Journal
SCIENCE OF THE TOTAL ENVIRONMENT
Volume 593, Issue -, Pages 704-712Publisher
ELSEVIER
DOI: 10.1016/j.scitotenv.2017.03.192
Keywords
Persulfate; SO2 extrusion products; Smiles-type rearrangement; Sulfate radical-based oxidation; Sulfonamide antibiotics
Categories
Funding
- Natural Science Foundation of Jiangsu Province-China [BK20160709]
- National Natural Science Foundation of China [NSFC21607077]
- Fundamental Research Funds for Central Universities [KJQN201741]
- Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institute
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The widespread occurrence of sulfonamide antibiotics in the environment has raised great concerns about their potential to proliferate antibacterial resistance. Sulfate radical (SO4) based advanced oxidation processes (SRAOPs) are promising in-situ chemical oxidation (ISCO) technologies for remediation of soil and groundwater contaminated by antibiotics. The present study reported that thermally activated persulfate oxidation of sulfon-amides (SAs) bearing six-membered heterocyclic rings, e.g., sulfamethazine (SMZ), sulfapyridine (SPD), sulfadiazine (SDZ), sulfadimethoxine (SDM), and sulfachloropyridazine (SCP), all produced SO2 extrusion products (SEPs), a phenomenon that is of potential importance, but not systematically studied. As an electrophilic oxidant, SO4 tends to attack the aniline moiety, the reactive site of SAs, via electro-transfer mechanism. The resulting anilinyl radical cations are subjected to further intermolecular Smiles-type rearrangement to produce SEPs. Formation of SEPs is expected to occur in other SR-AOPs as well. The temperature-dependent evolution pattern of SEP of SMZ, 4-(2-imino-4,6-dimethylpyrimidin-1(2H)-yl)aniline, can be well fitted by kinetic modeling concerning sequential formation and transformation of intermediate product. The presence of natural organic matter (NOM) influenced the evolution patterns of 4-(2-imino-4,6-dimethylpyrimidin-1(2H)-yl)aniline significantly. Toxicological effects of SEPs on ecosystem and human health remain largely unknown, thus, further monitoring studies are highly desirable. (C) 2017 Elsevier B.V. All rights reserved.
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