Hydrogen Bonding Enhances the Electrochemical Hydrogenation of Benzaldehyde in the Aqueous Phase

Sanyal, Udishnu; Yuk, Simuck F.; Koh, Katherine; Lee, Mal‐Soon; Stoerzinger, Kelsey; Zhang, Difan; Meyer, Laura C.; Lopez‐Ruiz, Juan A.; Karkamkar, Abhi; Holladay, Jamie D.; Camaioni, Donald M.; Nguyen, Manh‐Thuong; Glezakou, Vassiliki‐Alexandra; Rousseau, Roger; Gutiérrez, Oliver Y.; Lercher, Johannes A.

doi:10.1002/anie.202008178

Hydrogen Bonding Enhances the Electrochemical Hydrogenation of Benzaldehyde in the Aqueous Phase

Journal Article · Tue Oct 27 00:00:00 EDT 2020 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.202008178· OSTI ID:1690294

^[1]; ^[1]; Koh, Katherine ^[1]; ^[1]; ^[2]; ^[1]; ^[1]; ^[1]; Karkamkar, Abhi ^[1]; Holladay, Jamie D. ^[1]; ^[1]; ^[1]; ^[1]; ^[1]; ^[1]; ^[3]

Institute for Integrated Catalysis Pacific Northwest National Laboratory P.O. Box 999 Richland WA 99352 USA
Institute for Integrated Catalysis Pacific Northwest National Laboratory P.O. Box 999 Richland WA 99352 USA, School of Chemical, Biological and Environmental Engineering Oregon State University Corvallis OR 97331 USA
Institute for Integrated Catalysis Pacific Northwest National Laboratory P.O. Box 999 Richland WA 99352 USA, Department of Chemistry and Catalysis Research Center Institution TU München Lichtenbergstrasse 4 85747 Garching Germany

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Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: AC05-76RL01830

OSTI ID:: 1690294

Alternate ID(s):: OSTI ID: 1771311
OSTI ID: 1786201

Report Number(s):: PNNL-SA--155228

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 1 Vol. 60; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: Germany

Language:: English

References (55)

