Fate and effects of picric acid and 2,6-DNT in marine environments: Toxicity of degradation products

Nipper, Marion; Carr, R. Scott; Biedenbach, James M.; Hooten, Russell L.; Miller, Karen D.

doi:10.1016/j.marpolbul.2005.04.019

Cited by 71 publications

(43 citation statements)

References 15 publications

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“…10 d). These findings corroborate well with few other previous studies where a reduction of toxicity was observed following anaerobic treatment of petroleum hydrocarbon contaminated wastewater (Xiong et al, 2012;Cooper et al, 2010;Bautista et al, 2009;Nipper et al, 2005). Toxicity data together with other experimental evidence provided earlier in sections 3.1.1 and 3.1.3 further demonstrate the effectiveness of this novel tubular MFC in the in situ treatment of petroleum hydrocarbons especially in deep aquifers with contaminated groundwater.…”

Section: Toxicity Reduction During Mfc Operationsupporting

confidence: 91%

Treatment of phenanthrene and benzene using microbial fuel cells operated continuously for possible in situ and ex situ applications

Adelaja

Keshavarz

Kyazze

2017

International Biodeterioration & Biodegradation

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Bioelectrochemical systems could have potential for bioremediation of contaminants either in situ or ex situ. The treatment of a mixture of phenanthrene and benzene using two different tubular microbial fuel cells (MFCs) designed for either in situ and ex situ applications in aqueous systems was investigated over long operational periods (up to 155 days). For in situ deployments, simultaneous removal of the petroleum hydrocarbons (>90% in term of degradation efficiency) and bromate, used as catholyte, (up to 79 %) with concomitant biogenic electricity generation (peak power density up to 6.75 mWm -2 ) were obtained at a hydraulic retention time (HRT) of 10 days. The tubular MFC could be operated successfully at copiotrophic (100 ppm phenanthrene, 2000 ppm benzene at HRT 30 days) and oligotrophic (phenanthrene and benzene, 50 ppb each, HRT 10 days) substrate conditions suggesting its effectiveness and robustness at extreme substrate concentrations in anoxic environments. In the MFC designed for ex situ deployments, optimum MFC performance was obtained at HRT of 30 h giving COD removal and maximum power output of approximately 77% and 6.75 mWm -2 respectively. The MFC exhibited the ability to resist organic shock loadings and could maintain stable MFC performance. Results of this study suggest the potential use of MFC technology for possible in situ/ex situ hydrocarbon-contaminated groundwater treatment or refinery effluents clean-up, even at extreme contaminant level conditions.

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Section: Toxicity Reduction During Mfc Operationsupporting

confidence: 91%

Treatment of phenanthrene and benzene using microbial fuel cells operated continuously for possible in situ and ex situ applications

Adelaja

Keshavarz

Kyazze

2017

International Biodeterioration & Biodegradation

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“…The toxicity of 2,4-DNP was higher than that of picramic acid for macroalga zoospores, but both chemicals exhibited similar toxicity to copepod for reproduction (Nipper et al 2005). The potential reasons for higher toxicity of picric acid to macroalga zoospores observed in Nipper et al (2001) when compared to results reported in Nipper et al (2005) were not discussed in the more recent study. The concentrations of picric acid eliciting mortality to freshwater fish (Table 4.8) were similar to concentrations reported as toxic to marine fish.…”

Section: Toxicity Of Nitrophenolic MCmentioning

confidence: 85%

“…Under aerobic conditions, the mono-or dinitrophenol can then be oxygenated with subsequent ring cleavage (Monteil-Rivera 2009). The fate of picric acid in marine sediments was investigated by Nipper et al (2005). Transformation rates were highest in incubated, fine-grained sediment and major transformation products included 4-dinitrophenol, aminodinitrophenols (including picramic acid), 3,4-diaminophenol, amino nitrophenol, and nitrodiaminophenol.…”

Section: Nitroaromaticsmentioning

confidence: 99%

“…Oysters were also tolerant to the lethal effects of picric acid (Goodfellow et al 1983). The reduction of picric acid to picramic acid promoted substantial toxicity increase as the main breakdown products of picric acid, 2,4-DNP and picramic acid, were more toxic to copepods, oysters, and macroalga zoospores than the parent compound (Nipper et al 2005;Goodfellow et al 1983). The toxicity of 2,4-DNP was higher than that of picramic acid for macroalga zoospores, but both chemicals exhibited similar toxicity to copepod for reproduction (Nipper et al 2005).…”

