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Nitrobenzol Produkt Beschreibung

Nitrobenzene Struktur
98-95-3
CAS-Nr.
98-95-3
Bezeichnung:
Nitrobenzol
Englisch Name:
Nitrobenzene
Synonyma:
NCI-C60082;Nitrobenzen;NITROBENZOL;MYRBANE OIL;MIRBANE OIL;Nitrobenzeen;nitro-benzen;Mitrobenzole;NITROBENZENE;oilofmyrbane
CBNumber:
CB7854756
Summenformel:
C6H5NO2
Molgewicht:
123.11
MOL-Datei:
98-95-3.mol

Nitrobenzol Eigenschaften

Schmelzpunkt:
5-6 °C (lit.)
Siedepunkt:
210-211 °C (lit.)
Dichte
1.196 g/mL at 25 °C (lit.)
Dampfdichte
4.2 (vs air)
Dampfdruck
0.15 mm Hg ( 20 °C)
Brechungsindex
n20/D 1.551(lit.)
Flammpunkt:
190 °F
storage temp. 
Store below +30°C.
Löslichkeit
1.90g/l
pka
3.98(at 0℃)
Aggregatzustand
Liquid
Farbe
Clear yellow
PH
8.1 (1g/l, H2O, 20℃)
Relative polarity
4.5
Explosionsgrenze
1.8-40%(V)
Wasserlöslichkeit
slightly soluble
Merck 
14,6588
BRN 
507540
Henry's Law Constant
9.86 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)
Expositionsgrenzwerte
TLV-TWA 1 ppm (~5 mg/m3) (ACGIH, MSHA, and OSHA); IDLH 200 ppm (NIOSH).
Stabilität:
Stable. Incompatible with strong oxidizing agents, strong reducing agents, strong bases. Flammable. Note wide explosion limits.
CAS Datenbank
98-95-3(CAS DataBase Reference)
NIST chemische Informationen
Benzene, nitro-(98-95-3)
IARC
2B (Vol. 65) 1996
EPA chemische Informationen
Nitrobenzene (98-95-3)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher T,N,F,Xn
R-Sätze: 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
S-Sätze: 28-36/37-45-61-28A-16-7-27-53-26
RIDADR  UN 1662 6.1/PG 2
WGK Germany  2
RTECS-Nr. DA6475000
Selbstentzündungstemperatur 899 °F
TSCA  Yes
HazardClass  6.1
PackingGroup  II
HS Code  29042010
Giftige Stoffe Daten 98-95-3(Hazardous Substances Data)
Toxizität LD50 orally in rats: 600 mg/kg (PB91-108398)
Bildanzeige (GHS)
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H225 Flüssigkeit und Dampf leicht entzündbar. Entzündbare Flüssigkeiten Kategorie 2 Achtung P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H227 Combustible liquid Flammable liquids Category 4 Warnung P210, P280, P370+P378, P403+P235,P501
H300 Lebensgefahr bei Verschlucken. Akute Toxizität oral Kategorie 2 Achtung P264, P270, P301+P310, P321, P330,P405, P501
H310 Lebensgefahr bei Hautkontakt. Acute toxicity,dermal Category 1, 2 Achtung P262, P264, P270, P280, P302+P350,P310, P322, P361, P363, P405, P501
H330 Lebensgefahr bei Einatmen. Akute Toxizität inhalativ Kategorie 1 Achtung P260, P271, P284, P304+P340, P310,P320, P403+P233, P405, P501
H351 Kann vermutlich Krebs verursachen. Karzinogenität Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
H361 Kann vermutlich die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen. Reproduktionstoxizität Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
H370 Schädigt die Organe. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 1 Achtung P260, P264, P270, P307+P311, P321,P405, P501
H372 Schädigt bei Hautkontakt und Verschlucken die Organe bei längerer oder wiederholter Exposition. Spezifische Zielorgan-Toxizität (wiederholte Exposition) Kategorie 1 Achtung P260, P264, P270, P314, P501
H401 Toxic to aquatic life Hazardous to the aquatic environment, acute hazard Category 2 P273, P501
H411 Giftig für Wasserorganismen, mit langfristiger Wirkung. Langfristig (chronisch) gewässergefährdend Kategorie 2
H412 Schädlich für Wasserorganismen, mit langfristiger Wirkung. Langfristig (chronisch) gewässergefährdend Kategorie 3 P273, P501
Sicherheit
P201 Vor Gebrauch besondere Anweisungen einholen.
P210 Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P304 BEI EINATMEN
P308+P313 BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.
P370+P378 Bei Brand: zum Löschen verwenden.
P403+P235 An einem gut belüfteten Ort aufbewahren. Kühl halten.

