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Nitrobenzol
NITROBENZOL · Nitrobenzen · MIRBANE OIL · Nitrobenzeen · 1-Nitrobenzene · PhSO3H · NCI-C60082 · MYRBANE OIL
Identifikatoren & physikalische Daten
| CAS No. | 98-95-3 |
|---|---|
| Summenformel | C6H5NO2 |
| Durchschnittliche Molmasse | 123,11 g/mol |
| Monoisotopische Masse | 123,0320284 g/mol |
| SMILES | O=[N+]([O-])c1ccccc1 |
| InChIKey | LQNUZADURLCDLV-UHFFFAOYSA-N |
| PubChem CID | 7416 |
| ChEMBL | CHEMBL15750 |
| ChEBI | CHEBI:27798 |
| EC No. | 202-716-0 |
| DTXSID | DTXSID3020964 |
| Lokaler Name | Nitrobenzol |
Chemische & physikalische Eigenschaften
| XLogP | 1,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 45,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 102 |
| Stoffklassen | Hazardous Air Pollutants (HAPs)Nitrogen Compounds -> Nitros, AromaticCarcinogensVolatile Organic Compound (VOC) and(or) Semi-Volatile Organic Compound (SVOC) |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Duftstoffe | Fragrance substance (Nitrobenzene) -> IFRA amendment 40 |
| Pestizide | Pesticide -> EPA IRIS |
| LogP (Verteilungskoeffizient) | log Kow = 1.851.86 |
| Geruch | Odor of volatile oil almondPungent odor like paste shoe polish |
| Geschmack | Aqueous solutions are sweet tasting |
| Dichte | 1.2037 at 68 °F (EPA, 1998) - Denser than waterwill sink1.2037 g/cu cm at 20 °CDensity: 1.199 g/cu cm at 25 °C/4 °CSpecific heat: 1.509 J/g at 30 °CRelative density (water = 1): 1.21.205 @ 15°C1.196 g/mL at 25 °C (lit.) |
| Viscosity | 1.863 mPa-s at 25 °C |
| Color/Form | Greenish-yellow crystals or yellow, oily liquidColorless to yellow, oily liquid (Note: A solid below 42 degrees F).Bright-yellow crystals or pale-yellow to colorless, oily liquid |
| Löslichkeit | Insoluble (<1 mg/ml at 75 °F) (NTP, 1992)Slightly soluble in carbon tetrachloridevery soluble in ethanol, diethyl ether, acetone, benzeneSoluble in ~500 parts waterfreely soluble in alcohol, benzene, ether, oilsReadily soluble in most organic solvents and is completely miscible with diethyl ether, benzene, and alcohol.Slightly soluble in water with a solublity of 0.19% at 20 °C and 0.8% at 80 °CIn water, 2.09X10+3 mg/L at 25 °C1.90g/l |
| Flammpunkt | 190.4 °F (EPA, 1998)88 °C190 °F (88 °C) (Closed cup)88 °C c.c. |
| Schmelzpunkt | 5-6 °C (lit.) |
| Siedepunkt | 210-211 °C (lit.) |
| Dampfdichte | 4.2 (vs air) |
| Dampfdruck | 0.15 mm Hg ( 20 °C) |
| Brechungsindex | n20/D 1.551(lit.) |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 3.98(at 0℃) |
| Aggregatzustand | Liquid |
| Farbe | Clear yellow |
| pH | 8.1 (1g/l, H2O, 20℃) |
| Explosionsgrenze | 1.8-40%(V) |
| Spezifische Wärmekapazität | Cp(liquid): 1.51 J/(g·K)Cp(gas): 0.98 J/(g·K), at 25℃ |
| Merck | 14,6588 |
| BRN | 507540 |
| Henry-Konstante | 9.86 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) |
| Dielektrizitätskonstante | 35.7(20℃) |
| Stabilität | Stable. Incompatible with strong oxidizing agents, strong reducing agents, strong bases. Flammable. Note wide explosion limits. |
| InChI | 1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H |
| InChIKey | LQNUZADURLCDLV-UHFFFAOYSA-N |
| SMILES | [O-][N+](=O)c1ccccc1 |
| LogP (Verteilungskoeffizient) | 1.86 at 24.5℃ and pH7.9 |
| Oberflächenspannung | 43.9mN/m at 20°C |
| CAS Datenbank | 98-95-3(CAS DataBase Reference) |
| NIST chemische Informationen | Benzene, nitro-(98-95-3) |
| EPA chemische Informationen | Nitrobenzene (98-95-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P203, P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P318, P319, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)H301+H311+H331 (10%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]P203, P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P318, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Benzene, nitro-Hazard Traits - CarcinogenicityEndocrine ToxicityHematotoxicityHepatotoxicity and Digestive System ToxicityNephrotoxicity and Other Toxicity to the Urinary SystemNeurotoxicityReproductive ToxicityRespiratory ToxicityBenzene, nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, nitro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 09-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14701Substance: NitrobenzeneNitrobenzene: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzene, nitro-: Human health tier II assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Moderate explosion hazard when exposed to heat or flame. Reacts violently with nitric acid, aluminum trichloride plus phenol, aniline plus glycerine, silver perchlorate and nitrogen tetroxide. Avoid aluminum trichloridegycerolsulfuric acidoxidantsphosphorus pentachloridepotassiumpotassium hydroxide. Avoid sunlight, physical damage to container, freezing, and intense heat. (EPA, 1998)· Combustible material: may burn but does not ignite readily.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 88 °C explosive vapour/air mixtures may be formed. Risk of fire and explosion. See Chemical Dangers. |
