nitrophenols and nitrobenzene

Topics: Acetylcholinesterase; Biomarkers; Cholinesterase Inhibitors; Chromatography, High Pressure Liquid; Environmental Exposure; Environmental Monitoring; Humans; Insecticides; Mass Spectrometry; Methyl Parathion; Nitrobenzenes; Nitrophenols; Parathion; Reference Values; Specimen Handling

Nitrobenzene compounds are highly toxic pollutants with good stability, and they have a major negative impact on both human health and the ecological environment. Herein, it was found for the first time that fluorescent DNA-silver nanoclusters (DNA-AgNCs) can catalyze the reduction of toxic and harmful nitro compounds into less toxic amino compounds with excellent tolerance to high temperature and organic solvents. In this study, the reduction of p-nitrophenol (4-NP) as a model was systematically investigated, followed by expending the substrate to disclose the versatility of this reaction. This report not only expanded the conditions for utilizing catalytic reduction conditions of DNA-AgNCs as an efficient catalyst in the control of hazardous chemicals but also widened the substrate range of DNA-AgNCs reduction, providing a new angle for the application of noble metal nanoclusters.

Topics: Catalysis; DNA; Hot Temperature; Metal Nanoparticles; Nitrobenzenes; Nitrophenols; Silver

To improve catalytic performance and stability of Ag nanoparticles (Ag NPs), a facile ultrasonication-assisted chemical reduction method was developed to fabricate reduced graphene oxide (rGO) aerogels loaded with 1-3 nm Ag NPs under the normal temperature and pressure. The ultrasonication facilitated the dispersion of Ag(I) in the form of silver ammonia and anchored onto GO nanosheets. Ag(I) and GO were simultaneously reduced to Ag(0) immobilizing onto 3D rGO hydrogels within the heterogeneous liquid phase, and ultimately formed 3D rGO-Ag NPs aerogels. The 3D rGO-Ag NPs aerogels displayed superb catalytic performance for the reduction of nitrobenzene (NB), 1,3-dinitrobenzene (DNB) and 4-nitrophenol (NP) into aniline, 1,3-diaminobenzene and 4-aminophenol, respectively. The individual reduction rate K

Topics: Aminophenols; Carrier Proteins; Catalysis; Dipeptides; Graphite; Metal Nanoparticles; Neoplasm Proteins; Nitrobenzenes; Nitrophenols; Silver

We report the design and realization of yolk-shell structured nanospheres with periodic mesoporous organosilica (PMO) nanospheres or noble metal nanoparticles encapsulated in mesoporous silica shells via a selective etching method. These architectures have well controlled structure, size and morphology. The yolk-shell structured PMO@SiO2 nanoparticles can be precisely functionalized with different catalytic functionalities, even incompatible acidic and basic groups: the PMO core with amino (-NH2) groups and the mesoporous silica shell with sulfonic acid (-SO3H) groups. As a nanoreactor, the as-synthesized Au@SiO2 nanospheres show faster reduction of 4-nitrophenol than that of nitrobenzene. Furthermore, the prepared PMO-NH2@SiO2-SO3H nanoparticles can be used as bifunctional catalysts with highly efficient catalytic performance for catalyzing the deacetalization-Henry cascade reaction.

Topics: Catalysis; Gold; Metal Nanoparticles; Microscopy, Electron, Transmission; Nanospheres; Nitrobenzenes; Nitrophenols; Organogold Compounds; Particle Size; Porosity; Silicon Dioxide; Sulfonic Acids; Water

The simplicity and easy manipulation of a porous substrate-based ESI-MS technique have been widely applied to the direct analysis of different types of samples in positive ion mode. However, the study and application of this technique in negative ion mode are sparse. A key challenge could be due to the ease of electrical discharge on supporting tips upon the application of negative voltage. The aim of this study is to investigate the effect of supporting materials, including polyester, polyethylene and wood, on the detection sensitivity of a porous substrate-based negative ESI-MS technique. By using nitrobenzene derivatives and nitrophenol derivatives as the target analytes, it was found that the hydrophobic materials (i.e., polyethylene and polyester) with a higher tendency to accumulate negative charge could enhance the detection sensitivity towards nitrobenzene derivatives via electron-capture ionization; whereas, compounds with electron affinities lower than the cut-off value (1.13 eV) were not detected. Nitrophenol derivatives with pKa smaller than 9.0 could be detected in the form of deprotonated ions; whereas polar materials (i.e., wood), which might undergo competitive deprotonation with the analytes, could suppress the detection sensitivity. With the investigation of the material effects on the detection sensitivity, the porous substrate-based negative ESI-MS method was developed and applied to the direct detection of two commonly encountered explosives in complex samples.

