Influence of the catalyst surface chemistry on the electrochemical self-coupling of biomass-derived benzaldehyde into hydrobenzoin
Gong L, Zhao S, Yu J, Li J, Arbiol J, Kallio T, Calcabrini M, Martínez-Alanis PR, Ibáñez M, Cabot A. 2024. Influence of the catalyst surface chemistry on the electrochemical self-coupling of biomass-derived benzaldehyde into hydrobenzoin. Energy Advances.
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https://doi.org/10.1039/D4YA00334A
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Journal Article
| Epub ahead of print
| English
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Author
Gong, Li;
Zhao, Shiling;
Yu, Jing;
Li, Junshan;
Arbiol, Jordi;
Kallio, Tanja;
Calcabrini, MarianoISTA ;
Martínez-Alanis, Paulina R.;
Ibáñez , MariaISTA ;
Cabot, Andreu
Department
Abstract
The electroreduction of biomass-derived benzaldehyde (BZH) provides a potentially cost-effective route to produce benzyl alcohol (BA). This reaction competes with the electrochemical self-coupling of BZH to hydrobenzoin (HDB), which holds significance as a biofuel. Herein, we demonstrate the selectivity towards one or the other product strongly depends on the surface chemistry of the catalyst, specifically on its ability to adsorb hydrogen, as showcased with Cu2S electrocatalysts. We particularly analyze the effect of surface ligands, oleylamine (OAm), on the selective conversion of BZH to BA or HDB. The effect of the electrode potential, electrolyte pH, and temperature are studied. Results indicate that bare Cu2S exhibits higher selectivity towards BA, while OAm-capped Cu2S promotes HDB formation. This difference is explained by the competing adsorption of protons and BZH. During the BZH electrochemical conversion, electrons first transfer to the C in the C[double bond, length as m-dash]O group to form a ketyl radical. Then the radical either couples with surrounding H+ to form BA or self-couple to produce HDB, depending on the H+ availability that is affected by the electrocatalyst surface properties. The presence of OAm inhibits the H adsorption on the electrode surface therefore reducing the formation of high-energy state Had and its combination with ketyl radicals to form BA. Instead, the presence of OAm promotes the outer sphere reaction for obtaining HDB.
Publishing Year
Date Published
2024-07-12
Journal Title
Energy Advances
Acknowledgement
L. Gong and J. Yu thank the China Scholarship Council for the scholarship support. ICN2 acknowledges funding from Generalitat de Catalunya 2021SGR00457. This study is part of the Advanced Materials programme and was supported by MCIN with funding from European Union NextGenerationEU (PRTR-C17.I1) and by Generalitat de Catalunya. The authors thank support from the project NANOGEN (PID2020-116093RB-C43), funded by MCIN/AEI/10.13039/501100011033/and by “ERDF A way of making Europe”, by the “European Union”. ICN2 is supported by the Severo Ochoa program from Spanish MCIN/AEI (Grant No.: CEX2021-001214-S) and is funded by the CERCA Programme/Generalitat de Catalunya. Part of the present work has been performed in the framework of Universitat Autònoma de Barcelona Materials Science PhD program. Authors acknowledge the use of instrumentation as well as the technical advice provided by the Joint Electron Microscopy Center at ALBA (JEMCA). ICN2 acknowledges funding from Grant IU16-014206 (METCAM-FIB) funded by the European Union through the European Regional Development Fund (ERDF), with the support of the Ministry of Research and Universities, Generalitat de Catalunya. ICN2 is founding member of e-DREAM.
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Cite this
Gong L, Zhao S, Yu J, et al. Influence of the catalyst surface chemistry on the electrochemical self-coupling of biomass-derived benzaldehyde into hydrobenzoin. Energy Advances. 2024. doi:10.1039/d4ya00334a
Gong, L., Zhao, S., Yu, J., Li, J., Arbiol, J., Kallio, T., … Cabot, A. (2024). Influence of the catalyst surface chemistry on the electrochemical self-coupling of biomass-derived benzaldehyde into hydrobenzoin. Energy Advances. Royal Society of Chemistry. https://doi.org/10.1039/d4ya00334a
Gong, Li, Shiling Zhao, Jing Yu, Junshan Li, Jordi Arbiol, Tanja Kallio, Mariano Calcabrini, Paulina R. Martínez-Alanis, Maria Ibáñez, and Andreu Cabot. “Influence of the Catalyst Surface Chemistry on the Electrochemical Self-Coupling of Biomass-Derived Benzaldehyde into Hydrobenzoin.” Energy Advances. Royal Society of Chemistry, 2024. https://doi.org/10.1039/d4ya00334a.
L. Gong et al., “Influence of the catalyst surface chemistry on the electrochemical self-coupling of biomass-derived benzaldehyde into hydrobenzoin,” Energy Advances. Royal Society of Chemistry, 2024.
Gong L, Zhao S, Yu J, Li J, Arbiol J, Kallio T, Calcabrini M, Martínez-Alanis PR, Ibáñez M, Cabot A. 2024. Influence of the catalyst surface chemistry on the electrochemical self-coupling of biomass-derived benzaldehyde into hydrobenzoin. Energy Advances.
Gong, Li, et al. “Influence of the Catalyst Surface Chemistry on the Electrochemical Self-Coupling of Biomass-Derived Benzaldehyde into Hydrobenzoin.” Energy Advances, Royal Society of Chemistry, 2024, doi:10.1039/d4ya00334a.
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