Characterization of products from the biotransformation of 2,4- dinitrotoluene by denitrifying enrichment cultures

Water Environment Research

Volumn 69, Issue 3, 1997, Pages 260-268

  Noguera, Daniel R ^a,b   Freedman, David L ^a,c  

^a University of Illinois at Urbana Champaign   (United States)

^b University of Wisconsin Madison   (United States)

^c CLEMSON UNIVERSITY   (United States)

Author keywords

acetylation; aromatics; denitrification; dinitrotoluene; munitions wastes; nitroaromatics

Indexed keywords

TOLUENE DERIVATIVE;

ACTIVATED SLUDGE; ARTICLE; DENITRIFICATION; DRUG DEGRADATION; DRUG DETOXIFICATION; PRIORITY JOURNAL; WASTE WATER MANAGEMENT;

EID: 0030902778     PISSN: 10614303     EISSN: None     Source Type: Journal    
DOI: 10.2175/106143097X125434     Document Type: Article

References (46)

1. Alvarez, M. A., Hanners, J. L., Botsford, J. L., Unkefer, P. J. (1994) Isolation and Characterization of a 2,4,6-Trinitrotoluene-Degrading Microorganism. Abstracts 94th General Meet. Am. Soc. Microbiol., Las Vegas, Nevada, Abstract No. Q-199, 408.
2. Behr, L. C. (1967) Indazoles and Condensed Types. In: Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings. R. H. Wiley (Ed.), Interscience Publishers, New York, 289.
3. Berchtold, S. R., VanderLoop, S. L., Suidan, M. T., Maloney, S. W. (1995) Treatment of 2,4-Dinitrotoluene using a Two-Stage System: Fluidized-Bed Anaerobic Granular Activated Carbon Reactors and Aerobic Activated Sludge Reactors. Water Environ. Res., 67, 1081.
4. Boopathy, R., Kulpa, C. F., Wilson, M. (1993) Metabolism of 2,4,6-Trinitrotoluene (TNT) by Desulfovibrio sp. (B Strain). Appl. Microbiol. Biotechnol., 39, 270.
5. Caldwell, J., (1982) Conjugation Reactions of Nitrogen Centers. In Metabolic Basis of Detoxication. W. B. Jakoby, J. R. Bend, J. Caldwell (Ed.), Academic Press, New York, 292.
6. Corbett, M. D., and Corbett, B. R. (1981) Metabolism of 4-Chloronitrobenzene by the Yeast Rhodosporidium sp. Appl. Environ. Microbiol., 41, 942.
7. Corbett, M. D., and Corbett, B. R. (1995) Bioorganic Chemistry of the Arylhydroxylamine and Nitrosoarene Functional Groups. In Biodegradation of Nitroaromatic Compounds. J. C. Spain (Ed.), Plenum Press, New York, 151.
8. Crawford, R. L. (1995) Biodegradation of Nitrated Munition Compounds and Herbicides by Obligately Anaerobic Bacteria. In Biodegradation of Nitroaromatic Compounds. J. C. Spain (Ed.), Plenum Press, New York, 87.
9. Duque, E., Haidour, A., Godoy, F., Ramos, J. L. (1993) Construction of a Pseudomonas Hybrid Strain That Mineralizes 2,4,6-Trinitrotoluene. J. Bacteriol., 175, 2278.
10. Engelhardt, G., Wallnofer, P., Fuchsbichler, G., Baumeister, W. (1977) Bacterial Transformations of 4-Chloroaniline. Chemosphere (G.B.), 2, (3), 85.
11. Fernando, T., Bumpus, J. A., Aust, S. D. (1990) Biodegradation of TNT (2,4,6-Trinitrotoluene) by Phanerochaete chrysosporium. Appl. Environ. Microbiol., 56, 1666.
12. Freedman, D. L., and Noguera, D. R. (1995) An Evaluation of Biotransformation Products from 2,4-Dinitrotoluene Under Nitrate-Reducing Conditions. U.S. Army Research Office, Final Report, DAAH04-94-G-0264.