Topics: Explosive Agents; Limit of Detection; Models, Molecular; Nitrobenzenes; Nitrophenols; Polyesters; Polyethylene; Porosity; Spectrometry, Mass, Electrospray Ionization; Static Electricity; Wood

This work is an attempt to establish if aromatic nitration processes are always associated with an increase of genotoxicity. We determined the mutagenic and genotoxic effects of Benzene (B), Nitrobenzene (NB), Phenol (P), 2-Nitrophenol (2-NP), 2,4-Dinitrophenol (2,4-DNP), Pyrene (Py), 1-Nitropyrene (1-NPy), 1,3-Dinitropyrene (1,3-DNPy), 1,6-Dinitropyrene (1,6-DNPy), and 1,8-Dinitropyrene (1,8-DNPy). The mutagenic activities were evaluated with umuC test in presence and in absence of metabolic activation with S9 mix. Then, we used both cytokinesis-blocked micronucleus (CBMN) assay, in combination with fluorescent in situ hybridization (FISH) of human pan-centromeric DNA probes on human lymphocytes in order to evaluate the genotoxic effects. Analysis of all results shows that nitro polycyclic aromatic hydrocarbons (PAHs) are definitely environmental genotoxic/mutagenic hazards and confirms that environmental aromatic nitration reactions lead to an increase in genotoxicity and mutagenicity properties. Particularly 1-NPy and 1,8-DNPy can be considered as human potential carcinogens. They seem to be significant markers of the genotoxicity, mutagenicity, and potential carcinogenicity of complex PAHs mixtures present in traffic emission and industrial environment. In prevention of environmental carcinogenic risk 1-NPy and 1,8-DNPy must therefore be systematically analyzed in environmental complex mixtures in association with combined umuC test, CBMN assay, and FISH on cultured human lymphocytes. © 2010 Wiley Periodicals, Inc. Environ Toxicol, 2012.

Topics: Benzene; Carcinogens; DNA Damage; Humans; In Situ Hybridization, Fluorescence; Lymphocytes; Mutagenicity Tests; Nitrobenzenes; Nitrophenols; Pyrenes; Salmonella typhimurium

The adsorption of phenol, p-nitrophenol, aniline, and nitrobenzene onto a commercial granular activated carbon (GAC: F400) preloaded with tannic acid (TA), a model background contaminant, was investigated. Compared with virgin GAC, the adsorption capacities of the four selected aromatic organic compounds (AOCs) onto GACs preloaded with TA at three densities were affected significantly. Also, the relationship between the adsorption capacities of AOCs and the characteristics of GACs was further discussed and clarified in this manuscript. The differences in the functional groups attached to the AOCs did not affect the similar linear relationship between the micropore surface area and their capacities to AOCs. However, the adsorption capacities of AOCs on TA-loaded GAC were affected by the different functional groups on the four AOCs: 67.6% of the capacity of aniline for virgin F400 remained on F400c (a preloaded GAC), compared with 23.8, 25.9, and 36.5% of phenol, p-nitrophenol, and nitrobenzene, respectively. The diversity of adsorption behavior of the four AOCs with different substituents was the result of hybrid contributions, such as hydrogen bonding, hydrophobic effect and aromatic stacking.

Topics: Adsorption; Charcoal; Nitrobenzenes; Nitrophenols; Organic Chemicals; Phenol; Water Purification

Nitrobenzene is a synthetic compound, more than 95% of which is used in the production of aniline. Nitrobenzene has been demonstrated to be substantially metabolized to p-Nitrophenol, p-Aminophenol and p-Nitroaniline in food animals (e.g., bovines, fowls). There have been no studies on the acute toxicity and the mutagenesis of the mixture of the three metabolites mentioned above. The aim of the present study is to testify the acute toxicity and the mutagenesis of the three metabolites mixture. Seventy Kunming mice (half male, half female) received an intragastric administration exposure to metabolites-containing suspension of 750, 638, 542, 461, 392, 333 mg kg(-1) body weight and 0.5% sodium carboxymethyl cellulose (control), followed by a 14-day observation. The medial lethal dose (LD(50)) concentration for nitrobenzene metabolites mixture in this study was 499.92 mg/kg. Their mutagenic toxicology was studied through micronucleus and sperm abnormality test. Kunming mice were twice intragastrically exposed to 1/5 LD(50), 1/10 LD(50), 1/20 LD(50) mg kg(-1) nitrobenzene metabolites-containing suspension spaced 24-h apart. Cyclophosphamide, pure water and sodium carboxymethyl cellulose served as doses of the positive group, the negative group and the solvent control group, respectively. The incidence of micronucleus and sperm abnormality increased significantly in the 1/5 LD(50) and 1/10 LD(50) group compared with the negative and solvent control group. A dose-related increase in the incidence of micronucleus and sperm abnormality was noted. In conclusion, the three metabolites mixture of nitrobenzene was secondary toxicity and mutagenic substances in mice.