Nitrobenzol Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD

HELLGELBE, öLIGE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH.

CHEMISCHE GEFAHREN

Beim Verbrennen Bildung von giftigen und ätzenden Rauchen mit Stickoxiden. Reagiert sehr heftig mit starken Oxidationsmittelnund Reduktionsmitteln unter Feuer- und Explosionsgefahr. Reagiert sehr heftig mit starken Säuren und Stickoxiden unter Explosionsgefahr.

ARBEITSPLATZGRENZWERTE

TLV: 1 ppm (als TWA); Hautresorption; Krebskategorie A3 (bestätigte krebserzeugende Wirkung beim Tier mit unbekannter Bedeutung für den Menschen); BEI vorhanden; (ACGIH 2005).
MAK: Hautresorption; Krebserzeugend Kategorie 3B; BAT vorhanden; (DFG 2006).
EG Arbeitsplatz-Richtgrenzwerte: 1 mg/m? 0.2 ppm (als TWA); Hautresorption; (EG 2006)

AUFNAHMEWEGE

Aufnahme in den Körper durch Inhalation über die Haut und durch Verschlucken

INHALATIONSGEFAHREN

Beim Verdampfen bei 20°C tritt langsam eine gesundheitsschädliche Kontamination der Luft ein, viel schneller jedoch beim Versprühen oder Dispergieren.

WIRKUNGEN BEI KURZZEITEXPOSITION

WIRKUNGEN BEI KURZZEITEXPOSITION:
Möglich sind Auswirkungen auf Blut mit nachfolgender Methämoglobinbildung. Exposition kann Bewusstseinstrübung verursachen. Die Auswirkungen treten u.U. verzögert ein. ärztliche Beobachtung notwendig.

WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION

Möglich sind Auswirkungen auf Blut, Milz und Leber. Möglicherweise krebserzeugend für den Menschen. Tierversuche zeigen, dass die Substanz möglicherweise fruchtbarkeitsschädigend oder entwicklungsschädigend wirken kann.

LECKAGE

Persönliche Schutzausrüstung: Vollschutzanzug mit umgebungsluftunabhängigem Atemschutzgerät. Ausgelaufene Flüssigkeit möglichst in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. NICHT in die Umwelt gelangen lassen.

R-Sätze Betriebsanweisung:

R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R40:Verdacht auf krebserzeugende Wirkung.
R48/23/24:Giftig: Gefahr ernster Gesundheitsschäden bei längerer Exposition durch Einatmen und durch Berührung mit der Haut.
R51/53:Giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R62:Kann möglicherweise die Fortpflanzungsfähigkeit beeinträchtigen.
R39/23/24/25:Giftig: ernste Gefahr irreversiblen Schadens durch Einatmen, Berührung mit der Haut und durch Verschlucken.
R11:Leichtentzündlich.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-Sätze Betriebsanweisung:

S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S16:Von Zündquellen fernhalten - Nicht rauchen.
S7:Behälter dicht geschlossen halten.
S27:Beschmutzte, getränkte Kleidung sofort ausziehen.

Aussehen Eigenschaften

C8H5NO2; Benzalin, Mirban-Essenz, Mirbanöl, Mononitrobenzol, falsches Bittermandelöl. Sehr giftige, farblos bis gelbliche Flüssigkeit. Schwerer als Wasser und kaum wasserlöslich. Bittermandelgeruch. Wässrige Lösungen schmecken intensiv süß.

