Unraveling the electrocatalytic reduction mechanism of enols on copper in aqueous media

Zhihao Cui, Xing’an Dong, Sung Gu Cho, Modeste N. Tegomoh, Weidong Dai, Fan Dong and Anne C. Co ()
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Zhihao Cui: The Ohio State University
Xing’an Dong: University of Electronic Science and Technology of China
Sung Gu Cho: The Ohio State University
Modeste N. Tegomoh: The Ohio State University
Weidong Dai: University of Electronic Science and Technology of China
Fan Dong: University of Electronic Science and Technology of China
Anne C. Co: The Ohio State University

Nature Communications, 2022, vol. 13, issue 1, 1-12

Abstract: Abstract Deoxygenation of aldehydes and their tautomers to alkenes and alkanes has implications in refining biomass-derived fuels for use as transportation fuel. Electrochemical deoxygenation in ambient, aqueous solution is also a potential green synthesis strategy for terminal olefins. In this manuscript, direct electrochemical conversion of vinyl alcohol and acetaldehyde on polycrystalline Cu to ethanol, ethylene and ethane; and propenol and propionaldehyde to propanol, propene and propane is reported. Sensitive detection was achieved using a rotating disk electrode coupled with gas chromatography-mass spectrometry. In-situ attenuated total reflection surface-enhanced infrared absorption spectroscopy, and in-situ Raman spectroscopy confirmed the adsorption of the vinyl alcohol. Calculations using canonical and grand-canonical density functional theory and experimental findings suggest that the rate-determining step for ethylene and ethane formation is an electron transfer step to the adsorbed vinyl alcohol. Finally, we extend our conclusions to the enol reaction from higher-order soluble aldehyde and ketone. The products observed from the reduction reaction also sheds insights into plausible reaction pathways of CO2 to C2 and C3 products.

Date: 2022
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DOI: 10.1038/s41467-022-33620-2

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