| Brandpotenzial | /Fire hazard is/ moderate when exposed to heat, flame, or oxidizers. |
| Gesundheitsgefahren | Can cause death due to respiratory failure. Classified as extremely toxic. The mean lethal oral dose is probably between 1 and 5 grams. Systemic effects may be delayed for a few hours. This compound is rapidly absorbed through the skin. It is a powerful methemoglobin former. Ethyl alcohol aggravates intoxication caused by nitrobenzene exposure. (EPA, 1998)· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin. |
| Gefahrenübersicht | Nitrobenzene is an industrial chemical. It is an oily yellow liquid with an almond-like odor. It dissolves only slightly in water and will evaporate to air. It is produced in large quantities for use in industry. Most of the nitrobenzene produced in the United States is used to manufacture a chemical called aniline. Nitrobenzene is also used to produce lubricating oils such as those used in motors and machinery. A small amount of nitrobenzene is used in the manufacture of dyes, drugs, pesticides, and synthetic rubber.Nitrobenzene is used to manufacture aniline. Acute (short-term) and chronic (long-term) inhalation, oral, and dermal exposure of humans to nitrobenzene result in effects on the blood (i.e., methemoglobinemia). At low nitrobenzene concentrations, symptoms include fatigue, weakness, dyspnea, headache, and dizziness. At higher concentrations, depressed respiration, bluish-gray skin, disturbed vision, and coma may occur. No information is available on the reproductive, developmental, or carcinogenic effects of nitrobenzene in humans. Animal studies indicate that inhalation exposure to nitrobenzene does not result in developmental effects, while reproductive effects, such as a decrease in fertility, reduced testicular weights, and decreased sperm production, have been noted. EPA has classified nitrobenzene as a Group D, not classifiable as to human carcinogenicity.Liquid causes first degree burns on short exposure[CHRIS] Most cases of nitrobenzene-induced methemoglobinemia are probably mild. Severe methemoglobinemia and liver damage have been reported after occupational exposure. Anemia is the most common finding seen after chronic poisoning. Methemoglobinemia has been produced by inhalation of nitrobenzene at 5 ppm in animals and 6 ppm in humans. There is no evidence that dermal exposure in the industrial environment could induce significant methemoglobinemia. [ACGIH] In high-dose reproductive studies of animals, nitrobenzene causes testicular damage. [Frazier, p. 347] Inhalation of high concentrations can cause CNS depression[ICSC] |
| DOT-Nummer und Handbuch | 1662 152 |
| Reaktive Gruppe | Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| EG-Einstufung | Symbol: T, NR: 23/24/25-40-48/23/24-51/53-62S: (1/2)-28-36/37-45-61 |
| UN-Einstufung | UN Hazard Class: 6.1UN Pack Group: II |
| Special Reports | USEPAAmbient Water Quality Criteria Doc: Nitrobenzene (1980) EPA 440/5-80-061.WHOEnvironmental Health Criteria 230: Nitrobenzene (2003). EHC are designed for scientists and administrators responsible for the establishment of safety standards and regulations and provide basic scientific risk evaluations of a wide range of chemicals and groups of chemicals.[http://www.inchem.org/pages/ehc.html]DHHS/ATSDRToxicological Profile for Nitrobenzene (1990) ATSDR/TP-90/19. The ATSDR toxicological profile succinctly characterizes the toxicologic and adverse health effects information for a hazardous substance.[Available from, as of November 18, 2009: http://www.atsdr.cdc.gov/toxprofiles/tp140.html]IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Nitrobenzene, in Printing Processes and Printing Inks, Carbon Black and Some Nitro Compounds, vol 65. p.381-408 (1996). IARC Monographs provide critical reviews of data on carcinogenicity for agents to which humans are known to be exposed and on specific exposure situations.[Available from, as of November 18, 2009: http://monographs.iarc.fr/ENG/Monographs/vol65/index.php]National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Nitrobenzene (98-95-3) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s121zntb.pdf] |