Gefahren für Mensch und Umwelt

Sehr giftig beim Einatmen, Verschlucken und Berührung mit der Haut. Gefahr kumulativer Wirkungen.
Starke Methämoglobinbildung. Rasche Aufnahme auch durch Einatmen oder die Haut.
Wird im Körper über Nitrosobenzol zum entsprechenden Hydroxylamin reduziert, das dann als Methämoglobinbildner wirkt. Alkohol oder heiße Bäder können Cyanose lebensbedrohend verstärken.
Leber-, Haut- und ZNS-Schäden sowie Anämie möglich.
Nicht mit Reduktionsmitteln, Laugen, Alkalimetallen, starken Säuren, Peroxidverbindungen und Salpetersäure in Berührung bringen.
LD50 (oral, Ratte): 489 mg/kg.

Schutzmaßnahmen und Verhaltensregeln

Schutzhandschuhe als kurzzeitiger Spritzschutz.

Verhalten im Gefahrfall

Mit flüssigkeitsbindendem Material z. B. Rench Rapid aufnehmen. Der Entsorgung zuführen. Nachreinigen.
Kohlendioxid, Schaum, Pulver.
Brennbar. Mit Luft Bildung explosionsfähiger Gemische möglich. Dämpfe schwerer als Luft. Im Brandfall Entstehung nitroser Gase möglich.

Erste Hilfe

Nach Hautkontakt: Mit reichlich Wasser und Seife abwaschen. Abtupfen mit Polyethylenglycol 400.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 10 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
Nach Einatmen: Frischluft.
Nach Verschlucken: Viel Wasser trinken lassen, möglichst mit Aktivkohlezusatz. Erbrechen auslösen. Sofort Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung sofort entfernen.
Ersthelfer: siehe gesonderten Anschlag

Sachgerechte Entsorgung

Als halogenfreie, organische Lösemittelabfälle.

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.

Chemische Eigenschaften

yellow liquid

Chemische Eigenschaften

Nitrobenzene is a pale yellow to dark brown oily liquid whose odor resembles bitter almonds (or black paste shoe polish).

Chemische Eigenschaften

Aromatic nitro compounds mixed with nitrobenzene are explosives of high sensitivity and detonation velocities and are spark detonatable).

Physikalische Eigenschaften

Clear, light yellow to brown, oily liquid with an almond-like or shoe polish odor. May darken on exposure to air. An experimentally determined odor threshold concentration of 4.7 ppbv was reported by Leonardos et al. (1969). A detection odor threshold concentration of 9.6 mg/m3 (1.9 ppmv) was determined by Katz and Talbert (1930).

Verwenden

Most nitrobenzene (97%) is used in the manufacture of aniline (IARC 1996, HSDB 2009). Miscellaneous uses include the manufacture of benzidine, quinoline, azobenzene, pyroxylin compounds, isocyanates, pesticides, rubber chemicals, pharmaceuticals, and dyes such as nigrosines and magenta. Nitrobenzene is found in soaps and shoe and metal polishes and is used as a solvent for cellulose ester, in modifying esterification of cellulose acetate, and in refining lubricating oils (HSDB 2009). Nitrobenzene also is used as a solvent in petroleum refining and the synthesis of other organic compounds, such as acetaminophen (ATSDR 1990).

Verwenden

The primary use of nitrobenzene is in the captive production of aniline, with about 97.5% of nitrobenzene production consumed in this process. The major use of aniline is in the manufacture of polyurethanes. Nitrobenzene is also used as a solvent in petroleum refining, in the manufacture of cellulose ethers and acetate, and in Friedel-Crafts reactions to hold the catalyst in solution. It is also used in the synthesis of other organic compounds including acetaminophen, which is an over-the-counter analgesic commonly known as Tylenol?.
Nitrobenzene is used as a flavoring agent, a perfume for soaps and as a solvent for shoe dyes.

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.

Verwenden

For the manufacture of aniline; in soaps, shoe polishes; for refining lubricating oils; manufacture of pyroxylin Compounds.

Vorbereitung Methode

Nitrobenzene is produced by the direct nitration of benzene with a mixture of sulfuric and nitric acids. U.S. capacity for nitrobenzene production is approximately 1.5 billion pounds . The most important use for nitrobenzene is in the production of aniline. Nearly 98% of the nitrobenzene produced in the U.S. is converted to aniline.

