Photodegradation of halobenzenes in water ice

  • Petr Klán
  • David Del Favero
  • Alena Ansorgová
  • Jana Klánová
  • Ivan Holoubek
Research Articles

Abstract

Results from the photolysis ofo, p-dichlorobenzene, bromobenzene, andp-dibromobenzene in water ice are reported. All phototransformations appeared to be based on dehalogenation, coupling, and rearrangement reactions in ice cavities. No photosolvolysis products, i.e. products from intermolecular reactions between organic and water molecules, were found. Many of the products were very toxic substances of a high environmental risk, such as PCBs. The results support our model, in which secondary, very toxic, pollutants can be formed in ice, snow, and atmospheric ice particles from primary pollutants through the action of solar irradiation. The photoproducts may be released to the environment by ice melting and evaporation.

Keywords

Long-range transport photochemistry photodegradation ice snow water chlorobenzenes bromobenzenes persistent organic pollutants (POPs) polychlorobiphenyls (PCB) POPs 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Allamandola LJ, Sandford SA, Wopenka B (1987): Interstellar Polycyclic Aromatic Hydrocarbons and Carbon in Interplanetary Dust Particles and Meteorites. Science 237, 56–59CrossRefGoogle Scholar
  2. Arnold DR, Wong PC (1977): The Photochemistry of Chloroaromatic Compounds. Is ‘Pi-Chlorobenzene’ an Intermediate? J Am Chem Soc 99, 3361–3366CrossRefGoogle Scholar
  3. Bernstein MP, Dworkin JP, Sandford SA, Allamandola LJ (2001): Ultraviolet Irradiation of Naphthalene in H2O Ice: Implications for Meteorites and Biogenesis. Meteor Planet Sci 36, 351–358CrossRefGoogle Scholar
  4. Bernstein MP, Sandford SA, Allamandola LJ, Gillette JS, Clemen SJ, Zare RN (1999): UV Irradiation of Polycyclic Aromatic Hydrocarbons in Ices: Production of Alcohols, Quinones, and Ethers. Science 283, 1135–1138CrossRefGoogle Scholar
  5. Boule P, Tissot A, Lemaire J (1985): Photochemistry and Environment 11. Orientation Rules of the Photohydrolysis of Chlorinated Aromatic Derivatives. Chemosphere 14, 1789–1793CrossRefGoogle Scholar
  6. Bunce NJ (1994): In: Organic Photochemistry and Photobiology, Horspool WM and Song PS, Eds, CRC Press, Boca Raton, pp 1181–1192 and references thereinGoogle Scholar
  7. Bunce NJ, Bergsma JP, Bergsma MD, De Graaf W, Kumar Y, Ravanal L (1980): Structure and Mechanism in the Photoreduction of Aryl Chlorides in Alkane Solvents. J Org Chem 45, 3708–3713CrossRefGoogle Scholar
  8. Bunce NJ, Gallacher JC (1982): Photolysis of Aryl Chlorides with Dienes and with Aromatic Amines. J Org Chem 47, 1955–1958CrossRefGoogle Scholar
  9. Bunce NJ, Landers JP, Langshaw J-A, Nakai JS (1989): An Assessment of the Importance of Direct Solar Degradation of some Simple Chlorinated Benzenes and Biphenyls in the Vapor Phase. Environ Sci Technol 23, 213–218CrossRefGoogle Scholar
  10. Choudhry GG, van den Broecke JA, Webster GRB, Hutzinger O (1986): Photochemistry of Halogenated Benzene Derivatives 7. Photoincorporation of Polychlorobenzenes with Humic Model Monomers in Aqueous Acetonitrile Solutions. Environ Toxicol Chem 5, 625–635CrossRefGoogle Scholar