Palladium-Catalyzed Hydrolytic Cleavage of Aromatic C−O Bonds Wang, Meng; Shi, Hui; Camaioni, Donald M. Angewandte Chemie, Vol. 129, Issue 8 https://doi.org/10.1002/ange.201611076	journal	January 2017
Electrochemically Tunable Proton‐Coupled Electron Transfer in Pd‐Catalyzed Benzaldehyde Hydrogenation Koh, Katherine; Sanyal, Udishnu; Lee, Mal‐Soon Angewandte Chemie, Vol. 132, Issue 4 https://doi.org/10.1002/ange.201912241	journal	December 2019
Palladium-Catalyzed Hydrolytic Cleavage of Aromatic C−O Bonds Wang, Meng; Shi, Hui; Camaioni, Donald M. Angewandte Chemie International Edition, Vol. 56, Issue 8 https://doi.org/10.1002/anie.201611076	journal	January 2017
Electrochemically Tunable Proton‐Coupled Electron Transfer in Pd‐Catalyzed Benzaldehyde Hydrogenation Koh, Katherine; Sanyal, Udishnu; Lee, Mal‐Soon Angewandte Chemie International Edition, Vol. 59, Issue 4 https://doi.org/10.1002/anie.201912241	journal	January 2020
Structure Sensitivity in Hydrogenation Reactions on Pt/C in Aqueous‐phase Sanyal, Udishnu; Song, Yang; Singh, Nirala ChemCatChem, Vol. 11, Issue 1 https://doi.org/10.1002/cctc.201801344	journal	October 2018
Electrocatalytic Hydrogenation and Deoxygenation of Glucose on Solid Metal Electrodes Kwon, Youngkook; Koper, Marc T. M. ChemSusChem, Vol. 6, Issue 3 https://doi.org/10.1002/cssc.201200722	journal	January 2013
Electricity Storage in Biofuels: Selective Electrocatalytic Reduction of Levulinic Acid to Valeric Acid or γ-Valerolactone Xin, Le; Zhang, Zhiyong; Qi, Ji ChemSusChem, Vol. 6, Issue 4 https://doi.org/10.1002/cssc.201200765	journal	March 2013
Electrocatalytic Hydrogenation of Oxygenates using Earth-Abundant Transition-Metal Nanoparticles under Mild Conditions Carroll, Kyler J.; Burger, Thomas; Langenegger, Lukas ChemSusChem, Vol. 9, Issue 15 https://doi.org/10.1002/cssc.201600290	journal	June 2016
Electrolytic hydrogenation of phenols in aqueous acid solutions Sasaki, Kazuo; Kunai, Atsutaka; Harada, Junji Electrochimica Acta, Vol. 28, Issue 5 https://doi.org/10.1016/0013-4686(83)85062-2	journal	May 1983
Cathodic Hydrogen Evolution Reaction on Gold Catalyzed by Proton-Carriers Creju, Raluca; Kellenberger, Andrea; Medeleanu, Mihai International Journal of Electrochemical Science, Vol. 9, Issue 8 https://doi.org/10.1016/S1452-3981(23)08106-3	journal	August 2014
Aqueous phase electrocatalysis and thermal catalysis for the hydrogenation of phenol at mild conditions Song, Yang; Gutiérrez, Oliver Y.; Herranz, Juan Applied Catalysis B: Environmental, Vol. 182 https://doi.org/10.1016/j.apcatb.2015.09.027	journal	March 2016
Electro-reduction of organics on metal cathodes: A multiscale-modeling study of benzaldehyde on Au (111) Nguyen, Manh-Thuong; Akhade, Sneha A.; Cantu, David C. Catalysis Today, Vol. 350 https://doi.org/10.1016/j.cattod.2019.05.067	journal	June 2020
Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes Zhao, Chen; He, Jiayue; Lemonidou, Angeliki A. Journal of Catalysis, Vol. 280, Issue 1 https://doi.org/10.1016/j.jcat.2011.02.001	journal	May 2011
Integrated catalytic and electrocatalytic conversion of substituted phenols and diaryl ethers Song, Yang; Chia, Shao Hua; Sanyal, Udishnu Journal of Catalysis, Vol. 344 https://doi.org/10.1016/j.jcat.2016.09.030	journal	December 2016
Hydrogenation of benzaldehyde via electrocatalysis and thermal catalysis on carbon-supported metals Song, Yang; Sanyal, Udishnu; Pangotra, Dhananjai Journal of Catalysis, Vol. 359 https://doi.org/10.1016/j.jcat.2017.12.026	journal	March 2018