Definition

ChEBI: A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.

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.

Definition

A yellow organic oil obtained by refluxing benzene with a mixture of concentrated nitric and sulfuric acids. The reaction is a typical electrophilic substitution on the benzene ring by the nitryl cation (NO2+).

Definition

nitrobenzene: A yellow oily liquid,C6H5NO2; r.d. 1.2; m.p. 6°C; b.p.211°C. It is made by the nitration ofbenzene using a mixture of nitricand sulphuric acids.

Synthesis Reference(s)

Journal of the American Chemical Society, 95, p. 5198, 1973 DOI: 10.1021/ja00797a017
Tetrahedron Letters, 27, p. 2335, 1986 DOI: 10.1016/S0040-4039(00)84522-0

Air & Water Reaktionen

Very slightly soluble in water.

Reaktivität anzeigen

Aluminum chloride added to Nitrobenzene containing about 5% phenol caused a violent explosion [Chem. Eng. News 31:4915. 1953]. Heating a mixture of Nitrobenzene, flake sodium hydroxide and a little water led to an explosion, discussed in [Bretherick's 5th ed. 1995]. Mixed with oxidants, i.e. dinitrogen tetraoxide, fluorodinitromethane, nitric acid, peroxodisulfuric acid, sodium chlorate, tetranitromethane, uranium perchlorate, etc., forms highly sensitive explosive, [Bretherick 5th ed, 1995]. Heated mixtures of Nitrobenzene and tin(IV) chloride produce exothermic decomposition with gas production [Bretherick, 5th Ed., 1995].

Hazard

Toxic by ingestion, inhalation, and skin absorption. Methemoglobinemia. Possible carcinogen.

Health Hazard

The routes of entry of nitrobenzene intothe body are the inhalation of its vaporsor absorption of the liquid or the vaporthrough the skin and, to a much lesserextent, ingestion. The target organs are theblood, liver, kidneys, and cardiovascular system. Piotrowski (1967) estimated that in anexposure period of 6 hours to a concentration of 5 mg/m3, 18 mg of nitrobenzene wasabsorbed through the lungs and 7 mg throughthe skin in humans. Furthermore, about 80%of inhaled vapor is retained in the respiratorytract. The dermal absorption rate at this concentration level is reported as 1 mg/h, whilethe subcutaneous absorption of the liquidis between 0.2 and 0.3 mg/cm3/h (ACGIH1986).
The symptoms of acute toxicity are headache, dizziness, nausea, vomiting, and dyspnea. Subacute and chronic exposure cancause anemia. Nitrobenzene effects the conversion of hemoglobin to methemoglobin. Itis metabolized to aminophenols and nitrophenols to about 30%, which are excreted.

Brandgefahr

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 trichloride; aniline; gycerol; sulfuric acid; oxidants; phosphorus pentachloride; potassium; potassium hydroxide. Avoid sunlight, physical damage to container, freezing, and intense heat.

Industrielle Verwendung

Nitrobenzene is mainly utilized for aniline production. The aniline is used primarily for the manufacture of 4,4'-methylenebis (phenyl isocyanate) and polymers thereof (50%). The second largest use of aniline is in the manufacture of chemicals for rubber production (30%). Dyes and dye intermediates, hydroquinone and drugs account for about 8% of the aniline produced, while 10% of the aniline is converted to agricultural products such as pesticides and defoliants (Northcott 1978). It also is used as a solvent for cellulose ethers and an ingredient in polishes for metals and shoes (HSDB 1988).

