A novel approach to modeling the reaction kinetics of tetracycline antibiotics with aqueous ozone

Science of the Total Environment

Volumn 468-469, Issue , 2014, Pages 337-344

  Hopkins, Zachary R ^a   Blaney, Lee ^a  

^a Baltimore County   (United States)

Author keywords

Antibiotics; Chlortetracycline; Oxytetracycline; Ozone; Reaction kinetics; Tetracycline

Indexed keywords

ASSOCIATION REACTIONS; KINETICS; OZONE; OZONE WATER TREATMENT; RATE CONSTANTS; REACTION KINETICS;

CHLORTETRACYCLINE; OXYTETRACYCLINES (OTC); OZONE DISINFECTION; PRIMARY OBJECTIVE; SECOND-ORDER RATE CONSTANTS; TETRACYCLINE; TETRACYCLINE ANTIBIOTICS; WATER TREATMENT PROCESS;

ANTIBIOTICS;

CHLORTETRACYCLINE; DOXYCYCLINE; OXYTETRACYCLINE; OZONE; ROLITETRACYCLINE; TETRACYCLINE; TETRACYCLINE DERIVATIVE;

ANTIBIOTICS; DISINFECTION; NUMERICAL MODEL; OZONE; REACTION KINETICS; REACTION RATE; SPECIATION (CHEMISTRY); WATER TREATMENT;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION KINETICS; OZONATION; PH; PRIORITY JOURNAL;

ANTIBIOTICS; CA; CHLORTETRACYCLINE; CINNAMIC ACID; CTC; DAD; DC; DEIONIZED WATER; DI; DIODE ARRAY DETECTOR; DOXYCYCLINE; ELECTROSPRAY IONIZATION; ESI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HPLC; MS/MS; OTC; OXYTETRACYCLINE; OZONE; REACTION KINETICS; ROLITETRACYCLINE; RTC; T-BUOH; TANDEM MASS SPECTROMETRY; TC; TERT-BUTANOL; TET; TETRACYCLINE; TETRACYCLINE ANTIBIOTICS; WASTEWATER TREATMENT PLANT; WWTP;

ANTI-BACTERIAL AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROGEN-ION CONCENTRATION; KINETICS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; OZONE; TANDEM MASS SPECTROMETRY; TETRACYCLINE; WATER POLLUTANTS, CHEMICAL; WATER PURIFICATION;

EID: 84884177913     PISSN: 00489697     EISSN: 18791026     Source Type: Journal    
DOI: 10.1016/j.scitotenv.2013.08.032     Document Type: Article

References (70)