Topics: Aminophenols; Aniline Compounds; Animals; Body Weight; Bone Marrow Cells; Female; Lethal Dose 50; Male; Mice; Micronucleus Tests; Mutagenesis; Mutagens; Nitrobenzenes; Nitrophenols; Spermatozoa; Toxicity Tests, Acute

In this study, the acute toxicities of nitrobenzene (NB) and para nitrophenol (p-NP) were investigated in a high rate sequential anaerobic migrating blanket (AMBR)/aerobic completely stirred tank reactor (CSTR) using Microtox and Daphnia magna tests. After sequential anaerobic and aerobic treatments, the inhibitions in the Microtox bacteria decreased from an initial 78.10-48.20% and 4.00%, respectively, in wastewater containing 40.00 mg/L p-NP. The inhibitions of the influent wastewater containing 60.00 mg/L NB decreased from 72.10% to 45.30% and to 4.00% after anaerobic and aerobic treatment, respectively. The acute toxicity removals were 94% and 93% in the effluent of the whole sequential system, for p-NP and NB, respectively. The acute toxicity in the influent was dependent on the parent NB and p-NP concentrations and ons their physicochemical properties such as hydrophobicity, octanol/water partition coefficient and vapour density for both Microtox bacteria and Daphnia magna while the toxicity in the effluent of the anaerobic reactor was strongly dependent on the metabolites of p-NP (p-amino phenol, phenol, NH(4)-N) and NB (aniline) for Microtox test. This effluent was not toxic to Daphnia magna.

Topics: Aerobiosis; Anaerobiosis; Animals; Daphnia; Nitrobenzenes; Nitrophenols; Photobacterium

p(4-vinylpyridine) (p(4-VP)) hydrogels were prepared in bulk (macro, 5 × 6 mm) and in nanosizes (370 nm) dimensions. The prepared hydrogels were used to remove organic aromatic contaminates such as 4-nitrophenol (4-NP), 2-nitrophenol (2-NP), phenol (Ph) and nitrobenzene (NB) from an aqueous environment. Important parameters affecting the absorption phenomena, such as the initial concentration of the organic species and the absorbent, absorption rate, absorption capacity, pH and the temperature of the medium, were evaluated for both hydrogel sizes. The absorption capacity of bulk and microgels were found to be 4-NP>2-NP>Ph>NB. Furthermore, p(4-VP) microgels were embedded in poly(acrylamide) (p(AAm)) bulk hydrogel as a microgel-hydrogel interpenetrating polymer network and proved to be very practical in overcoming the difficulty of using the microgels in real applications. Moreover, it was demonstrated that separately prepared magnetic ferrite particles inserted inside p(4-VP) microgels during synthesis allowed for trouble-free removal of p(4-VP)-magnetic composite microgels from the aqueous environment by an externally applied magnetic field upon completion of their task.

Topics: Hydrogels; Magnetic Fields; Magnets; Nitrobenzenes; Nitrophenols; Pyridines; Water Pollutants, Chemical; Water Pollution; Water Purification

Our previous studies have shown that major metabolites of nitrobenzene in bovine and fowl were p-nitrophenol, p-aminophenol, and p-nitroaniline. There are few reports about the subacute toxicity of the three metabolites. The aim of this study was to investigate the subacute toxicity of these compounds. A suspension containing three metabolites at 50, 25, and 5 mg kg(-1) body weight was administrated introgastrically to Sprague-Dawley rats of both sexes for 4 weeks. All four groups survived to the end of the 4-week treatment period. Compared to the control group, there was a significant difference in body-weight increases in rats administered nitrobenzene metabolites at 50 and 25 mg kg(-1) (P < 0.01). ALT, AST, ALP, T-CHO, TP, albumin, and creatinine were significantly increased in the 50-mg kg(-1) group and tended to increase in the 25-mg kg(-1) group, compared with controls. There was no significant difference in glucose between treatment groups and controls. RBC counts and concentration of Hb decreased significantly in the 50- and 25-mg kg(-1) groups, compared with controls, whereas WBC and Ret counts increased in the 50- and 25-mg kg(-1) groups and LYM only in the 50-mg kg(-1) group. There were no significant differences in MONO and neutrophil counts, compared with controls. Methemoglobin concentrations were significantly increased on day 21 of treatment in the 50-mg kg(-1) group and on day 28 in the 25- and 50-mg kg(-1) groups. The subacute toxicity was characterized by lesions affecting the liver, kidneys, spleen, cerebellum, and hematopoietic system.