| Brandbekämpfung | Move container from fire area if you can do it without risk. Fight fire from maximum distance. Dike fire control water for later disposaldo not scatter the material. Keep unnecessary people awayisolate hazard area and deny entry. Stay upwindkeep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. Remove and isolate contaminated clothing at the site.Use water spray, alcohol-resistant foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give a slurry of activated charcoal in water to drink. Rest. Refer for medical attention . |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| Erste Hilfe | Warning: Effects may be delayed. Caution is advised. Prior alcohol consumption aggravates the effects of nitrobenzene poisoning.General First Aid:(General first aid procedures) |
| Sichere Lagerung | Separated from combustible substances, reducing agents, strong oxidants, strong acids and food and feedstuffs. Store in an area without drain or sewer access. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA).Biological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or end of shift0.1 [ppm] |
| Brandbekämpfungsverfahren | Water, foam, carbon dioxide, or dry chemicalUse dry chemical, foam, carbon dioxide, or water spray. Use water spray to keep fire-exposed containers cool. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products.If material is on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. |
| Lagerbedingungen | Store in a cool, dry, well-ventilated, dark location. Separate from acids, bases, oxidizing materials, and metals.PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/ |
| Reinigungsverfahren | SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.1. Ventilate area of spill or leak. 2. If in liq form, for small quantities, absorb on paper towels. Evaporate in safe place (such as fume hood). Allow sufficient time for evaporating vapors to completely clear hood ductwork. Burn paper in suitable location away from combustible materials. Large quantities can be collected and atomized in suitable combustion chamber equipped with an appropriate effluent gas cleaning device. 3. If in solid form, allow to melt and handle as indicated in ... /phrase 2/ above.Environmental considerations: Land spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be contained with a flexible impermeable membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash or cement powder.Environmental considerations: Water spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.For more Cleanup Methods (Complete) data for NITROBENZENE (7 total), please visit the HSDB record page. |
| Freisetung ohne Brand | Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]: |
| Entsorgungsverfahren | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U169, F004, and D036 must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.Nitrobenzene is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration. Incineration (1800 °F, 2.0 sec minimum) with scrubbing for nitrogen oxide abatement.A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.A comparison was made of various methods for treating petrochemical wastewater. Among these are wet air oxidation, carbon adsorption, chemical oxidation, and biological treatment. Among the biological treatment methods are stripping of volatile organic carbon, sorption on biomass, and biodegradation. Nitrobenzene was among the priority pollutants commonly present in oil refinery wastewater which show >95% biodegradation.For more Disposal Methods (Complete) data for NITROBENZENE (13 total), please visit the HSDB record page. |
| Verschüttetes entsorgen | Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Toxikologische Informationen | CDC-ATSDR Toxicological Profile |
| Cancer Sites | Endocrine |