1. AHI Antibiotics sales: sales of disease fighting animal medicines rise. Animal Health Institute press release (November, 14, 2008) 2008, [Accessed at on June 26, 2013., 2008].
2. Auerbach E.A., Seyfried E.E., McMahon K.D. Tetracycline resistance genes in activated sludge wastewater treatment plants. Water Res 2007, 41:1143-1151.
3. Bader H., Hoigné J. Determination of ozone in water by the indigo method. Water Res 1981, 15:449-456.
4. Batt A.L., Kim S., Aga D.S. Comparison of the occurrence of antibiotics in four full-scale wastewater treatment plants with varying designs and operations. Chemosphere 2007, 68:428-435.
5. Ben W., Qiang Z., Pan X., Nie Y. Degradation of veterinary antibiotics by ozone in swine wastewater pretreated with sequencing batch reactor. J Environ Eng 2012, 138:272-277.
6. Bobrowski K., Raghavan N.V. Pulse radiolytic and product analysis studies of the reaction of hydroxyl radicals with cinnamic acid. The relative extent of addition to the ring and side chain. J Phys Chem 1982, 86:4432-4435.
7. Buxton G.V., Greenstock C.L., Helman W.P., Ross A.B. Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (·OH/O-) in aqueous solution. J Phys Chem Ref Data 1988, 17:513-886.
8. ChemAxon [Accessed on June 26, 2013]. http://www.chemicalize.org.
9. Chen J., Fei Z., Tao W., Zhang G. Adsorption and desorption of tetracycline on activated carbons. Adv Mater Res 2011, 233-235:561-566.
10. Choi K.J., Kim S.G., Kim S.H. Removal of antibiotics by coagulation and granular activated carbon filtration. J Hazard Mater 2008, 151:38-43.
11. Choi K.J., Kim S.G., Kim S.H. Removal of tetracycline and sulfonamide classes of antibiotic compound by powdered activated carbon. Environ Technol 2008, 29:333-342.
12. Chopra I., Hawkey P.M., Hinton M. Tetracyclines, molecular and clinical aspects. J Antimicrob Chemother 1992, 29:245-277.
13. Dalmazio I., Almeida M.O., Augusti R., Alves T.M.A. Monitoring the degradation of tetracycline by ozone in aqueous medium via atmospheric pressure ionization mass spectrometry. J Am Soc Mass Spectrom 2007, 18:679-687.
14. Dodd M.C., Buffle M.O., von Gunten U. Oxidation of antibacterial molecules by aqueous ozone: moiety-specific reaction kinetics and application to ozone-based wastewater treatment. Environ Sci Technol 2006, 40:1969-1977.
15. Dorfman L.M., Adams G.E. Reactivity of the hydroxyl radical in aqueous solutions. Nat Stand Ref Data Ser, Nat Bur Stand 1973, 46:1-59.
16. Fu H., Yang L., Wan Y., Xu Z., Zhu D. Adsorption of pharmaceuticals to microporous activated carbon treated with potassium hydroxide, carbon dioxide, and steam. J Environ Qual 2011, 40:1886-1894.
17. Gao P., Munir M., Xagoraraki I. Correlation of tetracycline and sulfonamide antibiotics with corresponding resistance genes and resistant bacteria in a conventional municipal wastewater treatment plant. Sci Total Environ 2012, 421-422:173-183.
18. Gomez-Pacheco C.V., Sanchez-Polo M., Rivera-Utrilla J., Lopez-Penalver J. Tetracycline removal from waters by integrated technologies based on ozonation and biodegradation. Chem Eng J 2011, 178:115-121.
19. Gottschall N., Topp E., Metcalfe C., Edwards M., Payne M., Kleywegt S., et al. Pharmaceutical and personal care products in groundwater, subsurface drainage, soil, and wheat grain, following a high single application of municipal biosolids to a field. Chemosphere 2012, 87:194-203.
20. Grote M., Schwake-Anduschus C., Michel R., Stevens H., Heyser W., Langenkaemper G., et al. Incorporation of veterinary antibiotics into crops from manured soil. Landbauforsch Voelkenrode 2007, 57:25-32.
21. Gu C., Karthikeyan K.G. Interaction of tetracycline with aluminum and iron hydrous oxides. Environ Sci Technol 2005, 39:2660-2667.
22. Hamad B. The antibiotics market. Nat Rev Drug Discov 2010, 9:675-676.
23. Hamscher G., Sczesny S., Hoper H., Nau H. Determination of persistent tetracycline residues in soil fertilized with liquid manure by high-performance liquid chromatography with electrospray ionization tandem mass spectrometry. Anal Chem 2002, 74:1509-1518.