Topics: Administration, Oral; Alanine Transaminase; Alkaline Phosphatase; Aminophenols; Aniline Compounds; Animals; Aspartate Aminotransferases; Blood Cell Count; Body Weight; Cholesterol; Creatinine; Female; Male; Methemoglobin; Nitrobenzenes; Nitrophenols; Organ Size; Random Allocation; Rats; Rats, Sprague-Dawley; Serum Albumin

Experiments have been performed with a semicontinuous batch reactor to compare the degradation efficiency of nitrobenzene in aqueous solution by the ultrasonic processes of single field, opposite dual fields, and orthogonal dual fields. Ultrasound with dual fields can improve the degradation efficiency of nitrobenzene compared to that of single field, and the improvement phenomenon is even more pronounced in the orthogonal dual-field system. The degradation reactions of nitrobenzene in the three processes all follow the pseudofirst-order kinetic model. The mechanism investigation indicates the degradation proceeds via hydroxyl radical (*OH) oxidation. The enhancement efficiency of orthogonal dual fields is attributed to an obvious synergetic effect, which accelerates the *OH initiation from 0.28 micromol L(-1) min(-1) for a single field to 0.98 micromol L(-1) min(-1) compared with 0.42 micromol L(-1) min(-1) for opposite dual fields, resulting in rapid formation of an increased diversity of byproducts and an advanced degree of mineralization of total organic carbon (TOC). The introduction of an ultrasonic field placed in the different spatial position causes a variable kinetic order during the removal of TOC. The degradation byproducts are identified by gas chromatography mass spectrometry and ion chromatography, including p-, m-nitrophenol, malonic acid, nitrate ion, 4-nitrocatechol, phenol, maleic acid, oxalic acid, hydroquinone, 1,2,3-trihydroxy-5-nitrobenzene, and acetic acid.

Topics: Acetic Acid; Carbon; Catechols; Chromatography, Gas; Hydroquinones; Hydroxyl Radical; Ions; Kinetics; Maleates; Malonates; Nitrates; Nitrobenzenes; Nitrophenols; Oxalic Acid; Ultrasonics; Water

This article attempts to discern the physical (or mechanistic) features of the sonochemical degradation of two major and ubiquitous nitroaromatic pollutants, viz. nitrobenzene and p-nitrophenol. The fundamental physical phenomenon behind sonochemical degradation of pollutants is radial motion of cavitation bubbles. This study implements a dual approach to the problem, i.e. results of the experiments under different conditions have been coupled to a mathematical model that addresses physics and chemistry of the cavitation bubbles. Various experimental techniques applied in this study influence important physical parameters related to cavitation phenomenon in the liquid medium such as extent of radical production from the bubble, thickness of the liquid shell surrounding the bubble that gets heated up during transient collapse, the concentration of the pollutant in the interfacial region and extent of radical scavenging in the medium. Concurrent analysis of the experimental and simulation results reveal that overall degradation of the pollutant achieved for a given combination of experimental conditions is a function of competing (and sometimes conflicting) effect of these parameters. A semi-quantitative account of the relative influence of these parameters and the interrelations between them is presented.

Topics: Algorithms; Models, Theoretical; Nitrobenzenes; Nitrophenols; Ultrasonics; Waste Disposal, Fluid; Water Pollutants, Chemical

For understanding the mechanism of biodegradation in a SBR reactor treating nitrogen-containing aromatic wastewater, the reactor sludge samples were used for PCR-DGGE analysis. Meanwhile, 90 strains were isolated from the sludge sample after the start-up stage, 36 strains can degrade nitrogen-containing aromatic compounds. 5 strains nitrogen-containing aromatic degraders were further performed aromatic ring cleavage dioxygenase analysis. Result showed that bacterial diversity in the reactor were changed during the start-up stage, Acidobacteria (SBR1, SBR7), Actinobacteria (SBR4) and beta-Proteobacteria (SBR6) may play important role in biodegradation of nitrogen-containing aromatic compounds, among the isolates. Different bacterial diversity research method all have bias, and reflected different part of the bacterial structure. Among the isolates, Actinobacteria were the majority, by analysis the ring cleavage enzyme activity, further understood how the four nitrogen-containing aromatic compound were degraded in the reactor. The results provided valuable references for studying microbiological degradation mechanism in the reactor, and enriched microbial resources of nitrogen-containing aromatic degrader.

