Electrochemical Reduction of the Benzene Ring

Abstract

Reduction of benzene and tetrahydronaphthalene (tetralin) was achieved by electrolysis in ethylenediamine saturated with lithium chloride. This reduction could also be carried out with tetrabutylammonium iodide as the supporting electrolyte. In the absence of a substrate, electrolysis of a solution of lithium chloride in ethylenediamine produced the blue color of the solvated metal.) unless CC License in place (see abstract).

The role of supporting electrolyte during the electrocatalytic hydrogenation of aromatic compounds

“…In these experiments, the predominant product was the 1,4-dihydro derivative, with current efficiencies near 90%. When benzene was electrochemically reduced via solvated electrons on Pt in ethylenediamine saturated with LiCI, cyclohexadiene was produced in a divided cell [14], whereas cyclohexadiene and cyclohexane were synthesized in an undivided cell [15]. Pasquariello el al.…”

Cold field emission in microreactors to perform chemical reactions

“…Therefore our data cannot be compared with reported data based on AFM probing, a method by means of which only a single CNT (or a few CNTs) may be electrically characterized [8,9,25] .…”

“…In 1963, Sternberg et al showed the reduction of benzene by electrolyzing a solution of ethylamine saturated with lithium chloride [25] . Using this process, the reduction of benzene and tetralin to the dihydro-products was achieved, avoiding the use of low temperatures and alkali metals.…”

“…A combinatorial approach was used by Ng et al to analyze the influence of various adhesion metals underneath thin layers of Fe, Ni, Co and Fe/Ni alloy catalysts [25] . [26] , and found that Ta, independent of its layer thickness, is the more stable Ni/Ti thin films on oxidized silicon and fused silica supports [24,28] by means of HR-SEM and Raman spectroscopy.…”

“…We hypothesize that for the applied electrical fields during the reaction, electron emission at the cathode is not the only phenomenon that takes place, but that also charge carrier injection occurs in proximity of the electrodes thereby forming cations and anions. The relatively low reaction yield obtained by using field emission instead of an electrochemical method are due to 3 reasons [13,25,26] : (i) the presence of contaminants in the solvent reduces the lifetime of the excess of electrons in the solution, thereby decreasing the amount of aromatic radical anions formed during the reaction; (ii) the reaction is performed in continuous flow, with a quite low residence time of ca. 0.25 sec; (iii) during the reaction hydrogen evolution can occur at the electrodes decreasing the proton donator source.…”