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Atmospheric Reactions of PAHs Including Formation of Nitroarenes

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PAHs and Related Compounds

Part of the book series: The Handbook of Environmental Chemistry ((HEC3,volume 3 / 3I))

Abstract

The effect of phase distribution on the atmospheric fates of the PAHs, the important atmospheric loss processes, and the resulting atmospheric lifetimes of the PAHs are discussed. Gasphase PAH reactions are emphasized because it is these reactions which control the in-situ formation of nitroarenes in ambient atmospheres. Results from laboratory studies of PAH reactions and data on ambient nitroarene profiles are presented. Hydroxyl (OH) radical-initiated reactions of gas-phase PAHs generally limit their atmospheric lifetimes to less than 1 day. Both daytime OH radical-initiated and nighttime nitrate (NO3) radical-initiated reactions of gas-phase PAHs lead to the formation of nitroarenes, which depending upon their vapor pressures may become particle-associated. Two classes of PAH atmospheric reaction products, nitroarenes and nitroarene lactones, have been found to contribute significantly to the mutagenic activity of ambient atmospheres suggesting that comprehensive risk assessments for atmospheric PAHs should include the potential health effects of their atmospheric reaction products.

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References

  1. Alfheim I, Löfroth G, Moller M (1983) Bioassay of extracts of ambient particulate matter. Environ Health Perspect 47: 227

    CAS  Google Scholar 

  2. Ames BN, McCann J, Yamasaki E (1975) Methods for detecting carcinogens and mutagens with the Salmonella mammalian-microsome mutagenicity test. Mutat Res 31: 347

    CAS  Google Scholar 

  3. Arey J, Zielinska B, Atkinson R, Winer AM, Ramdahl T, Pitts JN Jr (1986) The formation of nitro-PAH from the gas-phase reactions of fluoranthene and pyrene with the OH radical in the presence of NO.. Atmos Environ 20: 2339

    CAS  Google Scholar 

  4. Arey J, Zielinska B, Atkinson R, Winer AM (1987) Polycyclic aromatic hydrocarbon and nitroarene concentrations in ambient air during a winter-time high-NOx episode in the Los Angeles basin. Atmos Environ 21: 1437

    CAS  Google Scholar 

  5. Arey J, Zielinska B, Atkinson R, Winer AM (1988) Formation of nitroarenes during ambient high-volume sampling. Environ Sci Technol 22: 457

    CAS  Google Scholar 

  6. Arey J, Zielinska B, Harger WP, Atkinson R, Winer AM (1988) The contribution of nitrofluoranthenes and nitropyrenes to the mutagenic activity of ambient particulate organic matter collected in southern California. Mutat Res 207: 45

    CAS  Google Scholar 

  7. Arey J, Atkinson R, Zielinska B, McElroy PA (1989) Diurnal concentrations of volatile polycyclic aromatic hydrocarbons and nitroarenes during a photochemical air pollution episode in Glendora, California. Environ Sci Technol 23: 321

    Google Scholar 

  8. Arey J, Zielinska B, Atkinson R, Aschmann SM (1989) Nitroarene products from the gas-phase reactions of volatile polycyclic aromatic hydrocarbons with the OH radical and N205. Int J Chem Kinet 21: 775

    CAS  Google Scholar 

  9. Arey J, Atkinson R, Aschmann SM, Schuetzle D (1990) Experimental investigation of the atmospheric chemistry of 2-methyl-l-nitronaphthalene and a comparison of predicted nitroarene concentrations with ambient air data. Polycyclic Aromatic Compounds 1: 33

    Google Scholar 

  10. Arey J, Harger WP, Helmig D, Atkinson R (1992) Bioassay-directed fractionation of mutagenic PAH atmospheric photooxidation products and ambient particulate extracts. Mutat Res 281: 67

    CAS  Google Scholar 

  11. Atkinson R, Arey J, Zielinska B, Aschmann SM (1987) Kinetics and products of the gas-phase reactions of OH radicals and N2O5 with naphthalene and biphenyl. Environ Sci Technol 2 1: 1014

