Metallic Impurities in Electrolysis: Catalytic Effect of Pb Traces in Reductive Amination and Acetone Reduction

The electrochemical hydrogenation (e‐hydrogenation) of unsaturated compounds like imines or carbonyls presents a benign reduction method. It enables direct use of electrons as reducing agent, water as proton source, while bypassing the need for elevated temperatures or pressures. In this contributio...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2024-12, Vol.63 (49), p.e202411532-n/a
Main Authors: Kümper, Justus, Mürtz, Sonja D., Guan, Yani, Kumari, Simran, Hausoul, Peter J. C., Kurig, Nils, Sautet, Philippe, Palkovits, Regina
Format: Article
Language:English
Subjects:
Acetone
Amination
Carbonyl compounds
Carbonyls
Catalysis
Chemical reduction
e-Hydrogenation
Electrochemistry
Electrode materials
Electrolysis
High temperature
Hydrogenation
Imines
Impurities
Lead
Methylamine
Reducing agents
Reduction
Reduction (electrolytic)
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Summary:The electrochemical hydrogenation (e‐hydrogenation) of unsaturated compounds like imines or carbonyls presents a benign reduction method. It enables direct use of electrons as reducing agent, water as proton source, while bypassing the need for elevated temperatures or pressures. In this contribution, we discuss the active species in electrocatalytic reductive amination with the transformation of acetone and methylamine as model reaction. Surprisingly, lead impurities in the ppm‐range proved to possess a significant effect in e‐hydrogenation. Accordingly, the influence of applied potential and cathode material in presence of 1 ppm Pb was investigated. Finally, we transferred the insights to the reduction of acetone manifesting comparable observations as for imine reduction. The results suggest that previous studies on electrochemical reduction in the presence of lead electrodes should be re‐evaluated. Studying the reductive amination of acetone with methylamine as nitrogen source using electrochemistry revealed the catalytic activity of 1 ppm Pb. In addition, the effects of the applied potential and the cathode materials on the reaction were investigated. Finally, the results were transferred to the electrochemical hydrogenation of acetone.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202411532