Oxidation of Antibiotic Agent Trimethoprim by Chlorine Dioxide: Reaction Kinetics and Pathways
Publication: Journal of Environmental Engineering
Volume 138, Issue 3
Abstract
Trimethoprim (TMP) is a widely prescribed antibiotic frequently detected in the aquatic environment. This study investigates the reactions of TMP and two sub structure model compounds [2, 4-diamino-5-methylpyrimidine (DAMP) and 3, 4, 5-trimethoxytoluene (TMT)] with chlorine dioxide (), one of the common water disinfection oxidants, in batch reactors. A second-order kinetic model that incorporates the organic compounds’ acid-base speciation can sufficiently describe the reaction kinetics and is used to evaluate molecules’ reactive sites. TMP’s apparent second-order rate constant () with ranges at from pH 2.7 to 9.1, corresponding to a half-life of 40.8 min at pH 7 and of . The reaction’s pH dependence is linked to protonation of the ring nitrogens on TMP’s 2, 4-diaminopyrimidinyl moiety. Comparison among TMP, DAMP, and TMT reveals that the reactivity of TMP to resides mostly in its diaminopyrimidinyl moiety at neutral to alkaline pH, but centers in its trimethoxybenzyl moiety at acidic conditions. LC/MS analysis shows that oxidation of TMP by generates Cl and OH substitutions at both diaminopyrimidinyl and trimethoxybenzyl moieties and other products. The reaction rate constants obtained in clean water matrix can be used to model the decay of TMP by in surface water samples, but overestimate the decay in wastewater samples. Overall, transformation of TMP by can be expected under typical disinfection conditions.
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Acknowledgments
Financial support for P.W. from the China Scholarship Council is acknowledged. The materials and supplies for this study were available from a project funded by National Science Foundation (NSFCBET 0229172).
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Published In
Journal of Environmental Engineering
Volume 138 • Issue 3 • March 2012
Pages: 360 - 366
Copyright
© 2012 American Society of Civil Engineers.
History
Received: Dec 1, 2010
Accepted: Apr 28, 2011
Published online: Apr 30, 2011
Published in print: Mar 1, 2012
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