    Google Scholar 

  12. Atkinson R, Arey J, Winer AM, Zielinska B, Dinoff TM, Harger WP, McElroy PA (1988) A survey of ambient concentrations of selected polycyclic aromatic hydrocarbons (PAH) at various locations in California. Final Report for California Air Resources Board Contract No. A5–185–32, Sacramento, CA

    Google Scholar 

  13. Atkinson R (1989) Kinetics and mechanisms of the gas-phase reactions of the hydroxyl radical with organic compounds. J Phys Chem Ref Data Monograph 1

    Google Scholar 

  14. Atkinson R, Aschmann SM, Arey J, Zielinska B, Schuetzle D (1989) Gas-phase atmospheric chemistry of 1- and 2-nitronaphthalene and 1,4-naphthoquinone. Atmos Environ 23: 2679

    CAS  Google Scholar 

  15. Atkinson R,Arey J, Zielinska B, Aschmann SM (1990) Kinetics and nitro-products of the gas-phase OH and NO3 radical-initiated reactions of naphthalene-d8, fluoranthene-d10 and pyrene. Int J Chem Kinet 22: 999

    Google Scholar 

  16. Atkinson R, Tuazon EC, Arey J (1990) Reactions of naphthalene in N2O5 - NO3 -NO2 - air mixtures. Int J Chem Kinet 22: 1071

    CAS  Google Scholar 

  17. Atkinson R (1991) Kinetics and mechanisms of the gas-phase reactions of the NO3 radical with organic compounds. J Phys Chem Ref Data 20: 459

    CAS  Google Scholar 

  18. Atkinson R, Baulch DL, Cox RA, Hampson RF Jr, Kerr JA, Troe J (1992) Evaluated kinetic and photochemical data for atmospheric chemistry. Supplement IV. IUPAC subcommittee on gas kinetic data evaluation for atmospheric chemistry. J Phys Chem Ref Data 21: 1125

    Google Scholar 

  19. Atkinson R (1994) Gas-phase tropospheric chemistry of organic compounds. J Phys Chem Ref Data Monograph 2

    Google Scholar 

  20. Atkinson R, Arey J (1994) Atmospheric chemistry of gas-phase polycyclic aromatic hydrocarbons: formation of atmospheric mutagens. Environ Health Perspect 102: 117

    CAS  Google Scholar 

  21. Atkinson R, Aschmann SM (1994) Products of the gas-phase reactions of aromatic hydrocarbons: effect of NO2 concentration. Int J Chem Kinet 26: 929

    CAS  Google Scholar 

  22. Atkinson R, Tuazon EC, Bridier I, Arey J (1994) Reactions of NO3-naphthalene adducts with 02 and NO2. Int J Chem Kinet 26: 605

    CAS  Google Scholar 

  23. Atkinson R (1995) Gas-phase tropospheric chemistry of organic compounds. In: Hester RE, Harrison RM (eds) Volatile organic compounds in the atmosphere. The Royal Society of Chemistry, Cambridge, UK, p 65

    Google Scholar 

  24. Ayers GP, Penkett SA, Gillett RW, Bandy B, Galbally IE, Meyer CP, Elsworth CM, Bentley ST, Forgan BW (1992) Evidence for photochemical control of ozone concentrations in unpolluted marine air. Nature 360: 446

    CAS  Google Scholar 

  25. Behymer TD, Hites RA (1988) Photolysis of polycyclic aromatic hydrocarbons adsorbed on fly ash. Environ Sci Technol 22: 1311

    CAS  Google Scholar 

  26. Bidleman TF (1988) Atmospheric processes: wet and dry deposition of organic compounds are controlled by their vapor-particle partitioning. Environ Sci Technol 22: 361

    CAS  Google Scholar 

  27. Bunce NJ, Zhu J (1994) Products from photochemical reactions of naphthalene in air. Polycyclic Aromatic Compounds 5: 123

    CAS  Google Scholar 

  28. Busby WF Jr, Penman BW, Crespi CL (1994) Human cell mutagenicity of mono-and dinitropyrenes in metabolically competent MCL-5 cells. Mutat Res 322: 233

    CAS  Google Scholar 

  29. Ciccioli P, Cecinato A, Cabella R, Brancaleoni E, Buttini, P (1993) The contribution of gas-phase reactions to the nitroarene fraction of molecular weight 247 present in carbon particles sampled in an urban area of northern Italy. Atmos Environ 27A: 1261

    Google Scholar 

  30. Ciccioli P, Cecinato A, Brancaleoni E, Frattoni M, Zacchei P, De Castro Vasconcellos P (1995) The ubiquitous occurrence of nitro-PAH of photochemical origin in airborne particles. Annali di Chimica 85: 455.

