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Anilin Produkt Beschreibung

Aniline Struktur
62-53-3
CAS-Nr.
62-53-3
Bezeichnung:
Anilin
Englisch Name:
Aniline
Synonyma:
Anyvim;Kyanol;Anilin;blueoil;ci76000;Anilina;ANILINE;Benzidam;Blue Oil;benzamine
CBNumber:
CB7169544
Summenformel:
C6H7N
Molgewicht:
93.13
MOL-Datei:
62-53-3.mol

Anilin Eigenschaften

Schmelzpunkt:
-6.2 °C
Siedepunkt:
184 °C(lit.)
Dichte
1.022 g/mL at 25 °C(lit.)
Dampfdichte
3.22 (185 °C, vs air)
Dampfdruck
0.7 mm Hg ( 25 °C)
Brechungsindex
n20/D 1.586(lit.)
Flammpunkt:
76 °C
storage temp. 
2-8°C
Löslichkeit
water: soluble
pka
4.63(at 25℃)
Aggregatzustand
Liquid
Farbe
APHA: ≤250
Wichte
1.021
Relative polarity
0.42
PH
8.8 (36g/l, H2O, 20℃)
Geruch (Odor)
Sweet, amine-like odor detectable at 0.6 to 10 ppm
Explosionsgrenze
1.2-11%(V)
Wasserlöslichkeit
36 g/L (20 ºC)
Merck 
14,659
BRN 
605631
Henry's Law Constant
1.91 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)
Expositionsgrenzwerte
TLV-TWA skin 2 ppm (~8 mg/m3) (ACGIH), 5 ppm (~19 mg/m3) (MSHA, OSHA, and NIOSH); IDLH 100 ppm (NIOSH).
Stabilität:
Stable. Incompatible with oxidizing agents, bases, acids, iron and iron salts, zinc, aluminium. Light sensitive. Combustible.
CAS Datenbank
62-53-3(CAS DataBase Reference)
NIST chemische Informationen
Aniline(62-53-3)
EPA chemische Informationen
Benzenamine(62-53-3)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher T,N,F
R-Sätze: 23/24/25-40-41-43-48/23/24/25-50-68-48/20/21/22-39/23/24/25-11
S-Sätze: 26-27-36/37/39-45-46-61-63-36/37-16
RIDADR  UN 1547 6.1/PG 2
WGK Germany  2
RTECS-Nr. BW6650000
8-9
Selbstentzündungstemperatur 615 °C
TSCA  Yes
HS Code  2921 41 00
HazardClass  6.1
PackingGroup  II
Giftige Stoffe Daten 62-53-3(Hazardous Substances Data)
Toxizität LD50 orally in rats: 0.44 g/kg (Jacobson)
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
H301 Giftig bei Verschlucken. Akute Toxizität oral Kategorie 3 Achtung P264, P270, P301+P310, P321, P330,P405, P501
H311 Giftig bei Hautkontakt. Akute Toxizität dermal Kategorie 3 Achtung P280, P302+P352, P312, P322, P361,P363, P405, P501
H317 Kann allergische Hautreaktionen verursachen. Sensibilisierung der Haut Kategorie 1A Warnung P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H318 Verursacht schwere Augenschäden. Schwere Augenschädigung Kategorie 1 Achtung P280, P305+P351+P338, P310
H330 Lebensgefahr bei Einatmen. Akute Toxizität inhalativ Kategorie 1 Achtung P260, P271, P284, P304+P340, P310,P320, P403+P233, P405, P501
H341 Kann vermutlich genetische Defekte verursachen. Keimzellmutagenität Kategorie 2 Warnung P201,P202, P281, P308+P313, P405,P501
H351 Kann vermutlich Krebs verursachen. Karzinogenität 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
H373 Kann die Organe schädigen bei längerer oder wiederholter Exposition. Spezifische Zielorgan-Toxizität (wiederholte Exposition) Kategorie 2 Warnung P260, P314, P501
H400 Sehr giftig für Wasserorganismen. Kurzfristig (akut) gewässergefährdend Kategorie 1 Warnung P273, P391, P501
H410 Sehr giftig für Wasserorganismen mit langfristiger Wirkung. Langfristig (chronisch) gewässergefährdend Kategorie 1 Warnung P273, P391, P501
H412 Schädlich für Wasserorganismen, mit langfristiger Wirkung. Langfristig (chronisch) gewässergefährdend Kategorie 3 P273, P501
Sicherheit
P210 Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P260 Dampf/Aerosol/Nebel nicht einatmen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P370+P378 Bei Brand: zum Löschen verwenden.
P403+P233 An einem gut belüfteten Ort aufbewahren. Behälter dicht verschlossen halten.