  11. Choudhry GG, Webster GRB, Hutzinger O (1986): Environmentally Significant Photochemistry of Chlorinated Benzenes and Their Derivatives in Aquatic Systems. In Toxicological and Environmental Chemistry. Gordon and Breach, Science Publishers, Inc, 13, pp 27–83 and references thereinGoogle Scholar
  12. de Voogt P, Jansson B (1993): Vertical and Long-range Transport of Persistent Organics in the Atmosphere. Rev Environ Contam Toxicol 132, 1–27Google Scholar
  13. Dubowski Y, Hoffmann MR (2000): Photochemical Transformations in Ice: Implications for the Fate of Chemical Species. Geophys Res Lett 27, 3321–3324CrossRefGoogle Scholar
  14. Dulin D, Drossman H, Mill T (1986): Products and Quantum Yields for Photolysis of Chloroaromatics in Water. Environ Sci Technol 20, 72–77CrossRefGoogle Scholar
  15. Georgiou S, Koubenakis A, Labrakis J, Lassithiotaki M (1998a): Photoproduct Desorption Dynamics in the UV Ablation of Model Molecular Solids. Ablation of Chlorobenzene Films at 248 nm. Appl Surface Sci 127–129, 122–127CrossRefGoogle Scholar
  16. Georgiou S, Koubenakis A, Labrakis J, Lassithiotaki M (1998b): Formation and Desorption Dynamics of Photoproducts in the Ablation of van der Waals Films of Chlorobenzene at 248 nm. J Chem Phys 109, 8591–8600CrossRefGoogle Scholar
  17. Ghormley JA, Hochanadel CJ (1971): Production of H, OH, and H2O2 in the Flash Photolysis of Ice. J Phys Chem 75, 40–44CrossRefGoogle Scholar
  18. Hoffmann MR (1996): Possible chemical Transformations in Snow and Ice Induced by Solar (UV Photons) and Cosmic Irradiation (Muons). In: Chemical Exchange between the Atmosphere and Polar Snow, NATO ASI Series I, 43, 353–377Google Scholar
  19. Holoubek I, Klán P, Ansorgová A, Del Favero D (2000): Photochemistry of PBT Compounds in Ice — New Potential Source of Ice Contamination? Organohalogen Compounds 46, 228–231Google Scholar
  20. Ichimura T, Mori Y (1973): Photolysis of Monochlorobenzene in Gas Phase. J Chem Phys 58, 288–292CrossRefGoogle Scholar
  21. Juang L-Ch, Tseng D-H, Lee J-F (1998): Photolytic Mechanism of Monochlorobenzene in an Aqueous UV7H2O2 System. Chemosphere 36, 1187–1199 and references thereinCrossRefGoogle Scholar
  22. Klán P, Ansorgová A, Del Favero D, Holoubek I (2000): Photochemistry of Chlorobenzene in Ice. Tetrahedron Lett 41, 7785–7789CrossRefGoogle Scholar
  23. Klán P, Janosek J, Kriz Z (2000): Photochemistry of Valerophenone in Solid Solutions. J Photochem Photobiol A, Chemistry 134, 37–44CrossRefGoogle Scholar
  24. Kojima M, Sakuragi H, Tokumaru K (1981): Photolysis of Chlorobenzene — Phenylation of Chlorobenzene with Anomalous Orientation. Chem Lett 1539–1540Google Scholar
  25. Mackay D, Shiu WY (1981): A Critical Review of Henry’s Law Constants for Chemicals of Environmental Interest. J Phys Chem Ref Data 10, 1175–1199CrossRefGoogle Scholar
  26. Mackay D, Shiu WY, Ma KC (1992): Illustrated Handbook of Physical Chemical Properties and Environmental Fate for Organic Chemicals. Vol I, Lewis Publishers/CRC Press, Boca Raton, FLGoogle Scholar
  27. Matsuura T, Omura K (1966): Photo-induced Reactions. III The Synthesis of Biphenyls from Aromatic Bromo-Compounds. Bull Chem Soc Jpn 39, 944–947CrossRefGoogle Scholar