Carbon-supported Pt during aqueous phenol hydrogenation with and without applied electrical potential: X-ray absorption and theoretical studies of structure and adsorbates Singh, Nirala; Nguyen, Manh-Thuong; Cantu, David C. Journal of Catalysis, Vol. 368 https://doi.org/10.1016/j.jcat.2018.09.021	journal	December 2018
A mechanistic investigation on the electrocatalytic reduction of aliphatic ketones at platinum Bondue, C. J.; Koper, M. T. M. Journal of Catalysis, Vol. 369 https://doi.org/10.1016/j.jcat.2018.11.019	journal	January 2019
Aqueous phase catalytic and electrocatalytic hydrogenation of phenol and benzaldehyde over platinum group metals Singh, Nirala; Sanyal, Udishnu; Ruehl, Griffin Journal of Catalysis, Vol. 382 https://doi.org/10.1016/j.jcat.2019.12.034	journal	February 2020
Cyclic-voltammetry behavior of Pt(111) in aqueous HClO4+C6H6: Influence of C6H6 concentration, scan rate and temperature Obradović, Maja D.; Lessard, Jean; Jerkiewicz, Gregory Journal of Electroanalytical Chemistry, Vol. 649, Issue 1-2 https://doi.org/10.1016/j.jelechem.2010.04.022	journal	November 2010
Low-Temperature Electrochemical Upgrading of Bio-oils Using Polymer Electrolyte Membranes Lister, Tedd E.; Diaz, Luis A.; Lilga, Michael A. Energy & Fuels, Vol. 32, Issue 5 https://doi.org/10.1021/acs.energyfuels.8b00134	journal	April 2018
Electrocatalytic Hydrogenation of Oxygenated Compounds in Aqueous Phase Sanyal, Udishnu; Lopez-Ruiz, Juan; Padmaperuma, Asanga B. Organic Process Research & Development, Vol. 22, Issue 12 https://doi.org/10.1021/acs.oprd.8b00236	journal	September 2018
Ab Initio-Based Kinetic Modeling for the Design of Molecular Catalysts: The Case of H ₂ Production Electrocatalysts Ho, Ming-Hsun; Rousseau, Roger; Roberts, John A. S. ACS Catalysis, Vol. 5, Issue 9 https://doi.org/10.1021/acscatal.5b01152	journal	August 2015
Electrocatalytic Conversion of Furanic Compounds Kwon, Youngkook; Schouten, Klaas Jan P.; van der Waal, Jan C. ACS Catalysis, Vol. 6, Issue 10 https://doi.org/10.1021/acscatal.6b01861	journal	September 2016
A Combined Experimental and Theoretical Study on the Activity and Selectivity of the Electrocatalytic Hydrogenation of Aldehydes Cantu, David C.; Padmaperuma, Asanga B.; Nguyen, Manh-Thuong ACS Catalysis, Vol. 8, Issue 8 https://doi.org/10.1021/acscatal.8b00858	journal	June 2018
Kinetic Significance of Proton–Electron Transfer during Condensed Phase Reduction of Carbonyls on Transition Metal Clusters Shangguan, Junnan; Chin, Ya-Huei Cathy ACS Catalysis, Vol. 9, Issue 3 https://doi.org/10.1021/acscatal.8b03470	journal	January 2019
Quantifying Adsorption of Organic Molecules on Platinum in Aqueous Phase by Hydrogen Site Blocking and in Situ X-ray Absorption Spectroscopy Singh, Nirala; Sanyal, Udishnu; Fulton, John L. ACS Catalysis, Vol. 9, Issue 8 https://doi.org/10.1021/acscatal.9b01415	journal	June 2019
Understanding the Role of Metal and Molecular Structure on the Electrocatalytic Hydrogenation of Oxygenated Organic Compounds Lopez-Ruiz, Juan A.; Andrews, Evan; Akhade, Sneha A. ACS Catalysis, Vol. 9, Issue 11 https://doi.org/10.1021/acscatal.9b02921	journal	September 2019
Water-Mediated Heterogeneously Catalyzed Reactions Li, Gengnan; Wang, Bin; Resasco, Daniel E. ACS Catalysis, Vol. 10, Issue 2 https://doi.org/10.1021/acscatal.9b04637	journal	December 2019
Synthetic Organic Electrochemistry: An Enabling and Innately Sustainable Method Horn, Evan J.; Rosen, Brandon R.; Baran, Phil S. ACS Central Science, Vol. 2, Issue 5 https://doi.org/10.1021/acscentsci.6b00091	journal	May 2016