13. Funk, S. B., Roberts, D. J., Crawford, D. L., Crawford, R. L. (1993) Initial-Phase Optimization for Bioremediation of Munition Compound-Contaminated Soils. Appl. Environ. Microbiol., 9, 2171.
14. 14C]Trifluralin in Soil. J. Agric. Food Chem., 7, 163.
15. Haigler, B. E., and Spain, J. C. (1993) Biodegradation of 4-Nitrotoluene by Pseudomonas sp. Strain 4NT. Appl. Environ. Microbiol., 9, 2239.
16. Haigler, B. E., Wallace, W. H., Spam, J. C. (1994) Biodegradation of 2-Nitrotoluene by Pseudomonas sp. Strain JS42. Appl. Environ. Microbioi., 0, 3466.
17. Heijman, C. G., Grieder, E., Holliger, C., Schwarzenbach, R. P (1995) Reduction of Nitroaromatic Compounds Coupled to Microbial Iron Reduction in Laboratory Aquifer Columns. Environ. Sci. Technol., 9, 775.
18. Hallas, L. E., and Alexander, M. (1983) Microbial Transformation of Nitroaromatic Compounds in Sewage Effluent. Appl. Environ. Microbioi., 5, 1234.
19. IT Environmental Programs, (1991) Removal of DNT from Wastewaters at Radtord Army Ammunition Plant. U.S. Army Corps of Engineers. Toxic and Hazardous Materials Agency, Final Report No. CETHA-TS-CR-91031.
20. Jenkins, F., Bauer, C. F., Leggett, D. C., Grant, C. L. (1984) Reverse phase HPLC method for analysis of TNT, RDX, HMX, and 2,4-DNT in munitions wastewater. U.S. Army Corps of Engineers, CRREL Report 84-29.
21. Laanio, T. L., Kearney, P. C., Kaufman, D. D. (1973) Microbial Metabolism of Dinitramine. Pestic. Biochem. Physiol., , 271.
22. Low, G. K.-C., Bartha, A., Billiet, H. A. H., Galan, L. D. (1989) Systematic Procedure for the Determination of the Nature of the Solutes Prior to the Selection of the Mobile Phase Parameters for Optimization of Reversed-Phase Ion-Pairing Chromatographic Separations. J. Chromatogr., 78, 21.
23. Maloney, S. W., May, E., Suidan, M. T., Berchtold, S. R., Heffinger, J. G. (1994a) DNT Abatement in Propellant Production Wastewater On-Site Using Expanded Bed Granular Activated Carbon Anaerobic Reactors. Proc. 19th Environ. Symp. Exhibit., Am. Defen. Preparedness Assoc., "Federal Agency Environmental Vision - 2000 DOD/DOE/EPA/USCG: Can Current Technology Get us There?," Albuquerque, NM, 304.
24. Maloney, S. W., VanderLoop, S., Suidan, M. T., Moteleb, M., (1994b) Two Phase Biodegradation of Ordnance Waste: Bench-Scale and Pilot Studies. 67th Annual Conf. Expo. Water Environ. Fed., Chicago, IL, 387.
25. McCormick, N. G., Cornell, J. H., Kaplan, A. M. (1978) Identification of Biotransformation Products from 2,4-Dinitrotoluene. Appl. Environ. Microbioi., 35, 945.
26. McCormick, N. G., Feeherry, F. E., Levinson, H. S. (1976) Microbial Transformation of 2,4,6-Trinitrotoluene and Other Nitroaromatic Compounds. Appl. Environ. Microbiol., 31, 949.
27. McLafferty, F. W., and Turecek, F. (1993) Interpretation of Mass Spectra. Fourth edition, University Science Books, Mill Valley, CA.
28. Naumova, R. P., Selivanovskaya, S. Y., Cherepneva, I. E. (1986) Conversion of 2,4,6-Trinitrotoluene under Conditions of Oxygen and Nitrate Respiration of Pseudomonas fluorescens. Prikl. Biokhim. Mikrobiol. (USSR), 24, 493.
29. Noguera, D. R. (1996) Biological Transformation of 2,4-Dinitrotoluene Under Denitrifying Conditions. Ph.D. thesis, University of Illinois at Urbana-Champaign, Urbana.
