The bromination kinetics of phenolic compounds in aqueous solution

Journal of Hazardous Materials

Volumn 170, Issue 2-3, 2009, Pages 645-651

  Guo, Gaimei ^a,b   Lin, Fengkai ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b Zhejiang Water Conservancy and Hydropower University   (China)

Author keywords

Bromination; Drinking water; Kinetics; Phenolic compounds; Rate constants

Indexed keywords

3-CHLOROPHENOL; AQUEOUS SOLUTIONS; BROMINATION; DRINKING WATER; HAMMETT CORRELATION; HYPOBROMITE; HYPOBROMOUS ACID; OVERALL REACTIONS; PH RANGE; PHENOLIC COMPOUNDS; PHENOXIDE IONS; SECOND-ORDER RATE CONSTANTS; SUBSTITUTED PHENOL; THREE ORDERS OF MAGNITUDE;

BROMINE; BROMINE COMPOUNDS; CHLORINE; CHLORINE COMPOUNDS; IONS; ORGANIC COMPOUNDS; OZONE; PH EFFECTS; PHENOLS; POTABLE WATER; SOLUTIONS;

RATE CONSTANTS;

3 METHOXYPHENOL; CHLORINE; CHLOROPHENOL; DRINKING WATER; HYPOBROMOUS ACID; INORGANIC ACID; OZONE; PHENOL DERIVATIVE; PHENOXIDE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; BROMINE; DRINKING WATER; PH; PHENOLIC COMPOUND; REACTION KINETICS; REACTION RATE;

AQUEOUS SOLUTION; ARTICLE; BROMINATION; CONTROLLED STUDY; OZONATION; PH; WATER MANAGEMENT; WATER TREATMENT;

AMMONIA; BROMATES; CHLORINE; HALOGENATION; HYDROGEN-ION CONCENTRATION; INDICATORS AND REAGENTS; KINETICS; PHENOLS; REFERENCE STANDARDS; SOLUTIONS; WATER; WATER SUPPLY;

EID: 69049087632     PISSN: 03043894     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2009.05.017     Document Type: Article

References (35)

