Alkali Hydrolysis of Trinitrotoluene

  • Christian Karasch
  • Milan Popovic
  • Mohamed Qasim
  • Rakesh K. Bajpai
Chapter
Part of the Applied Biochemistry and Biotechnology book series (ABAB)

Abstract

Data for alkali hydrolysis of 2,4,6-trinitrotoluene (TNT) in aqueous solution at pH 12.0 under static (pH-controlled) as well as dynamic (pH-uncontrolled) conditions are reported. The experiments were conducted at two different molar ratios of TNT to hydroxylions at room temperature. The TNT disappeared rapidly from the solution as a first-order reaction. The complete disappearance of aromatic structure from the aqueous solution within 24 h was confirmed by the ultraviolet-visible (UV-VIS) spectra of the samples. Cuvet experiments in a UV-VIS spectrophotometer demonstrated the formation of Meisenheimer complex, which slowly disappeared via formation of aromatic compounds with fewer nitro groups. The known metabolites of TNT were found to accumulate only in very small quantities in the liquid phase.

Index Entries

2,4,6-Trinitrotoluene alkali hydrolysis ultraviolet-visible spectra metabolites 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Spain, J. C. (2000), in Biodegradation of Nitroaromatic Compounds and Explosives, Spain, J. C., Hughes, J. B., and Knackmuss, H.-J., eds., CRC Press, Boca Raton, FL, pp. 7–61.Google Scholar
  2. 2.
    Boopathy R., Manning J. (1999), Water Environ. Res. 71, 19–24.CrossRefGoogle Scholar
  3. 3.
    Li, Z. M., Shea, P. J., and Comfort, S. D. (1997), J. Environ. Quality 26, 480–487.CrossRefGoogle Scholar
  4. 4.
    Dodard, S. G., Renoux, A. Y., Hawari, J., Ampleman, G., Thiboutot, S., and Sunahara, G. I. (1999), Chemosphere 38, 2071–2079.PubMedCrossRefGoogle Scholar
  5. 5.
    Robidoux, P.Y., Hawari, J., Thiboutot, S., Ampleman, G., and Sunahara, G. I. (1999), Ecotoxicol. Environ. Safety 44, 311–321.PubMedCrossRefGoogle Scholar
  6. 6.
    Sciences International (1995), Toxicological Profile for 2,4,6-Trinitrotoluene, US Department of Health and Human Services, Alexandria, VA.Google Scholar
  7. 7.
    Hermann D. H. (1994), ‘35’ Sprengstofftypischen Verbindungen und Abbauprodukten in Böden und Trinkwasser, Insitut für Wasser-, Boden-, und Lufthygiene des Bundesgesundheitsamtes, Berlin, Germany.Google Scholar
  8. 8.
    Lachance, B., Robidoux, P. Y., Hawari, J., Ampleman, G., Thiboutot, S., and Sunahara, G. I. (1999), Genet. Toxicol. Environ. Mutagen., Mutat. Res. 444, 25–39.CrossRefGoogle Scholar
  9. 9.
    Honeycutt, M. E., Jarvis, A. S., and McFairland, V. A., (1996), Exotoxicol. Environ. Safety 35, 282–287.CrossRefGoogle Scholar
  10. 10.
    Arienzo, M. (1999), Chemosphere 39, 1629–1638.CrossRefGoogle Scholar
  11. 11.
    Arienzo, M. (2000), Chemosphere 40, 331–337.PubMedCrossRefGoogle Scholar
  12. 12.
    Hundal, L. S., Singh, J., Bier, E. L., Shea, P. J., Comfort, S. D., and Powers, W. L. (1997), Environ. Pollut. 97, 55–64.PubMedCrossRefGoogle Scholar
  13. 13.
    Meharg, A. A., Dennis, G. R., and Cairney, J. W. G. (1997), Chemosphere 35, 513–521.CrossRefGoogle Scholar
  14. 14.
    Sembries, S. and Crawford, R. L. (1997), Appl. Environ. Microbiol. 63, 2100–2104.PubMedGoogle Scholar
  15. 15.
    Spain, J. C. (1995), Annu. Rev. Microbiol. 49, 523–555.PubMedCrossRefGoogle Scholar
  16. 16.
    Haderlein, S. B., Hofstetter, T. B., and Schwarzenbach, R. P. (2000), in Biodegradation of Nitroaromatic Compounds and Explosives, Spain, J. C., Hughes, J. B., and Knackmuss, H.-J, eds., CRC Press, Boca Raton, FL.Google Scholar
  17. 17.
    Vorbeck, C., Lenke, H., Fischer, P., and Knackmuss, H.-J. (1994), J. Bacteriol. 176, 932–934.PubMedGoogle Scholar
  18. 18.
    Bernasconi, C. F. (1971), J. Org. Chem. 36, 1671–1679.CrossRefGoogle Scholar
  19. 19.
    Shipp, K. G., Kaplan, L. A., and Sitzmann, M. E. (1972), J. Org. Chem. 37, 1966–1970.CrossRefGoogle Scholar
  20. 20.
    Emmrich, M. (1999), Environ. Sci. Technol. 33, 3802–3805.CrossRefGoogle Scholar
  21. 21.
    Emmrich, M. (2001), Environ. Sci. Technol. 35, 874–877.PubMedCrossRefGoogle Scholar
  22. 22.
    Qasim, M., Bajpai, R., and Hansen, L. (1999), Nucleophilic Reactions of TNT with Hydroxide Ions (OH-) for Enhancement of Biodegradation, paper presented at the 4th International Conference on TiO2 Photocatalytic Purification and Treatment of Water and Air, Albuquerque, NM.Google Scholar

Copyright information

© Springer Science+Business Media New York 2002

Authors and Affiliations

  • Christian Karasch
    • 1
  • Milan Popovic
    • 1
  • Mohamed Qasim
    • 2
  • Rakesh K. Bajpai
    • 3
  1. 1.Technische FachhochschuleBerlinGermany
  2. 2.US Army Engineer Research and Development CenterVicksburgUSA
  3. 3.Chemical Engineering DepartmentUniversity of MissouriColumbiaUSA

Personalised recommendations