Reconstruction of Cu–ZnO catalyst by organic acid and deactivation mechanism in liquid-phase hydrogenation of dimethyl succinate to 1,4-butanediol

doi:10.1007/s11705-022-2281-9

Front. Chem. Sci. Eng.

2023, Vol. 17

Issue (9) : 1311-1319 https://doi.org/10.1007/s11705-022-2281-9

COMMUNICATION

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

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Abstract

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.

Keywords liquid phase hydrogenation Cu–ZnO deactivation mechanism 1,4-butanediol diester

Corresponding Author(s): Yan Xu,Yujun Zhao

About author:

^* These authors contributed equally to this work.

Online First Date: 06 April 2023 Issue Date: 29 August 2023

Cite this article:

Fan Sun,Huijiang Huang,Wei Liu, et al. Reconstruction of Cu–ZnO catalyst by organic acid and deactivation mechanism in liquid-phase hydrogenation of dimethyl succinate to 1,4-butanediol[J]. Front. Chem. Sci. Eng., 2023, 17(9): 1311-1319.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-022-2281-9
https://academic.hep.com.cn/fcse/EN/Y2023/V17/I9/1311

Scheme1 Reaction pathway for the hydrogenation of (a) dialkyl maleate and (b) formation of polyesters.

Scheme2 Reaction pathway for the formation of DMSA.

Fig.1 SEM images of (a) Cu–ZnO–F and (b) Cu–ZnO–P.

Tab.1 Textural and physicochemical properties of catalysts employed in the reconstruction process.

Fig.2 TEM images of (a, e) Cu–ZnO–F and (i, m) Cu–ZnO–P and corresponding EDS mapping (blue part: Cu; red part: Zn; pink part: overlap of Cu and Zn).

Fig.3 (a) XPS and (b) Cu LMM spectra of Cu–ZnO–F and Cu–ZnO–P.

Fig.4 Plausible process for the organic acid reconstruction.

Fig.5 Liquid phase hydrogenation of (a) DMSA on Cu–ZnO–F and (b) Cu–ZnO–P. Reaction conditions: t = 200 °C, P = 8 MPa, H₂/DMSA = 50, WHSV = 0.5 h^–1. Reactant: 10 wt % DMSA in 1,4-dioxane.

Tab.2 Textural and physicochemical properties of catalysts in the hydrogenation of DMSA

Fig.6 MALDI-TOFMS analysis of the polyesters existing on the spent catalysts. The number near the peak presents the molecular weight of the compound detected, and the intensity of the peaks represents the relative content.

Fig.7 Plausible reaction pathways for the liquid phase hydrogenation of DMSA and transesterification between DMSA and BDO on Cu–ZnO. ZnO strongly interacting with (a) Cu, (b) Cu–ZnO with weakly interacted ZnO and (c) isolated ZnO.

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