Abstract
The influence of zinc chloride on the chlorination of naphthalene by electrolysis in a water-methylene chloride emulsion and using tetrabutylammonium ion as a phase transfer catalyst is described. It is shown that when the aqueous medium contains both NaCl and ZnCl2 it is the anion ZnCl 4 2− which transfers into the organic phase and it is confirmed that the presence of ZnCl2 in the electrolyte is, indeed, beneficial. The electrolyses have been carried out in both divided and undivided cells and in both the organic yield of 1-chloronaphthalene can exceed 80% but the former is better from the viewpoint of speed of electrolysis; in the divided cell, the conversion was 85% (cf. typically 60% in the undivided cell) after the passage of 2.3 F mol−1 of naphthalene. Possible mechanisms for the effect of ZnCl[in2] are discussed.
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