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Oxidation of antibacterial molecules by aqueous ozone: Moiety-specific reaction kinetics and application to ozone-based wastewater treatment

机译:臭氧水溶液对抗菌分子的氧化:基团特异性反应动力学及其在臭氧废水处理中的应用

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Ozone and hydroxyl radical (center dot OH) reaction kinetics were measured for 14 antibacterial compounds from nine structural families, to determine whether municipal wastewater ozonation is likely to result in selective oxidation of these compounds' biochemically essential moieties. Each substrate is oxidized by ozone with an apparent second-order rate constant, k(O3,app)' > 1 x 10(3) M-1 s(-1), at pH 7, with the exception of N(4)-acetylsulfamethoxazole (k(O3,app)' is 2.5 x 10(2) M-1 s(-1)) k(O3,app)' values (pH 7) for macrolides, sulfamethoxazole, trimethoprim, tetracycline, vancomycin, and amikacin appear to correspond directly to oxidation of biochemically essential moieties. Initial reactions of ozone with N(4)-acetylsulfamethoxazole, fluoroquinolones, lincomycin, and beta-lactams do not lead to appreciable oxidation of biochemically essential moieties. However, ozone oxidizes these moieties within fluoroquinolones and lincomycin via slower reactions. Measured k(O3,app)' values and second-order center dot OH rate constants, k(center dot OH,app') were utilized to characterize pollutant losses during ozonation of secondary municipal wastewater effluent. These losses were dependent on k(O3,app)', but independent of k(center dot OH,app)". H,app- Ozone doses >= 3 mg/L yielded >= 99% depletion of fast-reacting substrates (k(O3,app)' > 5 x 10(4) M-1 s(-1)) at pH 7.7. Ten substrates reacted predominantly with ozone; only four were oxidized predominantly by center dot OH. These results indicate that many antibacterial compounds will be oxidized in wastewater via moiety-specific reactions with ozone.
机译:对来自9个结构族的14种抗菌化合物的臭氧和羟基自由基(中心点OH)反应动力学进行了测定,以确定市政废水的臭氧化是否可能导致这些化合物的生物化学基本部分的选择性氧化。每个底物均被臭氧氧化,其表观二级速率常数k(O3,app)'> 1 x 10(3)M-1 s(-1),在pH 7下,N(4)除外-大环内酯类,磺胺甲恶唑,甲氧苄啶,四环素,万古霉素和-的乙酰基磺胺甲恶唑(k(O3,app)'为2.5 x 10(2)M-1 s(-1))k(O3,app)'值(pH 7)阿米卡星似乎直接对应于生化必需部分的氧化。臭氧与N(4)-乙酰基磺胺甲基恶唑,氟喹诺酮,林可霉素和β-内酰胺的初始反应不会导致生物化学上必要部分的明显氧化。但是,臭氧会通过较慢的反应氧化氟喹诺酮类和林可霉素中的这些部分。测量的k(O3,app)'值和二阶中心点OH速率常数k(中心点OH,app')用于表征二级市政废水的臭氧化过程中的污染物损失。这些损失取决于k(O3,app)',但与k(中心点OH,app)“无关。H,app-臭氧剂量> = 3 mg / L产生> = 99%的快速反应底物消耗(在pH值为7.7时k(O3,app)'> 5 x 10(4)M-1 s(-1))。十种底物主要与臭氧反应;只有四种主要被中心点OH氧化。这些结果表明许多抗菌剂化合物将通过与臭氧的特定部分反应在废水中被氧化。

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