| Wechselwirkungen | Experiments pertaining to the influence of gut microflora on the metabolism of nitrobenzene, included an in vivo protocol in which normal or antibiotic-treated male F344 (COBS CDF/CrlBR) rats were gavaged with 225 mg/kg nitrobenzene (containing 0.1 uCi/mg (14C)-nitrobenzene). Rats were kept in metabolic cages for up to 72 hours after treatment, during which urine, feces, and expired air were collected. To the extent possible, the excretory products were characterized and measured by high-performance liquid chromatography. ... A statistically significant decrease in p-hydroxyacetanilide (a reductive metabolite of nitrobenzene) and a slight increase in p- and m-nitrophenol (oxidative metabolites) were observed in antibiotic-treated rats versus controls. Antibiotic pretreatment ameliorated the nitrobenzene-induced methemoglobinemia following a single oral dose of 300 mg/kg. Moreover, antibiotic-treated animals exposed to 300 mg/kg nitrobenzene had metHb concentrations of 2.1+ or - 0.4%, 2.8 + or - 0.5%, and 1.9 + or - 1.9% at 6, 24, and 96 hours after the dose. However, nitrobenzene-exposed vehicle-control rats still had elevated metHb concentrations (20.0 + or - 7.9%) 96 hours after the dose.Synergism between orally administered nitrobenzene and six other common industrial compounds (formalin, butylether, aniline, dioxane, acetone, and carbon tetrachloride) was demonstrated in rat studies using death as the end-point.When alcohol was given orally and nitrobenzene was given intravenously, there was increased toxicity in rabbits. Alcohol also enhanced the neural toxicity of nitrobenzene in rabbits when nitrobenzene was applied to the skin.To determine whether nitro reduction by the gut flora can play an important role in chem toxicity, methemoglobin formation was measured after admin of nitrobenzene to germ-free rats and to germ-free rats acclimatized to the normal animal room. When nitrobenzene (200 mg/kg in sesame oil) was admin to normal male Sprague Dawley rats ip, about 30-40% of blood hemoglobin was converted to methemoglobin within 1-2 hr. When same dose was given to germ-free or antibiotic pretreated rats, no measurable methemoglobin formation occurred even up to 7 hr after admin. Since germ-free animals are free from microbial flora, gut flora present in normal and acclimatized animals may be responsible for redn of nitrobenzene in vivo and subsequent methemoglobin formation. |
| Zielorgane | Cancer, Hematological (Blood Forming), Hepatic (Liver), Renal (Urinary System or Kidneys), Reproductive (Producing Children), Respiratory (From the Nose to the Lungs)Eyes, skin, blood, liver, kidneys, cardiovascular system, reproductive system |
| Ökotoxizitätswerte | EC50Species: Chlorella pyrenoidosa (Green algae, log growth phase, 2x10+8 cells/L)Conditions: freshwater, static, 25 °C, pH 6.6Concentration: 18000 ug/L for 96 hr (95% confidence interval: 15000-22000 ug/L)Effect: growth, general /formulation/Species: Chlorella pyrenoidosa (Green algae, 2x10+6 cells/mL)Conditions: freshwater, static, 22 °C, pH 7.4Concentration: 28000 ug/L for 72 hr (95% confidence interval: 23000-36000 ug/L)Effect: decreased population growth rate />99.5% purity/Species: Lymnaea stagnalis (snail)Concentration: 116 (98-139) mg/L for 1 dayEffect: mortality /Conditions of bioassay not specified in source/Species: Scenedesmus obliquus (green algae)Conditions: staticConcentration: 67.7 mg/L for 48 hrEffect: growth inhibitionFor more Ecotoxicity Values (Complete) data for NITROBENZENE (52 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 30.6(2) to 370(3), indicate that nitrobenzene is expected to have very high to moderate mobility in soil(SRC). Volatilization of nitrobenzene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.4X10-5 atm-cu m/mole(4). Nitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.245 mm Hg(5). Nitrobenzene had a half-life of 56 days in an aerobic soil column (sandy loam, pH 7.1)(6). An aerobic soil microcosm, planted with reed canary grass, was set up to mimic the fate of nitrobenzene in municipal wastewater applied to soil>99.9% of the added nitrobenzene was removed during passage through the microcosm (<1% due to volatilization, <1% found in microcosm effluent)(7) suggesting that nitrobenzene is readily biodegraded(SRC).AQUATIC FATE: Based on a recommended classification scheme(1), a measured Koc value of 89, determined for a river sediment(2), indicates that nitrobenzene is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 2.4X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 44 hours and 17 days, respectively(SRC). The half-life of nitrobenzene in the Rhine River in The Netherlands was estimated as 1 day by measuring the concn reduction between sampling points(5). According