Electrochemical Conversion of Muconic Acid to Biobased Diacid Monomers Matthiesen, John E.; Carraher, Jack M.; Vasiliu, Monica ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 6 https://doi.org/10.1021/acssuschemeng.6b00679	journal	May 2016
Electrochemical Conversion of Biologically Produced Muconic Acid: Key Considerations for Scale-Up and Corresponding Technoeconomic Analysis Matthiesen, John E.; Suástegui, Miguel; Wu, Yutong ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 12 https://doi.org/10.1021/acssuschemeng.6b01981	journal	October 2016
Kinetic Investigation of the Sustainable Electrocatalytic Hydrogenation of Benzaldehyde on Pd/C: Effect of Electrolyte Composition and Half-Cell Potentials Lopez-Ruiz, Juan A.; Sanyal, Udishnu; Egbert, Jonathan ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 12 https://doi.org/10.1021/acssuschemeng.8b02637	journal	October 2018
Liquid-Phase Hydrogenation Kinetics of Multicomponent Aromatic Mixtures on Ni/Al ₂ O ₃ Lylykangas, Mikko S.; Rautanen, Petri A.; Krause, A. Outi I. Industrial & Engineering Chemistry Research, Vol. 41, Issue 23 https://doi.org/10.1021/ie0202930	journal	November 2002
Kinetics of Aqueous-Phase Hydrogenation of Organic Acids and Their Mixtures over Carbon Supported Ruthenium Catalyst Chen, Yuqing; Miller, Dennis J.; Jackson, James E. Industrial & Engineering Chemistry Research, Vol. 46, Issue 10 https://doi.org/10.1021/ie0614632	journal	May 2007
Competitive Catalytic Hydrogenation of Benzene, Toluene and the Polymethylbenzenes on Platinum Rader, Charles P.; Smith, Hilton A. Journal of the American Chemical Society, Vol. 84, Issue 8 https://doi.org/10.1021/ja00867a021	journal	April 1962
Ni-Catalyzed Cleavage of Aryl Ethers in the Aqueous Phase He, Jiayue; Zhao, Chen; Lercher, Johannes A. Journal of the American Chemical Society, Vol. 134, Issue 51, p. 20768-20775 https://doi.org/10.1021/ja309915e	journal	December 2012
First-Principles Study of Phenol Hydrogenation on Pt and Ni Catalysts in Aqueous Phase Yoon, Yeohoon; Rousseau, Roger; Weber, Robert S. Journal of the American Chemical Society, Vol. 136, Issue 29 https://doi.org/10.1021/ja501592y	journal	July 2014
Proton-Coupled Electron Transfer: Moving Together and Charging Forward Hammes-Schiffer, Sharon Journal of the American Chemical Society, Vol. 137, Issue 28 https://doi.org/10.1021/jacs.5b04087	journal	July 2015
Mechanisms of Furfural Reduction on Metal Electrodes: Distinguishing Pathways for Selective Hydrogenation of Bioderived Oxygenates Chadderdon, Xiaotong H.; Chadderdon, David J.; Matthiesen, John E. Journal of the American Chemical Society, Vol. 139, Issue 40 https://doi.org/10.1021/jacs.7b06331	journal	September 2017
Correlations and Predictions of p K _a Values of Fluorophenols and Bromophenols Using Hydrogen-Bonded Complexes with Ammonia Han, Jun; Tao, Fu-Ming The Journal of Physical Chemistry A, Vol. 110, Issue 1 https://doi.org/10.1021/jp052824e	journal	January 2006
Interfacial water reorganization as a pH-dependent descriptor of the hydrogen evolution rate on platinum electrodes Ledezma-Yanez, Isis; Wallace, W. David Z.; Sebastián-Pascual, Paula Nature Energy, Vol. 2, Issue 4 https://doi.org/10.1038/nenergy.2017.31	journal	March 2017
Solvent-mediated charge separation drives alternative hydrogenation path of furanics in liquid water Zhao, Zheng; Bababrik, Reda; Xue, Wenhua Nature Catalysis, Vol. 2, Issue 5 https://doi.org/10.1038/s41929-019-0257-z	journal	April 2019