Anilin Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD

FARBLOSE öLIGE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH. VERFäRBT SICH BRAUN BEI KONTAKT MIT LUFT ODER LICHT.

CHEMISCHE GEFAHREN

Zersetzung beim Erhitzen auf Temperaturen über 190 °C unter Bildung giftiger und ätzender Rauche (Ammoniak, Stickstoffoxide) und entzündlicher Dämpfe. Schwache Base. Reagiert sehr heftig mit starken Oxidationsmitteln. Feuer- und Explosionsgefahr! Reagiert heftig mit starken Säuren. Greift Kupfer und seine Legierungen an.

ARBEITSPLATZGRENZWERTE

TLV: 2 ppm (als TWA); Hautresorption; Krebskategorie A3 (bestätigte krebserzeugende Wirkung beim Tier mit unbekannter Bedeutung für den Menschen); BEI vorhanden; (ACGIH 2005).
MAK: 2 ppm, 7,7 mg/m? Spitzenbegrenzung: überschreitungsfaktor II(2); Hautresorption; Sensibilisierung der Haut; Krebserzeugend Kategorie 4; Schwangerschaft: Gruppe C; (DFG 2006).

AUFNAHMEWEGE

Aufnahme in den Körper durch Inhalation, über die Haut und durch Verschlucken, auch als Dampf!

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:
Die Substanz reizt die Augen und die Haut. Möglich sind Auswirkungen auf das Blut mit nachfolgender Methämoglobinbildung. Exposition in hohen Konzentrationen kann zum Tode führen. ärztliche Beobachtung notwendig. Die Auswirkungen sind u.U. verzögert. (s. Anm.)

WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION

Wiederholter oder andauernder Hautkontakt kann zu Sensibilisierung führen. Möglich sind Auswirkungen auf das Blut mit nachfolgender Methämoglobinbildung.

LECKAGE

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

R-Sätze Betriebsanweisung:

R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R40:Verdacht auf krebserzeugende Wirkung.
R41:Gefahr ernster Augenschäden.
R43:Sensibilisierung durch Hautkontakt möglich.
R48/23/24/25:Giftig: Gefahr ernster Gesundheitsschäden bei längerer Exposition durch Einatmen, Berührung mit der Haut und durch Verschlucken.
R50:Sehr giftig für Wasserorganismen.
R68:Irreversibler Schaden möglich.
R48/20/21/22:Gesundheitsschädlich: Gefahr ernster Gesundheitsschäden bei längerer Exposition durch Einatmen, Berührung mit der Haut und durch Verschlucken.
R39/23/24/25:Giftig: ernste Gefahr irreversiblen Schadens durch Einatmen, Berührung mit der Haut und durch Verschlucken.
R11:Leichtentzündlich.

S-Sätze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S27:Beschmutzte, getränkte Kleidung sofort ausziehen.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S46:Bei Verschlucken sofort ärztlichen Rat einholen und Verpackung oder Etikett vorzeigen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S63:Bei Unfall durch Einatmen: Verunfallten an die frische Luft bringen und ruhigstellen
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.

Aussehen Eigenschaften

C6H7N; Farblose, ölige Flüssigkeit mit aromatischem Geruch; färbt sich an der Luft rasch braun.

Gefahren für Mensch und Umwelt

Gefährliche Reaktionen mit starken Oxydationsmitteln und anorganischen Säuren; mit Dibenzoylperoxid und rauchender Salpetersäure explosionsartige Reaktionen möglich! Bildung nitroser Gase beim Verbrennen.
Kann möglicherweise Krebs erzeugen. Giftig beim Einatmen, Verschlucken und Berührung mit der Haut. Gefahr kumulativer Wirkungen. Irreversibler Schaden möglich.
Anilin wirkt akut und chronisch als Blut-, Ferment- und Nervengift. Die durch Oxydation entstehenden Stoffwechselprodukte greifen als Methämoglobinbildner in das Fermentsystem der roten Blutkörperchen ein. Die akute Vergiftung zeigt neben einer unterschiedlich ausgeprägten zentralen Erregung eine graublaue Verfärbung der Haut. Übelkeit, Durst, Erbrechen sind u.a. auftretende Begleiterscheinungen. In schweren Fällen auch ausgeprägte Wirkung auf das ZNS. Bei chronischer Vergiftung allgemeine Schwäche, leichte bis mäßige Cyanose, Urämie. Gleichzeitiger Alkoholgenuß kann die Giftwirkung des Anilins um das 7 - 20-fache steigern.
Wassergefährdender Stoff (WGK 2).