24. Hoigné J., Bader H. Rate constants of reactions of ozone with organic and inorganic compounds in water. I. Nondissociating organic compounds. Water Res 1983, 17:173-183.
25. Huettenrauch R., Keiner I. Analysis of antibiotics. IX. Dissociation constants of Mannich bases of tetracycline antibiotics. Arch Pharm Ber Dtsch Pharm Ges 1968, 301:97-102.
26. Ji L., Chen W., Duan L., Zhu D. Mechanisms for strong adsorption of tetracycline to carbon nanotubes: a comparative study using activated carbon and graphite as adsorbents. Environ Sci Technol 2009, 43:2322-2327.
27. Karthikeyan K.G., Meyer M.T. Occurrence of antibiotics in wastewater treatment facilities in Wisconsin, USA. Sci Total Environ 2006, 361:196-207.
28. Khan M.H., Bae H., Jung J.-Y. Tetracycline degradation by ozonation in the aqueous phase: proposed degradation intermediates and pathway. J Hazard Mater 2010, 181:659-665.
29. Kim T.-H., Kim S.D., Kim H.Y., Lim S.J., Lee M., Yu S. Degradation and toxicity assessment of sulfamethoxazole and chlortetracycline using electron beam, ozone and UV. J Hazard Mater 2012, 227-228:237-242.
30. Kolpin D.W., Furlong E.T., Meyer M.T., Thurman E.M., Zaugg S.D., Barber L.B., et al. Pharmaceuticals, hormones, and other organic wastewater contaminants in U.S. streams, 1999-2000: a national reconnaissance. Environ Sci Technol 2002, 36:1202-1211.
31. Kumar K., Gupta S.C., Baidoo S.K., Chander Y., Rosen C.J. Antibiotic uptake by plants from soil fertilized with animal manure. J Environ Qual 2005, 34:2082-2085.
32. Lange F., Cornelissen S., Kubac D., Sein M.M., von Sonntag J., Hannich C.B., et al. Degradation of macrolide antibiotics by ozone: a mechanistic case study with clarithromycin. Chemosphere 2006, 65:17-23.
33. Lee H., Lee E., Lee C.-H., Lee K. Degradation of chlorotetracycline and bacterial disinfection in livestock wastewater by ozone-based advanced oxidation. J Ind Eng Chem 2011, 17:468-473.
34. Leitzke A., Reisz E., Flyunt R., von Sonntag C. The reactions of ozone with cinnamic acids: formation and decay of 2-hydroperoxy-2-hydroxyacetic acid. J Chem Soc, Perkin Trans 2 2001, 793-797.
35. Lemke T.L., Williams D.A. Foye's principles of medicinal chemistry 2008, 6th ed.
36. Leung H.W., Minh T.B., Murphy M.B., Lam J.C.W., So M.K., Martin M., et al. Distribution, fate and risk assessment of antibiotics in sewage treatment plants in Hong Kong, South China. Environ Int 2012, 42:1-9.
37. Li B., Zhang T. Mass flows and removal of antibiotics in two municipal wastewater treatment plants. Chemosphere 2011, 83:1284-1289.
38. Li D., Yang M., Hu J., Ren L., Zhang Y., Li K. Determination and fate of oxytetracycline and related compounds in oxytetracycline production wastewater and the receiving river. Environ Toxicol Chem 2008, 27:80-86.
39. Lide D.R. CRC handbook of chemistry and physics 2008, Taylor & Francis Group, Boca Raton, FL. 89th ed.
40. Lin A.Y.-C., Tsai Y.-T. Occurrence of pharmaceuticals in Taiwan's surface waters: impact of waste streams from hospitals and pharmaceutical production facilities. Sci Total Environ 2009, 407:3793-3802.
41. Martindale P. The complete drug reference 1999, Pharmaceutical Press, London. 32nd ed.
42. Miao X.S., Bishay F., Chen M., Metcalfe C.D. Occurrence of antimicrobials in the final effluents of wastewater treatment plants in Canada. Environ Sci Technol 2004, 38:3533-3541.
43. Mispagel H., Gray J.T. Antibiotic resistance from wastewater oxidation ponds. Water Environ Res 2005, 77:2996-3002.
44. Motoyama M., Nakagawa S., Tanoue R., Sato Y., Nomiyama K., Shinohara R. Residues of pharmaceutical products in recycled organic manure produced from sewage sludge and solid waste from livestock and relationship to their fermentation level. Chemosphere 2011, 84:432-438.
45. Munir M., Xagoraraki I. Levels of antibiotic resistance genes in manure, biosolids, and fertilized soil. J Environ Qual 2011, 40:248-255.
46. Munir M., Wong K., Xagoraraki I. Release of antibiotic resistant bacteria and genes in the effluent and biosolids of five wastewater utilities in Michigan. Water Res 2011, 45:681-693.
