Reaction of polycyclic aromatic hydrocarbons adsorbed on silica in aqueous chlorine

Environmental Science and Technology

Volumn 41, Issue 7, 2007, Pages 2190-2195

  Nakamura, Hideyuki ^a   Tomonaga, Yuzo ^a   Miyata, Kana ^a   Uchida, Mitsuo ^a   Terao, Yoshiyasu ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS CHLORINE; BROMINATED DERIVATIVES; HALOGENATING AGENTS;

ADSORPTION; CHLORINE; DERIVATIVES; OXIDATION; SILICA GEL; SOLUTIONS;

POLYCYCLIC AROMATIC HYDROCARBONS;

1 BROMOPYRENE; 9 (1 TERT BUTYLAMINO 3 HYDROXY 2 PROPYLOXYIMINO)FLUORENE; CHLORINE DERIVATIVE; FLUORANTHENE; FLUORENE; HYPOCHLORITE SODIUM; INFUSORIAL EARTH; POLYCYCLIC AROMATIC HYDROCARBON; PYRENE; SILICON DIOXIDE; UNCLASSIFIED DRUG; WATER;

ADSORPTION; CHLORINE; DERIVATIVES; OXIDATION; POLYCYCLIC AROMATIC HYDROCARBONS; SILICA GEL; SOLUTIONS;

ADSORPTION; AQUEOUS SOLUTION; CHLORINE; DIATOMITE; HYDROPHOBICITY; PAH; SEDIMENT; SILICA;

ADSORPTION; ARTICLE; BROMINATION; CHEMICAL REACTION KINETICS; CHLORINATION; ELECTROPHILICITY; HALOGENATION; HYDROPHOBICITY; OXIDATION; REACTION ANALYSIS; SEDIMENTOLOGY; SURFACE PROPERTY; WATER POLLUTION;

ADSORPTION; BROMIDES; CHLORINE; ENVIRONMENTAL POLLUTANTS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; KINETICS; MOLECULAR STRUCTURE; POLYCYCLIC HYDROCARBONS, AROMATIC; POTASSIUM COMPOUNDS; SILICON DIOXIDE; SODIUM HYPOCHLORITE;

EID: 34247110523     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es062005n     Document Type: Article

References (37)