Schutzmaßnahmen und Verhaltensregeln

Latex- oder Neopren-Schutzhandschuhe tragen (nur als kurzzeitigen Spritzschutz).

Verhalten im Gefahrfall

Verschüttet Substanz mit Chemikalienbinder (z.B. Rench-Rapid) aufnehmen und als Sonderabfall entsorgen.
Brände mit CO2-Löscher bekämpfen.
Assistenten verständigen!
Vorsicht: Bildung nitroser Gase!

Erste Hilfe

Nach Hautkontakt: Sofort mit Polyethylenglycol 400 abwaschen, danach mit Wasser und Seife.
Nach Augenkontakt: Sofort mit viel Wasser mindestens 15 Minuten lang spülen. Arzt!
Nach Einatmen: Frischluft. Auxolisonspray verabreichen. Arzt!
Nach Verschlucken: Sofort Arzt aufsuchen!
Nach Kleidungskontakt: Benetzte Kleidung ausziehen.
Getränktes Leder (Schuhe!) zum Sondermüll!
Bei Unfall oder Unwohlsein ärztlichen Rat einholen.
Ersthelfer: siehe gesonderten Anschlag

Sachgerechte Entsorgung

Anilinhaltige Abfälle als Sonderabfall entsorgen.

Chemische Eigenschaften

Aniline,C6H5NH2, is slightly soluble in water,miscible in alcohol and ether,and turns yellow to brown in air. Aniline may be made(1) by the reduction, with iron or tin in HCI, of nitrobenzene, and(2) by the amination of chlorobenzene by heating with ammonia to a high temperature corresponding to a pressure of over 200 atmospheres in the presence of a catalyst(a mixture of cuprous chlorideandoxide).Aniline is the end point of reduction of most mononitrogen substituted benzene nuclei,as nitro benzene beta-phenyl hydroxylamine, azoxybenzene, azobenzene, hydrazobenzene. Aniline is detected by the violet coloration produced by a small amountof sodium hypochlorite. Aniline is used as a solvent, in the preparation of compound in the manufacture of dyes and their intermediates, and in the manufacture of medicinal chemicals.

Chemische Eigenschaften

Aniline was fi rst isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben. Aniline is oily and, although colorless, it slowly oxidizes and turns into a kind of resin in air, giving the sample a red-brown tint. At room temperature, aniline, the simplest aromatic amine, is a clear to slightly yellow, oily liquid that darkens to a brown color on exposure to air. Like most volatile amines, it possesses the somewhat unpleasant odor of rotten fi sh and also has a burning aromatic taste. It has a low vapor pressure at room temperature and ignites readily, burning with a smoky flame. It does not readily evaporate at room temperature. Aniline is slightly soluble in water and mixes readily with most organic solvents. It is synthesized by catalytic hydrogenation of nitrobenzene or by ammonolysis of phenol. Aniline is incompatible with strong acids, strong oxidizers, albumin, and solutions of iron, zinc, aluminum, toluene diisocyanate, and alkalis. It ignites spontaneously in the presence of red fuming nitric acid, and with sodium. Originally, the great commercial value of aniline was due to the readiness with which it yields, directly or indirectly, valuable dyestuffs. Currently, the largest market for aniline is in the preparation of methylene diphenyl diisocyanate (MDI), some 85% of aniline serving this market. In fact, in industry, aniline is an initiator or intermediary in the synthesis of aniline being used as a precursor to more complex chemicals. It is the starting material for many dyestuffs, known as aniline dyes. Its main application is in the manufacture of polyurethane foam, and a wide variety of products, such as MDI, agricultural chemicals, synthetic dyes, antioxidants, stabilizers for the rubber industry, varnishes, explosives, analgesics, and hydroquinone for photographic developing, and as an octane booster in gasoline. Aniline has also been detected in tobacco smoke and exposures to aniline have been reported among workers in related industrial workplaces, hazardous waste sites, and the general population through food and drinking water.

Chemische Eigenschaften

Aniline is a clear, colorless, oily liquid that darkens on exposure to light; with a characteristic amine-like odor.

Physikalische Eigenschaften

Colorless, oily liquid with a faint ammonia-like odor and burning taste. Gradually becomes yellow to reddish-brown on exposure to air or light. The lower and upper odor thresholds are 2 and 128 ppm, respectively (quoted, Keith and Walters, 1992). An odor threshold of 1.0 ppmv was reported by Leonardos et al. (1969).

