Reactions are known to take place between solid alkali halides and ionic organic compounds. Anion exchange between p-aminophenol hydrohalides and alkali halides has been studied recently. Organic acids are known to exchange cations with alkali halides under exceptional conditions, Duyckaerts noting that mechanochemical reactions convert benzoic acid and 2-aminonaphthalene-7-sulfonic acid to their K salts during prolonged grinding with KBr in a ball mill. Oxalic, malonic, and succinic acids form acid salts during intensive grinding for the preparation of alkali halide pellets, and also when they are fused in the presence of alkali halides.
B. Cleverley, "An Examination of Ion Exchange in Powdered Mixtures of Alkali Halides and Some Organic Acids, using Infrared Spectroscopy," Appl. Spectrosc. 30, 465-467 (1976)
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