Basic Knowledge and Perspectives on Biodegradation of 2,4,6-Trinitrotoluene and Related Nitroaromatic Compounds in Contaminated Soil

Rieger, Paul-Gerhard; Knackmuss, Hans‐Joachim

doi:10.1007/978-1-4757-9447-2_1

Cited by 208 publications

(199 citation statements)

References 44 publications

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“…Although never shown for the detachment of complex alkyl groups, ipso-substitution represents a general method by which bacteria and rat liver microsomes oxidatively detach substituents, such as halogen and nitro groups in ortho-or para-substituted phenols (23)(24)(25)(26)(27). ipso-Substitution starts with the hydroxylation of the ring anchor carbon, to which the substituent is attached (ipso-attack) (Fig.…”

mentioning

confidence: 99%

A Novel Metabolic Pathway for Degradation of 4-Nonylphenol Environmental Contaminants by Sphingomonas xenophaga Bayram

Gabriel

Heidlberger

Rentsch

et al. 2005

Journal of Biological Chemistry

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Several nonylphenol isomers with ␣-quaternary carbon atoms serve as growth substrates for Sphingomonas xenophaga Bayram, whereas isomers containing hydrogen atoms at the ␣-carbon do not (Gabriel, F. L. P., Giger, W., Guenther, K., and Kohler, H. Furthermore, two metabolites originating from 4-n-nonylphenol were identified as 4-hydroxy-4-nonyl-cyclohexa-2,5-dienone and 4-hydroxy-4-nonyl-cyclohex-2-enone by high pressure liquid chromatography-mass spectrometry. We conclude that nonylphenols were initially hydroxylated at the ipsoposition forming 4-alkyl-4-hydroxy-cyclohexa-2,5-dienones. Dienones originating from growth substrate nonylphenol isomers underwent a rearrangement that involved a 1,2-C,O shift of the alkyl moiety as a cation to the oxygen atom of the geminal hydroxy group yielding 4-alkoxyphenols, from which the alkyl moieties can be easily detached as alcohols by known mechanisms. Dienones originating from nongrowth substrates did not undergo such a rearrangement because the missing alkyl substituents at the ␣-carbon atom prevented stabilization of the putative ␣-carbocation. Instead they accumulated and subsequently underwent side reactions, such as 1,2-C,C shifts and dihydrogenations. The ipso-hydroxylation and the proposed 1,2-C,O shift constitute key steps in a novel pathway that enables bacteria to detach ␣-branched alkyl moieties of alkylphenols for utilization of the aromatic part as a carbon and energy source.

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confidence: 99%

A Novel Metabolic Pathway for Degradation of 4-Nonylphenol Environmental Contaminants by Sphingomonas xenophaga Bayram

Gabriel

Heidlberger

Rentsch

et al. 2005

Journal of Biological Chemistry

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“…However, it is doubtful that TAT would be produced and accumulated in plant cells. As discussed by Rieger and Knackmuss (1995), TAT formation requires a strong reducing potential, which is not present in plant cells. In addition, accumulation of TAT would be prevented by its auto-oxidation prior to polymerization.…”

Section: Reduction Reactionsmentioning

confidence: 99%

Biological remediation of explosives and related nitroaromatic compounds

Snellinx

Nepovím

Taghavi

et al. 2002

Environ. Sci. & Pollut. Res

118

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Abstract. Nitroaromatics form an important group of recalcitrant xenobiotics. Only few aromatic compounds, bearing one nitro group as a substituent of the aromatic ring, are produced as secondary metabolites by microorganisms. The majority of nitroaromadc compounds in the biosphere are industrial chemicals such as explosives, dyes, polyurethane foams, herbicides, insecticides and solvents. These compounds are generally recalcitrant to biological treatment and remain in the biosphere, where they constitute a source of pollution due to both toxic and mutagenic effects on humans, fish, algae and microorganisms. However, relatively few microorganisms have been described as being able to use nitroaromatic compounds as nitrogen and/or carbon and energy source. The best-known nitroaromatic compound is the explosive TNT (2,4,6-trinitrotoluene). This article reviews the bioremediation strategies for TNT-contaminated soil and water. It comes to the following conclusion: The optimal remediation strategy for nitroaromatic compounds depends on many site-specific factors. Composting and the use of reactor systems lend themselves to treating soils contaminated with high levels of explosives (e.g. at former ammunition production facilities, where areas with a high contamination level are common). Compared to composting systems, bioreactors have the major advantage of a short treatment time, but the disadvantage of being more labour intensive and more expensive. Studies indicate that biological treatment systems, which are based on the activity of the fungus Phanerochaete chrysosporium or on Pseudomonas sp. ST53, might be used as effective methods for the remediation of highly contaminated soil and water. Phytoremediation, although not widely used now, has the potential to become an important strategy for the remediation of soil and water contaminated with explosives. It is best suited where contaminant levels are low (e.g. at military sites where pollution is rather diffuse) and where larger contaminated surfaces or volumes have to be treated. In addition, phytoremediation can be used as a polishing method after other remediation treatments, such as composting or bioslurry, have taken place. This in-situ treatment method has the advantage of lower treatment costs, but has the disadvantage of a considerable longer treatment time. In order to improve the cost-efficiency, phytoremediation of nitroaromatics (and other organic xenobiotics) could be combined with bio-energy production. This requires, however, detailed knowledge on the fate of the contaminants in the plants as well as the development of efficient treatment methods for the contaminated biomass that minimise the spreading of the contaminants into the environment during post harvest treatment.

