New insights into the primary phototransformation of acetaminophen by UV/H2O2: photo-Fries rearrangement versus hydroxyl radical induced hydroxylation

Su, Feng; Zhang, Xu; Liu, Yanxiang

doi:10.1016/j.watres.2015.05.008

Cited by 27 publications

(4 citation statements)

References 24 publications

(36 reference statements)

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“…These results suggest that •OH gave a limited contribution to the transformation of these phenols in HA solution, consistent with the transformation of APAP in other NOM solutions . The small contribution of •OH mainly results from the very low steady-state concentration of •OH, offsetting the relatively high second order rate constant of the reaction of APAP and TMP with •OH. − …”

Section: Resultssupporting

confidence: 72%

Contribution of the Excited Triplet State of Humic Acid and Superoxide Radical Anion to Generation and Elimination of Phenoxyl Radical

Chen

Zhang

2018

Environ. Sci. Technol.

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Contributions of excited triplet state of humic acid (HA*) and superoxide radical anion (O), which is mainly generated via the reaction of O with HA-derived reducing intermediates (HA), to phenol transformation were revealed using acetaminophen, 2,4,6-trimethylphenol and tyrosine as probe molecules. Phenol transformation was initiated by HA*, leading to the formation of the phenoxyl radical (PhO•), but the distribution of transformation intermediates was codetermined byHA* and HA. The influence of HA essentially resulted from the production of O, which affected the fate of PhO•. PhO• could undergo dimerization, or react with O, leading to either phenol peroxide formation (radical addition) or phenol regeneration (electron transfer). In addition, PhO• could bind to HA or react with HA radicals, particularly in the absence of O and O. These PhO• reactions were dependent on the reduction potential and structure of PhO•. This study also proved that the reaction of phenol with O and the reaction of PhO• with O lead to the same oxidation product. The contributions of HA* and its generatedO, HA and its generated O to phenol transformation were pH-dependent.

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Section: Resultssupporting

confidence: 72%

Contribution of the Excited Triplet State of Humic Acid and Superoxide Radical Anion to Generation and Elimination of Phenoxyl Radical

Chen

Zhang

2018

Environ. Sci. Technol.

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“…These aromatics are the basic structures of APAP, suggesting that the degradation of APAP was mainly caused by the attack of the radicals on the ortho and para positions of aromatic ring . The intermediates were similar to those obtained in other studies …”

Section: Resultsmentioning

confidence: 99%

Structurally modified CuFe₂O₄/persulfate process for acetaminophen scavenging: high efficiency with low catalyst addition

Zhang

Dong

et al. 2018

J of Chemical Tech & Biotech

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BACKGROUND: Iron (Fe)-copper (Cu) bimetallic catalysts such as CuFe 2 O 4 , CuFeO 2 and CuO/Fe 3 O 4 have been widely applied in persulfate oxidization process. Among these catalysts, CuFe 2 O 4 has shown excellent performance in catalyzing peroxymonosulfate. However, because the catalytic effect of CuFe 2 O 4 on persulfate (PS) is not obvious, the application of CuFe 2 O 4 to activate persulfate has been investigated only rarely. Hence, structural modification has been applied in order to improve the catalytic activity of CuFe 2 O 4 on persulfate.RESULT: In this study, Oxygen (O)-deficient CuFe 2 O 4 was synthesized via the hydrogen reduction method and first used to activate PS for degrading acetaminophen (APAP) in aqueous solution with low catalyst concentration of 0.3 g L −1 . Results reveal that high-concentration APAP (100 mg L −1 ) could be efficiently removed by O-deficient CuFe 2 O 4 -activated PS, and 91% removal rate could be reached in 60 min using 0.8 g L −1 PS and 0.3 g L −1 catalyst under unadjusted pH. Dissolved O 2 and Cl − showed inhibitory effects on the degradation process. Radical scavenger experiments, in which methanol, tert-butyl alcohol (TBA) and nitrobenzene (NB) were used as radical trappers, indicated that SO 4 − and OH were the active radicals in the reaction, but the main radical was SO 4 − . Oxygen-deficient CuFe 2 O 4 showed strong reduction ability and could activate PS efficiently, and the electron transfer capability was remarkably enhanced after this structural modification. CONCLUSIONS: Results indicated that compared to the pristine crystal, the catalytic activity of CuFe 2 O 4 could be improved through structural modification. Additionally, the structurally modified catalyst showed high potential to treat wastewater with high antibiotic content under mild conditions. Romero A. Oxidation of priority and emerging pollutants with persulfate activated by iron: effect of iron valence and particle size. Chem Eng J 318:197-205 (2017).J Chem Technol Biotechnol 2019; 94: 785-794