to a classification scheme(6), 1.47(7), <10(8), 15(9), 6(10) and 28.32(11), measured in goldfish, golden orfe, fathead minnows, guppies, and carp, respectively, suggest that bioconcentration in aquatic organisms is low(SRC).AQUATIC FATE: Nitrobenzene may be degraded in water by photolysis (a half-life of 133 days(1)), by reaction with hydrated electrons in eutrophic lakes (a half-life of 22 days(2)), or by reaction with sunlight and nitrate (a measured half-life of 11 hours(3-4)). Nitrobenzene, present in anaerobic sediments, is expected to be rapidly reduced by abiotic mechanisms(5). In model waste stabilization ponds that were continuously fed with a synthetic waste feedstock and retained for 12 days, 89.5% of the added nitrobenzene was degraded, 4.9% volatilized, 2.3% adsorbed to sediment, 2.3% was lost in effluent, and 1% remained in the water column(6). The biodegradation half-life in the pond was 3.8 days(6). Results of aerobic aqueous screening tests for nitrobenzene have results ranging from rapid degradation(7-9) to no degradation(10-12). Nitrobenzene was rapidly biodegraded after a lag phase of 70 to 85 days in an aerobic aquifer test done with groundwater and sediment from 8 locations over a 149 day incubation period(13).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nitrobenzene, which has a vapor pressure of 0.245 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase nitrobenzene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 115 days(SRC), calculated from its rate constant of 1.4X10-13 cu cm/molecule-sec at 25 °C(3). Nitrobenzene will degrade in the atmosphere primarily by photolysis (38% degradation in 5 hr in laboratory tests)(4). Atmospheric removal of nitrobenzene through hydroxyl addition results in the formation of dinitrobenzene, nitrophenols, and dicarbonyls as reaction products(5). Results of modeling studies and field experiments suggest that wet deposition will have little effect on nitrobenzene loss in plumes within kilometers of a source(6). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Expositionspfade | The substance can be absorbed into the body by inhalation, through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contact |
| Toxizitätsübersicht | IDENTIFICATION: Nitrobenzene is a colorless to pale yellow oily liquid with an odor similar to bitter almonds or shoe polish. It is soluble in water and it represents a fire hazard. Nitrobenzene is a synthetic chemical. It does not occur naturally. Its main use is in the synthesis of aniline and is used as a chemical intermediate to produce polyurethane. It is used as a solvent during petroleum refining and in the manufacture of cellulose ethers and acetates. It is used to produce dinitrobenzenes, dichloroanilines and in the synthesis of other compounds including acetominophen. HUMAN EXPOSURE: Nitrobenzene can be inhaled or by skin penetration. Nitrobenzene has been detected in ambient air and water and in finished water supplies. Nitrobenzene is found in fish. Occupational exposure occurs in petroleum plants and other facilities that produce nitrobenzene. The spleen is the target organ in humans occupationally exposed to this chemical. The spleen in tender and enlarged. Liver effects including hepatic enlargement and tenderness and altered serum chemistries have been reported in a woman exposed to nitrobenzene by inhalation. Headache, confusion, vertigo and nausea were reported. Orally exposed persons have included symptoms of apnea and coma. ANIMAL/PLANT/BACTERIAL STUDIES: Nitrobenzene causes toxicity in multiple organs by all routes of exposure, This solvent causes methemoglobinemia based on all routes of administration. All exposure routes are associated with hemolytic anemia, splenic conjestion, liver, bone marrow and spleen hematopoiesis. In rats, nitrobenzene caused splenic capsular lesions via gavage or dermal application. Effects on the liver were noted in rats and mice after both gavage and dermal application of nitrobenzene with centrilobular hepatocyte necrosis, hepatocellular nucleolar enlargement, severe hydroscopic degeneration and pigment accumulation in Kupfer cells. Incleased vacuolation of the X zone of the adrenal gland was noted in female mice after oral administration and dermal dosing. In subchronic oral and dermal studies in rats and mice, central nervous system lesions in the cerebellum and brainstem was life threatening. These lesions