    CAS  Google Scholar 

  31. Ciccioli P, Cecinato A, Brancaleoni E, Frattoni M, Zacchei P, Miguel AH, de Castro Vasconcellos P (1996) Formation and transport of 2-nitrofluoranthene and 2-nitropyrene of photochemical origin in the troposphere. J Geophys Res 101: 19567

    CAS  Google Scholar 

  32. Coutant RW, Brown L, Chuang JC, Riggin RM, Lewis RG (1988) Phase distribution and artifact formation in ambient air sampling for polynuclear aromatic hydrocarbons. Atmos Environ 22: 403

    CAS  Google Scholar 

  33. Daisey JM, Lewandowski CG, Zorz M (1982) A photoreactor for investigations of the degradation of particle-bound polycyclic aromatic hydrocarbons under simulated atmospheric conditions. Environ Sci Technol 16: 857

    CAS  Google Scholar 

  34. Dockery, DW, Pope CA III, Xu X, Spengler JD, Ware JH, Fay ME, Ferris BG Jr, Speizer FE (1993) An association between air pollution and mortality in six U.S. cities. New Engl J Med 329: 1753

    CAS  Google Scholar 

  35. Dunstan TDJ, Mauldin RF, Jinxian Z, Hipps AD, Wehry EL, Mamantov G (1989) Adsorption and photodegradation of pyrene on magnetic, carbonaceous, and mineral subfractions of coal stack ash. Environ Sci Technol 23: 303

    CAS  Google Scholar 

  36. Eaborn C, Golborn P, Spillett RE, Taylor R (1968) Aromatic reactivity part XXXVII detritiation of substituted 1- and 2-tritionaphthalenes. J Chem Soc B: 1112

    Google Scholar 

  37. El-Bayoumy K, Hecht SS (1986) Mutagenicity of K-region derivatives of 1-nitropyrene; remarkable activity of 1- and 3-nitro-5H-phenanthro[4, 5-bcd]pyran-5-one. Mutat Res 170: 31

    CAS  Google Scholar 

  38. Fan Z, Kamens RM, Hu J, Zhang J, McDow S (1996) Photostability of nitro-polycyclic aromatic hydrocarbons on combustion soot particles in sunlight. Environ Sci Technol 30: 1358

    CAS  Google Scholar 

  39. Fan Z, Kamens RM, Zhang J, Hu J (1996) Ozone-nitrogen dioxide-NPAH heterogeneous soot particle reactions and modeling NPAH in the atmosphere. Environ Sci Technol 30: 2821

    CAS  Google Scholar 

  40. Fu PP, Herreno-Saenz D, Von Tungeln LS, Lay JO, Wu Y-S, Lai J-S, Evans FE (1994) DNA adducts and carcinogenicity of nitro-polycyclic aromatic hydrocarbons. Environ Health Perspect 102: 177

    CAS  Google Scholar 

  41. Goldring JM, Ball LM, Sangaiah R, Gold A (1988) Synthesis and biological activity of nitro-substituted cyclopenta-fused PAH. In: Cooke M, Dennis AJ (eds.) Polynuclear aromatic hydrocarbons: a decade of progress. Battelle Press, Columbus, p 285

    Google Scholar 

  42. Graedel TE, Weschler CJ (1981) Chemistry within aqueous atmospheric aerosols and raindrops. Rev Geophys Space Phys 19: 505

    CAS  Google Scholar 

  43. Graedel TE, Hawkins DT, Claxton LD (1986) Atmospheric chemical compounds: sources, occurrence, and bioassay. Academic Press, Orlando pp. 732