Section: Toxicity Of Nitrophenolic MCmentioning

confidence: 99%

“…The reduction of picric acid to picramic acid promoted substantial toxicity increase as the main breakdown products of picric acid, 2,4-DNP and picramic acid, were more toxic to copepods, oysters, and macroalga zoospores than the parent compound (Nipper et al 2005;Goodfellow et al 1983). The toxicity of 2,4-DNP was higher than that of picramic acid for macroalga zoospores, but both chemicals exhibited similar toxicity to copepod for reproduction (Nipper et al 2005). The potential reasons for higher toxicity of picric acid to macroalga zoospores observed in Nipper et al (2001) when compared to results reported in Nipper et al (2005) were not discussed in the more recent study.…”

Section: Toxicity Of Nitrophenolic MCmentioning

confidence: 99%

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Summary Review of the Aquatic Toxicology of Munitions Constituents

Lotufo¹,

Rosen²,

Wild³

et al. 2013

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Military munitions are present in waters around the world, including those waters located at current and former Department of Defense sites. This report provides a review of the aquatic ecotoxicology of munitions constituents (MC), including nitroaromatics (2,4,6-trinitrotoluene (TNT), dinitrotoluenes (DNTs), 1,3,5-trinitrobenzene (TNB), 2,4,6-trinitrophenylmethylnitramine (tetryl) and 2,4,6-trinitrophenol (picric acid)); nitrate esters (nitrocellulose (NC), pentaerythritoltetranitrate (PETN), nitroglycerine (NG)); and nitramines (hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX), and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX)). The major focus of this report is on the fate and effects of MC in the marine environment. Most MC observed in this study rapidly degraded in aqueous exposure systems and nitroaromatics showed a significant binding affinity with organic matter. To support the assessment of risk from MC in aquatic environments, laboratory-based toxicity data have been derived for a variety of aquatic species for both lethal and sublethal exposure endpoints using spiked water or sediment. Frequently, unrealistically high concentrations were used to derive toxicity benchmarks. In general, nitramines were less toxic than nitroaromatics, with a wide range of sensitivity among species. MC are weakly hydrophobic and bioaccumulative potential was low, as expected. High elimination rates for MC resulted in a virtually complete loss of body residue within hours to days following transfer to clean water. Uptake of TNT resulted in the substantial formation of bound residues. For fish, aqueous exposure was the dominant route of exposure to explosive compounds, with dietary uptake providing only minimal contribution. More realistic exposures using Composition B and multiple species found the presence of munitions in aquatic environments unlikely to result in biological effects. Verification of this conclusion should be pursued by determining site-specific exposure risk.

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Metal‐free hydroarylation derived ferrocene‐dihydrocoumarin as ultrasensitive dual‐channel probe selectively for picric acid

Srivastava

Tamrakar

Joshi

et al. 2023

Applied Organom Chemis

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4‐Ferrocenyl‐6,7‐dimethoxy‐3,4‐dihydrocoumarin (3) was synthesized by intermolecular hydroarylation of phenol from β‐ferrocene acrylic acid, and structure has been thoroughly characterized and confirmed by analysing X‐ray single‐crystal data. Compound 3 serves as highly selective fluorescent probe towards explosive picric acid (PA) through quenching of fluorescence in aqueous media. Probe 3 ensures high selectivity for PA in the background presence of various nitroaromatics, anions, cations and some phenols. The LoD for PA has been estimated to be 25.0 ppb using fluorescent probe 3. Binding stoichiometry and binding site of 3 towards PA have been supported by Job's plot, ESI‐mass, performing NMR titration and eventually by developing a model compound 4‐ferrocenyl‐3,4‐dihydrocoumarin 4, which strongly suggested 6,7‐dimethoxy groups as best probable binding site for PA. Overall, present approach deals with development of a ferrocenyl‐dihydrocoumarin conjugate for highly selective and ultrasensitive ‘turn‐off’ fluorescent probe for PA, which has been well‐supported through rational spectral analyses as well as through synthesizing a model compound.

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Fate and effects of picric acid and 2,6-DNT in marine environments: Toxicity of degradation products

Cited by 71 publications

References 15 publications

Treatment of phenanthrene and benzene using microbial fuel cells operated continuously for possible in situ and ex situ applications

Treatment of phenanthrene and benzene using microbial fuel cells operated continuously for possible in situ and ex situ applications

Summary Review of the Aquatic Toxicology of Munitions Constituents

Metal‐free hydroarylation derived ferrocene‐dihydrocoumarin as ultrasensitive dual‐channel probe selectively for picric acid

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