The nitration of pyrene adsorbed on silica particles by nitrogen dioxide

Chemosphere

Volumn 41, Issue 9, 2000, Pages 1479-1484

  Wang, Huimin ^a   Hasegawa, Kiyoshi ^a   Kagaya, Shigehiro ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Catalytic effect; Heterogeneous nitration; Nitration mechanism; Nitric acid; Nitrogen dioxide; Nitrous acid; Polycyclic aromatic hydrocarbons; Pyrene

Indexed keywords

NITRIC ACID; NITROGEN DIOXIDE; NITROUS ACID; POLYCYCLIC AROMATIC HYDROCARBON; PYRENE; SILICON DIOXIDE;

ADSORPTION; ARTICLE; ATMOSPHERE; CATALYSIS; CHEMICAL REACTION KINETICS; NITRATION; NONHUMAN;

ADSORPTION; GASES; NITRATES; NITRIC ACID; NITRITES; NITROGEN DIOXIDE; NITROUS ACID; PYRENES; SILICON DIOXIDE;

EID: 0033923422     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0045-6535(99)00523-8     Document Type: Article

References (33)

1. Ammann M., Kalberer M., Jose D.T., Tobler L., Rössler E., piguet D., Gäggeler H.W., Baltensperger U. Heterogeneous production of nitrous acid on soot in polluted air masses. Nature. 395:1998;157-160.
2. Bayliss N.S., Dingle R., Watts D.W., Wilkie R.J. The spectrophotometry of sodium nitrite solutions in aqueous sulphuric and perchloric acids and the equilibrium between nitrosonium ion and nitrous acid. Aust. J. Chem. 16:1963;933-942.
3. Carberry J.J. Some remarks on chemical equilibrium and kinetics in the nitrogen oxides-water system. Chem. Eng. Sci. 9:1959;189-194.
4. Committee on Biologic Effects of Atmospheric Air Pollutants, National Research Council, 1972. Particulate Polycyclic Organic Matter. National Academy of Sciences, Washinton, DC.
5. Cox R.A. The photolysis of gaseous nitrous acid. J. Photochem. 3:1974;175-188.
6. Eberson L., Radner F. Nitration of aromatics via electron transfer. II. On the reaction between naphthalene radical cation and nitrogen dioxide. Acta Chem. Scand. B. 34:1980;739-745.
7. Eberson L., Radner F. Electron transfer reactions in organic chemistry. IV. Possible role of electron transfer in aromatic nitration by nitrosonium and nitronium ion. Acta Chem. Scand. B. 38:1984;861-870.
8. Eberson L., Radner F. Nitration of polycyclic aromatic hydrocarbons by dinitrogen tetraoxide. II. Synthetic and mechanistic aspects. Acta Chem. Scand. B. 39:1985;343-356.
9. Eberson L., Radner F. Nitration of aromatics via electron transfer. IV. On the reaction between perylene radical cation and nitrogen dioxide or nitrite ion. Acta Chem. Scand. B. 39:1985;357-374.
10. Effenberger F., Kurtz W., Fischer P. Aminobenzole, IX Darstellung und reaktionen von 1, 3, 5-tris(dialkylamino)-2-nitrosobenzolen Chem. Ber. 107:1974;1285-1304.
11. +. J. Chem. Soc. 2620-2627.
12. Harrison R.M., Peak J.D., Collins G.M. Tropospheric cycle of nitrous acid. J. Geophys. Res. 101:1996;14429-14439.
13. 2. Atmos. Environ. 26A:1992;211-217.
14. Inazu K., Kobayashi T., Hisamatsu Y. Formation of 2-nitrofluoranthene in gas-solid heterogeneous photoreaction of fluoranthene supported on oxide particles in the presence of nitrogen dioxide. Chemosphere. 35:1997;607-622.
15. Kitto A.M.N., Harrison R.M. Nitrous and nitric acid measurements at sites in South-East England. Atmos. Environ. 26A:1992;235-241.