Sicherheitsprofil

Confirmed carcinogen. Human poison by an unspecified route. Poison experimentally by subcutaneous and intravenous routes. Moderately toxic by ingestion, skin contact, and intraperitoneal routes. Human systemic effects by ingestion: general anesthetic, respiratory stimulation, and vascular changes. An experimental teratogen. Experimental reproductive effects. Mutation data reported. An eye and skin irritant. Can cause cyanosis due to formation of methemoglobin. It is absorbed rapidly through the skin. The vapors are hazardous. to heat and flame. Moderate explosion hazard when exposed to heat or flame. Explosive reaction with solid or concentrated alkali + heat (e.g., sodium hydroxide or potassium hydroxide), aluminum chloride + phenol (at 12O°C), aniline + glycerol + sulfuric acid, nitric + sulfuric acid + heat. Forms explosive mixtures with aluminum chloride, oxidants (e.g., fluorodinitromethane, uranium perchlorate, tetranitromethane, sodium chlorate, nitric acid, nitric acid + water, peroxodsulfuric acid, dinitrogen tetraoxide), phosphorus pentachloride, potassium, sulfuric acid. Reacts violently with aniline + glycerin, N20, AgCLO4. To fight fne, use water, foam, CO2, dry chemical. Incompatible with potassium hydroxide. When heated to decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.

mögliche Exposition

Nitrobenzene is used in the manufacture of explosives and aniline dyes and as solvent and intermediate. It is also used in floor polishes; leather dressings and polished; and paint solvents, and to mask other unpleasant odors. Substitution reactions with nitrobenzene are used to form m-derivatives. Pregnant women may be especially at risk with respect to nitrobenzene as with many other chemical compounds, due to transplacental passage of the agent. Individuals with glucose-6-phosphate dehydrogenase deficiency may also be special risk groups. Additionally, because alcohol ingestion or chronic alcoholism can lower the lethal or toxic dose of nitrobenzene, individuals consuming alcoholic beverages may be at risk.

Carcinogenicity

Nitrobenzene is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

Environmental Fate

Biological. In activated sludge, 0.4% of the applied nitrobenzene mineralized to carbon dioxide after 5 d (Freitag et al., 1985). Under anaerobic conditions using a sewage inoculum, nitrobenzene degraded to aniline (Hallas and Alexander, 1983). When nitrobenzene (5 and 10 mg/L) was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, complete biodegradation with rapid acclimation was observed after 7 to 14 d (Tabak et al., 1981). In activated sludge inoculum, 98.0% COD removal was achieved in 5 d. The average rate of biodegradation was 14.0 mg COD/g?h (Pitter, 1976).
Razo-Flores et al. (1999) studied the fate of nitrobenzene (50 mg/L) in an upward-flow anaerobic sludge bed reactor containing a mixture of volatile fatty acids and/or glucose as electron donors. The nitrobenzene loading rate and hydraulic retention time for this experiment were 43 mg/L?d and 28 h, respectively. Nitrobenzene was effectively reduced (>99.9%) to aniline (92% molar yield) in stoichiometric amounts for the 100-d experiment.
Photolytic. Irradiation of nitrobenzene in the vapor phase produced nitrosobenzene and 4- nitrophenol (HSDB, 1989). Titanium dioxide suspended in an aqueous solution and irradiated with UV light (λ = 365 nm) converted nitrobenzene to carbon dioxide at a significant rate (Matthews, 1986). A carbon dioxide yield of 6.7% was achieved when nitrobenzene adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985).
Chemical/Physical. In an aqueous solution, nitrobenzene (100 μM) reacted with Fenton’s reagent (35 μM). After 15 min, 2-, 3-, and 4-nitrophenol were identified as products. After 6 h, about 50% of the nitrobenzene was destroyed. The pH of the solution decreased due to the formation of nitric acid (Lipczynska-Kochany, 1991). Augusti et al. (1998) conducted kinetic studies for the reaction of nitrobenzene (0.2 mM) and other monocyclic aromatics with Fenton’s reagent (8 mM hydrogen peroxide; [Fe+2] = 0.1 mM) at 25 °C. They reported a reaction rate constant of 0.0260/min.

