Reactions of tetracycline antibiotics with chlorine dioxide and free chlorine

化学 脱质子化 反应速率常数 反应性(心理学) 二氧化氯 动力学 无机化学 四环素类抗生素 四环素 药物化学 有机化学 抗生素 医学 离子 生物化学 物理 替代医学 病理 量子力学
作者
Pei Wang,Yiliang He,Ching‐Hua Huang
出处
期刊:Water Research [Elsevier BV]
卷期号:45 (4): 1838-1846 被引量:163
标识
DOI:10.1016/j.watres.2010.11.039
摘要

Tetracyclines (TCs) are a group of widely used antibiotics that have been frequently found in the aquatic environment. The potential reactions of TCs with common water disinfection oxidants such as chlorine dioxide (ClO2) and free available chlorine (FAC) have not been studied in depth and are the focus of this study. The oxidation kinetics of tetracycline, oxytetracycline, chlorotetracycline and iso-chlorotetracycline by ClO2 and FAC are very rapid (with large apparent second-order rate constants kapp = 2.24 × 105–1.26 × 106 M−1 s−1 with ClO2 and kapp = 1.12 × 104–1.78 × 106 M−1 s−1 with FAC at pH 7.0) and highly dependent on pH. Species-specific rate constants are obtained by kinetic modeling that incorporates pH-speciation of TCs and the oxidants (for FAC), and reveal that TCs primarily react with ClO2 and FAC by their unprotonated dimethylamino group and deprotonated phenolic-diketone group. The modest difference in reactivity among the four TCs toward the oxidants is consistent with expectation and can be explained by structural influences on the two reactive moieties. Product evaluation shows that oxidation of TCs by ClO2 leads to (hydr)oxylation and breakage of TC molecules, while oxidation of TCs by FAC leads to chlorinated and (hydr)oxylated products without any substantial ring breakage. Results of this study indicate that rapid transformation of TCs by oxidants such as ClO2 and FAC under water and wastewater treatment conditions can be expected.
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