Transformation of tetracycline during chloramination: Kinetics, products and pathways

To assess the potential adverse effects stemming from tetracycline (TC) in drinking water or disinfected wastewater, the kinetics of the chloramination of TC was investigated at room temperature, the transformation products and pathways of their generation were elucidated, and their growth inhibiting properties towards sludge bacteria were assessed. The chloramination of TC exhibited pseudo-first-order kinetics with the rate constants (kobs) ranging from 0.0082 to 0.041 min−1 at pH of 6-8. Chloramination of TC generated at least 13 discernible products, and the structures of 12 products, including five chlorinated compounds, were identified using LC-ESI-MS. Two main pathways for the generation of these products were proposed: (1) chlorine substitution reactions followed by dehydration; and (2) oxidization by chloramine. The chlorinated products were proposed to be further degraded to small molecules via the scission of benzene rings of TC, and two oxidization products (2,11a-dihydroxy-keto-TC and 6,11-epoxy-2,11a-dihydroxy-TC) were the final products obtained under the experimental conditions. The chlorinated solution, even without detection of TC, exhibited greater than 80% of TC inhibitory effects towards sludge bacteria, suggesting potential effects on microorganisms in aquatic environment.

Graphical abstractDownload full-size imageHighlights► Chloramination of TC exhibited pseudo-first-order kinetics. ► Chloramination of TC generated at least 13 discernible products. ► Two main pathways were proposed: chlorination and oxidization. ► TC inhibitory effects were observed after chloramination towards sludge bacteria.