Investigation of the degradation of cresols in the treatments with ozone

Water Research

Volumn 46, Issue 8, 2012, Pages 2795-2804

  Valsania, Maria C ^a   Fasano, Francesca ^a   Richardson, Susan D ^b   Vincenti, Marco ^a  

^a UNIVERSITY OF TURIN   (Italy)

^b U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

Author keywords

Chloroformates; Cresol; DBPs; Degradation intermediate; Disinfection by products; Ozone

Indexed keywords

ALDEHYDES; AROMATIC COMPOUNDS; DEGRADATION; GAS CHROMATOGRAPHY; IONIZATION OF GASES; ISOMERS; MASS SPECTROMETRY; OXALIC ACID; REACTION INTERMEDIATES; SOLUTIONS; SUBSTRATES;

AROMATIC RINGS; CHLOROFORMATES; CRESOL; DBP; DEGRADATION INTERMEDIATES; DEGRADATION KINETICS; DISINFECTION BY-PRODUCT; DISINFECTION BYPRODUCTS; HYDROXYBENZALDEHYDES; METHYL GROUP;

OZONE;

4 HYDROXYBENZALDEHYDE; 5 CHLORO 2,2,3,3,4,4,5,5 OCTAFLUORO 1 PENTYL CHLOROFORMATE; ALDEHYDE; CARBOXYLIC ACID; CITRACONIC ACID; CRESOL; HYDROXYBENZOIC ACID; HYDROXYL GROUP; ITACONIC ACID; MALIC ACID; METHYL GROUP; METHYLMUCONIC ACID; OXALIC ACID; OZONE; PHENOL; TARTRONIC ACID; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; DEGRADATION; DISINFECTION; HYPOTHESIS TESTING; OXIDATION; OZONE; PHENOLIC COMPOUND; REACTION KINETICS; WASTE TREATMENT;

ARTICLE; DEGRADATION; ELECTRON CAPTURE DETECTION; EXTRACTION; GAS CHROMATOGRAPHY; HYDROPHILICITY; IONIZATION; ISOMER; MASS SPECTROMETRY; OXIDATION; OZONATION; PRIORITY JOURNAL; RING OPENING; WATER TREATMENT;

EID: 84859004560     PISSN: 00431354     EISSN: 18792448     Source Type: Journal    
DOI: 10.1016/j.watres.2012.02.040     Document Type: Article

References (41)

