A novel environmentally friendly 2,4,6-trinitrotoluene (TNT) based explosive
DOI:
https://doi.org/10.20450/mjcce.2008.230Keywords:
2, 4, 6-trinitrotoluene (TNT), explosive, biotransformation, immobilization, humic monomersAbstract
A novel bioremediation technology has been developed. This technology involves the incorporation of a newly isolated Pseudomonas putida GG04 and Bacillus sp. SF into an explosive formulation to enhance biodegradation of TNT residues and explosives which fail to detonate due to technical problems. The incorporation of these microorganisms into the explosive did not affect the quality of the explosive in terms of detonation velocity while complete degradation of TNT moieties upon transfer in liquid media was observed after 4 days. The incorporated microorganisms sequentially reduced TNT leading to the formation of hydroxylamnidnitrotoluenes (HADNT), 4-amino-2,6- dinitrotoluenes; 2-amino-4,6-dinitrotoluenes, different azoxy compounds; 2,6-diaminonitrotoluenes and 2,4- diaminonitrotoluenes. Aminodinitrotoluenes (AMDNT) and diamninonitrotoluenes (DAMNT) constituted the predominant metabolites which steadily increased achieving 41μM and 63 μM in P. putida GG04 cultures and, 73 μM and 109 μM in Bacillus SF cultures, respectively. Although both microorganisms use NAD(P)H dependent enzymes to transform TNT, P. putida GG04 has a preference for NADPH. The accumulation of AMDNT and DAMNT was effectively prevented in the presence of guaiacol and catechol. A 89 % reduction of AMDNT and a 80 % of DAMNT was achieved in P. putida GG04 cultures, while in Bacillus sp. SF, 91 % and 70 % reduction was achieved. This demonstrates that biodegradation of TNT in the presence of humic material is effective in immobilizing TNT metabolites. Addition of acetonitrile (1:4) to TNT and to its biodegradation products with sequential freezing of the samples at –20 °C was effective in concentrating and enhancing detection signals to identify TNT contaminates sites.
References
B. van Aken, J. M. Yoon and J. L. Schnoor, Biodegradation of Nitro-Substituted Explosives 2,4,6-Trinitrotoluene, Hexahydro-1,3,5-Trinitro-1,3,5-Triazine, and Octahydro- 1,3,5,7-Tetranitro-1,3,5-Tetrazocine by a Phytosymbiotic Methylobacterium sp. Associated with Poplar Tissues (Populus deltoides x nigra DN34), Appl. Environ. Microbiol. 70(1), 508–517 (2004).
R. D. Harter, The use and importance of nitroaromatic compounds in the chemical industry. In: D. E. Rickert (ed.), Chemical Institute of Toxicology Series. Toxicity of nitroaromatic compounds. Hemisphere Publishing, Washington, D.C, 1985, pp. 1–14.
R. P. Mason, P. D. Josephy, Free radical mechanism of nitroreductase. In: Toxicity of Nitroaromatic Compounds. (Rickert D. E., ed), Hemisphere, New York, 1985, pp.121 – 140.
IARC(International Agency for Research of Cancer), 2,4,6-trinitrotoluene. In. Printing Processes and printing inks, Carbon black and some nitro compounds, Volume 65: IARC Monographs on the evaluation of carcinogens to humans. World Health Organization-International Agency for Reaearch on Cancer, 449–475 (1996).
G. S. Nyanhongo, M. Schroeder, W. Steiner, G. M. Gübitz, Biodegradation of 2,4,6-trinitrotoluene (TNT): An enzymatic perspective, Biocatalysis and Biotransformation, 23 (2), 53–69 (2005).
F. B. Smets, H. Yin, A. Esteve-Nuñez, TNT biotransformation: When chemistry confronts mineralization, Appl Microbiol Biotechnol., 76, 267–277 (2007).
G. Daun, H. Lenke, M. Reuss, H.J. Knackmuss, Biological treatment of TNT-contaminated soil. 1. Anaerobic cometabolic reduction and interaction of TNT and metabolites with soil components, Environ. Sci. Technol., 32, 1956–1963 (1998).
H. Lenke, G. Daun, K. Hund, U. Sieglen, U. Walter, H. J. Knackmuss, Biological treatment of TNT contaminated soil. 2 Biologically induced immobilization of the contaminants and full-scale application. Environ. Sci. Technol. 32, 1964–1971 (1998).
G. S. Nyanhongo, S. Rodrıguez Couto, G. M. Guebitz, Coupling of 2,4,6-trinitrotoluene (TNT) metabolites onto humic monomers by a new laccase from Trametes modesta, Chemosphere, 64, 359–370 (2006).
