Kinetics and transformation pathways on oxidation of fluoroquinolones with thermally activated persulfate

Chemical Engineering Journal

Volumn 292, Issue , 2016, Pages 82-91

  Guo, Hongguang ^a   Gao, Naiyun ^b   Yang, Ying ^a   Zhang, Yongli ^a  

^a SICHUAN UNIVERSITY   (China)

^b TONGJI UNIVERSITY   (China)

Author keywords

Fluoroquinolones; Kinetics; Mechanism; Sulfate radicals; Thermal activation

Indexed keywords

ANTIBIOTICS; CHEMICAL ACTIVATION; DEGRADATION; DRUG PRODUCTS; ENZYME KINETICS; HYDROGEN BONDS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MECHANISMS;

DEGRADATION MECHANISM; FLUOROQUINOLONES; FLUOROQUINOLONES (FQS); HYDROXYL SUBSTITUTION; LIQUID CHROMATOGRAPHY TANDEM MASS SPECTROMETRY (LC MS/MS); SULFATE RADICALS; THERMAL ACTIVATION; TRANSFORMATION PATHWAYS;

REACTION INTERMEDIATES;

EID: 84958543175     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2016.01.009     Document Type: Article

References (57)

1. Wammer K.H., Korte A.R., Lundeen R.A., Sundberg J.E., McNeill K., Arnold W.A. Direct photochemistry of three fluoroquinolone antibacterials: norfloxacin, ofloxacin, and enrofloxacin. Water Res. 2013, 47:439-448.
2. 2 process: kinetics, parameters, and products. Environ. Sci. Pollut. Res. 2013, 20:3202-3213.
3. Sturini M., Speltini A., Maraschi F., Profumo A., Pretali L., Irastorza E.A., Fasani E., Albini A. Photolytic and photocatalytic degradation of fluoroquinolones in untreated river water under natural sunlight. Appl. Catal. B Environ. 2012, 119:32-39.
4. Amorim C.L., Maia A.S., Mesquita R.B.R., Rangel A.O.S.S., van Loosdrecht M.C.M., Tiritan M.E., Castro P.M.L. Performance of aerobic granular sludge in a sequencing batch bioreactor exposed to ofloxacin, norfloxacin and ciprofloxacin. Water Res. 2014, 50:101-113.
5. Rutgersson C., Fick J., Marathe N., Kristiansson E., Janzon A., Angelin M., Johansson A., Shouche Y., Flach C.F., Larsson D.G.J. Fluoroquinolones and qnr genes in sediment water, soil, and human fecal flora in an environment polluted by manufacturing discharges. Environ. Sci. Technol. 2014, 48:7825-7832.
6. Karthikeyan K.G., Meyer M.T. Occurrence of antibiotics in wastewater treatment facilities in Wisconsin, USA. Sci. Total Environ. 2006, 361:196-207.
7. Wang P., He Y.L., Huang C.H. Oxidation of fluoroquinolone antibiotics and structurally related amines by chlorine dioxide: reaction kinetics, product and pathway evaluation. Water Res. 2010, 44:5989-5998.
8. Vieno N.M., Harkki H., Tuhkanen T., Kronberg L. Occurrence of pharmaceuticals in river water and their elimination a pilot-scale drinking water treatment plant. Environ. Sci. Technol. 2007, 41:5077-5084.
9. Watkinson A.J., Murby E.J., Costanzo S.D. Removal of antibiotics in conventional and advanced wastewater treatment: implications for environmental discharge and wastewater recycling. Water Res. 2007, 41:4164-4176.
10. Van Doorslaer X., Dewulf J., Van Langenhove H., Demeestere K. Fluoroquinolone antibiotics: an emerging class of environmental micropollutants. Sci. Total Environ. 2014, 500:250-269.
11. Sim W.J., Lee J.W., Lee E.S., Shin S.K., Hwang S.R., Oh J.E. Occurrence and distribution of pharmaceuticals in wastewater from households, livestock farms, hospitals and pharmaceutical manufactures. Chemosphere 2011, 82:179-186.
12. Al M., Aukidy P., Verlicchi A., Jelic M., Petrovic D. Barcelo, monitoring release of pharmaceutical compounds: occurrence and environmental risk assessment of two WWTP effluents and their receiving bodies in the Po Valley, Italy. Sci. Total Environ. 2012, 438:15-25.
13. Pomati F., Castiglioni S., Zuccato E., Fanelli R., Vigetti D., Rossetti C., Calamari D. Effects of a complex mixture of therapeutic drugs at environmental levels on human embryonic cells. Environ. Sci. Technol. 2006, 40:2442-2447.
14. Wilson B.A., Smith V.H., Denoyelles F., Larive C.K. Effects of three pharmaceutical and personal care products on natural freshwater algal assemblages. Environ. Sci. Technol. 2003, 37:1713-1719.
