Skip to main content
Log in

Aromatic photonitration in homogeneous and heterogeneous aqueous systems

  • Research Article — INCA
  • Published:
Environmental Science and Pollution Research Aims and scope Submit manuscript

Abstract

This work describes the nitration of aromatics upon near-UV photolysis of nitrate and nitrite in aqueous solution and upon photocatalytic oxidation of nitrite in TiO2 suspensions. Phenol is used in this work as a model aromatic molecule and as a probe for •NO2/N2O4. The photoinduced nitration of phenol in aqueous systems occurs upon the reaction between phenol and •NO2 or N2O4, and is enhanced by the photocatalytic oxidation of nitrite to •NO2 by TiO2. Aromatic photonitration in the liquid phase can play a relevant role in the formation of nitroaromatics in natural waters and atmospheric hydrometeors, thus being a potential pathway for the condensed-phase nitration of aromatics. Furthermore, the photoinduced oxidation of nitrite to nitrogen dioxide suggests a completely new role for nitrite in natural waters and atmospheric aerosols.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Enya T, Suzuki H, Watanabe T, Hirayama T, Himasatsu Y (1997): 3-Nitrobenzanthrone, a Powerful Bacterial Mutagen and Suspected Human Carcinogen Found in Diesel Exhaust and Airborne Particulates. Environ Sci Technol 31, 2772–2776

    Article  CAS  Google Scholar 

  2. Arey J (1998): Atmospheric Reactions of PAHs Including Formation of Nitroarenes. In: Neilson AH (Ed): PAHs and Related Compounds. Springer Verlag Berlin, Chapter 9, pp 347–382

    Google Scholar 

  3. Pitts Jr JN, Arey Sweetman J, Zielinska B, Winer A M, Atkinson R (1985): Determination of 2-Nitrofluoranthene and 2-Nitropyrene in Ambient Particulate Organic Matter: Evidence for Atmospheric Reactions. Atmospheric Environment 19, 1601–1608

    Article  CAS  Google Scholar 

  4. Finlayson-Pitts BJ, Pitts Jr JN ( 1997): Tropospheric Air Pollution: Ozone, Airborne Toxics, Polycyclic Aromatic Hydrocarbons, and Particles. Science 276, 1045–1052

    Article  CAS  Google Scholar 

  5. Boule P, Bolte M, Richard C (1999): Phototransformations Induced in Aquatic Media by NO3-/NO2-, Fem and Humic Substances. In: Boule P (Ed): The Handbook of Environmental Chemistry Vol 2L (Environmental Photochemistry). Springer Verlag Berlin, pp 181–215

    Google Scholar 

  6. Warneck P, Wurzinger C(1988): Product Quantum Yields for the 305-nm Photodecomposition of NO3- in Aqueous Solution. J Phys Chem 92, 6278–6283

    Article  CAS  Google Scholar 

  7. Fischer M, Warneck P (1996): Photodecomposition of Nitrite and Undissociated Nitrous Acid in Aqueous Solution. J Phys Chem 100, 18749–18756

    Article  CAS  Google Scholar 

  8. Vione D, Maurino V, Minero C, Pelizzetti E (2001): Phenol Photonitration upon UV Irradiation of Phenol and Nitrite in Aqueous Solution. I: Effects of Oxygen and 2-Propanol. Chemosphere 45, 893–902.

    Article  CAS  Google Scholar 

  9. Buxton GV, Greenstock CL, Helman WP, Ross AB (1988): Critical Review of Rate Constants for Reactions of Hydrated Electrons, Hydrogen Atoms and Hydroxyl Radicals (•OH/ •O-) in Aqueous Solution. J Phys Chem Ref Data 17, 1027–1284

    Google Scholar 

  10. Grätzel M, Henglein A, Lilie J, Beck G (1969): Pulsradiolyti-sche Untersuchung einiger Elementarprozesse der Oxydation und Reduktion des Nitritions. Ber Bunsenges Physik. Chem. 73, 646–653

    Google Scholar 

  11. Leuenberger C, Czuczwa J, Tremp J, Giger W (1988): Nitrated Phenols in Rain: Atmospheric Occurrence of Phyto- toxic Pollutants. Chemosphere 17, 511–515

    Article  CAS  Google Scholar 

  12. Platz J, Nielsen OJ, Wallington TJ, Ball JC, Hurley MD, Straccia AM, Schneider WF, Sehested J (1998): Atmospheric Chemistry of the Phenoxy Radical, C6H5O(•): UV Spectrum and Kinetics of Its Reaction with NO, NO2 and O2. J Phys Chem A 102, 7964–7974

    Article  CAS  Google Scholar 

  13. Niessen R, Lenoir D, Boule P (1988): Phototransformations of Phenol Induced by Excitation of Nitrate Ions. Chemosphere 17, 1977–1984

    Article  CAS  Google Scholar 

  14. Machado F, Boule P (1995): Photonitration and photonitro-sation of phenolic derivatives induced in aqueous solution by excitation of nitrite and nitrate ions. J Photochem Photobiol A: Chem 86, 73–80

    Article  CAS  Google Scholar 

  15. Vione D, Maurino V, Minero C, Vincenti M, Pelizzetti E (2001): Formation of Nitrophenols upon UV Irradiation of Phenol and Nitrate in Aqueous Solutions and in TiO2 Aqueous Suspensions. Chemosphere 44, 237–248

    Article  CAS  Google Scholar 

  16. Bahnemann D, Cunningham J, Fox M A, Pelizzetti E, Pichat P, Serpone N (1994): Photocatalytic Treatment of Water. In: Helz GR, Zepp RG, Crosby DG (Eds): Aquatic and Surface Photochemistry. Lewis Publishers, London, pp 261–316

    Google Scholar 

  17. Hoigné J (1990): Formulation and Calibration of Environmental Reaction Kinetics: Oxidations by Aqueous Photooxidants as an Example. In: Stumm W (Ed): Aquatic Chemical Kinetics. John Wiley and Sons, New York, Chapter 2, pp 43–70

    Google Scholar 

  18. Dzengel J, Theurich J, Bahnemann D (1999): Formation of Nitroaromatic Compounds in Advanced Oxidation Processes: Photolysis versus Photocatalysis. Environ Sci Technol 33, 294–300

    Article  CAS  Google Scholar 

  19. Vione D, Maurino V, Minero C, Pelizzetti E (2001): Phenol Photonitration upon UV Irradiation of Phenol and Nitrite in Aqueous Solution. II: Effects of pH and TiO2. Chemosphere 45, 903–910

    Article  CAS  Google Scholar 

  20. Vione D, Maurino V, Minero C, Pelizzetti E (2001): New processes in the Environmental Chemistry of Nitrite: Nitration of Phenol upon Nitrite Photoinduced Oxidation. Environ Sci Technol (in press)

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ezio Pelizzetti.

Additional information

Part of this work was presented at the ’4° Convegno Consorzio Interuniver-sitario Nazionale La Chimica per I’Ambiente (INCA)’, Santa Margherita Ligure (Italy) 25–28 February 2001

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vione, D., Maurino, V., Minero, C. et al. Aromatic photonitration in homogeneous and heterogeneous aqueous systems. Environ Sci & Pollut Res 10, 321–324 (2003). https://doi.org/10.1065/espr2001.12.104.1

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1065/espr2001.12.104.1

Keywords

Navigation