Aqueous chlorination of acebutolol: kinetics, transformation by-products, and mechanism

Khalit, Wan Nor Adira Wan; Tay, Kheng Soo

Aqueous chlorination of acebutolol: kinetics, transformation by-products, and mechanism

2016

Khalit, Wan Nor Adira Wan | Tay, Kheng Soo

This study investigated the reaction kinetics and the transformation by-products of acebutolol during aqueous chlorination. Acebutolol is one of the commonly used β-blockers for the treatment of cardiovascular diseases. It has been frequently detected in the aquatic environment. In the kinetics study, the second-order rate constant for the reaction between acebutolol and chlorine (k ₐₚₚ) was determined at 25 ± 0.1 °C. The degradation of acebutolol by free available chlorine was highly pH dependence. When the pH increased from 6 to 8, it was found that the k ₐₚₚ for the reaction between acebutolol and free available chlorine was increased from 1.68 to 11.2 M⁻¹ min⁻¹. By comparing with the reported k ₐₚₚ values, the reactivity of acebutolol toward free available chlorine was found to be higher than atenolol and metoprolol but lower than nadolol and propranolol. Characterization of the transformation by-products formed during the chlorination of acebutolol was carried out using liquid chromatography-quadrupole time-of-flight high-resolution mass spectrometry. Seven major transformation by-products were identified. These transformation by-products were mainly formed through dealkylation, hydroxylation, chlorination, and oxidation reactions.

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