15. P. Sukul, M. Spiteller, Fluoroquinolone Antibiotics in the Environment, in: G.W. Ware (Ed.) Reviews of Environmental Contamination and Toxicology, vol. 191, 2007, pp. 131-162.
16. Dodd M.C., Shah A.D., Von Gunten U., Huang C.H. Interactions of fluoroquinolone antibacterial agents with aqueous chlorine: reaction kinetics, mechanisms, and transformation pathways. Environ. Sci. Technol. 2005, 39:7065-7076.
17. Dewitte B., Dewulf J., Demeestere K., De Vyvere V.V., De Wispelaere P., Van Langenhove H. Ozonation of ciprofloxacin in water: HRMS identification of reaction products and pathways. Environ. Sci. Technol. 2008, 42:4889-4895.
18. 2) process: kinetics, parameters, and products. Environ. Sci. Pollut. R 2013, 20:3202-3213.
19. Paul T., Dodd M.C., Strathmann T.J. Photolytic and photocatalytic decomposition of aqueous ciprofloxacin: transformation products and residual antibacterial activity. Water Res. 2010, 44:3121-3132.
20. De Bel E., Dewulf J., De Witte B., Van Langenhove H., Janssen C. Influence of pH on the sonolysis of ciprofloxacin: biodegradability, ecotoxicity and antibiotic activity of its degradation products. Chemosphere 2009, 77:291-295.
21. Hu L.H., Stemig A.M., Wammer K.H., Strathmann T.J. Oxidation of antibiotics during water treatment with potassium permanganate: reaction pathways and deactivation. Environ. Sci. Technol. 2011, 45:3635-3642.
22. 2) composite: identification of iron oxide and the optimum pH for degradations. Chemosphere 2014, 95:550-555.
23. Zou J., Ma J., Chen L.W., Li X.C., Guan Y.H., Xie P.C., Pan C. Rapid acceleration of ferrous iron/peroxymonosulfate oxidation of organic pollutants by promoting Fe(III)/Fe(II) cycle with hydroxylamine. Environ. Sci. Technol. 2013, 47:11685-11691.
24. Anipsitakis G.P., Dionysiou D.D., Gonzalez M.A. Cobalt-mediated activation of peroxymonosulfate and sulfate radical attack on phenolic compounds. Implications of chloride ions. Environ. Sci. Technol. 2006, 40:1000-1007.
25. -) transfer mechanisms. Appl. Catal. B Environ. 2010, 96:290-298.
26. Liang C.J., Su H.W. Identification of sulfate and hydroxyl radicals in thermally activated persulfate. Ind. Eng. Chem. Res. 2009, 48:5558-5562.
27. Fang G.D., Dionysiou D.D., Al-Abed S.R., Zhou D.M. Superoxide radical driving the activation of persulfate by magnetite nanoparticles: implications for the degradation of PCBs. Appl. Catal. B Environ. 2013, 129:325-332.
28. 0 coupling with weak magnetic field: performance and mechanism. Water Res. 2014, 62:53-62.
29. Hori H., Nagano Y., Murayama M., Koike K., Kutsuna S. Efficient decomposition of perfluoroether carboxylic acids in water with a combination of persulfate oxidant and ultrasonic irradiation. J. Fluorine Chem. 2012, 141:5-10.
30. Furman O.S., Teel A.L., Watts R.J. Mechanism of base activation of persulfate. Environ. Sci. Technol. 2010, 44:6423-6428.
31. Ivanov K.L., Glebov E.M., Plyusnin V.F., Ivanov Y.V., Grivin V.P., Bazhin N.M. Laser flash photolysis of sodium persulfate in aqueous solution with additions of dimethylformamide. J. Photochem. Photobiol. A 2000, 133:99-104.
32. He X.X., de la Cruz A.A., Dionysiou D.D. Destruction of cyanobacterial toxin cylindrospermopsin by hydroxyl radicals and sulfate radicals using UV-254 nm activation of hydrogen peroxide, persulfate and peroxymonosulfate. J. Photochem. Photobiol. A 2013, 251:160-166.
33. Guan Y.H., Ma J., Li X.C., Fang J.Y., Chen L.W. Influence of pH on the formation of sulfate and hydroxyl radicals in the uv/peroxymonosulfate system. Environ. Sci. Technol. 2011, 45:9308-9314.
34. Fang G.D., Gao J., Dionysiou D.D., Liu C., Zhou D.M. Activation of persulfate by quinones: free radical reactions and implication for the degradation of PCBs. Environ. Sci. Technol. 2013, 47:4605-4611.
35. Ahmad M., Teel A.L., Watts R.J. Mechanism of persulfate activation by phenols. Environ. Sci. Technol. 2013, 47:5864-5871.
36. Yang S.Y., Yang X., Shao X.T., Niu R., Wang L.L. Activated carbon catalyzed persulfate oxidation of azo dye acid orange 7 at ambient temperature. J. Hazard. Mater. 2011, 186:659-666.
