Reconstruction of Cu–ZnO catalyst by organic acid and deactivation mechanism in liquid-phase hydrogenation of dimethyl succinate to 1,4-butanediol
Fan Sun, Huijiang Huang, Wei Liu, Lu Wang, Yan Xu(), Yujun Zhao()
Key Laboratory for Green Chemical Technology of Ministry of Education, Collaborative Innovation Center of Chemical Science and Engineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China
A reconstructed Cu–ZnO catalyst with improved stability was fabricated by organic acid treatment method for the liquid-phase hydrogenation of dimethyl succinate to 1,4-butanediol. According to the characterization results of the fresh Cu–ZnO and reconstructed Cu–ZnO, three different forms of ZnO were suggested to be presented on the catalysts: ZnO having strong interaction with Cu species, ZnO that weakly interacted with Cu species and isolated ZnO. The first form of ZnO was believed to be beneficial to the formation of efficient active site Cu+, while the latter two forms of ZnO took the main responsibility for the deactivation of Cu–ZnO catalysts in the liquid-phase hydrogenation of diesters. The reconstruction of the Cu–ZnO catalyst by the organic acid treatment method resulted in a new Cu–ZnO catalyst with more Cu+ and less ZnO species that leads to deactivation. Furthermore, the deactivation mechanism of Cu–ZnO catalysts in liquid-phase diester hydrogenation in continuous flow system was proposed: the deposition of the polyesters on the catalysts via transesterification catalyzed by weakly interacted ZnO and isolated ZnO leads to the deactivation. These results provided meaningful instructions for designing highly efficient Cu–Zn catalysts for similar ester hydrogenation systems.
. [J]. Frontiers of Chemical Science and Engineering, 2023, 17(9): 1311-1319.
Fan Sun, Huijiang Huang, Wei Liu, Lu Wang, Yan Xu, Yujun Zhao. Reconstruction of Cu–ZnO catalyst by organic acid and deactivation mechanism in liquid-phase hydrogenation of dimethyl succinate to 1,4-butanediol. Front. Chem. Sci. Eng., 2023, 17(9): 1311-1319.
S D Le, S Nishimura. Effect of support on the formation of CuPd alloy nanoparticles for the hydrogenation of succinic acid. Applied Catalysis B: Environmental, 2021, 282: 119619 https://doi.org/10.1016/j.apcatb.2020.119619
2
J J Shang, G Yao, R H Guo, W Zheng, L Gu, J W Lan. Synthesis and characterization of biodegradable thermoplastic elastomers derived from N′,N-bis(2-carboxyethyl)-pyromellitimide, poly(butylene succinate) and polyethylene glycol. Frontiers of Chemical Science and Engineering, 2018, 12(3): 457–466 https://doi.org/10.1007/s11705-018-1716-9
3
X M Zhou. Synthesis and characterization of polyester copolymers based on poly(butylene succinate) and poly(ethylene glycol). Materials Science and Engineering C, 2012, 32(8): 2459–2463 https://doi.org/10.1016/j.msec.2012.07.025
4
Z W Huang, K J Barnett, J P Chada, Z J Brentzel, Z R Xu, J A Dumesic, G W Huber. Hydrogenation of γ-butyrolactone to 1,4-butanediol over CuCo/TiO2 bimetallic catalysts. ACS Catalysis, 2017, 7(12): 8429–8440 https://doi.org/10.1021/acscatal.7b03016
5
C Delhomme, D Weuster-Botz, F E Kühn. Succinic acid from renewable resources as a C4 building-block chemical—a review of the catalytic possibilities in aqueous media. Green Chemistry, 2009, 11(1): 13–26 https://doi.org/10.1039/B810684C
6