Topics: Aniline Compounds; Bacteria; Biodegradation, Environmental; Biodiversity; Bioreactors; Hydrocarbons, Aromatic; Molecular Structure; Nitrobenzenes; Nitrogen; Nitrophenols; Waste Disposal, Fluid

This work combined selective adsorption and bioaugmentation to treat mixed wastewater of nitrobenzene and p-nitrophenol. The mixed wastewater of nitrobenzene (217 mg/L) and p-nitrophenol (500 mg/L) was adjusted its pH to 8 and then passed through the adsorption column at 100 mL/h. In effluent the nitrobenzene concentration was less than 4 mg/L. Without the toxic inhibition of nitrobenzene, p-nitrophenol in effluent could be degraded within 60 h through bioaugmentation. About 23 mg/g of nitrobenzene adsorbed the dry resin HU-05 could be desorbed and degraded through bioaugmentation. During this process the adsorption capacity of the resin HU-05 was recovered partly. The recovered extent was limited by nitrobenzene bioavailability. The performance of the resin HU-05 kept stably in the recycle experiments of 60 days.

Topics: Adsorption; Biodegradation, Environmental; Bioreactors; Biotechnology; Hydrogen-Ion Concentration; Industrial Waste; Nitrobenzenes; Nitrophenols; Polymers; Resins, Plant; Waste Disposal, Fluid; Water Microbiology; Water Pollutants, Chemical; Water Purification

Many nitrogen-containing aromatic compounds (NACs), such as nitrobenzene (NB), 4-nitrophenol (4-NP), aniline (AN), and 2,4-dinitrophenol (2,4-DNP), are environmentally hazardous, and their removal from contaminated water is one of the main challenges facing wastewater treatment plants. In this study, synthetic wastewater containing NB, 4-NP, 2,4-DNP, and AN at concentrations ranging from 50 to 180 mg/L was fed into a sequencing batch reactor (SBR). Analyses of the SBR system indicated that it simultaneously removed more than 99% of the NACs at loading rates of 0.36 kg NB/(m3 x d), 0.3 kg 4-NP/(m3 x d), 0.25 kg AN/(m3 x d), and 0.1 kg 2,4-DNP/(m3 x d). Bacterial groups of Bacteriodetes, Candidate division TM7, alpha-Proteobacteria, and beta-Proteobacteria were dominant in the clone libraries of 16S rRNA genes retrieved from the microbial communities in the SBR system. "Cycle tests" designed to alter feeding and aeration parameters of the SBR system demonstrated that the resident microbial biome of the SBR system responded rapidly to changing conditions. Consumption of O2 was concomitant with the apparent mineralization of NACs. Aromatic ring-cleaving dioxygenase activities suggested that (1) AN and NB were degraded via catechol 2,3-dioxygenase; (2) 4-NP was degraded via 1,2,4-benzentriol 1,2-dioxygenase; and (3) 2,4-DNP was degraded via an unresolved pathway.

Topics: Aniline Compounds; Bacteria; Bioreactors; Dioxygenases; DNA, Bacterial; Nitrobenzenes; Nitrogen; Nitrophenols; RNA, Ribosomal, 16S; Waste Disposal, Fluid; Water Pollutants, Chemical

Nitroaromatic compounds such as nitrobenzene and nitrophenols are largely synthesised and particularly often occur in water bodies as toxic pollutants. The degradation of these compounds in the environment via direct photolysis and by biological treatment is difficult and usually slow. In our two previous published papers, we have discussed the advanced oxidation of nitrobenzene and nitrophenols in aqueous solutions irradiated by direct photolysis using polychromatic light and by means of UV/H2O2 process. The experimental results suggested the UV/H2O2 process is an effective and efficient technology for complete mineralization of these organic compounds. Based on the results therein, comprehensive reaction mechanism for nitrobenzene photolysis was proposed with detailed discussions.