Verwenden

Aniline is used in the manufacture of dyes,pharmaceuticals, varnishes, resins, photo graphic chemicals, perfumes, shoe blacks,herbicides, and fungicides. It is also usedin vulcanizing rubber and as a solvent. Itoccurs in coal tar and is produced from thedry distillation of indigo. It is also producedfrom the biodegradation of many pesticides.Aniline is a metabolite of many toxic com pounds, such as nitrobenzene, phenacetin,and phenylhydroxylamine.

Verwenden

Rubber accelerators and antioxidants, dyes and intermediates, photographic chemicals (hydro- quinone), isocyanates for urethane foams, pharma- ceuticals, explosives, petroleum refining, dipheny- lamine, phenolics, herbicides, fungicides.

Verwenden

A thin, colorless oil prepared by reducing benzene with iron filings in the presence of hydrochloric or acetic acid and then separating the aniline formed by distillation. It is slightly soluble in water but dissolves easily in alcohol, ether, and benzene. Aniline is the base for many dyes used to increase the sensitivity of emulsions.

Definition

ChEBI: A primary arylamine in which an amino functional group is substituted for one of the benzene hydrogens.

Definition

(aminobenzene; phenylamine; C6H5NH2) A colorless oily substance made by reducing nitrobenzene ( C6H5NO2). Aniline is used for making dyes, pharmaceuticals, and other organic compounds.

Vorbereitung Methode

Aniline was obtained in 1826 by Unverdorben from distillation of indigo and was given the name aniline in 1841 by Fritzsche (Windholz et al 1983). The chemical was manufactured in the U. S. by the Bechamp reaction involving reduction of nitrobenzene in the presence of either copper/silica or hydrochloric acid/ferrous chloride catalysts; but in 1966, amination of chlorobenzene with ammonia was introduced (IARC 1982; Northcott 1978). Currently, aniline is produced in the U.S., several European countries and Japan by the catalytic hydrogenation of nitrobenzene in either the vapor phase or solvent system. This chemical is also produced by reacting phenol with ammonia (HSDB 1989). Production in 1982 amounted to 331,000 tons (HSDB 1989).

Allgemeine Beschreibung

A yellowish to brownish oily liquid with a musty fishy odor. Melting point -6°C; boiling point 184°C; flash point 158°F. Denser than water (8.5 lb / gal) and slightly soluble in water. Vapors heavier than air. Toxic by skin absorption and inhalation. Produces toxic oxides of nitrogen during combustion. Used to manufacture other chemicals, especially dyes, photographic chemicals, agricultural chemicals and others.

Air & Water Reaktionen

Darkens on exposure to air and light. Polymerizes slowly to a resinous mass on exposure to air and light. Slightly soluble in water.

Reaktivität anzeigen

Aniline is a heat sensitive base. Combines with acids to form salts. Dissolves alkali metals or alkaline earth metals with evolution of hydrogen. Incompatible with albumin, solutions of iron, zinc and aluminum, and acids. Couples readily with phenols and aromatic amines. Easily acylated and alkylated. Corrosive to copper and copper alloys. Can react vigorously with oxidizing materials (including perchloric acid, fuming nitric acid, sodium peroxide and ozone). Reacts violently with BCl3. Mixtures with toluene diisocyanate may ignite. Undergoes explosive reactions with benzenediazonium-2-carboxylate, dibenzoyl peroxide, fluorine nitrate, nitrosyl perchlorate, peroxodisulfuric acid and tetranitromethane. Violent reactions may occur with peroxyformic acid, diisopropyl peroxydicarbonate, fluorine, trichloronitromethane (293° F), acetic anhydride, chlorosulfonic acid, hexachloromelamine, (HNO3 + N2O4 + H2SO4), (nitrobenzene + glycerin), oleum, (HCHO + HClO4), perchromates, K2O2, beta-propiolactone, AgClO4, Na2O2, H2SO4, trichloromelamine, acids, FO3Cl, diisopropyl peroxy-dicarbonate, n-haloimides and trichloronitromethane. Ignites on contact with sodium peroxide + water. Forms heat or shock sensitive explosive mixtures with anilinium chloride (detonates at 464° F/7.6 bar), nitromethane, hydrogen peroxide, 1-chloro-2,3-epoxypropane and peroxomonosulfuric acid. Reacts with perchloryl fluoride form explosive products. .