included petechial hemorrhages and hepatic toxicity. Dose dependent neurological effects included ataxia, head tilt, arching, loss of righting reflex, tremors, coma and consulsions were noted. Other target organs included kidney (increased kidney weight, glomerular and tubular epithelial swelling, pigmentation of tubular epithelial cells), nasal epithellium (glandularization of respiratory epithelium, pigment disposition and degeneration of olfactory epithellium), thyroid (follicular cell hyperplasia), thymus (involution) and pancreas (mononuclear cell infiltration) while lung pathology (emphysema, atelectasis and bronchiolization of alveolar celll walls) was reported in rabbits. In an inhalation study using male and female B6C3F1 mice and male and female Fischer 344 rats and male Sprague Dawley rats, survival was not adversely affected at the concentrations tested for micebut nitrobenzene was toxic and carcinogenic in both species and both rat strains including a spectrum of benign and malignant (lung, thyroid, mammary gland, liver and kidney) neoplasms. Nitrobenzene was not genotoxic in bacteria and mammalian ceells in vitro and mammalian cells in vivo. Studies reported DNA damage in repair assays, genetic mutation assays, chromosomal effects assays and cell transformation assays. Nitrobenzene was a testicular toxicant. Nitrobenzene appears to be toxic to bacteria and may adversely affect sewage facilities. The toxicity of nitrobenzene to fresh water invertebrates, Daphnia, marine invertebrates and fish indicate high acute toxicity.[ |
| Average Daily Intake | The lowest annual average concentration occurring within 2 km of a specific US point source has been estimated as 3.6X10-5 ug/cu m, affecting 4,510,613 persons(1). |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ 21 day Daphnia reproduction tests were conducted in line with the provisional procedure proposed by the Federal Environmental Agency (Umweltbundesamt, FRG), as of Jan 1, 1984. Groups of 20, 24 hr old Daphnia magna were exposed to 1.6 to 200 mg/L nitrobenzene in semi-static test vessels. Parent animals in the test and control vessels had to be pipetted 3 times/wk in freshly prepared test and control media at the corresponding concentration level. The no observed effect concentration (NOEC) was determined from the parameters of mortality of the parent animals, reproduction rate and appearance of the first offspring during the test period. In preliminary acute Daphnia tests, the 24 hr EC50 was 60 mg/L for nitrobenzene, the EC0 was 19 mg/L. The nominal 21 day no observed effect concentration was 13 mg/L, with the most sensitive parameter being the reproductive rate./AQUATIC SPECIES/ Toxicity threshold /as determined by/ (cell multiplication inhibition test): bacteria (Pseudomonas putida) 7 mg/Lalgae (Microcystis aeruginosa) 1.9 mg/Lgreen algae (Scenedesmus quadricauda) 33 mg/Lprotozoa (Entosiphon sulcatum and Uronema parduczi) 1.9 mg/L and 15 mg/L, respectively./PLANTS/ Eight species of plants were exposed to nitrobenzene in a hydroponic solution. Four species experienced no depression of either transpiration or photosynthetic rates, while one was rapidly killed and the other three were temporarily affected but recovered from the treatment. Uptake of nitrobenzene was passive and was shown to be proportional to the rate of water flux in each species. The transpiration stream concentration factor (TSCF) was 0.72. The root concentration factor (RCF) was variable between the species and was higher than expected, presumably due to deposits of insoluble metabolic products. All of the species examined displayed a capacity to chemically alter nonpolar nitrobenzene into both polar and insoluble products. Volatilization of nitrobenzene from the leaves was a major route of chemical loss. |
| Animal Concentrations | Nitrobenzene was measured in the eggs of birds in the Selenga river estuary of Lake Baikal region, Russia(species, concn ug/kg dry weight) mallard (Anas platyrhynchos), 156pintail (Anas acuta), <5shoveler (Anas clypeata), 144tufted duck (Aythya fuligula), 80pochard (Aythya ferina), <5goose (Anser anser), 122.4domestic fowl (Gallus gallus), 84 and 14.4heron (Ardea cinerea), 18herring gull (Larus argentatus), <5common gull (Larus canus), <5common tern(Sterna hirundo), 39.2black headed gull (Larus ridibundus), 12liapwing (Vanellus vanellus) 40.8Slavonian grebe (Podiceps auritus), 132marsh sandpiper (Tringa stagnatilis), <5(1). |
