41-48.
[15]	Da Ke, Minjia Wang, Jiancheng Ruan, Xinzhi Chen, Shaodong Zhou. Efficient, continuous oxidation of durene to pyromellitic dianhydride mediated by a V-Ti-P ternary catalyst: The remarkable doping effect [J]. Chinese Journal of Chemical Engineering, 2023, 55(3): 156-164.