Hazard

An allergen. Toxic if absorbed through the skin. Combustible. Skin irritant. Questionable car- cinogen.

Health Hazard

Exposures to aniline on inhalation, ingestion and/or through skin contact cause adverse health effects. Exposures to liquid aniline cause mild irritation to the skin and eyes. Aniline is a blood toxin and its absorption through the skin and by inhalation of its vapor results in systemic toxicity, damage to the kidney, liver, bone marrow and of methemoglobinemia. The symptoms of poisoning include, but are not limited to, drowsiness, dizziness, severe headache, nausea, tiredness, bluish discoloration of the lips and tongue, loss of appetite, irregular heart beat, mental confusion, and shock. A prolonged period of exposure to the vapor results in respiratory paralysis, convulsions, coma, and death.

Health Hazard

Aniline is classified as very toxic. Probable oral lethal dose in humans is 50-500 mg/kg for a 150 lb. person. Aniline poisoning is characterized by methemoglobin formation in the blood and resulting cyanosis or blue skin. The formation of methemoglobin interferes with the oxygen-carrying capacity of the blood. The approximate minimum lethal dose for a 150 lb. human is 10 grams. Serious poisoning may result from ingestion of 0.25 mL. People at special risk include individuals with glucose-6-phosphate-dehydrogenase deficiency and those with liver and kidney disorders, blood diseases, or a history of alcoholism.

Health Hazard

The most prominent symptoms of acute aniline intoxication in man was cyanosis, lacrimation, tremors, tachypnea, and lethargy due to methemoglobin, low levels of sulfhemoglobin and Heinz body formation (Jenkins et al 1972).

Health Hazard

hemolytic anemia. Acute poisoning arisesdue possibly to methemoglobin formation,which may result in cyanosis. Overexposuremay lead to death from respiratory paralysis.Inhalation of 250 ppm aniline in air for 4hours was lethal to rats. The concentrationof aniline in samples of rapeseed foodoil that caused Spanish toxic oil syndromewas determined to be within the range of110–1300 ppb (Hill et al. 1987). Contact ofthe pure liquid on the skin can producemoderate irritation, while the effect on theeyes can be severe. The oral LD50 value inanimals varied with the species. An LD50value in mice is 464 mg/kg. Ingestion of1 or 2 g aniline may possibly cause deathto humans. Toxicity of aniline in aqueousspecies was very high. An LC50 value basedon static acute toxicity was calculated tobe 0.17 mg/L to daphnids (Daphnia magna)(Gersich and Mayes 1986).Khan et al. (2003) have studied the selec tive toxicity of aniline to the spleen in rats.The oxidative damage to spleen from ani line is attributed to a mechanism involvingformation of peroxynitrite and nitrotyrosinefrom the reaction of nitric oxide.Aniline is metabolized to aminophenols,phenylhydroxylamine, and their glucuronideand sulfate derivatives, and excreted. p Aminophenol is the major metabolite inhumans and is excreted in urine.Methylene blue (tetramethylthionine chlo ride) is an antidote to aniline poisoning. Thestandard dose is 1–2 mg/kg body weight or0.1 to 0.2 mL/kg of a 1% solution to be givenintravenously over 5–10 minutes (ATSDR).This antidote is recommended when there aresigns and symptoms of hypoxia (other thancyanosis) or when the methemoglobin lev els exceeds 30%. The 24- hour dose mustnot exceed 7 mg/kg. In case of ingestion aslurry of activated charcoal may be admin istered (1 g/kg body weight). Do not induceemesis.Aniline administered to rats by the oralroute caused tumors in the kidney andbladder. The evidence of carcinogenicity inanimals, however, is inadequate. Any cancer causing action of aniline in humans is notknown.

Health Hazard

Aniline is a moderate skin irritant, a moderate to severe eye irritant, and a skin sensitizer in animals. Aniline is moderately toxic via inhalation and ingestion. Symptoms of exposure (which may be delayed up to 4 hours) include headache, weakness, dizziness, nausea, difficulty breathing, and unconsciousness. Exposure to aniline results in the formation of methemoglobin and can thus interfere with the ability of the blood to transport oxygen. Effects from exposure at levels near the lethal dose include hypoactivity, tremors, convulsions, liver and kidney effects, and cyanosis. Aniline has not been found to be a carcinogen or reproductive toxin in humans. Some tests in rats demonstrate carcinogenic activity. However, other tests in which mice, guinea pigs, and rabbits were treated by various routes of administration gave negative results. Aniline produced developmental toxicity only at maternally toxic dose levels but did not have a selective toxicity for the fetus. It produces genetic damage in animals and in mammalian cell cultures but not in bacterial cell cultures.

