Structure-reactivity relationship in the degradation of three representative fluoroquinolone antibiotics in water by electrogenerated active chlorine

Serna-Galvis, Efraím A.; Jojoa-Sierra, Sindy D.; Berrio-Perlaza, Karen E.; Ferraro, Franklin; Torres-Palma, Ricardo A.

doi:10.1016/j.cej.2017.01.062

Cited by 61 publications

(18 citation statements)

References 44 publications

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“…45 Indeed, PMS can react with Cl − to form HOCl and Cl2, which exhibit great selectivity towards compounds containing electron-rich organic moieties. 46,47 In addition, Clmay convert SO4 •− into HO • radicals, as previously reported. 48 Indeed, fast reaction of SO4 •− with Cl − yields chlorine atoms (Cl • ) as primary products, which in turn initiates a cascade of subsequent reactions depending on pH.…”

Section: Accepted Manuscriptsupporting

confidence: 63%

Nano-sized iron oxides supported on polyester textile to remove fluoroquinolones in hospital wastewater

Coulibaly

Rtimi

Assadi

et al. 2020

Environ. Sci.: Nano

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Section: Accepted Manuscriptsupporting

confidence: 63%

Nano-sized iron oxides supported on polyester textile to remove fluoroquinolones in hospital wastewater

Coulibaly

Rtimi

Assadi

et al. 2020

Environ. Sci.: Nano

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“…Processes such as UVC photolysis or UVC/persulfate are more affected than ultrasound by matrix components for antibiotics degradation [17]. On the other hand, anodic oxidation using Ti/IrO 2 as anode and sodium chloride as supporting electrolyte induces the formation of chlorinated degradation products in the treatment of fluoroquinolones [47], which may be toxic substances. Meanwhile, during the treatment of these antibiotics with high frequency ultrasound such chlorinated transformation products were not found here; which is other advantage of the sonochemical process.…”

Section: Treatment Of Complex Matricesmentioning

confidence: 99%

Sonochemical degradation of antibiotics from representative classes-Considerations on structural effects, initial transformation products, antimicrobial activity and matrix

Serna-Galvis

Montoya-Rodríguez

Isaza-Pineda

et al. 2019

Ultrasonics Sonochemistry

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In this work, the sonochemical treatment (at 354 kHz and 88 W L) of six relevant antibiotics belonging to fluoroquinolones (ciprofloxacin and norfloxacin), penicillins (oxacillin and cloxacillin) and cephalosporins (cephalexin and cephadroxyl) classes was evaluated. Firstly, the ability of the process to eliminate them was tested, showing that sonodegradation of these antibiotics is strongly chemical structure-dependent. Thus, correlations among initial degradation rate of pollutants (Rd), solubility in water (Sw), water-octanol partition coefficient (Log P) and topological polar surface area (TPSA) were tested. Rd exhibited a good correlation with Log P (i.e., the hydrophobicity degree of antibiotics). The considered penicillins had the fastest elimination and from the constitutional analysis using Lemke method was clear that the functional groups arrangement on these antibiotics made them highly hydrophobics. The penicillins were degraded closer at cavitation bubble than the fluoroquinolones or cephalosporins. The investigation of degradation products showed that sonogenerated hydroxyl radical primary attacked the β-lactam ring of cloxacillin and cephalexin, whereas on norfloxacin induced a decarboxylation. On the other hand, the evolution of antimicrobial activity was also followed. It was evidenced the process capacity to remove antimicrobial activity from treated solutions, which was associated to the transformations of functional groups on antibiotics with important role for interaction with bacteria. Additionally, degradation of antibiotics having the highest (the most hydrophobic, i.e., cloxacillin) and lowest (the most hydrophilic, i.e., cephadroxyl) Rd, was performed in synthetic matrices (hospital wastewater and seawater). Ultrasound degraded both antibiotics; for cloxacillin in such waters higher eliminations than in distilled water were observed (probably due to a salting-out effect exerted by matrix components). Meanwhile, for cephadroxyl a moderate inhibition of degradation in hospital wastewater and seawater respect to distilled water was found, this was related to competition by hydroxyl radical of the other substances in the matrices. These results show the quite selectivity of high frequency ultrasound to eliminate antibiotics form different classes even in complex matrices.

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“…It can be inferred that the benzene ring structure is both the electron donor of the E2 molecule and the main acceptor part of the electron (Hu et al 2002). The HOMO of a molecule is more susceptible to attack by electrophiles to generate an electrophilic reaction, and the nucleophile is more likely to attack the atom with a higher charge density on the LUMO (Serna-Galvis et al 2017). This paper calculates the atomic net charge distribution in the E2 molecular structure, and the main reactive sites on E2 are inferred.…”

Section: Reaction Centers Recognition Of E2mentioning

confidence: 99%

Degradation of 17β-estradiol by UV/persulfate in different water samples

Zhu

Shao

Wei

et al. 2021

Journal of Water and Health

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Sulfate radical (•SO4−)-based advanced oxidation processes are widely used for wastewater treatment. This study explored the potential use of UV/persulfate (UV/PS) system for the degradation of 17β-estradiol (E2). The pH of the reaction system can affect the degradation rate of E2 by UV/PS and the optimum pH was 7.0; Br− and Cl− in water can promote the degradation rate, HCO3− has an inhibitory effect on the reaction, SO42− and cations (Na+, Mg2+, K+) have no effect on the degradation rate. The degradation of E2 by UV/PS was a mineralization process, with the mineralization rate reaching 90.97% at 8 h. E2 in the UV/PS system was mainly degraded by hydroxylation, deoxygenation, and hydrogenation. E2 reaction sites were mainly located on benzene rings, mainly carbonylation on quinary rings, and bond breakage between C10 and C5 resulted in the removal of benzene rings and carboxyl at C2 and C3 sites. In the presence of halogen ions, halogenated disinfection by-products were not formed in the degradation process of E2 by UV/PS. E2 in the UV/PS system could inhibit the formation of bromate. The results of this study suggest that UV/PS is a safe and reliable method to degrade E2.

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Structure-reactivity relationship in the degradation of three representative fluoroquinolone antibiotics in water by electrogenerated active chlorine

Cited by 61 publications

References 44 publications

Nano-sized iron oxides supported on polyester textile to remove fluoroquinolones in hospital wastewater

Nano-sized iron oxides supported on polyester textile to remove fluoroquinolones in hospital wastewater

Sonochemical degradation of antibiotics from representative classes-Considerations on structural effects, initial transformation products, antimicrobial activity and matrix

Degradation of 17β-estradiol by UV/persulfate in different water samples

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