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“…(Spanggord et al, 1991). However, no aerobic bacteria capable of degrading 2,6-DNT has been reported (Rieger and Knackmuss, 1995).…”

Section: Introductionmentioning

confidence: 99%

“…(Crawford, 1995). It has been suggested that TNT can be treated using a continuous anaerobic-aerobic process (Rieger and Knackmuss, 1995).…”

Section: Introductionmentioning

confidence: 99%

Treatment of Industrial Process Effluents & Contaminated Groundwater Using the Biological Granular Activated Carbon-Fluidized Bed Reactor (GAC-FBR) Process. Volume I

Benovska¹,

Cook²,

Groshko³

et al. 1996

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Public reporting burden for this collection of information is estimated to average 1 hour per response, including the time for reviewing instructions, searching existing data sources, gathering and maintaining the data needed, and completing and reviewing this collection of information. Send comments regarding this burden estimate or any other aspect of this collection of information, including suggestions for reducing this burden to Washington Headquarters Services, Directorate for Information Operations and Reports, 1215 Jefferson Davis Highway, Suite 1204, Arlington, VA 22202-4302, and 11313. ABSTRACT (Maximum 200 Words) In 1992, Congress allocated funds for development of expertise in applied environmental bioremediation restoration technology including work on process integration, scale-up and demonstration of the Granular Activated Carbon-Fluidized Bed Reactor (GAC-FBR) process. Specific targets included the treatment of chlorinated solvents, nitrated compounds and aromatic hydrocarbons. The goal of this SERDP funded project was to conduct experimental work at the bench-scale through field demonstration using the GAC-FBR as the platform for degradation of these compounds of concern.In this report are the results of a three-year program designed to test and demonstrate the GAC-DBR process for a number of problem wastewaters facing the U.S. Armed Forces. Both laboratory-pilot and field demonstrations using small commercial scale GAC-FBR systems were conducted. S14633] including work on process integration, scale-up and demonstration of the Granular Activated Carbon-Fluidized Bed Reactor (GAC-FBR) process. Specific targets included the treatment of chlorinated solvents, nitrated compounds and aromatic hydrocarbons. The goal of this SERDP funded project was to conduct experimental work at the bench-scale through field demonstration using the GAC-FBR as the platform for degradation of these compounds of concern.The GAC-FBR process is a high-rate platform for performing biologically catalyzed reactions. The process can be operated as an aerobic, anoxic (denitrifying) or anaerobic system. The use of an adsorptive biomass carrier in the form of granular activated carbon (GAC) affords the process robustness during adverse environmental conditiofts beyond that possible with other biological fixed film systems. This makes the process an ideal candidate for ensuring compliance with effluent discharge limits for wastewaters produced during munitions manufacturing and remediation operations.In this report are the results of a three-year program designed to test and demonstrate the GAC-FBR process for a number of problem wastewaters facing the U.S. Armed Forces. Both laboratory-pilot and field demonstrations using small commercial scale GAC-FBR systems were conducted.Based on needs identified at a kickoff meeting held with representatives of the U.S. Army, Navy and Air Force, four laboratory-pilot tests were conducted. The intent was to determine the potential of the GAC-FBR to meet the treatment needs for differe...

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Basic Knowledge and Perspectives on Biodegradation of 2,4,6-Trinitrotoluene and Related Nitroaromatic Compounds in Contaminated Soil

Cited by 208 publications

References 44 publications

A Novel Metabolic Pathway for Degradation of 4-Nonylphenol Environmental Contaminants by Sphingomonas xenophaga Bayram

A Novel Metabolic Pathway for Degradation of 4-Nonylphenol Environmental Contaminants by Sphingomonas xenophaga Bayram

Biological remediation of explosives and related nitroaromatic compounds

Treatment of Industrial Process Effluents & Contaminated Groundwater Using the Biological Granular Activated Carbon-Fluidized Bed Reactor (GAC-FBR) Process. Volume I

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