30. Noguera, D. R., and Freedman, D. L. (1996) Reduction and Acetylation of 2,4-Dinitrotoluene by a Pseudomonas aeruginosa Strain. Appl. Environ. Microbiol., 62, 2257.
31. Noguera, D. R., and Freedman, D. L. (1995b) Characterization of the Metabolites Produced during the Biotransformation of 2,4-Dinitrotoluene under Nitrate Reducing Conditions. Abstracts 95th General Meet. Am. Soc. Microbiol., Washington D.C., Abstract No. Q-182, 431.
32. Patterson, J. W., Shapira, N. I., Brown, J. (1976) Pollution Abatement in the Military Explosives Industry. Proc. 31st Industrial Waste Conference. Purdue Univ. Lafayette, Indiana, 385.
33. Preuss, A., Fimpel, J., Diekert, G. (1993) Anaerobic Transformation of 2,4,6-trinitrotoluene (TNT). Arch. Mikrobiol. (Ger.), 159, 345.
34. Rhys-Williams, W., Taylor, S. C., Williams, P. A. (1993) A Novel Pathway for the Catabolism of 4-Nitrotoluene by Pseudomonas. J. Gen. Microbiol., 139, 1967.
35. Rickert, D. E. (1985) Mammalian and Bacterial Metabolism of Nitroaromatic Compounds. In Toxicity of Nitroaromatic Compounds. D. E. Rickert (Ed.), Hemisphere Publishing Corp., Washington, D.C., 87.
36. Rieger, P.-G., and Knackmuss, H.-J. (1995) Basic Knowledge and Perspectives on Biodegradation of 2,4,6-Trinitrotoluene and Related Nitroaromatic Compounds in Contaminated Soil. In Biodegradation of Nitroaromatic Compounds. J. C. Spain (Ed.). Plenum Press, New York, 1.
37. Schackmann, A., and Müller, R. (1991) Reduction of Nitroaromatic Compounds by Different Pseudomonas Species under Aerobic Conditions. Appl. Microbiol. Biotechnol., 34, 809.
38. Smith, R. H., Oliver, J. E., Lusby, W. R. (1979) Degradation of Pendimethalin and its N-Nitroso and N-Nitro Derivatives in Anaerobic Soil. Chemosphere (G.B.), 8, 855.
39. Smith, L. L., Carrazza, J., Wong, K. (1982) Biological Treatment for Waste Streams from Propellants and Explosives Manufacturing. J. Hazard. Mater., 5, 277.
40. Spanggord, R. J., Spain, J. C., Nishino, S. F., Mortelmans, K. E. (1991) Biodegradation of 2,4-Dinitrotoluene by a Pseudomonas sp. Appl. Environ. Microbiol., 57, 3200.
41. Swan, G. A., and Felton, D. G. I. (1957) Phenazines. Interscience Publishers, New York.
42. Valli, K., Brock, B. J., Joshi, D. K., Gold, M. H. (1992) Degradation of 2,4-Dinitrotoluene by the Lignin-Degrading Fungus Phanerochaete chrysosporium. Appl. Environ. Microbiol., 58, 221.
43. VanderLoop, S. L., Suidan, M. T., Moteleb, M. A., Maloney, S. W. (1994) Biodegradation of 2,4-Dinitrotoluene in a Two Stage System. In Critical Issues in Water and Wastewater Treatment. Proceedings of the 1994 National Conference on Environmental Engineering ASCE, Boulder, CO, 710.
44. Wallnofer, P. R., Tillmanns, G., Engelhardt, G. (1977) Degradation of Acylanilide Pesticides by Aspergillus niger. Pestic. Biochem. Physiol., , 481.
45. Young, L. Y. (1984) Anaerobic Degradation of Aromatic Compounds. In Microbial Degradation of Organic Compounds. D. T. Gibson (Ed.), Dekker, New York, 487.
46. Zeyer, J., Eicher, P., Dolfing, J., Schwarzenbach, R. P. (1990) Anaerobic Degradation of Aromatic Hydrocarbons. In Biotechnology and Biodegradation. D. Kamely, A. Chakrabarty, G. S. Onen (Eds.), Portfolio Publishing Company, The Woodlands, Texas, 33