Selective electrochemical oxidation of alkene: Recent progress and perspectives

doi:10.1016/S1872-2067(23)64522-X

Chinese Journal of Catalysis ›› 2023, Vol. 53: 34-51.DOI: 10.1016/S1872-2067(23)64522-X

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Selective electrochemical oxidation of alkene: Recent progress and perspectives

Jin Wang^a^,¹, Justin Zhu Yeow Seow^b^,¹, Zhichuan J. Xu^b^,^c^,^*(), Xiao Ren^a^,^*()

^aBeijing National Laboratory for Molecular Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
^bSchool of Materials Science and Engineering, Nanyang Technological University, Singapore 639798, Singapore
^cCentre for Advanced Catalysis Science and Technology, Nanyang Technological University, Singapore 639798, Singapore

Received:2023-07-13 Accepted:2023-09-20 Online:2023-10-18 Published:2023-10-25
Contact: *E-mail: renxiao_@pku.edu.cn (X. Ren), xuzc@ntu.edu.sg (Z. J. Xu).
About author:Zhichuan J. Xu is a professor at the School of Materials Science and Engieering, Nanyang Technological University, and a fellow of the Academy of Engineering, Singapore. He is a member of the International Society of Electrochemistry (ISE), the Electrochemistry Society (ECS), and a fellow of the Royal Society of Chemistry (FRSC). He serves as the president of ECS Singapore Section. His major research interest is electrocatalysis.
Xiao Ren is an associate research fellow at Peking University. After receiving his Ph.D. (2017) from the Institute of Physics, Chinese Academy of Sciences, China, Xiao Ren received postdoctoral training at Nanyang Technological University, Singapore (2017-2022). Dr. Ren joined the College of Chemistry and Molecular Engieering of Peking University in 2022. The central paradigm of his research is to develop magnetic materials for electrocatalytic reactions and to study electrochemical reaction processes involving electron spins. The main focus is on the changes in the reaction pathways and the kinetics of chemical reactions in which electron spin is involved.
¹Contributed equally to this work.
Supported by:
The National Natural Science Foundation of China(52202202);The Singapore MOE Tier 1 grant(RG78/22)

Abstract

Abstract:

Alkene oxidation is an important industrial process that produces considerable quantities of commodity chemicals, notably ethylene oxide and propylene oxide. However, typical thermal oxidation processes are characterized by harsh reaction conditions and limited selectivity. Thus, electrochemical alternatives with enhanced product selectivity emerge as promising solutions with the possibility of using renewable input energy sources. Herein, we discuss strategies to improve the selectivity of alkene electrooxidation, specifically focusing on the regulation of the geometric and electronic structures of electrocatalysts, as well as the application of mediated indirect oxidation. Furthermore, we also provide an overview of the current challenges and problems requiring further investigation in improving industrial feasibility of electrochemical alkene oxidation.

Key words: Alkene oxidation, Electrocatalysis, Overoxidation, Electronic structure, Indirect oxidation

Jin Wang, Justin Zhu Yeow Seow, Zhichuan J. Xu, Xiao Ren. Selective electrochemical oxidation of alkene: Recent progress and perspectives[J]. Chinese Journal of Catalysis, 2023, 53: 34-51.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(23)64522-X

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Figures/Tables 11

Fig. 1. Schematic illustration of the proposed electrocatalytic system for alkene oxidation powered by electricity from renewable power sources.

Scheme 1. (a-c) Possible mechanisms of alkene electrooxidation as exemplified by ethylene electrooxidation, and possible electrooxidation products of (d) ethylene, (e) propylene, (f) cyclohexene, (g) cyclooctene and (h) styrene.

Fig. 2. (a) Schematic illustration of modulating available active sites. (b) Proposed formation mechanism of *OCClO* species. Reprinted with permission from Ref. [16]. Copyright 2021, American Chemical Society. (c) Proposed catalytic cycles for overoxidation and partial oxidation of ethylene. Reprinted with permission from Ref. [16]. Copyright 2021, American Chemical Society. (d) Geometric effects of increasing surface coverage of organic species formed in situ on the catalyst. Reprinted with permission from Ref. [17]. Copyright 2019, Royal Society of Chemistry.