Insight on Tafel slopes from a microkinetic analysis of aqueous electrocatalysis for energy conversion Shinagawa, Tatsuya; Garcia-Esparza, Angel T.; Takanabe, Kazuhiro Scientific Reports, Vol. 5, Issue 1 https://doi.org/10.1038/srep13801	journal	September 2015
Integrated electrocatalytic processing of levulinic acid and formic acid to produce biofuel intermediate valeric acid Qiu, Yang; Xin, Le; Chadderdon, David J. Green Chem., Vol. 16, Issue 3 https://doi.org/10.1039/C3GC42254B	journal	January 2014
New insights into the electrochemical hydrogen oxidation and evolution reaction mechanism Durst, J.; Siebel, A.; Simon, C. Energy Environ. Sci., Vol. 7, Issue 7 https://doi.org/10.1039/C4EE00440J	journal	January 2014
Electrocatalytic upgrading of model lignin monomers with earth abundant metal electrodes Lam, Chun Ho; Lowe, Christy B.; Li, Zhenglong Green Chemistry, Vol. 17, Issue 1 https://doi.org/10.1039/C4GC01632G	journal	January 2015
Impedance spectroscopy of H and OH adsorption on stepped single-crystal platinum electrodes in alkaline and acidic media Schouten, K. J. P.; van der Niet, M. J. T. C.; Koper, M. T. M. Physical Chemistry Chemical Physics, Vol. 12, Issue 46 https://doi.org/10.1039/c0cp00104j	journal	January 2010
Organic electrosynthesis: a promising green methodology in organic chemistry Frontana-Uribe, Bernardo A.; Little, R. Daniel; Ibanez, Jorge G. Green Chemistry, Vol. 12, Issue 12 https://doi.org/10.1039/c0gc00382d	journal	January 2010
Computational study of the adsorption and dissociation of phenol on Pt and Rh surfaces Honkela, Maija L.; Björk, Jonas; Persson, Mats Physical Chemistry Chemical Physics, Vol. 14, Issue 16 https://doi.org/10.1039/c2cp24064e	journal	January 2012
Competitive Catalytic Hydrogenation in the Liquid Phase on Solid Catalysts Červený, Libor; Růžička, Vlastimil Catalysis Reviews, Vol. 24, Issue 4 https://doi.org/10.1080/03602458208079662	journal	January 1982
Aromatic adsorption on metals via first-principles density functional theory Jenkins, S. J. Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 465, Issue 2110 https://doi.org/10.1098/rspa.2009.0119	journal	July 2009
Octahedral palladium nanoparticles as excellent hosts for electrochemically adsorbed and absorbed hydrogen Zalineeva, Anna; Baranton, Stève; Coutanceau, Christophe Science Advances, Vol. 3, Issue 2 https://doi.org/10.1126/sciadv.1600542	journal	February 2017
Trends in the Exchange Current for Hydrogen Evolution Nørskov, J. K.; Bligaard, T.; Logadottir, A. Journal of The Electrochemical Society, Vol. 152, Issue 3 https://doi.org/10.1149/1.1856988	journal	January 2005
An Examination of the Electrochemical Behavior of Palladium in Base Burke, L. D.; Casey, J. K. Journal of The Electrochemical Society, Vol. 140, Issue 5 https://doi.org/10.1149/1.2220973	journal	May 1993
Hydrogen Oxidation and Evolution Reaction Kinetics on Carbon Supported Pt, Ir, Rh, and Pd Electrocatalysts in Acidic Media Durst, Julien; Simon, Christoph; Hasché, Frédéric Journal of The Electrochemical Society, Vol. 162, Issue 1 https://doi.org/10.1149/2.0981501jes	journal	November 2014

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
benzaldehyde
cathodic potential
electrocatalytic hydrogenation
electrochemistry
electron transfer
hydrogen bonding
metal catalysts
phenol
reduction
supported catalysts

Hydrogen Bonding Enhances the Electrochemical Hydrogenation of Benzaldehyde in the Aqueous Phase

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