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“…A large number of AOTs have been considered for eliminating different PhACs from water [16][17][18][19][20]. Nevertheless, most of them have investigated the degradation of individual drugs dissolved in water, without considering the potential effects of PhAC mixtures on the performance of treatment processes [13].…”

Section: Introductionmentioning

confidence: 99%

Low Pressure UV Photolysis of the Pharmaceutical Compounds Acetaminophen, Atenolol, Bezafibrate, Diclofenac and Ibuprofen

Katsumata

Parizi

Lastre-Acosta

et al. 2022

Water

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Pharmaceutically active compounds (PhACs) are continuously introduced into the environment by human and livestock excretion, hospital sewage and pharmaceutical effluents. While the performance of UV photolysis regarding PhACs degradation may be limited by low quantum yields, it may be efficient when the contaminants significantly absorb UV radiation. In this work, the direct photolysis under 254 nm UVC radiation of acetaminophen (ACT), atenolol (ATL), bezafibrate (BZF), diclofenac (DIC) and ibuprofen (IBU), isolated and in mixture, was investigated. The results showed that PhAC photolysis followed apparent first-order kinetics, with removals ranging from 32% to 99% after 60 min, while all the compounds exhibited lower photolysis rates when mixed in solution. Less than 13% mineralization was achieved. The toxicity of irradiated solutions of Vibrio fischeri remained the same or slightly decreased for ATL, BZF and IBU, increased for ACT, and notably decreased for DIC; nevertheless, the solution of mixed PhACs became very toxic following irradiation, showing the need for oxidant addition for removing residual toxicity.

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New insights into the primary phototransformation of acetaminophen by UV/H2O2: photo-Fries rearrangement versus hydroxyl radical induced hydroxylation

Cited by 27 publications

References 24 publications

Contribution of the Excited Triplet State of Humic Acid and Superoxide Radical Anion to Generation and Elimination of Phenoxyl Radical

Contribution of the Excited Triplet State of Humic Acid and Superoxide Radical Anion to Generation and Elimination of Phenoxyl Radical

Structurally modified CuFe₂O₄/persulfate process for acetaminophen scavenging: high efficiency with low catalyst addition

Low Pressure UV Photolysis of the Pharmaceutical Compounds Acetaminophen, Atenolol, Bezafibrate, Diclofenac and Ibuprofen

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New insights into the primary phototransformation of acetaminophen by UV/H2O2: photo-Fries rearrangement versus hydroxyl radical induced hydroxylation

Cited by 27 publications

References 24 publications

Contribution of the Excited Triplet State of Humic Acid and Superoxide Radical Anion to Generation and Elimination of Phenoxyl Radical

Contribution of the Excited Triplet State of Humic Acid and Superoxide Radical Anion to Generation and Elimination of Phenoxyl Radical

Structurally modified CuFe2O4/persulfate process for acetaminophen scavenging: high efficiency with low catalyst addition

Low Pressure UV Photolysis of the Pharmaceutical Compounds Acetaminophen, Atenolol, Bezafibrate, Diclofenac and Ibuprofen

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Structurally modified CuFe₂O₄/persulfate process for acetaminophen scavenging: high efficiency with low catalyst addition