    Google Scholar 

  44. Grosjean D, Fung K, Harrison J (1983) Interactions of polycyclic aromatic hydrocarbons with atmospheric pollutants. Environ Sci Technol 17: 673

    CAS  Google Scholar 

  45. Gundel LA, Daisey JM, de Carvalho LRF, Kado NY, Schuetzle D (1993) Polar organic matter in airborne particles: chemical characterization and mutagenic activity. Environ Sci Technol 27: 2112

    CAS  Google Scholar 

  46. Gupta P (1995) The contribution of methylnitronaphthalenes to the vapor-phase mutagenicity observed in ambient air samples collected at Redlands, California. Master’s Thesis, University of California, Riverside.

    Google Scholar 

  47. Gupta P, Harger WP, Arey J (1996) The contribution of nitro-and methylnitro-naphthalenes to the vapor-phase mutagenicity of ambient air samples. Atmos Environ 30: 3157

    CAS  Google Scholar 

  48. Hannigan MP, Cass GR, Lafleur AL, Longwell JP, Thilly WG (1994) Bacterial mutageni-city of urban organic aerosol sources in comparison to atmospheric samples. Environ Sci Technol 28: 2014

    CAS  Google Scholar 

  49. Harger WP, Arey J, Atkinson R (1992) The mutagenicity of HPLC-separated vapor-phase and particulate organics in ambient air. Atmos Environ 26A: 2463

    Google Scholar 

  50. HEI (1995) Diesel exhaust: a critical analysis of emissions, exposure, and health effects. Health Effects Institute, Cambridge, MA

    Google Scholar 

  51. Helmig D, Arey J, Atkinson R, Harger WP, McElroy PA (1992) Products of the OH radical-initiated gas-phase reaction of fluorene in the presence of NOI. Atmos Environ 26A: 1735

    Google Scholar 

  52. Helmig D, Arey J, Harger WP, Atkinson R, López-Cancio J (1992) Formation of mutagenic nitrodibenzopyranones and their occurrence in ambient air. Environ Sci Technol 26: 622

    CAS  Google Scholar 

  53. Helmig D, López-Cancio J, Arey J, Harger WP, Atkinson R (1992) Quantification of ambient nitrodibenzopyranones: further evidence for atmospheric mutagen formation. Environ Sci Technol 26: 2207

    CAS  Google Scholar 

  54. Herreno-Saenz D, Evans FE, Heinze T, Lewtas J, Fu PP (1992) In vitro metabolism and DNA adduct formation from the mutagenic environmental contaminant 2-nitrofluoranthene. Chem Res Toxicol 5: 863

    CAS  Google Scholar 

  55. Howard PC, Hecht SS, Beland FA (eds) (1990) Nitroarenes - occurrence, metabolism, and biological impact. Plenum, New York

    Google Scholar 

  56. Hueper WC, Kotin P, Tabor EC, Payne WW, Falk H, Sawicki E (1962) Carcinogenic bioassay on air pollutants. Arch Pathol 74: 89

    CAS  Google Scholar 

  57. IARC (1984) Polynuclear aromatic compounds, part 2, carbon blacks, mineral oils and some nitroarenes. In: IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans, Vol 33. International Agency for Research on Cancer, Lyon

    Google Scholar 

  58. IARC (1989) Diesel and gasoline engine exhausts and some nitroarenes. In: IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans, Vol 46. International Agency for Research on Cancer, Lyon

    Google Scholar 

  59. Jong M, McDow SR (1995) Benz[a]anthracene photodegradation in the presence of known organic constituents of atmospheric aerosols. Environ Sci Technol 29: 2654

    Google Scholar 

  60. Kado NY, Langley D, Eisenstadt E (1983) A simple modification of the Salmonella liquid-incubation assay. Mutat Res 121: 25

    CAS  Google Scholar 

  61. Kado NY, Wong, JM, Kuzmicky PA, Woodrow JE, Ning H, Seiber JN, Hsieh DPH (1992) Quantitative integration of the Salmonella microsuspension assay with supercritical fluid extraction of model airborne vapor-phase mutagens. Mutat Res 271: 253

