Abstract
Contamination of ground and surface water with 2,4,6-trinitrotoluene (TNT) and its biological and chemical transformation products are a persisting problem at former TNT production sites. We have investigated the photochemical degradation of TNT and its aminodinitro-(ADNT) and diaminonitrotoluene (DANT) metabolites using OH-radical generating systems like Fenton and hydrogen peroxide irradiated with UV, in order to compare the degradation and mineralization rate of ADNT- and DANT-isomers with TNT itself. As a result, we find that the aminoderivatives were mineralized much faster than TNT. Consequently, as ADNTs and DANTs are the known dead-end products of biological TNT degradations, we have combined our photochemical procedure with a preceding biological treatment of TNT by a mixed culture from sludge of a sewage plant. This consecutive degradation procedure, however, shows a reduced mineralization rate of the ADNTa and DANTs in the biologically derived supernatant as compared to the pure substances, suggesting that during the biological TNT treatment by sludge competing substrates are released into the solution, and that a more defined biological procedure would be necessary in order to achieve an effective, ecologically and economically acceptable mineralization of TNT from aqueous systems.
Similar content being viewed by others
References
Baker A, Spencer RG (2004) Characterization of dissolved organic matter from source to sea using fluorescence and absorbance spectroscopy. Sci Total Environ 333:217–232
Bruns-Nagel D, Breitung J, Steinbach K, Gemsa D, von Low E, Gorontzy T, Blotevogel KH (1997) Bioremediation of 2,4,6-trinitrotoluene-contaminated soil by anaerobic/aerobic and aerobic methods. In: Alleman BC, Leeson A (Eds) In situ and On-Site Bioremediation, 9–14
Burlinson N, Sitzmann M, Kaplan L, Kayser E (1979) Photochemical generation of the 2,4,6-trinitrobenzyl anion. J Org Chem 44:3695–3698
Carey JH (1992) An introduction to advanced oxidation processes (AOP) for destruction of organics in wastewater. Water Pollut Res J Can 27:1–21
Claus H, Bausinger T, Lehmler I, Perret N, Fels G, Dehner U, Preuß J, König H (2006). Bacterial elimination of 2,4,6-trinitrotoluene (TNT) by Raoultella terrigena. Biodegradation (in press)
Crawford RL (1995) The microbiology and treatment of nitroaromatic compounds. Curr Opin Biotechnol 6:329–336
Dillert R, Siebers U, Renwrantz A, Bahnemann D (1997) Oxidation von Nitro- und Aminoaromaten mit Wasserstoffperoxid. Verbundvorhaben biologische Sanierung von Rüstungsaltlasten, Tagungsband zum 3 Statusseminar am 26 und 27 02 in Berlin (Hrsg: Umweltbundesamt), BMBF, Bonn Kapitel G
Ederer M, Lewis TA, Crawford RL (1997) 2,4,6-Trinitrotoluene (TNT) transformation by Clostidia isolated from a munition-fed bioreactor: comparison with non-adapted bacteria. J Ind Microbiol Biotechnol 18:75–80
Edwards JO, Curci R (1992) Fenton type activation and chemistry of hydroxyl radical. In: Strukul G (Ed) Catalytic oxidations with hydrogen peroxide. Kluwer Academic Publishers, Dordrecht
Eilers A, Rüngeling E, Stuendl UM, Gottschalk G (1999) Metabolism of TNT by the white-rot fungus bjerkanda dausta dsm 3375 depends on cytochrome p 450. Appl Microbiol Biotechnol 53:75–80
Emmrich M (1999) Kinetics of the alkaline hydrolysis of 2,4,6-trinitrotoluene in aqueous solution and highly contaminated soils. Environ Sci Technol 33:3802–3805
Esteve-Núñez A, Caballero A, Ramos JL (2001) Biological degradation of 2,4,6-trinitrotoluene. Microbiol Mol Biol Rev 335–352