1. Westerhoff P., Chao P., and Mash H. Reactivity of natural organic matter with aqueous chlorine and bromine. Water Res. 38 (2004) 1502-1513
2. Pourmoghaddas H., Stevens A.A., Kinman R.N., Dressman R.C., Moore L.A., and Ireland J.C. Formation of brominated trihalomethanes in drinking water. J. Am. Water Works Assoc. 85 (1993) 82-87
3. Trussell R., and Umphres D. The formation of trihalomethanes. J. Am. Water Work Assoc. 11 (1978) 606-612
4. Rook J., Gras A., van der Heijden G., and de Wee J. Bromide oxidation and organic substitution in water treatment. Environ. Sci. Health. A13 2 (1978) 91-116
5. M. Rebhun, L. Heller-Grossman, J. Manka, D. Kimel, B. Limoni, Trihalomethane formation and distribution in bromide-rich and ammonia-containing lake water, in: Water chlorination: Environmental Impact and Health Effects, 6 (2002) 665-680.
6. Shukairy H.M., Miltner R.J., and Summers R.S. Bromide's effect on DBP formation speciation and control: part 2, biotreatment. J. Am. Water Works Assoc. 87 (2001) 71-82
7. Minear R.A., and Amy G.L. Disinfection By-products in Water Treatment: The Chemistry of Their Formation and Control (1996), Lewis Publishers, Boca Raton, FL p. 502
8. Glaze W.H., Andelman J.B., Bull R.J., Conolly R.B., Hertz C.D., Hood R.D., and Pegram R.A. Determining health risks associated with disinfectants and disinfection by-products-research needs. J. Am. Water Works Assoc. 85 (2003) 53-56
9. Simmons J.E., Richardson S.D., Speth T.F., Miltner R.J., Rice G., Schenck K.M., Hunter E.S., and Teuschler L.K. Development of a research strategy for integrated technology-based toxicological and chemical evaluation of complex mixtures of drinking water disinfection byproducts. Environ. Health Perspect. 110 (2002) 1013-1024
10. Bull R.J., and Kopfler F.C. Health Effects of Disinfectant and Disinfection By-products (1991), American Water Works Association Research Foundation, Denver, CO
11. Boorman G.A., Dellarco V., Dunnick J.K., Chapin R.E., Hunter S., Hauchman F., Gardner H., Cos M., and Silss R. Drinking water disinfection byproducts: review and approach to toxicity evaluation. Environ. Health Perspect. 107 Supple 1 (2000) 207-217
12. USEPA, National primary drinking water regulations: disinfectants and disinfection by-products rule: final rule, Fed. Reg., 63, 241, 68390, December 16, 1998.
13. Legube B. A survey of bromate ion in European drinking water. Ozone Sci. Eng. 18 (2000) 325-348
14. Gunten U.V., and Oliveras Y. Advanced oxidation of bromide-containing waters: bromate formation mechanisms. Environ Sci. Technol. 32 (2000) 63-70
15. Federal Register, National Primary Drinking Water Regulations: Disinfection and Disinfection Byproducts: Final Rule, 40CFR Parts 9, 141 and 142, December 16, 1998.
16. Thurman E.M. Organic Geochemistry of Natural Waters (1985), Martinus Nijhoff/Dr. Junk Publishers, Boston, MA
17. Reckhow D.A., Singer P.C., and Malcolm R.L. Chlorination of humic materials-byproduct formation and chemical interpretations. Environ. Sci. Technol. 24 (2001) 1655-1664
18. Gallard H., and Gunten U.V. Chlorination of phenols: kinetics and formation of chloroform. Environ. Sci. Technol. 36 (2002) 884-890
19. Rook J.J. Formation of haloforms during chlorination of nature water. J. Water Treat. Exam. 23 (1974) 234-243
20. Rostad C.E., Martin B.S., Barber L.B., Leenheer J.A., and Daniel S.R. Effect of constructed wetland on disinfection byproducts: removal processes and production of precursors. Environ. Sci. Technol. 34 (2000) 2703-2710
21. Soper F.G., and Smith G.F. The halogenation of phenols. J. Chem. Soc. (1926) 1582-1591
22. Merlet N., de Laat J., and Dore M. Oxydation des bromures au cours de la chloration des eaux de surface, incidence sur la production decomposes organohalogenes. Revue Fr Sci Eau 1 (2002) 215-231
23. Symons M., Krasner W., Simms A., and Sclimenti M. Measurement of THM and precursor concentrations revisited: the effect of bromide ion. J. Am. Water Works Assoc. 85 (2003) 51-62
24. Boyce D., Barefoot C., Britton R., and Horning F. Formation of trihalomethanes from the halogenation of 1,3-dihydroxybenzenes in dilute aqueous solution synthesis of 2-13Cresorcinol and its reaction with chlorine and bromine. Water Chlorination Environmental and Health Effects vol. 4 (1983), Ann Arbor Science Publishers, Ann Arbor, MI pp. 253-267
25. Pinkernell U., and Gunten U.V. Bromate minimization during ozonation mechanistic considerations. Environ. Sci. Technol. 35 (2001) 2525-2531
26. Tee O.S., Paventi M., and Bennett J.M. Kinetics and mechanism of the brominatio of phenols and phenoxide ions in aqueous solution. Diffusion-controlled rates. J. Am. Chem. Soc. 111 (2002) 2233-2240
27. de La Mare P.B.D. Electrophilic halogenation (1976), Cambridge University Press, London
28. Bell R.P., and Rawlinson D.J. Kinetics of the bromination of some anisoles and Phenols. J. Chem. Soc. (1961) 63-68
29. Pinkernell U., Nowack B., Gallard H., and Gunten U.V. Methods for the photometric determination of reactive bromine and chlorine species with ABTS. Water Res. 34 (2000) 4343-4350
30. Troy R.C., and Margerum D.W. Nonmetal redox kinetics hypobromite and hypobromous acid reactions with iodide and with sulfite and the hydrolysis of bromosulfate. Inorg. Chem. 30 (2001) 3538-3543
31. Palin A.T. Current DPD methods for residual halogen compounds in water. J. Am. Water Works Assoc. 67 (1975) 32-33
32. Saguinsin J.L.S., and Morris J.C. The chemistry of aqueous nitrogen chloride. In: Johnson J.D. (Ed). Disinfection Water and Wastewater (1975), Ann Arbor Science Publishers, Inc, Ann Arbor, MI
33. Gallard H., Pellizzari F., Philippe Croue J., and Legube B. Rate constants of reactions of bromine with phenols in aqueous solution. Water Res. 37 (2003) 2883-2892
34. Bischel Y., and Gunten U.V. Formation of iodotrihalomethanes during disinfection and oxidation of iodide-containing waters. Environ. Sci. Technol. 34 (2000) 2784-2791
35. Rebenne L.M., Gonzalez A.C., and Olson T.M. Aqueous chlorination kinetics and mechanism of substituted dihydroxybenzenes. Environ. Sci. Technol. 30 (2004) 2235-2242