G. S. Nyanhongo, A. Erlacher, M. Schroeder, G. M. Gubitz, Enzymatic immobilization of 2,4,6-trinitrotoluene (TNT) biodegradation products onto model humic substances, Enzyme Microbiol Technol., 39, 1197–1204 (2006).
J. Maier, A. Kandelbauer, A. Erlacher, A. Cavaco-Paulo, G. M. Gübitz, A New Alkali-Thermostable Azoreductase from Bacillus sp. Strain SF, Environ. Microbiol., 70(2), 837–844 (2004).
D. Gunnison, J. C. Pennington, C. B. Price, G. B. Myrick, "Screening test and isolation procedure for TNT-degrading microorganisms", Technical Report IRRP-93-2, U.S. Army Engineer Waterways Experiment Station, Vicksburg, MS. NTIS No. AD A269 124, 1–32 (1993).
N. G. McCormick, F. E. Feeherry, H. S. Levinson, Microbial transformation of 2,4,6-TNT and other nitroaromatic compounds, Appl. Environ. Microbiol., 31, 949– 958 (1976).
A. M. Tope, K. Jamil, T. R. Baggi, Transformation of 2,4,6-trinitrotoluene (TNT) by immobilized and resting cells of Arthrobacter sp., J. Harzadous Substances Res., 2, 3–9 (1999).
C. Held,• A. Kandelbauer, M. Schroeder, A. Cavaco- Paulo, G. M. Guebitz, Biotransformation of phenolics with laccase containing bacterial spores, Environ. Chem. Lett., 3, 74–77 (2005).
A. M. Malik, Long-term preservation of some Rhodospirillaceae by freeze-drying, J. Microbiol. Methods, 8, 259–271 (1998).
T. Kalafut, M. E. Wales, V. K. Rastogi, R. P. Naumova, S. K. Zaripova, J. R. Wild, Biotransformation patterns of 2,4,6-trinitrotoluene by aerobic bacteria, Curr. Microbiol., 36, 45–54 (1998).
J. W. Pak, K. L. Knoke, D. R. Noguera, B. G. Fox, G. H. Chambliss, Transformation of 2,4,6-trinitrotoluene by purified xenobiotic reductase B from Pseudomonas fluorescens I-C, Appl. Environ. Microbiol., 66, 4742–4750 (2000).
A. Haidour, J. L. Ramos, Identification of products resulting from the biological reduction of 2,4,6-trinitrotoluene; 2,4-dinitrotoluene and 2,6-dinitrotoluene by Pseudomonas sp., Environ. Sci. Technol., 30, 2365–2370 (1996).
C. Vorbeck, H. Lenke, P. Fischer, H. J. Knackmuss, Identification of a hydride-Meisenheimer complex as a metabolite of 2,4,6-trinitrotoluene by a Mycobacterium strain, J. Bacteriol., 176, 932–934 (1994).
C. E. French, S. Nicklin, N. C. Bruce, Aerobic degradation of 2,4,6-trinitrotoluene by Enterobacter cloacae PB2 and by pentaerythritol tetranitrate reductase, Appl. Environ. Microbiol., 64, 2864–2868 (1998).
G. Heiss, H. J. Knackmuss, Bioelimination of trinitroaromatic compounds: Immobilization versus mineralization, Cur. Opinion Microbiol., 5, 282–287 (2002).
S. Thiele, E. Fernandes, and J. M. Bollag, Enzymatic transformation and binding of labelled 2,4,6-trinitrotoluene to humic substances during an anaerobic/aerobic incubation, J. Environ. Qual. 31, 437–444 (2002)
C. Achtnich, E. Fernandes, J. M. Bollag, H. J. Knackmuss, H. Lenke, Covalent binding of reduced metabolites of
N3] TNT to soil organic matter during a bioremediation process analyzed by 15NMR spectroscopy, Environ. Sci. Technol., 33, 4448–4456 (1999).
K. A. Thorn, J. C. Pennington, and C. A. Hayes, 15N NMR Investigation of the reduction and binding of TNT in an aerobic bench scale reactor simulating windrow composting, Environ. Sci. Technol., 36, 3797–3805 (2002).
A.P. Mackenzie, Comparative studies on the freezedrying survival of various bacteria: Gram type, suspending medium and freezing rate, Develop. Biol. Standard, 36, 263–277 (1977).
Downloads
Published
How to Cite
Issue
Section
License
The authors agree to the following licence: Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)
- Share — copy and redistribute the material in any medium or format
- Adapt — remix, transform, and build upon the material
- for any purpose, even commercially.
Under the following terms:
Attribution — You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.
- NonCommercial — You may not use the material for commercial purposes.