Fukushima M, Tatsumi K, Nagao S (2001) Degradation characteristics of humic acids during photo-Fenton processes. Environ Sci Technol 35:3683–3690
Glover DJ, Hoffsommer JC, Kubose DA, (1977) Anal Chim Acta 88: 381–384
Hampton ML, Sisk WE (1997) Environmental stability of windrow composting of explosives-contaminated soils. In: Tedder DW (Ed) Emerging Technologies in Hazardous Waste Management IX, Division of Industrial and Engineering Chemistry, 252–257
Hawari J, Beaudet S, Halasz A, Thiboutot S, Ampleman G (2000) Microbial degradation of explosives: biotransformation versus mineralization. Appl Microbiol Biotechnol 54:605–618
Heiss G, Knackmuss HJ (2002) Bioelimination of trinitroaromatic compounds: immobilization versus mineralization. Curr Opin Microbiol 5:282–287
Hess TF, Lewis TA, Crawford RL, Katamneni S, Wells JH, Watts RJ (1998) Combined photocatalytic and fungal treatment for the destruction of 2,4,6-trinitrotoluene (TNT). Wat Res 32:1481–1491
Hess TF, Schrader PS (2002) Coupled abiotic-biotic mineralization of 2,4,6-trinitrotoluene (TNT). J Environ Qual 31:736–744
Ho PC (1986) Photooxidation of 2,4-dinitrotoluene in the presence of hydrogen peroxide. Environ Sci Technol 20:260–267
Hofrichter M, Scheibner K, Schneegaβ I, Fritsche W (1998) Enzymatic combustion of aromatic and aliphatic compounds by manganese peroxidase from nematoloma frowardii. Appl Environ Microbiol 64:399–404
Honeycutt ME, Jarvis AS, McFarland VA (1996) Cytotoxicity and mutagenicity of 2,4,6-trinitrotuene and its metabolites. Ecotox Environ Safety 35:282–287
Hwang HM, Slaughter LF, Cook SM, Cui H (2000a) Degradation of TNT in a freshwater environment. Bull Environ Contam Toxicol 65:228–235
Hwang HM, Slaughter LF, Cook SM, Cui H (2000b) Photochemical and microbial degradation of 2,4,6-trinitrotoluene (TNT) in a freshwater environment. Bull Environ Contam Toxicol 65:228–235
Kearney PC, Zeng Q, Ruth JM (1983) Oxidative pretreatment accelerates TNT metabolism in soils. Chemosphere 12:1583–1597
Kröger M, Fels G (2000) 14C-TNT synthesis reinvestigated. J Label Compds Radiopharm 43:217–227
Kröger M, Fels G (2002) Microbiotic synthesis of 14C-ringlabelled aminodinitrotoluenes (ADNT) and diaminonitrotoluenes (DANT). J Label Compds Radiopharm 45:249–255
Kröger M, Schumacher ME, Risse H, Fels G (2004) Biological reduction of TNT as part of a combined biological-chemical procedure for mineralization. Biodegradation 15:241–248
Lachance B, Robidoux PY, Hawari J, Ampleman G, Thiboutout S, Sunahara GI (1999) Cytotoxic and genotoxic effects of energetic compounds on bacterial and mammalian cells in vitro. Mutat Res 444:25–39
Legrini O, Oliveros E, Braun AM (1993) Photochemical processes for water treatment. Chem Rev 93:671–698
Lenke H, Achtnich C, Knackmuss HJ (2000) Perspectives of bioelimination of polynitroaromatic compounds. In: Spain JC, Hughes JB, Knackmus HJ (Eds) Biodegradation of nitroaromatic compounds and explosives. CRC Press, Boca Raton, pp. 91–126
Lewis TA, Crawford RL, Katamneni S, Wells JH, Watts, RJ, Hess TF (1998) Wat Res 32:1481–1491
Lewis TA, Newcombe DA, Crawford RL (2004) Bioremediation of soils contaminated with explosives. J Environ Managem 70:291–307
Li AZ, Marx KA, Walker J, Kaplan DL (1997) Trinitrotoluene and metabolites binding to humic acid. Environ Sci Technol 31:584–589
Li ZM, Comfort SD, Shea PJ (1997) Destruction of 2,4,6-trinitrotoluene by Fenton oxidation. J Environ Qual 26:480–487
Li ZM, Shea PJ, Comfort SD (1998) Nitrotoluene destruction by UV-catalyzed Fenton oxidation. Chemosphere 36:1849–1865
Lindsey ME, Tarr MA (2000) Inhibition of hydroxyl radical reaction with aromatics by dissolved organic matter. Environ Sci Technol 34:444–449