  28. Nagaoka S, Takemura T, Baba H (1985): Nucleophilic Photoreaction of Chlorobenzene in Methanol as Studied by Emission Spectroscopy. Bull Chem Soc Jpn 58, 2082–2087CrossRefGoogle Scholar
  29. Nakada M, Miura C, Nishiyama H, Higashi F, Mori T, Hirota M, Ishii T (1989): Photoreactions of Polyhalonenzenes in Benzene - Formation of Terphenyls. Bull Chem Soc Jpn 62, 3122–3126CrossRefGoogle Scholar
  30. Paasivirta J; Knuutila M, Paukku R (1985): Study of Organochlorine Pollutants in Snow at North Pole and Comparison to the Snow at North, Central and South Finland. Chemosphere 14, 1741–1748CrossRefGoogle Scholar
  31. Park H-R, Yang I-J, Kim M-S (1998): Photolysis of Chlorobenzene in Aqueous Solution. Bull Korean Chem Soc 19, 1265–1268Google Scholar
  32. Perovich DK, Govoni JW (1991): Absorption Coefficients of Ice from 250 to 400 nm. Geophys Res Lett 18, 1233–1235CrossRefGoogle Scholar
  33. Petrenko VF, Whitworth RW (1999): Physics of Ice. Oxford University Press, OxfordGoogle Scholar
  34. Sax NI (1968): Dangerous Properties of Industrial Materials. 3rd ed, pp 149–151, Van-Nostrand-Reinhold, New YorkGoogle Scholar
  35. Soumillion JP, DeWolf B (1981): A Link between Photoreduction and Photosubstitution of Chloroaromatic Compounds. J Chem Soc, Chem Commun 436–437Google Scholar
  36. Scheringer M, Wegmann F, Fenner K, Hungerbühler K (2000): Investigation of the Cold Condensation of Persistent Organic Pollutants with a Global Multimedia Fate Model. Environ Sci Technol 34, 1842–1850CrossRefGoogle Scholar
  37. Tissot A, Boule P, Lemaire J (1983): Photochemistry and Environment 5. Photohydrolysis of Monochlorobenzene in Dilute Aqueous Solution. Chemosphere 12, 859–872CrossRefGoogle Scholar
  38. Tissot A, Boule P, Lemaire J (1984): Photochemistry and Environment 7. Photohydrolysis of Chlorobenzene — Studies of the Excited State Involved. Chemosphere 13, 381–389CrossRefGoogle Scholar
  39. Uyeta M, Taue S, Chikasawa K, Mazaki M (1976): Photoformation of Polychlorinated Biphenyls from Chlrinated Benzenes. Nature 264, 583–584CrossRefGoogle Scholar
  40. Wania F (1999): On the Origin of Elevated Levels of Persistent Chemicals in the Environment. ESPR — Environ Sci Pollut Res 6, 11–19CrossRefGoogle Scholar
  41. Wania F, Hoff JT, Jia CQ, Mackay D (1998): The Effects of Snow and Ice on the Environmental Behaviour of Hydrophobie Organic Chemicals. Environ Pollut 102, 25–41CrossRefGoogle Scholar
  42. Wania F, Mackay D (1993): Global Fractionation and Cold Condensation of Low Volatility Organochlorine Compounds in Polear Regions. Ambio 22, 10–18Google Scholar
  43. Weiss RG, Ramamurthy V, Hammond GS (1993): Photochemistry in Organized Media: A Model. Acc Chem Res 26, 530–536CrossRefGoogle Scholar

Copyright information

© Ecomed Publishers 2001

Authors and Affiliations

  • Petr Klán
    • 1
  • David Del Favero
    • 2
  • Alena Ansorgová
    • 2
  • Jana Klánová
    • 2
  • Ivan Holoubek
    • 2
  1. 1.Department of Organic Chemistry, Faculty of ScienceMasaryk UniversityBrnoCzech Republic
  2. 2.RECETOX-TOCOEN & AssociatesBrnoCzech Republic

Personalised recommendations