Topics: Hydrocarbons, Aromatic; Hydrogen Peroxide; Molecular Structure; Nitrobenzenes; Nitrogen Compounds; Nitrophenols; Photolysis; Ultraviolet Rays; Water; Water Pollutants, Chemical

Photolysis of nitroaromatic compounds in aqueous solution is a very slow and inefficient process. As already observed for a variety of organic pollutants, considerably faster degradation rates of nitrobenzene (NBE), 1-chloro-2,4-dinitrobenzene (CDNB), 2,4-dinitrophenol (DNP), and 4-nitrophenol (PNP) could be achieved, when the oxidative degradation of these compounds was initiated by hydroxyl radicals produced by UV-C photolysis of H2O2. Analysis of intermediate products formed during irradiation by HPLC and IC showed that cleavage of the aromatic ring should occur at an early stage of the oxidation process and that organic nitrogen was almost completely converted to nitrate. The optimal initial concentration of hydrogen peroxide ([H2O2]OPT) leading to the fastest oxidation rate, which depends on the initial substrate concentration ([S]0), could be evaluated using a simplified expression based on the main reactions involved in the first stages of the degradation process. Using only a minimum of kinetic and analytical information, this expression shows that the ratio R(OPT) (= [H2O2]OPT/[S]0) is related to the bimolecular rate constants for the reactions of hydroxyl radicals with substrate (kS) and H2O2 (kHP) and to the corresponding molar absorption coefficients (epsilonS, epsilonHP). Competition experiments between selected pairs of the substrates showed that their relative reactivity toward hydroxyl radicals could be correctly predicted using the same simplified approach. The results of our investigations as well as literature data support the general validity of the proposed procedure for optimizing oxidation rates of the UV/H2O2 process.

Topics: 2,4-Dinitrophenol; Air Pollution; Chromatography, High Pressure Liquid; Dinitrochlorobenzene; Humans; Hydrogen Peroxide; Nitrobenzenes; Nitrophenols; Oxidation-Reduction; Photolysis; Ultraviolet Rays; Water Pollutants, Chemical

Electron beam irradiations of aqueous solutions containing 15-30 mg/L of nitrobenzene at 60 kGy dose removed 78% of the contaminant. Three mononitrophenols were detected as by-products of electron beam treatment of nitrobenzene. A mixed culture enriched on a mixture of 2-, 3-, and 4-nitrophenol degraded both the residual nitrobenzene and the nitrophenol products. Percentage removal of nitrobenzene increased with increasing electron beam dose. This observation led to the conceptual design of a two-stage electron beam microbial process for degradation of nitrobenzene. Three groups of pure isolates were characterized from the mixed culture based on their abilities to grow on cor- responding nitrophenol substrates: Group A, 2NP(-)3NP(-)4NP(+); Group B, 2NP(+)3NP(+)4NP(-); and Group C, 2NP(-)3NP(+)4NP(-). Bacteria that grew on 3-NP transformed nitrobenzene into ammonia in the electron beam-treated nitrobenzene samples.

Topics: Biotransformation; Chromatography, Gas; Chromatography, High Pressure Liquid; Electrons; Nitrobenzenes; Nitrophenols; Pseudomonas; Water Microbiology; Water Purification

Twenty-one microorganisms were screened for their ability to convert nitroaromatics into 3-nitrocatechol as a result of the action of an oxygenase. Cultures containing toluene dioxygenases and phenol monooxygenases accumulated 3-nitrocatechol during incubation with nitrobenzene and nitrophenol, respectively. Nocardia S3 was selected and studied in more detail. Toluene-pregrown cultures were able to degrade nitrobenzene with a concomitant formation of 3-nitrocatechol. The rates of nitrobenzene utilization decreased throughout the biotransformation period and finally the accumulation ceased. The gradual deterioration of the biotransformation rates was not a consequence of depletion of the NADH pool, but was due to the accumulation of 3-nitrocatechol. The inhibition of nitrobenzene biotransformation by 3-nitrocatechol greatly impacts 3-nitrocatechol production processes.

Topics: Biotransformation; Catechols; Culture Media; Nitrobenzenes; Nitrophenols; Nocardia; Oxidoreductases; Oxygen Consumption; Oxygenases; Toluene

Using a mixture of three mono nitrophenols as sole carbon, nitrogen and energy sources, mixed cultures were enriched from municipal activated sludge to degrade both nitrophenols and nitrobenzene. Bacterial growth and degradation rate could be increased by supplementing the medium with 0.1% YE. Microorganisms were isolated from the nitrophenols enrichment, and they were identified as strains of Comamonas testosteroni and Acidovorax delafieldii. These strains showed broad degradation ability toward nitrophenols and nitrobenzene.