    CAS  Google Scholar 

  62. Kamens RM, Guo Z, Fulcher JN, Bell DA (1988) Influence of humidity, sunlight, and temperature on the daytime decay of polyaromatic hydrocarbons on atmospheric soot particles. Environ Sci Technol 22: 103

    CAS  Google Scholar 

  63. Kleindienst TE, Shepson PB, Edney EO, Claxton LD, Cupitt LT (1986) Wood smoke: measurement of the mutagenic activities of its gas-and particulate-phase photo-oxidation products. Environ Sci Technol 20: 493

    CAS  Google Scholar 

  64. Kleindienst TE, Smith DF, Hudgens EE, Snow RF, Perry E, Claxton LD, Bufalini JJ, Black FM, Cupitt LT (1992) The photo-oxidation of automobile emissions: measurements of the transformation products and their mutagenic activity. Atmos Environ 26A: 3039

    Google Scholar 

  65. Knispel R, Koch R, Siese M, Zetzsch C (1990) Adduct formation of OH radicals with benzene, toluene, and phenol and consecutive reactions of the adducts with NOI and 02. Ber Bunsenges Phys Chem 94: 1375

    CAS  Google Scholar 

  66. Korfmacher WA, Wehry EL, Mamantov G, Natusch DFS, (1980) Resistance to photochemical decomposition of polycyclic aromatic hydrocarbons vapor-adsorbed on coal fly ash. Environ Sci Technol 14: 1094

    CAS  Google Scholar 

  67. Kwok ESC, Atkinson R, Arey J (1994) Kinetics and mechanisms of the gas-phase reactions of the NO3 radical with aromatic compounds. Int J Chem Kinet 26: 511

    CAS  Google Scholar 

  68. Kwok ESC, Harger WP, Arey J, Atkinson R (1994) Reactions of gas-phase phenanthrene under simulated atmospheric conditions. Environ Sci Technol 28: 521

    CAS  Google Scholar 

  69. Kwok ESC, Atkinson R, Arey J (1997) Kinetics of the gas-phase reactions of indan, indene, fluorene and 9,10-dihydroanthracene with OH radicals, NO3 radicals and 03. Int J Chem Kinet, 29: 299

    CAS  Google Scholar 

  70. Lane DA, Tang H (1994) Photochemical degradation of polycyclic aromatic compounds. I. naphthalene. Polycyclic Aromatic Compounds 5: 131

    Google Scholar 

  71. Leiter J, Shimkin MB, Shear MJ (1942) Production of subcutaneous sarcomas in mice with tars extracted from atmospheric dusts. J Natl Cancer Inst 3: 155

    CAS  Google Scholar 

  72. Lewtas J (1993) Airborne carcinogens. Pharmacol & Toxicol 72: 55 supplement 1

    Google Scholar 

  73. Lewtas J (1994) Human exposure to complex mixtures of air pollutants. Toxicol Let 72: 163

    CAS  Google Scholar 

  74. Ligocki MP, Pankow JF (1989) Measurements of the gas/particle distributions of atmospheric organic compounds. Environ Sci Technol 23: 75

    CAS  Google Scholar 

  75. Logan JA (1985) Tropospheric ozone: seasonal behavior, trends, and anthropogenic influence. J Geophys Res 90: 10463

    Google Scholar 

  76. Madronich S, Hastie DR, Ridley BA, Schiff HI (1983) Measurement of the photodissociation coefficient of NO2 in the atmosphere: I. method and surface measurements. J Atmos Chem 1: 3

    Google Scholar 

  77. Madronich S, McKenzie RL, Caldwell MM, Björn LO (1995) Changes in ultraviolet radiation reaching the Earth’s surface. Ambio 24: 143

    Google Scholar 

  78. McDow SR, Sun Q, Vartiainen M, Hong Y, Yao Y, Fister T, Yao R, Kamens RM (1994) Effect of composition and state of organic components on polycyclic aromatic hydrocarbon decay in atmospheric aerosols. Environ Sci Technol 28: 2147

    CAS  Google Scholar 

  79. Möller L (1994) In vivo metabolism and genotoxic effects of nitrated polycyclic aromatic hydrocarbons. Environ Health Perspect 102: 139