Brandgefahr

Combustion can produce toxic fumes including nitrogen oxides and carbon monoxide. Aniline vapor forms explosive mixtures with air. Aniline is incompatible with strong oxidizers and strong acids and a number of other materials. Avoid heating. Hazardous polymerization may occur. Polymerizes to a resinous mass.

Brandgefahr

Aniline is a combustible liquid (NFPA rating = 2). Smoke from a fire involving aniline may contain toxic nitrogen oxides and aniline vapor. Toxic aniline vapors are given off at high temperatures and form explosive mixtures in air. Carbon dioxide or dry chemical extinguishers should be used to fight aniline fires.

Flammability and Explosibility

Aniline is a combustible liquid (NFPA rating = 2). Smoke from a fire involving aniline may contain toxic nitrogen oxides and aniline vapor. Toxic aniline vapors are given off at high temperatures and form explosive mixtures in air. Carbon dioxide or dry chemical extinguishers should be used to fight aniline fires.

Chemische Reaktivität

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water and rinse with dilute acetic acid; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Industrielle Verwendung

Aniline, the simplest primary aromatic amine, consists of a nitrogen atom with two attached hydrogen atoms affixed to a benzene ring. This aromatic amine is a weaker base than the aliphatic amines but aniline does undergo many of the same reactions in the realm of synthetic chemistry. Aniline is used to prepare agricultural chemicals, antioxidants, fungicides, herbicides, isocyanates, and other commercially important chemicals.
Aniline is used as a chemical intermediate to prepare isocyanates for making polyurethanes, antioxidants, and vulcanization accelerators, as well as in the manufacture of agricultural fungicides, herbicides and insecticides and in the preparation of certain dyes.

Industrielle Verwendung

In 1979 approximately 50% of the U.S. production of aniline was used in the preparation of 4,4'-methylene diphenyldiisocyanate (MDI) and polymethylene polyphenylisocyanate (polymeric MDI); 27% for production of rubber chemicals; 5% for hydroquinone production; 3% for production of drugs;and 9% for miscellaneous applications, including synthesis of herbicides and fibers (IARC 1982, Northcott 1978). Aniline is used in the manufacture of resins, perfumes and shoe blacks (Windholz et al 1983). It is also used as a chemical intermediate for the production of rubber processing chemicals such as accelerators; for dyes and pigments such as basic Orange 2 and manganese sulfate-coproduct; for pesticides such as alachlor; and for pharmaceuticals such as sulfonamide (HSDB 1989).

Sicherheitsprofil

Suspected carcinogen with experimental neoplastigenic data. A human poison by an unspecified route. Poison experimentally by most routes incluhng inhalation and ingestion. Experimental reproductive effects. A skin and severe eye irritant, and a rmld sensitizer. In the body, aniline causes formation of methemoglobin, resulting in prolonged anoxemia and depression of the central nervous system; less acute exposure causes hemolysis of the red blood cells, followed by stimulation of the bone marrow. The liver may be affected with resulting jaundice. Long-term exposure to a d n e dye manufacture has been associated with malignant bladder growths. A common air contaminant, A combustible liquid when exposed to heat or flame. To fight fire, use alcohol foam, CO2, dry chemical. It can react vigorously with oxidizing materials. When heated to decomposition it emits highly toxic fumes of NOx. Spontaneously explosive reactions occur with benzenediazonium-2-carboxylate, dibenzoyl peroxide, fluorine nitrate, nitrosyl perchlorate, red fuming nitric acid, peroxodisulfuric acid, and tetranitromethane. Violent reactions with boron trichloride, peroxyformic acid, dhsopropyl peroxydicarbonate, fluorine, trichloronitromethane (145℃), acetic anhydride, chlorosulfonic acid, hexachloromelamine, (HNO3 + N2O4 + H2SO4), (nitrobenzene + glycerin), oleum, (HCHO + HClO4), perchromates, K2O2, ppropiolactone, AgClO4, Na2On, H2SO4, trichloromelamine, acids, peroxydisulfuric acid, F03Cl, diisopropyl peroxy-dicarbonate, n-haloimides, and trichloronitromethane. Ignites on contact with sodium peroxide + water. Forms heator shock-sensitive explosive mixtures with anhnium chloride (detonates at 240°C/7.6 bar), nitromethane, hydrogen peroxide, 1 -chloro-2,3- epoxypropane, and peroxomonosulfuric acid. Reactions with perchloryl fluoride, perchloric acid, and ozone form explosive products.

mögliche Exposition

Aniline is widely used as an intermediate in the synthesis of dyestuffs. It is also used in the manufacture of rubber accelerators and antioxidants, pharmaceuticals, marking inks; tetryl, optical whitening agents; photographic developers; resins, varnishes, perfumes, shoe polishes, and many organic chemicals.