Stoffwechsel

Nitrobenzene vapor is readily absorbed through the skin and lungs. At an airborne nitrobenzene concentration of 10 mg/m3 humans may absorb 18 to 25 mg in 6 h through the lungs and from 8 to 19 mg through the skin in the same length of time .
Urine is the major route of excretion of nitrobenzene metabolites in rabbits , rats and mice . The most abundant metabolite in earlier studies in rabbits and rats was p-aminophenol. This compound, or its glucuronide or sulfate conjugates, accounted for 19% to 31% of the dose. In a later study in rats in which the acid hydrolysis step employed by earlier workers to cleave conjugates was replaced by enzyme hydrolysis, no p-aminophenol was found in the urine of male Fischer-344 or CD rats .
About 9% of a nitrobenzene dose was excreted by B6C3F1 mice as the sulfate conjugate. The major metabolites found in Fischer-344 rat urine were p-hydroxyacetanilide sulfate (19% of the dose), p-nitrophenol sulfate (20% of the dose) and m-nitrophenol sulfate (10% of the dose) .
In addition, an unidentified metabolite accounted for about 10% of the dose .
Male CD rats excreted the same metabolites after an oral dose of nitrobenzene, but in slightly different proportions. They excreted about half as much of the dose as the glucuronide or sulfate conjugates of P-hydroxyacetanilide (9% of the dose) and P-nitrophenol (13% of the dose), approximately the same amount of m-nitrophenol (8% of the dose), and about twice as much as the unidentified metabolite. Interestingly, whereas Fischer-344 rats excreted the phenolic metabolites of nitrobenzene exclusively as sulfates, CD rats excreted the same metabolites in the free form (15-17% of the total metabolite) and as glucuronides (4-20% of the total metabolite).
Approximately 4% of the dose also was excreted as p-hydroxyacetanilide by B6C3F1 mice and as p- and m-nitrophenol (7% and 6% of the dose, respectively) sulfates, glucuronides and free metabolites .
Clearly, ring hydroxylation and reduction are important metabolic steps in the biotransformation of nitrobenzene in rabbits, rats, mice and humans . Since no significant isotope effect was found in the metabolism of deuterated nitrobenzene to these products in rats in vivo , the o- and p-nitrophenols may be formed through an arene oxide intermediate. A significant isotope effect was noted in the formation of m-nitrophenol from deuterated nitrobenzene in the same rats, leading to the conclusion that m-nitrophenol is formed by a direct oxygen insertion mechanism or by some other mechanism which does not involve an arene oxide intermediate. The reduction of nitrobenzene in vivo is largely, if not exclusively, due to the action of anaerobic intestinal microflora. Treatment with antibiotics totally eliminated the ability of cecal contents of Fischer-344 rats to reduce nitrobenzene in vitro, and rats treated with antibiotics eliminated p-hydroxyacetanilide as 0.9% of an oral dose of nitro-benzene. Normal rats excreted 16.2% of an oral dose of nitrobenzene as that metabolite .
The reduction of most nitro compounds by hepatic microsomes is not detectable under aerobic conditions, but is readily observable under anaerobic conditions. Mason and Holtzman proposed that the first intermediate in the microsomal reduction of nitroaromatic compounds is the nitro anion radical, the product of a one electron transfer to nitrobenzene or other nitroaromatic compound. Oxygen would rapidly oxidize the radical to yield the parent nitro compound and Superoxide anion. Both the nitro anion radical and Superoxide anion are potentially toxic compounds.
Both P-nitrophenol and P-aminophenol have been detected in human urine after exposure to nitrobenzene. p-Aminophenol has been found only after large accidental exposures and acid hydrolysis of urine. Since acid conditions convert p-acetamidophenol to P-aminophenol, the identit

Versand/Shipping

UN1662 Nitrobenzene, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

läuterung methode

Common impurities include nitrotoluene, dinitrothiophene, dinitrobenzene and aniline. Most impurities can be removed by steam distillation in the presence of dilute H2SO4, followed by drying with CaCl2, and shaking with, then distilling at low pressure from BaO, P2O5, AlCl3 or activated alumina. It can also be purified by fractional crystallisation from absolute EtOH (by refrigeration). Another purification process includes extraction with aqueous 2M NaOH, then water, dilute HCl, and water, followed by drying (CaCl2, MgSO4 or CaSO4) and fractional distillation under reduced pressure. The pure material is stored in a brown bottle, in contact with silica gel or CaH2. It is very hygroscopic. [Beilstein 5 H 233, 5 I 124, 5 II 171, 5 III 591, 5 IV 708.]

