Alkaline Hydrolysis/Polymerization of 2,4,6-Trinitrotoluene: Characterization of Products by 13C and 15N NMR

Environmental Science and Technology

Volumn 38, Issue 7, 2004, Pages 2224-2231

  Thorn, Kevin A ^a   Thorne, Philip G ^b   Cox, Larry G ^a  

^a DENVER FEDERAL CENTER   (United States)

^b APPLIED RESEARCH ASSOCIATES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PRECIPITATION (CHEMICAL); SOIL POLLUTION; SUBSTITUTION REACTIONS; TOLUENE;

ALKALINE HYDROLYSIS; NUCLEOPHILIC SUBSTITUTIONS;

ENVIRONMENTAL IMPACT;

ALCOHOL; AMIDE; AMINE; AMMONIA; AZOXY DERIVATIVE; CALCIUM HYDROXIDE; CARBENE; CARBON; CARBON 13; CARBOXYL GROUP; DIPHENYL METHYLENE; ETHER DERIVATIVE; EXPLOSIVE; HYDROXIDE; HYDROXYLAMINE; IMINE; INDOLE; KETONE; METHYL GROUP; NITRITE; NITRO DERIVATIVE; NITROGEN 15; TRINITROTOLUENE; UNCLASSIFIED DRUG;

ALKALINITY; HYDROLYSIS; POLYMERIZATION;

ARTICLE; BIOREMEDIATION; CHEMICAL REACTION; DEGRADATION; FILTRATION; FRACTIONATION; HYBRIDIZATION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PRECIPITATION; SOIL POLLUTION;

CARBON ISOTOPES; ENVIRONMENTAL MONITORING; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; NITROGEN ISOTOPES; POLYMERS; PRECIPITATION; SOIL POLLUTANTS; TRINITROTOLUENE;

EID: 1842779037     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es030655a     Document Type: Article

References (36)

