Skip to main content
Log in

Inhibitory effect of dissolved organic matter on triplet-induced oxidation of aquatic contaminants

  • Paper
  • Published:
Photochemical & Photobiological Sciences Aims and scope Submit manuscript

Abstract

Excited triplet states of organic chromophores, in particular aromatic ketones, are capable of inducing oxidation of a variety of organic compounds. These reactions probably play an important role in the degradation of organic contaminants in sunlit natural waters. The effect of dissolved natural organic matter (DOM) on the oxidation rate of twenty-two aquatic organic contaminants, including phenols, anilines, phenylurea and s-triazine herbicides, and some pharmaceuticals, was investigated using photoexcited benzophenone-4-carboxylate (CBBP) as the oxidant. For about half of the studied compounds, a decrease in depletion rate was observed in the presence of Suwannee River fulvic acid, used as a reference DOM. Also, depletion rates decreased with increasing DOM concentration, as verified for five selected compounds. Such an inhibitory effect of DOM on oxidation is attributed to its antioxidant properties, whereby oxidation intermediates of the contaminants are supposed to be reduced back to their parent compounds. The presented screening study shows that DOM may be a relevant factor for inhibiting the oxidation of many organic contaminants in surface waters and possibly in engineered water treatment systems.

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. S. Canonica, U. Jans, K. Stemmler and J. Hoigne’, Transformation kinetics of phenols in water: Photosensitization by dissolved natural organic material and aromatic ketones, Environ. Sci. Technol., 1995, 29, 1822–1831.

    Article  CAS  Google Scholar 

  2. S. Canonica, B. Hellrung and J. Wirz, Oxidation of phenols by triplet aromatic ketones in aqueous solution, J. Phys. Chem. A, 2000, 104, 1226–1232.

    Article  CAS  Google Scholar 

  3. S. Canonica, B. Hellrung, P. Müller and J. Wirz, Aqueous oxidation of phenylurea herbicides by triplet aromatic ketones, Environ. Sci. Technol., 2006, 40, 6636–6641.

    Article  CAS  Google Scholar 

  4. A. C. Gerecke, S. Canonica, S. R. Müller, M. Schärer and R. P. Schwarzenbach, Quantification of dissolved natural organic matter (DOM) mediated phototransformation of phenylurea herbicides in lakes, Environ. Sci. Technol., 2001, 35, 3915–3923.

    Article  CAS  Google Scholar 

  5. S. Canonica, Oxidation of aquatic organic contaminants induced by excited triplet states, Chimia, 2007, 61, 641–644.

    Article  CAS  Google Scholar 

  6. C. Richard and S. Canonica, Aquatic phototransformation of organic contaminants induced by coloured dissolved natural organic matter, in The Handbook of Environmental Chemistry, ed. O. Hutzinger, Springer, Berlin, Germany, 2005, vol. 2, Part M, Pp. 299–323.

    CAS  Google Scholar 

  7. R. G. Zepp, J. Hoigne and H. Bader, Nitrate-induced photooxidation of trace organic chemicals in water, Environ. Sci. Technol., 1987, 21, 443–450.

    Article  CAS  Google Scholar 

  8. P. L. Brezonik and J. Fulkerson-Brekken, Nitrate-induced photolysis in natural waters: Controls on concentrations of hydroxyl radical photo-intermediates by natural scavenging agents, Environ. Sci. Technol., 1998, 32, 3004–3010.

    Article  CAS  Google Scholar 

  9. R. A. Larson and R. G. Zepp, Reactivity of the carbonate radical with aniline derivatives, Environ. Toxicol. Chem., 1988, 7, 265–274.

    Article  CAS  Google Scholar 

  10. S. Canonica, T. Kohn, M. Mac, F. J. Real, J. Wirz and U. Von Gunten, Photosensitizer method to determine rate constants for the reaction of carbonate radical with organic compounds, Environ. Sci. Technol., 2005, 39, 9182–9188.

    Article  CAS  Google Scholar 

  11. I. Loeff, J. Rabani, A. Treinin and H. Linschitz, Charge-transfer and reactivity of np* and pp* organic triplets, including anthraquinone-sulfonates, in interactions with inorganic anions: A comparative study based on classical Marcus theory, J. Am. Chem. Soc., 1993, 115, 8933–8942.

    Article  CAS  Google Scholar 

  12. M. Wegelin, S. Canonica, K. Mechsner, T. Fleischmann, F. Pesaro and A. Metzler, Solar water disinfection: Scope of the process and analysis of radiation experiments, J. Water Supply Res. Technol.-Aqua, 1994, 43, 154–169.

    Google Scholar 

  13. B. C. Faust and J. Hoigne, Sensitized photooxidation of phenols by fulvic acid and in natural waters, Environ. Sci. Technol., 1987, 21, 957–964.

    Article  CAS  Google Scholar 

  14. K. J. Lin and D. J. Carlson, Photoinduced degradation of tracer phenols added to marine surface microlayers, Mar. Chem., 1991, 33, 9–22.

    Article  CAS  Google Scholar 

  15. H. Kawaguchi, Rates of sensitized photooxidation of 2,4,6-trimethylphenol by humic acid, Chemosphere, 1993, 27, 2177–2182.

    Article  CAS  Google Scholar 

  16. S. Canonica and J. Hoigne, Enhanced oxidation of methoxy phenols at micromolar concentration photosensitized by dissolved natural organic material, Chemosphere, 1995, 30, 2365–2374.

    Article  CAS  Google Scholar 

  17. S. Canonica and M. Freiburghaus, Electron-rich phenols for probing the photochemical reactivity of freshwaters, Environ. Sci. Technol., 2001, 35, 690–695.

    Article  CAS  Google Scholar 

  18. C. Richard, O. Trubetskaya, O. Trubetskoj, O. Reznikova, G. Afanas’eva, J. P. Aguer and G. Guyot, Key role of the low molecular size fraction of soilhumic acids for fluorescence and photoinductive activity, Environ. Sci. Technol., 2004, 38, 2052–2057.

    Article  CAS  Google Scholar 

  19. J. P. Aguer, D. Tetegan and C. Richard, Humic substances mediated phototransformation of 2,4,6-trimethylphenol: a catalytic reaction, Photochem. Photobiol. Sci., 2005, 4, 451–453.

    Article  CAS  Google Scholar 

  20. S. Halladja, A. Ter Halle, J. P. Aguer, A. Boulkamh and C. Richard, Inhihition of humic substances mediated photooxygenation of furfuryl alcohol by 2,4,6-trimethylphenol. Evidence for reactivity of the phenol with humic triplet excited states, Environ. Sci. Technol., 2007, 41, 6066–6073.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

This paper was published as part of the themed issue in honour of Jakob Wirz.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Canonica, S., Laubscher, HU. Inhibitory effect of dissolved organic matter on triplet-induced oxidation of aquatic contaminants. Photochem Photobiol Sci 7, 547–551 (2008). https://doi.org/10.1039/b719982a

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/b719982a

Navigation