Topics: Biodegradation, Environmental; Gram-Negative Aerobic Rods and Cocci; Nitrobenzenes; Nitrophenols; Sewage

Peroxynitrite, the reaction product of nitric oxide (NO.) and superoxide anion (O2.-) produced during immune activation by a variety of inflammatory cells, may contribute to genotoxicity of benzene through its ability to carry out hydroxylation and nitration. After exposure of benzene to synthesised peroxynitrite, phenol, nitrophenols (p-nitrophenol, o-nitrophenol and m-nitrophenol) and nitrobenzene were identified in the reaction mixture by HPLC separation and single UV wavelength and diode array detection. The formation of phenol, nitrophenols and nitrobenzene showed a linear relationship with both benzene and peroxynitrite concentrations. The molar ratio for phenol/(nitrobenzene and nitrophenols) was approximately 9/5 with a total product yield of 14% hydroxylated and nitrated products as based on peroxynitrite. The physiological relevance of the chemical reaction between benzene and peroxynitrite was tested by detecting the reaction products in human neutrophils (2.5 x 10(7)cells/ml) incubated with 10 mM benzene for 25 min. The concentration of phenol and p-nitrophenol were found to be 1.29+/-0.22 and 1.56+/-0.61 microM (mean+/-SD) in the incubation medium of the neutrophils pretreated with phorbol myristate acetate (500 nM) for 5 min, respectively, whereas no metabolites were detected if the neutrophils were not pretreated. Nitrated aromatic compounds are known to be more carcinogenic than the parent compounds. It is reported that acute and chronic infection increases the risk of cancer at various sites; and that anti-inflammatory agents decrease benzene myelotoxicity. We suggest that the increased production of peroxynitrite during chronic inflammation combined with benzene exposure may increase the carcinogenicity of benzene by a mechanism that includes the formation of metabolites from the chemical reaction between benzene and peroxynitrite. Thus, peroxynitrite mediated hydroxylation and nitration of benzene during immune activation represent a novel in vivo mechanism for generation of proximal carcinogens of benzene.

Topics: Benzene; Carcinogens; Dose-Response Relationship, Drug; Humans; Neutrophils; Nitrates; Nitrobenzenes; Nitrophenols; Phenol; Spectrophotometry, Ultraviolet; Tetradecanoylphorbol Acetate

When male guinea pigs were given a single dose of Cd (2.0 mg Cd2+/kg, ip) 72 hr prior to sacrifice, the hepatic reduced glutathione (GSH) level did not change although glutathione S-transferase (GST) activities toward the substrates 1-chloro-2,4-dinitrobenzene (CDNB), 1,2-dichloro-4-nitrobenzene (DCNB), ethacrynic acid (EAA), and 1,2-epoxy-3-(p-nitrophenoxy) propane (ENPP) increased significantly as compared to controls. Cd did not change the renal GSH level and GST activities toward CDNB and EAA. However, significant increase was observed in the GST activity for DCNB whereas GST activity for ENPP was significantly inhibited by Cd. When the animals were given a single dose of Ni (14.8 mg Ni2+/kg, sc) 16 hr prior to sacrifice, significant increases were observed in hepatic GSH level and GST activities toward CDNB, DCNB, EAA and ENPP. Ni, however, depressed the renal GSH level and GST activities toward CDNB, DCNB and ENPP significantly. The renal GST activity toward EAA remained unaltered. For the combined treatment, guinea pigs received the single dose of Ni 56 hr after the single dose of Cd and then they were killed 16 hr later. In these animals, no significant alteration was observed in the hepatic GSH level. The augmentation of elevation was observed in hepatic GST activities toward CDNB and DCNB. Combined metal treatment did not potentiate the elevation of hepatic GST activities toward EAA and ENPP to any greater degree. The depression of renal GSH level was significantly ameliorated by the combined treatment. Combination treatment potentiated the depression of renal GST activity for ENPP but not for CDNB.(ABSTRACT TRUNCATED AT 250 WORDS)

Topics: Animals; Benzoates; Benzoic Acid; Cadmium; Dinitrochlorobenzene; Ethacrynic Acid; Glutathione Transferase; Guinea Pigs; Kidney; Liver; Male; Nickel; Nitrobenzenes; Nitrophenols; Organophosphorus Compounds; Substrate Specificity

A high-performance liquid chromatographic method is described for the simultaneous determination of six urinary metabolites of several aromatic chemicals: phenol (from benzene), hippuric acid (from toluene), 3-methylhippuric acid (from xylene), mandelic and phenylglyoxylic acid (from styrene) and 4-nitrophenol (from nitrobenzene). Reversed-phase liquid chromatography was performed in an isocratic mode at 1 ml/min on a 5-microns C18 column using two mobile phases: (A) acetonitrile-1% phosphoric acid (10:90); (B) acetonitrile-1% phosphoric acid (30:70). Phase A separates the six metabolites well, but phase B allows to a more rapid and reproducible simultaneous determination of phenolic compounds than phase A. For these compounds a prior enzymic hydrolysis step using Helix pomatia juice is performed to hydrolyse their sulphate and glucuronate conjugates. The reproducibility and the specificity are both excellent. Furthermore, the method is rapid, economical and easily automated. The proposed method appears very suitable for the routine monitoring of workers exposed to these chemicals on the basis of the biological threshold limit values.