Fig. 3. (a) Schematics of O-correlated and OH-correlated pathways. (b) Proposed mechanism for cyclooctene electrooxidation catalyzed by manganese oxide nanoparticles. Reprinted with permission from Ref. [19]. Copyright 2019, American Chemical Society. (c) Ir-doping on manganese oxide as a strategy to increase selectivity of cyclooctene epoxidation through facilitating Mn oxidation as demonstrated by X-ray absorption spectra (XAS). Reprinted from Ref. [22] under Creative Commons Attribution 4.0 International License: https://creativecommons.org/ licenses/by/4.0/.

Fig. 4. (a) Schematics of O-correlated and OH-correlated pathways for propylene (Pr) epoxidation on Ag3PO4. C, H, Ag, O and P atoms are colored in gray, white, blue, red and light pink. (b) Free energy diagrams of O-correlated and OH-correlated pathways on (100), (110) and (111) facets of Ag3PO4. Reprinted with permission from Ref. [23]. Copyright 2022, Springer Nature. (c) Possible reaction mechanism for ethylene electrooxidation to ethylene glycol on PdO (100), possible dopant positions and DFT-calculated free energy change from State IV to State V after doping, where # represents undoped catalyst. Reprinted with permission from Ref. [24]. Copyright 2020, Springer Nature.

Fig. 5. (a) Schematic of halide-mediated and H2O2-mediated electrocatalytic system. (b) Schematic of the electrocatalytic system for chloride-mediated ethylene-to-EO conversion. CER mechanism on Co3O4 nanoparticles in neutral NaCl electrolyte either without (c) or with (d) the presence of ethylene. Reprinted with permission from Ref. [26]. Copyright 2020, American Chemical Society.

Fig. 6. (a) Schematic illustration of the photo-electro-heterogeneous integrated catalytic system. Reprinted with permission from Ref. [36]. Copyright 2020, Springer Nature. (b) Schematic of H2O2-mediated alkene oxidation in H-cell. Reprinted with permission from Ref. [37]. Copyright 2021, John Wiley and Sons. (c) Schematic of the solid electrolyte reactor for H2O2 production. Reprinted with permission from Ref. [38]. Copyright 2023, Springer Nature. (d) Schematic of integrated three-chamber solid electrolyte reactor for alkene oxidation [39]. (e) Configurations of interfacial and conventional coupling systems. Reprinted with permission from Ref. [39]. Copyright 2023, Elsevier.

Fig. 7. Comparison of the key parameters of different catalytic systems. The ‘direct’ and ‘indirect’ labels stand for direct and indirect catalytic systems respectively.

Fig. 8. (a) Schematics of internal and external reflection mode for in-situ FTIR characterization incorporating electrolyte, working electrode (WE), counter electrode (CE) and reference electrode (RE). Reprinted with permission from Ref. [60]. Copyright 2022, Elsevier. (b) Electrochemical cell for XAS measurements in fluorescence mode. Reprinted from Ref. [66]. Under Creative Commons Attribution 4.0 International License: https://creativecommons.org/licenses/by/4.0/. (c) Schematics of EC-MS coupled with a flow electrolyzer. Reprinted with permission from Ref. [67]. Copyright 2021, John Wiley and Sons. (d) Schematics of the microfluidic electrochemical reaction cell for in-situ SIMS experiments. Reprinted with permission from Ref. [68]. Copyright 2017, American Chemical Society.

Fig. 9. TEA of the production of EO (a), EG (b), PO (c), and PG (d) at a current density of 100 mA cm-2. TEA of the production of EO at current densities of 10 mA cm-2 (e) and 500 mA cm-2 (f).

Fig. 10. Proposed directions for further research in improving electrochemical alkene oxidation.

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Selective electrochemical oxidation of alkene: Recent progress and perspectives

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