    Google Scholar 

  80. Nielsen T (1984) Reactivity of polycyclic aromatic hydrocarbons toward nitrating species. Environ Sci Technol 18: 157

    CAS  Google Scholar 

  81. Nielsen T, Seitz B, Ramdahl T (1984) Occurrence of nitro-PAH in the atmosphere in a rural area. Atmos Environ 18: 2159

    CAS  Google Scholar 

  82. Nielsen T, Ramdahl T (1986) Discussion on: determination of 2-nitrofluoranthene and 2-nitropyrene in ambient particulate matter: evidence for atmospheric reactions. Atmos Environ 20: 1507

    CAS  Google Scholar 

  83. Nikolaou K, Masclet P, Mouvier G (1984) Sources and chemical reactivity of polynuclear aromatic hydrocarbons in the atmosphere - a critical review. Sci Total Environ 32: 103

    CAS  Google Scholar 

  84. Nishioka MG, Howard CC, Contos DA, Ball LM, Lewtas J (1988) Detection of hydroxylated nitro aromatic and hydroxylated nitro polycyclic aromatic compounds in an ambient air particulate extract using bioassay-directed fractionation. Environ Sci Technol 22: 908

    CAS  Google Scholar 

  85. Odum JR, McDow SR, Kamens RM (1994) Mechanistic and kinetic studies of the photo-degradation of benz[a]anthracene in the presence of methoxyphenols. Environ Sci Technol 28: 1285

    CAS  Google Scholar 

  86. Oltmans SJ, Levy H,II (1994) Surface ozone measurements from a global network. Atmos Environ 28: 9

    CAS  Google Scholar 

  87. Pankow JF (1987) Review and comparative analysis of the theories on partitioning between the gas and aerosol particulate phases in the atmosphere. Atmos Environ 21: 2275

    CAS  Google Scholar 

  88. Pankow JF, Bidleman TF (1992) Interdependence of the slopes and intercepts from log-log correlations of measured gas-particle partitioning and vapor pressure- I. theory and analysis of available data. Atmos Environ 26A: 1071

    Google Scholar 

  89. Paputa-Peck MC, Marano RS, Schuetzle D, Riley TL, Hampton CV, Prater TJ, Skewes LM, Jensen TE, Ruehle PH, Bosch LC, Duncan WP (1983) Determination of nitrated polynuclear aromatic hydrocarbons in particulate extracts by capillary column gas chromatography with nitrogen selective detection. Anal Chem 55: 1946

    CAS  Google Scholar 

  90. Peters J, Seifert B (1980) Losses of benzo[a]pyrene under the conditions of high-volume sampling. Atmos Environ 14: 117

    CAS  Google Scholar 

  91. Pitts JN Jr, Grosjean D, Mischke TM, Simmon VF, Poole D (1977) Mutagenic activity of airborne particulate organic pollutants. Toxicol Lett 1: 65

    CAS  Google Scholar 

  92. Pitts JN Jr, Van Cauwenberghe KA, Grosjean D, Schmid JP, Fitz DR, Belser WL Jr, Knudson GB, Hynds PM (1978) Atmospheric reactions of polycyclic aromatic hydrocarbons: facile formation of mutagenic nitro derivatives. Science 202: 515

    Google Scholar 

  93. Pitts JN Jr, Winer AM, Lokensgard DM, Sweetman JA (1984) Identification of particulate mutagens in southern California’s atmosphere. Final Report for California Air Resources Board Contract No. A1–155–32, Sacramento, CA

    Google Scholar 

  94. Pitts JN Jr, Atkinson R, Sweetman JA, Zielinska B (1985) The gas-phase reaction of naphthalene with N2O5 to form nitronaphthalenes. Atmos Environ 19: 701

    CAS  Google Scholar 

  95. Pitts JN Jr, Sweetman JA, Zielinska B, Winer AM, Atkinson R (1985) Determination of 2nitrofluoranthene and 2-nitropyrene in ambient particulate organic matter: evidence for atmospheric reactions. Atmos Environ 19: 1601