L F Chen, P J Guo, L J Zhu, M H Qiao, W Shen, H L Xu, K N Fan. Preparation of Cu/SBA-15 catalysts by different methods for the hydrogenolysis of dimethyl maleate to 1,4-butanediol. Applied Catalysis A: General, 2009, 356(2): 129–136 https://doi.org/10.1016/j.apcata.2008.12.029
7
C Ohlinger, B Kraushaar-Czarnetzki. Improved processing stability in the hydrogenation of dimethyl maleate to γ-butyrolactone, 1,4-butanediol and tetrahydrofuran. Chemical Engineering Science, 2003, 58(8): 1453–1461 https://doi.org/10.1016/S0009-2509(02)00672-3
8
J T Ying, X Q Han, L Ma, C S Lu, F Feng, Q F Zhang, X N Li. Effects of basic promoters on the catalytic performance of Cu/SiO2 in the hydrogenation of dimethyl maleate. Catalysts, 2019, 9(9): 704–713 https://doi.org/10.3390/catal9090704
9
S P Müller, M Kucher, C Ohlinger, B Kraushaar-Czarnetzki. Extrusion of Cu/ZnO catalysts for the single-stage gas-phase processing of dimethyl maleate to tetrahydrofuran. Journal of Catalysis, 2003, 218(2): 419–426 https://doi.org/10.1016/S0021-9517(03)00157-X
10
S M Li, Y Wang, J Zhang, S P Wang, Y Xu, Y J Zhao, X B Ma. Kinetics study of hydrogenation of dimethyl oxalate over Cu/SiO2 catalyst. Industrial & Engineering Chemistry Research, 2015, 54(4): 1243–1250 https://doi.org/10.1021/ie5043038
11
W C Wang, H Wang, J W Zhang, L X Kong, H J Huang, W Liu, S P Wang, X B Ma, Y J Zhao. Determining roles of Cu0 in the chemosynthesis of diols via condensed diester hydrogenation on Cu/SiO2 catalyst. ChemCatChem, 2020, 12(15): 3849–3852 https://doi.org/10.1002/cctc.202000547
12
Y J Zhao, Z Y Guo, H J Zhang, B Peng, Y X Xu, Y Wang, J Zhang, Y Xu, S P Wang, X B Ma. Hydrogenation of diesters on copper catalyst anchored on ordered hierarchical porous silica: pore size effect. Journal of Catalysis, 2018, 357: 223–237 https://doi.org/10.1016/j.jcat.2017.11.006
13
J H Schlander, T Turek. Gas-phase hydrogenolysis of dimethyl maleate to 1,4-butanediol and γ-butyrolactone over copper/zinc oxide catalysts. Industrial & Engineering Chemistry Research, 1999, 38(4): 1264–1270 https://doi.org/10.1021/ie980606k
14
A Küksal, E Klemm, G Emig. Single-stage liquid phase hydrogenation of maleic anhydride to γ-butyrolactone, 1,4-butanediol and tetrahydrofurane on Cu/ZnO/Al2O3 catalysts. Studies in Surface Science and Catalysis, 2000, 130: 2111–2116 https://doi.org/10.1016/S0167-2991(00)80780-6
15
J Aubrecht, V Pospelova, O Kikhtyanin, M Lhotka, D Kubička. Understanding of the key properties of supported Cu-based catalysts and their influence on ester hydrogenolysis. Catalysis Today, 2022, 397–399: 173–181 https://doi.org/10.1016/j.cattod.2021.09.039
16
G Q Ding, Y L Zhu, H Y Zheng, W Zhang, Y W Li. Study on the reaction pathway in the vapor-phase hydrogenation of biomass-derived diethyl succinate over CuO/ZnO catalyst. Catalysis Communications, 2010, 11(14): 1120–1124 https://doi.org/10.1016/j.catcom.2010.06.007
X Y Wan, D Z Ren, Y J Liu, J Fu, Z Y Song, F M Jin, Z B Huo. Facile synthesis of dimethyl succinate via esterification of succinic anhydride over ZnO in methanol. ACS Sustainable Chemistry & Engineering, 2018, 6(3): 2969–2975 https://doi.org/10.1021/acssuschemeng.7b02598
19
N Karanwal, M G Sibi, M K Khan, A A Myint, B Chan Ryu, J W Kang, J Kim. Trimetallic Cu–Ni–Zn/H-ZSM-5 catalyst for the one-pot conversion of levulinic acid to high-yield 1,4-pentanediol under mild conditions in an aqueous medium. ACS Catalysis, 2021, 11(5): 2846–2864 https://doi.org/10.1021/acscatal.0c04216
