Application of ultrasound technology to electroorganic synthesis: Reduction of acetophenone

Electroreduction of acetophenone in an undivided cell was chosen as a model reaction to investigate the use of ultrasonication in organic electrosynthesis. The reaction was carried out in aqueous medium (water–methanol), at neutral pH and at a cadmium or zinc cathode. Electrochemical reduction of ac...

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Bibliographic Details
Published in:Chemical engineering science 2000-01, Vol.55 (14), p.2571-2578
Main Authors: Cognet, P., Ghanem-Lakhal, A., Berlan, J., Wilhelm, A.-M., Delmas, H., Fabre, P.-L.
Format: Article
Language:English
Subjects:
Acetophenone
Chemistry
Electrochemistry
Electroreduction
Exact sciences and technology
General and physical chemistry
Kinetics and mechanism of reactions
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Pinacol
Ultrasonic chemistry
Ultrasound
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Summary:Electroreduction of acetophenone in an undivided cell was chosen as a model reaction to investigate the use of ultrasonication in organic electrosynthesis. The reaction was carried out in aqueous medium (water–methanol), at neutral pH and at a cadmium or zinc cathode. Electrochemical reduction of acetophenone yields alcohol through a bielectronic transfer and pinacol through a monoelectronic transfer. Operating conditions permit to modify the reduction state of the reactant. On a cadmium cathode, the major product is the alcohol whereas on a zinc cathode, the pinacol is rather obtained. The ultrasonic activation has been studied as regards the faradaı̈c yield and the chemical selectivity. This work puts into evidence the interest of ultrasonication for electroorganic synthesis processes often submitted to passivation phenomena.
ISSN:0009-2509
1873-4405
DOI:10.1016/S0009-2509(99)00539-4