Toxicity evaluation

The intermediates and products of nitrobenzene reduction can cause methemoglobinemia (a condition in which the blood’s ability to carry oxygen is reduced) by accelerating the oxidation of hemoglobin to methemoglobin. Three primary metabolic mechanisms have been identified: reduction of nitrobenzene to aniline by intestinal microflora, its reduction to aniline occurring in hepatic microsomes and erythrocytes, and nitrobenzene oxidative metabolism to the nitrophenols by hepatic microsomes. Many of the toxicological effects are likely triggered by metabolites of nitrobenzene. For example, methemoglobinemia is caused by the interaction of hemoglobin with the products of nitrobenzene reduction (i.e., nitrosobenzene, phenylhydroxylamine, and aniline). The anaerobic metabolism occurring in the gastrointestinal track is much faster than reduction by the hepatic microsomal fraction; therefore, the action of bacteria normally present in the small intestine is an important element in the formation of methemoglobin.

Inkompatibilitäten

Concentrated nitric acid, nitrogen tetroxide; caustics; phosphorus pentachloride; chemically-active metals, such as tin or zinc. Violent reaction with strong oxidizers and reducing agents. Attacks many plastics. Forms thermally unstable compounds with many organic and inorganic compounds.

Waste disposal

Incineration (982℃, 2.0 seconds minimum) with scrubbing for nitrogen oxides abatement . Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

Nitrobenzol Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Nitrobenzol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 0)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate

98-95-3(Nitrobenzol)Verwandte Suche:


  • Benzene,nitro-
  • Essence of Mirbane
  • essenceofmirbane
  • NCI-C60082
  • Nitrobenzeen
  • Nitrobenzen
  • nitro-benzen
  • Oil of Myrbane
  • Mitrobenzole
  • 1-Nitrobenzene
  • NITROBENZENE 99+% A.C.S. REAGENT
  • NITROBENZENE OEKANAL, 250 MG
  • NITROBENZENE, 1X1ML, MEOH, 5000UG/ML
  • NITROBENZENE, ACS
  • NITROBENZENE,1X1ML, ACN 1000UG/ML
  • NITROBENZENE, REAGENTPLUS, 99%
  • NITROBENZENE, STANDARD FOR GC
  • NitrobenzeneGr
  • NitrobenzeneForSynthesis
  • Nitrobenzene,99%
  • Nitrobenzene, extra pure, 99%
  • Nitrobenzene, for analysis ACS, 99+%
  • NITROBENZENE REAGENT (ACS)
  • nitrobenzene solution
  • ssence of myrbane
  • Nitrobenzene (I, T)
  • NITROBENZENE pure
  • NITROBENZENE extrapure AR
  • Nitrobenzene, Reagent
  • Nitrobenzene, 99%, extra pure
  • Nitrobenzene, for analysis ACS
  • Nitrobenzene,99+%,for analysis ACS
  • Nitrobenzene,electronic grade
  • Nitrobenzene Standard
  • Nitrobenzene, reagent grade, ACS
  • Nitrobenzene, low in free acid
  • Nitrobenzene, extra pure, 99% 1LT
  • Nitrobenzene, extra pure, 99% 2.5LT
  • Nitrobenzene ACS reagent, >=99.0%
  • Nitrobenzene ReagentPlus(R), 99%
  • Nitrobenzene solution standard
  • NITROBENZOL
  • NITROBENZENE
  • OIL OF MIRBANE
  • MYRBANE OIL
  • MONONITROBENZENE
  • MIRBANE OIL
  • oilofmyrbane
  • Rcra waste number U169
  • rcrawastenumberu169
  • Nitrobenzene, 99.5%, for analysis
  • itrobenzene ACS reagent
  • ESSENCE OF MYRBANE
  • AKOS BBS-00004396
  • Nitrobenzene in Methanol
  • NITROBENZENE FOR SYNTHESIS 100 ML
  • NITROBENZENE FOR SYNTHESIS 1 L
  • NITROBENZENE FOR SYNTHESIS 33 KG
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