Topics: Benzene; Chromatography, High Pressure Liquid; Glyoxylates; Hippurates; Humans; Mandelic Acids; Nitrobenzenes; Nitrophenols; Occupational Exposure; Phenol; Phenols; Spectrophotometry, Ultraviolet; Styrene; Styrenes; Toluene; Xylenes

The percutaneous absorption of 2-nitro-p-phenylene-diamine, 4-amino-2-nitrophenol, nitrobenzene, p-nitroaniline, and 2,4-dinitrochlorobenzene was measured through human and monkey skin. Human studies were performed with excised skin in diffusion cells. Absorption through monkey skin was measured by in vivo and in vitro techniques. Results were compared with those from previously reported human in vivo studies on 2,4-dinitrochlorobenzene and nitrobenzene. Rapid penetration was observed with all compounds, with maximum absorption occurring the first few hours. No significant differences in absorption were found in values obtained by the different procedures except for the highly volatile (and therefore difficult to compare) compound nitrobenzene. A comparison of the human and monkey in vitro data showed a trend toward increased absorption through monkey skin, but the increase was not statistically significant. The monkey in vivo and in vitro results showed that absorption of all compounds except nitrobenzene was slightly less in the in vitro studies; however, the values were not significantly different. The relative volatility of these nitroaromatic compounds was measured by the loss of compound from epidermal discs at various time intervals. The greatest loss of applied material occurred with nitrobenzene; however, substantial amounts of the other compounds were lost, particularly during the first minute after application as the acetone vehicle evaporated. Monkey skin was found to be a good model for human skin for the determination of the percutaneous absorption of these compounds, and in vitro measurements of absorption agreed reasonably well with values obtained by in vivo techniques. A good correlation was not observed between the absorption of these compounds and their solubility properties.

Topics: Aniline Compounds; Animals; Dinitrochlorobenzene; Haplorhini; Humans; In Vitro Techniques; Kinetics; Nitro Compounds; Nitrobenzenes; Nitrophenols; Phenylenediamines; Skin Absorption; Volatilization

The sorption of benzoic acid, nitrobenzene, 4-nitrophenol, 2,4-dichlorophenoxyacetic acid (2,4-D), and naphthalene was determined for 10 Danish soils in laboratory studies. Measured equilibrium isotherms were of nonlinear Freundlich type for nearly all combinations of soil-test compounds. Adsorption was significantly correlated with the organic carbon content of the soils tested. No significant correlations with pH and cation-exchange capacity were observed. The adsorption of benzoic acid was found to be reversible and the sorption of naphthalene was reversible in 4 of 10 soils. A desorption-resistant fraction of adsorbed 2,4-D was estimated from interdependent adsorption and desorption isotherms.

Topics: 2,4-Dichlorophenoxyacetic Acid; Adsorption; Benzoates; Benzoic Acid; Denmark; Nitrobenzenes; Nitrophenols; Polychlorinated Biphenyls; Soil; Soil Pollutants; Temperature

Topics: Alanine Transaminase; Alkaline Phosphatase; Aminophenols; Aspartate Aminotransferases; Bilirubin; Blood Platelets; Cholesterol; Erythrocyte Count; Jaundice; Leukocyte Count; Methemoglobinemia; Nitrobenzenes; Nitrophenols; Phenols; Rats; Research; Reticulocytes; Serum Albumin; Serum Globulins; Toxicology; Urine

Topics: Body Fluids; Humans; Lung; Nitrobenzenes; Nitrophenols

Topics: Dinitrobenzenes; Nitrobenzenes; Nitrophenols; Organic Chemicals

Topics: Anti-Bacterial Agents; Dermatologic Agents; Dinitrophenols; Nitrobenzenes; Nitrophenols; Research

Topics: Animals; Nitrobenzenes; Nitrophenols; Rabbits

Topics: Aminophenols; Animals; Catechols; Nitrobenzenes; Nitrophenols; Rabbits