1. Simpson, C. D.; Mosi, A. A.; Cullen, W. R.; Reimer, K. J. Composition and distribution of polycyclic aromatic hydrocarbon contamination in surficial marine sediments from Kitimat Harbor, Canada. Sci. Total Environ. 1996, 181, 265-278.
2. Simpson, C. D.; Harrington, C. F.; Cullen, W. R.; Bright, D. A.; Reimer, K. J. Polycyclic aromatic hydrocarbon contamination in marine sediments near Kitimat, British Columbia. Environ. Sci. Technol. 1998, 32, 3266-3272.
3. Busetti, F.; Heitz, A.; Cuomo, M.; Badoer, S.; Traverso, P. Determination of sixteen polycyclic aromatic hydrocarbons in aqueous and solid samples from an Italian wastewater treatment plant. J. Chromatogr., A 2006, 1102, 104-115.
4. King, A. J.; Readman, J. W.; Zhou, J. L. Dynamic behaviour of polycyclic aromatic hydrocarbons in Brighton marina, UK. Mar. Pollut. Bull. 2004, 48, 229-239.
5. National Recommended Water Quality Criteria: 2002; 822-R-02-047; Health and Ecological Criteria Division, Office of Science and Technology, U.S. EPA: 2002.
6. Environmental Health Criteria 202. Selected Nonheterocyclic Polycyclic Aromatic Hydrocarbons; World Health Organization/International Program on Chemical Safety: Geneva, 1998.
7. Bigelow, S. W.; Nebert, D. W. The Ah regulatory gene product. Survey of nineteen polycyclic aromatic compounds' and fifteen benzo[a] pyrene metabolites' capacity to bind to the cytosolic receptor. Toxicol. Lett. 1982, 10, 109-118.
8. Jones, J. M.; Anderson, J. W. Relative potencies of PAHs and PCBs based on the response of human cells. Environ. Toxicol. Pharm. 1999, 7, 19-26.
9. Machala, M.; Vondracek, J.; Blaha, L.; Ciganek, M.; Neca, J. V. Aryl hydrocarbon receptor-mediated activity of mutagenic polycyclic aromatic hydrocarbons determined using in vitro reporter gene assay. Mutat. Res. 2001, 497, 49-62.
10. Piskorska-Pliszczynska, J.; Keys, B.; Safe, S.; Newman, M. S. The cytosolic receptor binding affinities and AHH induction potencies of 29 polynuclear aromatic hydrocarbons. Toxicol. Lett. 1986, 34, 67-74.
11. Ziccardi, M. H.; Gardner, I. A.; Denison, M. S. Application of the luciferase recombinant cell culture bioassay system for the analysis of polycyclic aromatic hydrocarbons. Environ. Toxicol. Chem. 2002, 21, 2027-2033.
12. Willett, K. L.; Gardinali, P. R.; Sericano, J. L.; Wade, T. L.; Safe, S. H. Characterization of the H4IIE rat hepatoma cell bioassay for evaluation of environmental samples containing polycyclic polynuclear aromatic hydrocarbons. Arch. Environ. Contam. Toxicol. 1997, 32, 442-448.
13. Fent, K.; Batscher, R. Cytochrome O4501A induction potencies of polycyclic aromatic hydrocarbons in a fish hepatoma cell line: Demonstration of additive interactions. Environ. Toxicol. Chem. 2000, 19, 2047-2058.
14. Santodonato, J. Review of the estrogenic and antiestrogenic activity of polycyclic aromatic hydrocarbons: Relationship to carcinogenicity. Chemosphere 1997, 34, 835-848.
15. Arcaro, K. F.; O'Keefe, P. W.; Yang, Y.; Clayton, W.; Gierthy, J. F. Antiestrogenicity of environmental polycyclic aromatic hydrocarbons in human breast cancer cells. Toxicology 1999, 133, 115-127.
16. Chaloupka, K.; Krishnan, V.; Safe, S. Polynuclear aromatic hydrocarbon carcinogens as antiestrogens in MCF-7 human breast cancer cells: Role of the Ah receptor. Carcinogenesis 1992, 13, 2233-2239.
17. Gozgit, J. M.; Nestor, K. M.; Fasco, M. J.; Pentecost, B. T.; Arcaro, K. F. Differential action of polycyclic aromatic hydrocarbons on endogenous estrogen-responsive genes and on a transfected estrogen-responsive reporter in MCF-7 cells. Toxicol. Appl. Pharm. 2004, 196, 58-67.
18. Charles, G. D.; Bartels, M. J.; Zacharewski, T. R.; Gollapudi, B. B.; Freshour, N. L.; Carney, E. W. Activity of benzo[a]pyrene and its hydroxylated metabolites in an estrogen receptor - a reporter gene assay. Toxicol. Sci. 2000, 55, 320-326.