1. Anderson L.J., Johnson J.D., Christman R.F. The reaction of ozone with isolated aquatic fulvic acid. Organic Geochemistry 1985, 8(1):65-69.
2. Bader H., Hoigné J. Determination of ozone in water by the indigo method. Water Research 1981, 15(4):449-456.
3. Coeur-Tourneur C., Henry F., Janquin M.-A., Brutier L. Gas-phase reaction of hydroxyl radicals with m-, o- and p-cresol. International Journal of Chemical Kinetics 2006, 38(9):553-562.
4. Coleman W.E., Munch J.W., Ringhand H.P., Kaylor W.H., Mitchell D.E. Ozonation/post-chlorination of humic acid: a model for predicting drinking water disinfection by-products. Ozone Science Engineering 1992, 14(1):51-69.
5. Flox C., Cabot P.L., Centellas F., Garrido J.A., Rodriguez R.M., Arias C., Brillas E. Solar photoelectro-Fenton degradation of cresols using a flow reactor with a boron-doped diamond anode. Applied Catalysis B: Environmental 2007, 75(1-2):17-28.
6. Galstyan G.A., Galstyan T.M., Sokolova S.M. Kinetics and mechanism of the reaction of ozone with methylbenzenes in acetic acid. Kinetics and Catalysis 1992, 33(4):623-630.
7. Glaze W.H., Weinberg H.S. Identification and Occurrence of Ozonation By-Products in Drinking Water 1993, American Water Works Works Association Research Foundation, Denver, CO.
8. Glaze W.H. Reaction products of ozone: a review. Environmental Health Perspectives 1986, 69:151-157.
9. Haag W.R., Hoigne J. Ozonation of bromide-containing waters-kinetics of formation of hypobromous acid and bromate. Environmental Science & Technology 1983, 17(5):261-267.
10. Hoigne J. Inter-calibration of OH radical sources and water quality parameters. Water Science and Technology 1997, 35(4):1-8.
11. Hoigne J., Bader H. Rate constants of reactions of ozone with organic and inorganic compounds in water-I. Non-dissociating organic compounds. Water Research 1983, 17(2):173-183.
12. Hoigne J., Bader H. Rate constants of reactions of ozone with organic and inorganic compounds in water-II. Dissociating organic compounds. Water Research 1983, 17(2):185-194.
13. Hsu Y.-C., Yang H.-C., Chen J.-H. The effects of preozonation on the biodegradability of mixed phenolic solution using a new gas-inducing reactor. Chemosphere 2005, 59(9):1279-1287.
14. 2 processes. Journal of Hazardous Materials 1995, 41(1):47-64.
15. Jung O.-J. Destruction of 2-chlorophenol from wastewater and investigation of by-products by ozonation. Bulletin Korean Chemical Society 2001, 22(8):850-856.
16. Kim H.-C., Yu M.-J. Characterization of aquatic humic substances to DBPs formation in advanced treatment processes for conventionally treated water. Journal of Hazardous Materials 2007, 143(1-2):486-493.
17. Komissarov V.C., Zimin Y.S., Khursan S.L. On the mechanism of phenol ozonolysis. Kinetics and Catalysis 2006, 47(6):850-854.
18. Legube B., Langlais B., Sohm B., Dore M. Identification of ozonation products of aromatic hydrocarbon micropollutants: effect on chlorination and biological filtration. Ozone: Science & Engineering 1981, 3(1):33-48.
19. Mvula E., von Sonntag C. Ozonolysis of phenols in aqueous solution. Organic & Biomolecular Chemistry 2003, 1(10):1749-1756.
20. Oh B.S., Kim K.S., Kang J.W. Ozonation of haloacetic acid precursor using phenol as a model compound: effect of ozonation by-products. Water Science Technology Water Supply 2006, 6(2):215-222.
21. Olariu R.I., Klotz B., Barnes I., Becker K.H., Mocanu R. FT-IR study of the ring-retaining products from the reaction of OH radicals with phenol, o-, m-, and p-cresol. Atmos. Environment 2002, 36(22):3685-3697.
22. Oturan M.A., Pimentel M., Oturan N., Sirés I. Reaction sequence for the mineralization of short-chain carboxylic acids usually formed upon cleavage of aromatics during electrochemical Fenton treatment. Electrochimica Acta 2008, 54(2):173-182.
23. Pimentel, M., 2010. Phenol and cresols treatment in aqueous solution by electro-Fenton process: application to the mineralization of aeronautic wastewater industry. Ph.D. thesis, Université Paris-Est Marne-la-Vallée, presented 2008, September 24, http://hal.archives-ouvertes.fr/docs/00/48/19/61/PDF/2008PEST0271_0_0.pdf.
24. Pimentel M., Oturan N., Dezotti M., Oturan M.A. Phenol degradation by advanced electrochemical oxidation process electro-Fenton using a carbon felt cathode. Applied Catalysis B: Environmental 2008, 83(1-2):140-149.
25. Poznyak T., Vivero J. Degradation of aqueous phenol and chlorinated phenols by ozone. Ozone: Science & Engineering 2005, 27(5):447-458.
26. Ramseier M.K., Peter A., Traber J., von Gunten U. Formation of assimilable organic carbon during oxidation of natural waters with ozone, chlorine dioxide, chlorine, permanganate, and ferrate. Water Research 2011, 45(5):2002-2010.
27. Ramseier M.K., von Gunten U. Mechanisms of phenol ozonation-kinetics of formation of primary and secondary reaction products. Ozone Science Engineering 2009, 31:201-215.
28. Razumovskii S.D. Reactions of ozone with aromatic compounds. Reaction and Properties of Monomers and Polymers 2006, 89-105. Nova Science Publishers Inc., New York, Chapter 5. A. D'Amore, G. Zaikov (Eds.).
29. Richardson S.D., Thruston A.D., Caughran T.V., Chen P.H., Collette T.W., Floyd T.L., Schenck K.M., Lykins B.W., Sun G.-R., Majetich G. Identification of new ozone disinfection byproducts formed in the presence of bromide. Environment Science Technology 1999, 33(19):3378-3383.
30. Richardson S.D., Thruston A.D., Caughran T.V., Chen P.H., Collette T.W., Floyd T.L., Schenck K.M., Lykins B.W., Sun G.-R., Majetich G. Identification of new ozone disinfection byproducts in drinking water. Environment Science Technology 1999, 33(19):3368-3377.
31. Richardson S.D., Plewa M.J., Wagner E.D., Schoeny R., DeMarini D.M. Occurrence, genotoxicity, and carcinogenicity of regulated and emerging disinfection by-products in drinking water: a review and roadmap for research. Mutation Research 2007, 636(1-3):178-242.
32. Richardson S.D. Disinfection by-products: formation and occurrence of drinking water. The Encyclopedia of Environmental Health 2011, vol. 2:110-136. Elsevier, Burlington.
33. Schulten H.R., Schnitzer M. A state-of-the-art structural concept for humic substances. Naturwissenschaften 1993, 80(1):29-30.
34. Singer P.C., Gurol M.D. Dynamics of the ozonation of phenol - I. experimental observations. Water Research 1983, 17(9):1163-1171.
35. Vincenti M., Ghiglione N., Valsania M.C., Davit P., Richardson S.D. Synthesis of highly fluorinated chloroformates and their use as derivatizing agents for hydrophilic compounds and drinking-water-disinfection by-products. Helvetica Chimica Acta 2004, 87(2):370-375.
36. Vincenti M., Biazzi S., Ghiglione N., Valsania M.C., Richardson S.D. Comparison of highly-fluorinated chloroformates as direct aqueous sample derivatizing agents for hydrophilic analytes and drinking-water disinfection by-products. Journal of the American Society for Mass Spectrometry 2005, 16(6):803-813.
37. Vincenti M., Fasano F., Valsania M.C., Guarda P., Richardson S.D. Application of the novel 5-chloro-2,2,3,3,4,4,5,5-octafluoro-1-pentyl chloroformate derivatizing agent for the direct determination of highly polar water disinfection byproducts. Analytical and Bioanalytical Chemistry 2010, 397(1):43-54.
38. von Gunten U. Ozonation of drinking water: part II. Disinfection and by-product formation in presence of bromide, iodide, or chlorine. Water Research 2003, 37(7):1469-1487.
39. von Gunten U. Ozonation of drinking water: part I. Oxidation kinetics and product formation. Water Research 2003, 37(7):1443-1467.
40. Wang K.H., Hsieh Y.H., Chen L.J. The heterogeneous photocatalytic degradation, intermediates and mineralization for the aqueous solution of cresols and nitrophenols. Journal of Hazardous Materials 1998, 59(2-3):251-260.
41. Yamamoto Y., Niki E., Shiokawa H., Kamiya Y. Ozonation of organic compounds. 2. Ozonation of phenol in water. Journal of Organic Chemistry 1979, 44(13):2137-2142.