37. Mahdi-Ahmed M., Chiron S. Ciprofloxacin oxidation by UV-C activated peroxymonosulfate in wastewater. J. Hazard. Mater. 2014, 265:41-46.
38. Ji Y.F., Ferronato C., Salvador A., Yang X., Chovelon J.M. Degradation of ciprofloxacin and sulfamethoxazole by ferrous-activated persulfate: implications for remediation of groundwater contaminated by antibiotics. Sci. Total Environ. 2014, 472:800-808.
39. Neta P., Huie R.E., Ross A.B. Rate constants for reactions of inorganic radicals in aqueous solution. J. Phys. Chem. Ref. Data 1988, 17:1027-1284.
40. 5-radicals. J. Am. Chem. Soc. 1972, 94:47-57.
41. F-. Inorg. Chem. 1991, 30:3582-3584.
42. Maruthamuthu P., Neta P. Radiolytic chain decomposition of peroxomonophosphoric and peroxomonosulfuric acids. J. Phys. Chem. 1977, 81:937-940.
43. Buxto G.V., Greenstoc C.L., Helman W.P., Ros A.B. Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals in aqueous solution. J. Phys. Chem. Ref. Data 1988, 17:513.
44. Liang C.-J., Huang S.-C. Kinetic model for sulfate/hydroxyl radical oxidation of methylene blue in a thermally-activated persulfate system at various pH and temperatures. Sustain. Environ. Res. 2012, 22:199-208.
45. Wols B.A., Hofman-Caris C.H.M. Review of photochemical reaction constants of organic micropollutants required for UV advanced oxidation processes in water. Water Res. 2012, 46:2815-2827.
46. Santoke H., Song W.H., Cooper W.J., Greaves J., Miller G.E. Free-radical-induced oxidative and reductive degradation of fluoroquinolone pharmaceuticals: kinetic studies and degradation mechanism. J. Phys. Chem. A 2009, 113:7846-7851.
47. El-Gamel N.E.A., Hawash M.F., Fahmey M.A. Structure characterization and spectroscopic investigation of ciprofloxacin drug. J. Therm. Anal. Calorim. 2012, 108:253-262.
48. Metry C.A., Maddox C.W., Dirikolu L., Johnson Y.J., Campbell K.L. Determination of enrofloxacin stability and in vitro efficacy against Staphylococcus pseudintermedius and Pseudomonas aeruginosa in four ear cleaner solutions over a 28 day period. Vet. Dermatol. 2012, 23:23-E26.
49. Golovnev N.N., Vasiliev A.D., Kirik S.D. Enrofloxacinium citrate monohydrate: preparation, crystal structure, thermal stability and IR-characterization. J. Mol. Struct. 2012, 1021:112-117.
50. Sustar B., Bukovec N., Bukovec P. Polymorphism and stability of norfloxacin, (1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinil)-3-quinolinocarboxylic acid. J. Therm. Anal. 1993, 40:475-481.
51. Naik P.N., Chimatadar S.A., Nandibewoor S.T. Kinetics and oxidation of fluoroquinoline antibacterial agent norfloxacin, by alkaline permanganate: a mechanistic study. Ind. Eng. Chem. Res. 2009, 48:2548-2555.
52. Hubicka U., Zmudzki P., Zuromska-Witek B., Zajdel P., Pawlowski M., Krzek J. Separation and characterization of ciprofloxacin, difloxacin, lomefloxacin, norfloxacin, and ofloxacin oxidation products under potassium permanganate treatment in acidic medium by UPLC-MS/MS. Talanta 2013, 109:91-100.
53. Liang C.J., Bruell C.J. Thermally activated persulfate oxidation of trichloroethylene: experimental investigation of reaction orders. Ind. Eng. Chem. Res. 2008, 47:2912-2918.
54. Liang C.J., Bruell C.J., Marley M.C., Sperry K.L. Thermally activated persulfate oxidation of trichloroethylene (TCE) and 1,1,1-trichloroethane (TCA) in aqueous systems and soil slurries. Soil Sediment Contam. 2003, 12:207-228.
55. Ge L.K., Chen J.W., Wei X.X., Zhang S.Y., Qiao X.L., Cai X.Y., Xie Q. Aquatic photochemistry of fluoroquinolone antibiotics: kinetics pathways, and multivariate effects of main water constituents. Environ. Sci. Technol. 2010, 44:2400-2405.
56. Li Y., Niu J.F., Wang W.L. Photolysis of enrofloxacin in aqueous systems under simulated sunlight irradiation: kinetics, mechanism and toxicity of photolysis products. Chemosphere 2011, 85:892-897.
57. Dodd M.C., Kohler H.P.E., Von Gunten U. Oxidation of antibacterial compounds by ozone and hydroxyl radical: elimination of biological activity during aqueous ozonation processes. Environ. Sci. Technol. 2009, 43:2498-2504.