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

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Abstract

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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Acknowledgments

This research was supported financially by the Fundamental Research Grant Scheme (FP043-2013A) of Ministry of Higher Education Malaysia, and University of Malaya (PPP PG075-2014B and UMRG RG342-15-AFR).

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Authors and Affiliations

  1. Environmental Research Group, Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia

    Wan Nor Adira Wan Khalit & Kheng Soo Tay

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  1. Wan Nor Adira Wan Khalit
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  2. Kheng Soo Tay
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Correspondence to Kheng Soo Tay.

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Responsible editor: Philippe Garrigues

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Khalit, W.N.A.W., Tay, K.S. Aqueous chlorination of acebutolol: kinetics, transformation by-products, and mechanism. Environ Sci Pollut Res 23, 2521–2529 (2016). https://doi.org/10.1007/s11356-015-5470-y

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  • DOI: https://doi.org/10.1007/s11356-015-5470-y

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