    CAS  Google Scholar 

  96. Pitts JN Jr, Paur H-R, Zielinska B, Arey J, Winer AM, Ramdahl T, Mejia V (1986) Factors influencing the reactivity of polycyclic aromatic hydrocarbons adsorbed on filters and ambient POM with ozone. Chemosphere 15: 675

    CAS  Google Scholar 

  97. Pope CA III, Bates DV, Raizenne ME (1995) Health effects of particulate air pollution: time for reassessment? Environ Health Perspect 103: 472

    Google Scholar 

  98. Prinn RG, Weiss RF, Miller BR, Huang J, Alyea FN, Cunnold DM, Fraser PJ, Hartley DE, Simmonds PG (1995) Atmospheric trends and lifetime of CH3CC13 and global OH concentrations. Science 269: 187

    CAS  Google Scholar 

  99. Ramdahl T, Zielinska B, Arey J, Atkinson R, Winer AM, Pitts JN, Jr (1986) Ubiquitous occurrence of 2-nitrofluoranthene and 2-nitropyrene in air. Nature 321: 425

    CAS  Google Scholar 

  100. Reichhardt T (1995) Weighing the health risks of airborne particulates. Environ Sci Technol 29: 360A

    Google Scholar 

  101. Rosenkranz HS (1996) Mutagenic nitroarenes, diesel emissions, particulate-induced mutations and cancer: an essay on cancer-causation by a moving target. Mutat Res 367: 65

    CAS  Google Scholar 

  102. Rowland FS (1991) Stratospheric ozone depletion. Annu Rev Phys Chem 42: 731

    CAS  Google Scholar 

  103. Ruehle, PH, Bosch LC, Duncan WP (1985) Synthesis of nitrated polycyclic aromatic hydrocarbons. In: White CM (ed) Nitrated polycyclic aromatic hydrocarbons. Hüthig, Heidelberg, p 169

    Google Scholar 

  104. Salmeen IT, Pero AM, Zator R, Schuetzle D, Riley TL (1984) Ames assay chromatograms and the identification of mutagens in diesel particle extracts. Environ Sci Technol 18: 375

    CAS  Google Scholar 

  105. Sasaki J, Arey J, Eastmond DA, Parks KK, Grosovsky AJ (1997) Genotoxicity induced in human lymphoblasts by atmospheric reaction products of naphthalene and phenanthrene. Mutat Res, in press

    Google Scholar 

  106. Sasaki J, Arey J, Harger WP (1995) Formation of mutagens from the photooxidations of 2–4-ring PAH. Environ Sci Technol 29: 1324

    CAS  Google Scholar 

  107. Sasaki J, Aschmann SM, Kwok ESC, Atkinson R, Arey J (1997) Products of the gas-phase OH and NO3 radical-initiated reactions of naphthalene. Environ Sci Technol. In press

    Google Scholar 

  108. Schroeder WH, Lane DA (1988) The fate of toxic airborne pollutants. Environ Sci Technol 22: 240

    CAS  Google Scholar 

  109. Schuetzle D (1983) Sampling of vehicle emissions for chemical analysis and biological testing. Environ Health Perspec 47: 65

    CAS  Google Scholar 

  110. Schuetzle D, Lewtas J (1986) Bioassay-directed chemical analysis in environmental research. Anal Chem 58: 1060A

    Google Scholar 

  111. Seckmeyer G, McKenzie RL (1992) Increased ultraviolet radiation in New Zealand (45°S) relative to Germany (48°N). Nature 359: 135

    Google Scholar 

  112. Shetter RE, McDaniel AH, Cantrell CA, Madronich S, Calvert JG (1992) Actinometer and eppley radiometer measurements of the NO2 photolysis rate coefficient during the Mauna Loa observatory photochemistry experiment. J Geophys Res 97: 10349

    CAS  Google Scholar 

  113. Sweetman JA, Zielinska B, Atkinson R, Ramdahl T, Winer AM, Pitts JN Jr (1986) A possible formation pathway for the 2-nitrofluoranthene observed in ambient particulate organic matter. Atmos Environ 20: 235