Source

Detected in distilled water-soluble fractions of regular gasoline (87 octane) and Gasohol at concentrations of 0.55 and 0.20 mg/L, respectively (Potter, 1996). Aniline was also detected in 82% of 65 gasoline (regular and premium) samples (62 from Switzerland, 3 from Boston, MA). At 25 °C, concentrations ranged from 70 to 16,000 μg/L in gasoline and 20 to 3,800 μg/L in watersoluble fractions. Average concentrations were 5.8 mg/L in gasoline and 1.4 mg/L in watersoluble fractions (Schmidt et al., 2002).
Based on laboratory analysis of 7 coal tar samples, aniline concentrations ranged from ND to 13 ppm (EPRI, 1990).
Aniline in the environment may originate from the anaerobic biodegradation of nitrobenzene (Razo-Flores et al., 1999).

Environmental Fate

Biological. Under anaerobic conditions using a sewage inoculum, 10% of the aniline present degraded to acetanilide and 2-methylquinoline (Hallas and Alexander, 1983). In a 56-d experiment, [14C]aniline applied to soil-water suspensions under aerobic and anaerobic conditions gave 14CO2 yields of 26.5 and 11.9%, respectively (Scheunert et al., 1987). A bacterial culture isolated from the Oconee River in North Georgia degraded aniline to the intermediate catechol (Paris and Wolfe, 1987). Aniline was mineralized by a soil inoculum in 4 d (Alexander and Lustigman, 1966).
Soil. A reversible equilibrium is quickly established when aniline covalently bonds with humates in soils forming imine linkages. These quinoidal structures may oxidize to give nitrogensubstituted quinoid rings. The average second-order rate constant for this reaction in a pH 7 buffer at 30 °C is 9.47 x 10-5 L/g?h (Parris, 1980). In sterile soil, aniline partially degraded to azobenzene, phenazine, formanilide, and acetanilide and the tentatively identified compounds nitrobenzene and p-benzoquinone (Pillai et al., 1982).
Surface Water. Aniline degraded in pond water containing sewage sludge to catechol, which then degrades to carbon dioxide. Intermediate compounds identified in minor degradative pathways include acetanilide, phenylhydroxylamine, cis,cis-muconic acid, β-ketoadipic acid, levulinic acid, and succinic acid (Lyons et al., 1984).
Photolytic. A carbon dioxide yield of 46.5% was achieved when aniline adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985). Products identified from the gas-phase reaction of ozone with aniline in synthetic air at 23 °C were nitrobenzene, formic acid, hydrogen peroxide, and a nitrated salt having the formula: [C6H5NH3]+NO3 - (Atnagel and Himmelreich, 1976). A second-order rate constant of 6.0 x 10-11 cm3/molecule?sec at 26 °C was reported for the vapor-phase reaction of aniline and OH radicals in air at room temperature (Atkinson, 1985).
Chemical/Physical. Alkali or alkaline earth metals dissolve in aniline with hydrogen evolution and the formation of anilides (Windholz et al., 1983). Laha and Luthy (1990) investigated the redox reaction between aniline and a synthetic manganese dioxide in aqueous suspensions at the pH range 3.7–6.5. They postulated that aniline undergoes oxidation by loss of one electron forming cation radicals. These radicals may undergo head-to-tail, tail-to-tail, and head-to-head couplings forming 4-aminophenylamine, benzidine, and hydrazobenzene, respectively. These compounds were additionally oxidized, in particular, hydrazobenzene to azobenzene at pH 4 (Laha and Luthy, 1990).