16. Lammel G., Perner D. The atmospheric aerosol as a source of nitrous acid in the polluted atmosphere. J. Aerosol. Sci. 19:1988;1199-1202.
17. Lee Y.-N., Schwartz S.E. Reaction kinetics of nitrogen dioxide with liquid water at low partial pressure. J. Phys. Chem. 85:1981;840-848.
18. Nielsen T. Reactivity of polycyclic aromatic hydrocarbons toward nitrating species. Environ. Sci. Technol. 18:1984;157-163.
19. Nielsen T., Jφrgensen H.E., Larsen J.C., Poulsen M. City air pollution of polycyclic aromatic hydrocarbons and other mutagens: occurrence, sources and health effects. Sci. Total Environ. 189/190:1996;41-49.
20. Ogata Y., Sawaki Y. Kinetics of the nitric acid oxidation of benzyl ethers to benzaldehydes. J. Am. Chem. Soc. 88:1966;5832-5837.
21. Pitts J.N. Jr. Formation and fate of gaseous and particulate mutagens and carcinogens in real and simulated atmospheres. Environ. Health. Perspect. 47:1983;115-140.
22. Pitts J.N. Jr., Sweetman J.A., Zielinska B., Winer A.M., Atkinson R. Determination of 2-nitrofluoranthene and 2-nitropyrene in ambient particulate organic matter: evidence for atmospheric reactions. Atmos. Environ. 19:1985;1601-1608.
23. Pitts J.N. Jr., Van Gauwenberghe K.A., Grosjean D., Schmid J.P., Fitz D.R., Belser W.L. Jr., Knudson G.B., Hynds P.M. Atmospheric reactions of polycyclic aromatic hydrocarbons: facile formation of mutagenic nitro derivatives. Science. 202:1978;515-519.
24. Pryor W.A., Gleicher G.J., Cosgrove J.P., Church D.F. Reaction of polycyclic aromatic hydrocarbons (PAH) with nitrogen dioxide in solution. Support for an electron-transfer mechanism of aromatic nitration based on correlations using simple molecular orbital theory. J. Org. Chem. 49:1984;5189-5194.
25. Ramdahl T., Bjφrseth A., Lokensgard D.M., Pitts J.N. Jr. Nitration of polycyclic aromatic hydrocarbons adsorbed to different carriers in a fluidized bed reactor. Chemosphere. 13:1984;527-534.
26. Rosenkranz H.S., Mermelstein R. Mutagenisity and genotoxicity of nitroarenes: all nitro-containing chemicals were not created equal. Mutat. Res. 114:1983;217-267.
27. Sakamaki F., Hatakeyama S., Akimoto H. Formation of nitrous acid and nitric oxide in the heterogeneous dark reaction of nitrogen dioxide and water vapor in a smog chamber. Int. J. Chem. Kinet. 15:1983;1013-1029.
28. Salmeen I.T., Durisen A.M., Prater T.J., Riley T., Schuetzle D. Contribution of 1-nitropyrene to direct acting Ames assay mutagenicities of diesel particulate extracts. Mutat. Res. 104:1982;17-28.
29. + and nitrous acid in aqueous perchloric acid. J. Chem. Soc. 3971-3974.
30. Tokiwa H., Ohnishi Y. Mutagenicity and carcinogenicity of nitroarenes and their sources in the environment. CRC Crit. Rev. Toxicol. 17:1986;23-60.
31. Wang, H., Hasegawa, K., Kagaya, S., 2000. Effect of nitrous acid gas on the nitration of pyrene adsorbed on silica particles by nitrogen dioxide. J. Environ. Sci. Health, Part A, in press.
32. Wang H., Hasegawa K., Kagaya S. Nitration of pyrene adsorbed on silica particles by nitrogen dioxide under simulated atmospheric conditions. Chemosphere. 39:1999;1923-1936.
33. Wu C.H., Niki H. Fluorescence spectroscopic study of kinetics of gas-surface reactions between nitrogen dioxide and adsorbed pyrene. Environ. Sci. Technol. 19:1985;1089-1094.