    CAS  Google Scholar 

  114. Talcott R, Wei E (1977) Airborne mutagens bioassayed in Salmonella typhimurium. J Nalt Cancer Inst 58: 449

    CAS  Google Scholar 

  115. Tokiwa H, Ohnishi Y (1986) Mutagenicity and carcinogenicity of nitroarenes and their sources in the environment. CRC Critical Rev Toxicol 17: 23

    CAS  Google Scholar 

  116. Wania F, Mackay D (1996) Tracking the distribution of persistent organic pollutants. Environ Sci Technol 30: 390A

    Google Scholar 

  117. Watanabe T, Kohan MJ, Walsh D, Ball LM, DeMarini DM, Lewtas J (1995) Mutagenicity of nitrodibenzopyranones in the Salmonella plate-incorporation and microsuspension assays. Mutat Res 345: 1

    CAS  Google Scholar 

  118. Watanabe T, Hirayama T, Lewtas J (1996) Mutagenicity and DNA adduct formation of air pollutants: nitrodibenzopyranone isomers and nitrodibenzofuran isomers. Jpn J Toxicol Environ Health 42: 4

    Google Scholar 

  119. White CM (ed) (1985) Nitrated polycyclic aromatic hydrocarbons. Hüthig, Heidelberg

    Google Scholar 

  120. Wilson NK, McCurdy TR, Chuang JC (1995) Concentrations and phase distributions of nitrated and oxygenated polycyclic aromatic hydrocarbons in ambient air. Atmos Environ 29: 2575

    CAS  Google Scholar 

  121. Yokley RA, Garrison AA, Wehry EL, Mamantov G (1986) Photochemical transformation of pyrene and benzo[a]pyrene vapor-deposited on eight coal stack ashes. Environ Sci Technol 20: 86

    CAS  Google Scholar 

  122. Yu S, Herreno-Saenz D, Miller DW, Kadlubar FF, Fu PP (1992) Mutagenicity of nitropolycyclic aromatic hydrocarbons with the nitro substituent situated at the longest molecular axis. Mutat Res 283: 45

    CAS  Google Scholar 

  123. Zielinska B, Arey J, Atkinson R, McElroy PA (1988) Nitration of acephenanthrylene under simulated atmospheric conditions and in solution and the presence of nitroacephenanthrylene(s) in ambient particles. Environ Sci Technol 22: 1044

    CAS  Google Scholar 

  124. Zielinska B, Arey J, Atkinson R, Winer AM (1989) The nitroarenes of molecular weight 247 in ambient particulate samples collected in southern California. Atmos Environ 23: 223

    CAS  Google Scholar 

  125. Zielinska B, Arey J, Atkinson R, McElroy PA (1989) Formation of methylnitro-naphthalenes from the gas-phase reactions of 1- and 2-methylnaphthalene with OH radicals and N205 and their occurrence in ambient air. Environ Sci Technol 23: 723

    CAS  Google Scholar 

  126. Zielinska B, Arey J, Atkinson R (1990) The atmospheric formation of nitroarenes and their occurrence in ambient air. In: Nitroarenes - occurrence, metabolism and biological impact. Howard PC, Hecht SS, Beland FA (eds.) Plenum, New York, p 73

    Google Scholar 

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Authors and Affiliations

  1. Statewide Air Pollution Research Center; and the Department of Soil & Environmental Sciences; and the Graduate Program in Environmental Toxicology, University of California, Riverside, Riverside, California, 92521, USA

    Janet Arey

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  1. Janet Arey
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  1. Research Institute, Swedish Environmental, P.O. Box 21060, S-10031, Stockholm, Sweden

    Alasdair H. Neilson

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© 1998 Springer-Verlag Berlin Heidelberg

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Arey, J. (1998). Atmospheric Reactions of PAHs Including Formation of Nitroarenes. In: Neilson, A.H. (eds) PAHs and Related Compounds. The Handbook of Environmental Chemistry, vol 3 / 3I. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-49697-7_9

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  • DOI: https://doi.org/10.1007/978-3-540-49697-7_9

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-08286-3

  • Online ISBN: 978-3-540-49697-7

  • eBook Packages: Springer Book Archive

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