47. Oleszczuk P., Pan B., Xing B. Adsorption and desorption of oxytetracycline and carbamazepine by multiwalled carbon nanotubes. Environ Sci Technol 2009, 43:9167-9173.
48. Qiang Z., Adams C. Potentiometric determination of acid dissociation constants (pKa) for human and veterinary antibiotics. Water Res 2004, 38:2874-2890.
49. Rakness K.L. Ozone in drinking water treatment: process design, operation, and optimization 2005, American Water Works Association, Denver, CO.
50. Rennecker J.L., Mariñas B.J., Owens J.H., Rice E.W. Inactivation of Cryptosporidium parvum oocysts with ozone. Water Res 1999, 33:2481-2488.
51. Rivas J., Encinas A., Beltran F., Graham N. Application of advanced oxidation processes to doxycycline and norfloxacin removal from water. J Environ Sci Health A Tox Hazard Subst Environ Eng 2011, 46:944-951.
52. Rivas J.F., Jose S., Angel E., Olga G. Contaminants abatement by ozone in secondary effluents - Evaluation of second-order rate constants. J Chem Technol Biotechnol 2011, 86:1058-1066.
53. Roberts M.C. Tetracycline resistance determinants: mechanisms of action, regulation of expression, genetic mobility, and distribution. FEMS Microbiol Rev 1996, 19:1-24.
54. Sanli S., Sanli N., Alsancak G. Determination of protonation constants of some tetracycline antibiotics by potentiometry and LC methods in water and acetonitrile-water binary mixtures. J Braz Chem Soc 2009, 20:939-946.
55. Shafrir M., Avisar D. Development method for extracting and analyzing antibiotic and hormone residues from treated wastewater sludge and composted biosolids. Water Air Soil Pollut 2012, 223:2571-2587.
56. Shao L., Ren Z., Zhang G., Chen L. Facile synthesis, characterization of a MnFe2O4/activated carbon magnetic composite and its effectiveness in tetracycline removal. Mater Chem Phys 2012, 135:16-24.
57. Sithole B.B., Guy R.D. Models for tetracycline in aquatic environments. Water Air Soil Pollut 1987, 32:303-314.
58. Sithole B.B., Guy R.D. Models for tetracycline in aquatic environments. Water Air Soil Pollut 1987, 32:315-321.
59. Sperry T. Court orders FDA to review antibiotic use in livestock 2012, CNN Health.
60. Spongberg A.L., Witter J.D., Acuña J., Vargas J., Murillo M., Umaña G., et al. Reconnaissance of selected PPCP compounds in Costa Rican surface waters. Water Res 2011, 45:6709-6717.
61. Stephens C.R., Murai K., Brunings K.J., Woodward R.B. Acidity constants of the tetracycline antibiotics. J Am Chem Soc 1956, 78:4155-4158.
62. Szczepanowski R., Linke B., Krahn I., Gartemann K.H., Gotzkow T., Eichler W., et al. Detection of 140 clinically relevant antibiotic resistance genes in the plasmid metagenome of wastewater treatment plant bacteria showing reduced susceptibility to selected antibiotics. Microbiology 2009, 155:2306-2319.
63. Thomas K.V., Dye C., Schlabach M., Langford K.H. Source to sink tracking of selected human pharmaceuticals from two Oslo city hospitals and a wastewater treatment works. J Environ Monit 2007, 9:1410-1418.
64. Tolls J. Sorption of veterinary pharmaceuticals in soils: a review. Environ Sci Technol 2001, 35:3397-3406.
65. Torres-Perez J., Gerente C., Andres Y. Sustainable activated carbons from agricultural residues dedicated to antibiotic removal by adsorption. Chin J Chem Eng 2012, 20:524-529.
66. Uslu M.O., Balcioglu I.A. Ozonation of animal wastes containing oxytetracycline. Ozone Sci Eng 2008, 30:290-299.
67. Wang Y., Zhang H., Chen L., Wang S., Zhang D. Ozonation combined with ultrasound for the degradation of tetracycline in a rectangular air-lift reactor. Sep Purif Technol 2012, 84:138-146.
68. Wei R., Ge F., Huang S., Chen M., Wang R. Occurrence of veterinary antibiotics in animal wastewater and surface water around farms in Jiangsu Province, China. Chemosphere 2011, 82:1408-1414.
69. Wickramanayake G.B., Rubin A.J., Sproul O.J. Effects of ozone and storage temperature on Giardia cysts. J Am Water Works Assoc 1985, 77:74-77.
70. Yalap K.S., Balcioglu I.A. Effects of inorganic anions and humic acid on the photocatalytic and ozone oxidation of oxytetracycline in aqueous solution. J Adv Oxid Technol 2009, 12:134-143.