| RCRA-Anforderungen | U169As stipulated in 40 CFR 261.33, when nitrobenzene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).F004When nitrobenzene is a spent solvent, it is classified as a hazardous waste from a nonspecific source (F004), as stated in 40 CFR 261.31, and must be managed according to State and/or Federal hazardous waste regulations.D036A solid waste containing nitrobenzene may or may not become characterized as a hazardous waste when subjected to the Toxicity Characteristic Leaching Procedure listed in 40 CFR 261.24, and if so characterized, must be managed as a hazardous waste. |
| TSCA-Anforderungen | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Nitrobenzene is included on this list. Effective date 10/4/82Sunset date: 10/4/92. |
| Luftstandards | This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Nitrobenzene is produced, as an intermediate or a final product, by process units covered under this subpart.Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Nitrobenzene is included on this list. |
| CERCLA-Meldepflichtmengen | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Nitrobenzene is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 10,000 lbs. |
| Clean Water Act Anforderungen | Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations.Nitrobenzene is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.Two approaches were used to derive criterion levels for nitrobenzene. Based on available toxicity data, to protect public health the derived level is 19.8 mg/l. Using available organoleptic data, to control undesirable taste and odor qualities of ambient water the estimated level is 30 ug/l ... Organoleptic data have limitations as a basis for establishing water criterion, and have no demonstrated relationship to potential adverse human health effects. |
| DHS Chemicals of Interest (COI) | NitrobenzeneA Commercial Grade100Explosive/Improvised Explosive Device Precursor material that, if stolen or diverted, can be converted into weapons using simple chemistry, equipment, or techniques. |
| Landesrichtlinien für Trinkwasser | (AZ) ARIZONA 3.5 ug/L(FL) FLORIDA 9.5 ug/L(ME) MAINE 3.5 ug/L |
| Berufliche Expositionsstufe (OEB) | B |
| Arbeitsplatzgrenzwert (OEL) | TWA: 1 ppm (5 mg/m3) [skin] |
| Wassergefährdungsklasse (WGK) | 2 |
| Sofort lebensgefährliche Konzentration | 200 ppm |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1662 |
| Zollcode | 29042010 |
| RTECS-Nr. | DA6475000 |
| R-Sätze (R) | 23/24/25-40-48/23/24-51/53-62-39/23/24/25-11-36/37/38-60-52/53-48/23/24/25-36-20/21/22 |
| Toxizität | LD50 orally in rats: 600 mg/kg (PB91-108398) |
| Gefahrensymbole | T,N,F,Xn |
| Sicherheitshinweise (S) | 28-36/37-45-61-28A-16-7-27-53-26 |
| Gefahrenklasse | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 3Carc. 2Repr. 1BSTOT RE 1 Inhalation |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Gefahrstoffdaten | 98-95-3(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 899 °F |
Anwendungen & Verwendung
Beschreibung
Nitrobenzene is a greenish-yellow crystal or yellow oily liquid, and is slightly soluble in water. The primary hazard of nitrobenzene is toxicity; however, it is also combustible. The boiling point is about 410°F, the flash point is 190°F, and the ignition temperature is 900°F. The specific gravity is 1.2, which is heavier than water, and the material will sink to the bottom. The vapor density is 4.3, which is heavier than air. Nitrobenzene is toxic by ingestion, inhalation, and skin absorption, with a TLV of 1 ppm in air. The four-digit UN identification number is 1652. The NFPA 704 designation is health 3, flammability 2, and reactivity 1. Nitrobenzene is a nitro hydrocarbon derivative, but it is not very explosive. The primary uses are as a solvent, an ingredient of metal polishes and shoe polishes, and in the manufacture of aniline.
Verwenden
Nitrobenzene is an organic compound used a standard for detection and analyses as well as its removal from the environment. The compound’s cytotoxic effects have been studied in a hepatocarcinoma cell line.
Herstellung & Synthese
synthetische
Nitrobenzene is produced commercially by the exothermic nitration of benzene with fuming nitric acid in the presence of a sulfuric acid catalyst at 50 to 65℃. The crude nitrobenzene is passed through washer-separators to remove residual acid and is then distilled to remove benzene and water.