Kinetics of oxidation of 4-hydroxy-4-methyl-2-pentanone by sodium N-chloro-p-toluenesulfonamide.

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The kinetics of oxidation of 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol) by sodium N-chloro-p-toluenesulfonamide (Chloramine-T, RNClNa) in presence of hydrochloric acid (0.05–0.6 M) has been studied at 30 °C. The reaction follows first order kinetics with respect to chloramine-T. The reaction rate depends on the square of the [H+] and independent of the alcohol concentration. The energy and entropy of activation have been found to be 65.56 kJ mol−1 and −73.81 JK−1 respectively. The rate of reaction has been affected by the addition of potassium chloride and dioxane to the reaction mixture. A mechanism has been proposed involving diacetone alcohol and H2OCl+ formed by the hydrolysis of chloramine-T. Applying steady state condition to RNHCl, a rate expression has been given to account for the observed results. Kinetic data have been used in the analytical estimation of diacetone alcohol in acidic medium.
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