19. Monoli, E.; Samara, C. Polycyclic aromatic hydrocarbons in natural waters: Sources, occurrence and analysis. Trends Anal. Chem. 1999, 18, 417-427.
20. Shiraishi, H.; Pilkington, N. H.; Otsuki, A; Fuwa, K. Occurrence of chlorinated polynuclear aromatic hydrocarbons in tap water. Environ. Sci. Technol. 1985, 19, 585-590.
21. Kveseth, K.; Sortlant, B.; Bokn, T. Polycyclic aromatic hydrocarbons in sewage, mussels and tap water. Chemosphere 1982, 11, 623-639.
22. Nagai, A.; Kano, Y.; Funasaka, R.; Nakamuro, K. Mutagenic characteristics and contribution of polycyclic aromatic hydrocarbons to mutagenicity of concentrates from municipal river water by blue chitin column. J. Health Sci. 2002, 48, 232-241.
23. Colmsjö, A.; Rannug, A.; Rannug, U. Some chloro derivatives of polynuclear aromatic hydrocarbons are potent mutagens in Salmonella typhimurium. Mutat. Res. 1984, 135, 21-29.
24. Onodera, S.; Igarashi, K.; Fukuda, A.; Ouchi, J.; Suzuki, S. Chemical changes of organic compounds in chlorinated water. VXI. Gas chromatographic-mass spectrometric studies of reactions of tricyclic aromatic hydrocarbons with hydrochlorite in dilute aqueous solution. J. Chromatogr., A 1989, 466, 233-249.
25. Oyler, A. R.; Liukkonen, R. J.; Lukasewycz, M. K.; Cox, D. A.; Peake, D. A.; Carlson, R. M. Implications of treating water containing polynuclear aromatic hydrocarbons with chlorine: A gas chromatographic mass spectrometric study. Environ. Health Perspect. 1982, 46, 73-86.
26. Oyler, A. R.; Liukkonen, R. J.; Lukasewycz, M. T.; Heikkila, K. E.; Cox, D. A.; Carlson, R. M. Chlorine disinfection chemistry of aromatic-compounds- polynuclear aromatic-hydrocarbons-Rates, products, and mechanisms. Environ. Sci. Technol. 1983, 17, 334-342.
27. Mori, Y.; Goto, S.; Onodera, S.; Naito, S.; Matsushita, H. Aqueous chlorination of tetracyclic aromatic hydrocarbons: Reactivity and product distribution. Chemosphere 1991, 22, 495-501.
28. Nikolaou, A. D.; Golfinopoulos, S. K.; Lekkas, T. D. Formation of organic byproducts during chlorination of natural water. J. Environ. Monit. 2002, 4, 910-916.
29. Cowman, G. A.; Singer, P. C. Effect of bromide ion on haloacetic acid speciation resulting from chlorination and chloramination of aquatic humic substances. Environ. Sci. Technol. 1996, 30, 16-24.
30. Hu, J.; Jin, X.; Kunikane, S.; Terao, Y.; Aizawa, T. Transformation of pyrene in aqueous chlorination in the presence and absence of bromide ion: Kinetics, products, and their aryl hydrocarbon receptor-mediated activities. Environ. Sci. Technol. 2006, 40, 487-493.
31. Voudrias, E. A.; Reinhard, M. Reactivities of hypochlorous and hypobromous acid, chlorine monoxide, hypobromous acidium ion, chlorine, bromine, and bromine chloride in electrophilic aromatic substitution reactions with p-xylene in water. Environ. Sci. Technol. 1988, 22, 1049-1056.
32. -. Environ. Sci. Technol 1988, 22, 1056-1062.
33. Ringwald, S. C.; Pemberton, J. E. Adsorption interactions of aromatics and heteroaromatics with hydrated and dehydrated silica surfaces by Raman and FTIR spectroscopies. Environ. Sci. Technol. 2000, 34, 259-265.
34. Kropp, P. J.; Breton, G. W.; Craig, S. L.; Crawford, S. D.; Durland, W. F., Jr.; Jones, J. E., III: Raleigh, J. S. Surface-mediated reactions. 6. Effects of silica gel and alumina on acid-catalyzed reactions. J. Org. Chem. 1995, 60, 4146-4152.
35. Patil, V. J.; Mavers, U. Wittig reactions in the presence of silica gel. Tetrahedron Lett. 1996, 37, 1281-1284.
36. Kotsuki, H.; Shimanouchi, T.; Ohshima, R.; Fujiwara, S. Solvent-free organic reactions on silica gel supports. Facile transformation of epoxides to β-halohydrins with lithium halides. Tetrahedron 1998, 54, 2709-2722.
37. Das, B.; Banerjee, J.; Ravindranath, N. A simple and facile stereoselective synthesis of (Z)- and (E)-allyl halides catalyzed by silica supported sodium hydrogen sulfate: factors influencing the yields and stereochemistry of allyl halides. Tetrahedron 2004, 60, 8357-8361.