20
L Zhang, J B Mao, S M Li, J M Yin, X D Sun, X W Guo, C S Song, J X Zhou. Hydrogenation of levulinic acid into gamma-valerolactone over in situ reduced CuAg bimetallic catalyst: strategy and mechanism of preventing Cu leaching. Applied Catalysis B: Environmental, 2018, 232: 1–10 https://doi.org/10.1016/j.apcatb.2018.03.033
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. Applied Catalysis A: General, 2017, 539: 59–69 https://doi.org/10.1016/j.apcata.2017.04.001
22
Y Q Yao, X Q Wu, O Y Gutierrez, J Ji, P Jin, S P Wang, Y Xu, Y J Zhao, S P Wang, X B Ma, J A Lercher. Roles of Cu+ and Cu0 sites in liquid-phase hydrogenation of esters on core-shell CuZnx@C catalysts. Applied Catalysis B: Environmental, 2020, 267: 118698 https://doi.org/10.1016/j.apcatb.2020.118698
23
B Zhang, Y Chen, J W Li, E Pippel, H M Yang, Z Gao, Y Qin. High efficiency Cu–ZnO hydrogenation catalyst: the tailoring of Cu–ZnO interface sites by molecular layer deposition. ACS Catalysis, 2015, 5(9): 5567–5573 https://doi.org/10.1021/acscatal.5b01266
24
X Q Dong, J W Lei, Y F Chen, H X Jiang, M H Zhang. Selective hydrogenation of acetic acid to ethanol on Cu-In catalyst supported by SBA-15. Applied Catalysis B: Environmental, 2019, 244: 448–458 https://doi.org/10.1016/j.apcatb.2018.11.062
25
J W Zhang, L X Kong, Y Chen, H J Huang, H H Zhang, Y Q Yao, Y X Xu, Y Xu, S P Wang, X B Ma, Y Zhao. Enhanced synergy between Cu0 and Cu+ on nickel doped copper catalyst for gaseous acetic acid hydrogenation. Frontiers of Chemical Science and Engineering, 2021, 15(3): 666–678 https://doi.org/10.1007/s11705-020-1982-1
26
T V Westen, R D Groot. Effect of temperature cycling on ostwald ripening. Crystal Growth & Design, 2018, 18(9): 4952–4962 https://doi.org/10.1021/acs.cgd.8b00267
27
S Yan, S O Salley, K Y Simon Ng. Simultaneous transesterification and esterification of unrefined or waste oils over ZnO-La2O3 catalysts. Applied Catalysis A: General, 2009, 353(2): 203–212 https://doi.org/10.1016/j.apcata.2008.10.053
28
S Yan, S Mohan, C DiMaggio, M Kim, K Y S Ng, S O Salley. Long term activity of modified ZnO nanoparticles for transesterification. Fuel, 2010, 89(10): 2844–2852 https://doi.org/10.1016/j.fuel.2010.05.023
29
I Istadi, S A Prasetyo, T S Nugroho. Characterization of K2O/CaO-ZnO catalyst for transesterification of soybean oil to biodiesel. Procedia Environmental Sciences, 2015, 23: 394–399 https://doi.org/10.1016/j.proenv.2015.01.056
30
N S Babu, R Sree, P S S Prasad, N Lingaiah. Room temperature transesterification of edible and nonedible oils using a heterogeneous strong basic Mg/La catalyst. Energy & Fuels, 2008, 22(3): 1965–1971 https://doi.org/10.1021/ef700687w
31
X M Wu, F F Zhu, J J Qi, L Y Zhao, F W Yan, C H Li. Challenge of biodiesel production from sewage sludge catalyzed by KOH, KOH/activated carbon, and KOH/CaO. Frontiers of Environmental Science & Engineering, 2017, 11(2): 3–13 https://doi.org/10.1007/s11783-017-0913-y
32
O Kikhtyanin, J Aubrecht, V Pospelova, D Kubička. On the origin of the transesterification reaction route during dimethyl adipate hydrogenolysis. Applied Catalysis A: General, 2020, 606: 117825 https://doi.org/10.1016/j.apcata.2020.117825
