Kinetics and Mechanism Studies of Oxidation of Dibromothymolsulfonphthalein Toxic Dye by Potassium Permanganate in Neutral Media with the Synthesis of 2-Bromo-6-isopropyl-3-methyl-cyclohexa-2,5-dienone

Abstract

The oxidation of 3′,3″-dibromothymolsulfonphthalein (DBTS) in neutral medium by potassium permanganate multi-equivalent oxidant has been studied spectrophotometrically. Pseudo-first-order plots showed inverted S-shape throughout the entire course of the reaction. The initial rates were found to be relatively fast in the early stages, followed by a decrease in the oxidation rates over longer time periods in the slow stage. Under pseudo-first-order conditions where [DBTS] ≫ 10 [MnO 4 – ], the experimental results showed a first-order dependence in [MnO 4 – ] and fractional-first-order kinetics in the [DBTS] concentration. The formation of 1:1 coordination intermediate complex prior to the rate-determining step was revealed kinetically. In addition, the intermediate species involving complexes of Mn(V) coordination has been detected. The oxidation product of DBTS was identified by Fourier transform infrared spectroscopy, ultraviolet–visible spectrophotometry, and gas chromatography–mass analysis. The obtained results indicated the formation of 2-bromo-6-isopropyl-3-methyl-cyclohexa-2,5-dienone as a derivative oxidation of DBTS.