1. Spain, J. C. Biodegradation of Nitroaromatic Compounds; Plenum Press: New York, 1995.
2. Spain, J. C.; Hughes, J. B.; Knackmuss, H.-J. Biodegradation of nitroaromatic compounds and explosives; Lewis Publishers: Boca Raton, FL, 2000.
3. Jerger, D. E.; Woodhull, P. M. In Biodegradation of Nitroaromatic Compounds and Explosives; Spain, J. C., Hughes, J. B., Knackmuss, H. J., Eds.; Lewis Publishers: Boca Raton, FL, 2000; pp 395-423.
4. Thorn, K. A.; Pennington, J. C.; Hayes, C. A. Environ. Sci. Technol. 2002, 36, 3797-3805.
5. Thorn, K. A.; Kennedy, K. R. Environ. Sci. Technol. 2002, 36, 3787-3796.
6. Achtnich, C.; Fernandes, E.; Bollag, J.-M. Environ. Sci. Technol. 1999, 33, 4448-4456.
7. Bruns-Nagel, D.; Knicker, H.; Drzyzga, O. Environ. Sci. Technol. 2000, 34, 1549-1556.
8. Saupe, A.; Garvens, H. J.; Heinze, L. Chemosphere 1998, 36, 1725-1744.
9. Emmrich, M. Environ. Sci. Technol. 1999, 33, 3802-3805.
10. Bishop, R. L.; Flesner, R. L.; Larson, S. A.; Bell, D. A. J. Energ. Mater. 2000, 18, 275.
11. Karasch, C.; Popovic, M.; Qasim, M.; Bajpai, R. K. Appl. Biochem. Biotechnol. 2002, 98, 1173-1185.
12. Felt, D. R.; Larson, S. L.; Valente, E. J. Chemosphere 2002, 49, 287-295.
13. Felt, D. R.; Larsen, S. L.; Hansen, L. D. Molecular Weight Distribution of the Final Products of TNT-Hydroxide Reaction; Report No. ERDC/EL TR-01-16; U.S. Army Corps of Engineers Engineer Research and Development Center: Vicksburg, MS, 2001.
14. Emmrich, M. Int. J. Environ. Anal. Chem. 2003, 83, 769-776.
15. Review and Evaluation of Alternative Technologies for Demilitarization of Assembled Chemical Weapons; The National Academies Press: Washington, DC, 1999; pp 213-229, http://books.nap.edu/books/0309066395/html/.
16. Effenberger, F.; Koch, M.; Streicher, W. Chem. Ber. 1991, 124, 163-173.
17. Beck, J. R. Tetrahedron 1978, 34, 2057-2068.
18. Newman, K. E. A Review of Alkaline Hydrolysis of Energetic Materials: Is it Applicable to Demilitarization of Ordnance?; Report No. IHTR 2167; Naval Surface Warfare Center Indian Head Division: Indian Head, MD, 1999.
19. Hammersley, V. L. Historical and Experimental Studies of Alkali and Trinitrotoluene Reaction; Report No. WQEC/C 75-192; Naval Weapons Support Center: Crane, IN, 1975.
20. Heilmann, H. M.; Wiesmann, U.; Stenstrom, M. K. Environ. Sci. Technol. 1996, 30, 1485-1492.
21. Emmrich, M. Environ. Sci. Technol. 2001, 35, 874-877.
22. Thorne, P. G.; Jenkins, T. F.; Brown, M. Continuous Treatment of Low Levels of TNT and RDX in Range Soils Using Surface Liming; Special Report; U.S. Army Corps of Engineers Cold Regions Research and Engineering Laboratory: Hanover, New Hampshire, in press.
23. Davis, J. Topical Lime Treatment for Containment of Source Zone Energetics Contamination; Strategic Environmental Research and Development Program, 2001; www.serdp.org/research/cu/cu-1230.pdf (accessed October 2003).
24. Review and Evaluation of Alternative Technologies for Demilitarization of Assembled Chemical Weapons; The National Academies Press: Washington, DC, 1999; pp 58-70; http://books.nap.edu/books/0309066395/html/.
25. Rose, K. D.; Francisco, M. A. Energy Fuels 1987, 1, 233.
26. Patt, S. L. J. Magn. Reson. 1982, 49, 161-163.
27. Buncel, E. In Supplement F The chemistry of amino, nitroso and nitro compounds and their derivatives Part 2; Patai, S., Ed.; John Wiley and Sons: New York, 1982; Vol. 2, pp 1225-1260.
28. Bunte, G.; Krause, H.; Hirth, T. J. Propellants, Explosives, Pyrotechnics 1997, 22, 160-164.
29. Thorn, K. A.; Steelink, C.; Wershaw, R. L. Org. Geochem. 1987, 11, 123-137.
30. Thorn, K. A.; Mikita, M. A. Sci. Total Environ. 1992, 113, 67-87.
31. Thorn, K.A.; Arterburn, J. B.; Mikita, M. A. Environ. Sci. Technol. 1992, 26, 107-116.
32. Thorn, K. A.; Pettigrew, P. J.; Goldenberg, W. S.; Weber, E. J. Environ. Sci. Technol. 1996, 30, 2764-2775.
33. Thorn, K. A.; Goldenberg, W. S.; Younger, S. J.; Weber, E. J. In Humic and Fulvic Acids: Isolation, Structure, and Environmental Role; Gaffney, J. S., Marley, N. A., Clark, S. B., Eds.; American Chemical Society: Washington, DC, 1996; pp 299-326.
34. Thorn, K. A.; Mikita, M. A. Soil Sci. Soc. Am. J. 2000, 64, 568-582.
35. Pennington, J. C.; Thorn, K. A.; Hayes, C. A.; Porter, B. E.; Kennedy, K. R. Immobilization of 2,4 - and 2,6-Dinirrotoluenes in Soils and Compost; Report No. ERDC/EL TR-03-2; U.S. Army Engineer Research and Development Center: Vicksburg, MS, 2003; http://www.wes.army.mil/el/elpubs/pdf/trel03-2.pdf.
36. Witanowski, M.; Stefaniak, L.; Januszewski, H.; Szymanski, S.; Webb, G. A. Tetrahedron 1973, 29, 2833-2836.