Liou MJ, Lu MC, Chen JN (2003) Oxidation of explosives by Fenton and photo-Fenton processes. Wat Res 37:3172–3179
Makarova O, Rajh T, Thurnauer MC, Martin A, Kemme PA, Cropek D (2000) Surface modification of TiO2 nanoparticles for photochemical reduction of nitrobenzene. Environ Sci Technol 34:4797–4803
Martinetz D, Rippen G (1990) TNT. In: Rippen, G (Ed), Handbuch Umweltchemikalien ecomed, Landsberg/Lech
Nahen M, Bahnemann R, Dillert R, Fels G (1997) Photocatalytc degradation of TNT: Reductive and oxidative pathways. J Photochem Photobiol A: Chemistry 110:191–199
Popesku JT, Singh A, Zhao JS, Hawari J, Ward OP (2004) Metabolite production during transformation of 2,4,6-trinitrotoluene (TNT) by a mixed culture acclimated and maintained on crude oil-containing media. Appl Microbiol Biotechnol 65:739–746
Preuss J, Eitelberg F (1999) Hallschlag-ISBN 3-88250-045-X (Erhältlich beim Geographischen Institut der Universität Mainz, Saarstr 21, 55121 Mainz)
Rieger PG, Knackmuss HJ (1995) Basic knowledge and perspectives on biodegradation of 2,4,6-trinitrotoluene and related nitroaromatic compounds in contaminated soil. Spain JC (Ed) Biodegradation of Nitroaromatic Compounds, 1–18
Robidoux PY, Svendsen C, Sarrazin MST, Ampleman G, Hawari J, Weeks JM, Sunahara GI (2005) Assessment of a 2,4,6-trinitrotoluene-contaminated site using Aporrectodea rosea and Eisenia andrei in mesocosms. Arch Environ Contam Toxicol 48:56–67
Rodgers JD, Bunce NJ (2001) Treatment methods for the remediation of nitroaromatic explosives. Wat Res 35:2101–2111
Scheibner K, Hofrichter M, Herre A, Michels J (1997) Screening for fungi intensively mineralizing TNT. Appl Microbiol Biotechnol 47:452–457
Schmelling DC, Gray KA, Kamat PV (1997) The influence of solution matrix on the photocatalytic degradation of TNT in TiO2 slurries. Wat Res 31:1439–1447
Schmidt A, Butte W (1999) Photocatalytic degradation of reduction products of TNT. Chemosphere 38:1293–1298
Schrader PS, Hess TF (2004) Coupled abiotic-biotic mineralization of 2,4,6-trinitrotoluene (TNT) in soil slurry. J Environ Qual 33:1202–1209
Simjouw JP, Minor EC, Mopper K (2005) Isolation and characterization of estuarine dissolved organic matter: Comparison of ultrafiltration and C-18 solid-phase extraction techniques. Marine Chem 96:219–235
Son HS, Lee SJ, Cho IH, Zoh KD (2004) Kinetics and mechanism of TNT degradation in TiO2 photocatalysis. Chemosphere 57:309–317
Spanggord RJ, Yao D, Mill T (2000) Kinetics of aminodinitrotoluene oxidations with ozone and hydroxyl radical. Environ Sci Technol 34:450–454
Szöcs A (1998). Geoökologische Systemanalyse und Bestimmung der Nitroaromaten-Mobilität auf dem großflächigen Rüstungsaltstandort Stadtallendorf bei Marburg. Diss FB Geowiss Uni Mainz
Thorn KA, Thorne PG, Cox LG (2004) Alkaline hydrolysis/polymerization of 2,4,6-trinitrotoluene: Characterization of products by 13C- and 15N-NMR. Environ Sci Technol 38:2224–2231
Yin H, Wood TK, Smets BF (2005) Reductive transformation of TNT by Escherichia coli: pathway description. Appl Microbiol Biotechnol 67:397–404
Zaripov SA, Naumov AV, Suvorova ES, Garusov AV, Naumova RP (2004) Initial Stages of 2,4,6-Trinitrotoluene Transformation by Microorganisms. Microbiol 73:398–403
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kröger, M., Fels, G. Combined biological–chemical procedure for the mineralization of TNT. Biodegradation 18, 413–425 (2007). https://doi.org/10.1007/s10532-006-9076-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10532-006-9076-4