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Kinetics and mechanism of cetyltrimethylammonium bromide catalyzed oxidation of diethylene glycol by chloramine-T in acidic medium

Bhagwat V.W. (School of Studies in Chemistry, Vikram University, Ujjain-456010, India)
Tiwari J. (School of Studies in Chemistry, Vikram University, Ujjain-456010, India)
Choube A. (IPCA Laboratories, Ratlam, India)
Pare B. (Madhav Science College, Vikram University, Ujjain-456010, India)

The kinetics and mechanism of the C16TABcatalyzed oxidation of diethylene glycol (2,2’-oxydiethanol) by chloramine-T in acidic medium has been studied. The reaction has a first-order dependence on chloramine-T. With excess concentrations of other reactants, the reaction rate follows fractional order kinetics with respect to [diethylene glycol]. The micellar effect due to cetyltrimethylammonium bromide, a cationic surfactant, has been studied. The reaction is catalyzed by chloride ions as well. The small salt effect and increase in the reaction rate with increasing dielectric constant suggest the involvement of neutral molecules in the rate determining step. Addition of p-toluenesulfonamide retards the reaction rate. On the basis of product analysis, a pertinent mechanism is proposed.

Keywords: diethylene glycol, chloramine-T, micellar catalysis.