Stoffwechsel

Aniline is absorbed from the skin and the gastrointestinal tract (BaranowskaDutkeiwicz 1982). It is excreted primarily in the urine of treated rabbits with only a small fraction (2%) of the administered dose excreted in the feces (Kao et al 1978; Parke 1960) and none in the expired air. Urinary metabolites of aniline include P-aminophenol, O-aminophenol, m-aminophenol, aniline-N-glucuronide, phenylsulfonic acid and acetanilide (Parke, 1960). Aminophenyl- and acetylaminophenyl-mercapturic acids also have been detected in the urine of rats and rabbits (IARC 1982). Excretion of aniline conjugates of P-aminophenol have been observed in human urine (Williams 1959) and urinary excretion of these conjugates has been found to reflect the extent of absorption of aniline vapor through the skin and respiratory tract (Kao et al 1978; Piotrowski 1972). The methemoglobinemia produced in humans by aniline is believed to result from its N-hydroxylation (IARC 1982). Aniline also is a weak inducer of hepatic microsomal enzymes. Subcutaneous injections of 5 mg/kg body weight for 30 days to rats impaired aniline metabolism in vivo but it increased its in vitro metabolism to p-aminophenol (Wisniewska-Knypl and Jablonska 1975; Wisniewska-Knypl et al 1975). Low protein diets decreased hepatic aniline hydroxylation in the rat (Kato et al 1968). Saturated fat increased aniline metabolism by rat liver independent of chemical composition of the fat used (Caster et al 1970). Highest initial concentrations of aniline derived radioactivity were found in blood, liver, kidney, bladder, and gastrointestinal tract of rat, given labelled compound i.v. After 0.5 h and 6 h, radioactivity concentrated in the stomach and jejunum and subsequently absorbed from the intestine indicating the presence of an enterogastric cycle in rats. Aniline was the predominant compound in the gastric contents of treated animals and acetanilide is the major metabolite found in the jejunal contents (Irons et al 1980).

Lager

Aniline should be kept stored against physical damage in a cool (but not freezing), dry, well-ventilated location, away from smoking areas and fi re hazard. It should be kept separated from incompatibles and the containers should be bonded and grounded for transfer to avoid static sparks

Versand/Shipping

UN1547 Aniline, Hazard Class: 6.1; Labels: 6.1- Poisonous materials. UN1548 Aniline hydrochloride, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

läuterung methode

Aniline is hygroscopic. It can be dried with KOH or CaH2, and distilled under reduced pressure. Treatment with stannous chloride removes sulfur-containing impurities, reducing the tendency to become coloured by aerial oxidation. It can be crystallised from Et2O at low temperatures. More extensive purifications involve preparation of derivatives, such as the double salt of aniline hydrochloride and cuprous chloride or zinc chloride, or N-acetylaniline (m 114o) which can be recrystallised from water. Redistilled aniline is dropped slowly into a strong aqueous solution ofrecrystallised oxalic acid. Aniline oxalate (m 174-175o) is filtered off, washed several times with water and recrystallised three times from 95% EtOH. Treatment with saturated Na2CO3 solution regenerated aniline which was distilled from the solution, dried and redistilled under reduced pressure [Knowles Ind Eng Chem 12 881 1920]. After refluxing with 10% acetone for 10hours, aniline is acidified with HCl (Congo Red as indicator) and extracted with Et2O until colourless. The hydrochloride is purified by repeated crystallisation before aniline is liberated by addition of alkali, then dried with solid KOH, and distilled. The product is sulfur-free and remains colourless in air [Hantzsch & Freese Chem Ber 27 2529, 2966 1894]. Non-basic materials, including nitro compounds, are removed from aniline in 40% H2SO4 by passing steam through the solution for 1hour. Pellets of KOH are then added to liberate the aniline which is steam distilled, dried with KOH, distilled twice from zinc dust at 20mm, dried with freshly prepared BaO, and finally distilled from BaO in an all-glass apparatus [Few & Smith J Chem Soc 753 1949]. Aniline is absorbed through skin and is TOXIC.[Beilstein 12 IV 223.]

Inkompatibilitäten

May form explosive mixture with air. Unless inhibited (usually methanol), aniline is readily able to polymerize. Fires and explosions may result from contact with halogens, strong acids; oxidizers, strong base organic anhydrides; acetic anhydride, isocyanates, aldehydes, sodium peroxide. Strong reaction with toluene diisocyanate. Reacts with alkali metals and alkali earth metals. Attacks some plastics, rubber and coatings; copper and copper alloys.

Waste disposal

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. Incineration with provision for nitrogen oxides removal from flue gases by scrubber, catalytic or thermal device.

Vorsichtsmaßnahmen

When using aniline, occupational workers should wear impervious protective clothing, including boots, gloves, laboratory coat, apron or coveralls, chemical safety goggles, and/ or a full face shield as appropriate, to prevent skin contact. Workplace facilities should maintain an eye-wash fountain and quick-drench facilities. Workers should not eat, drink, or smoke in the workplace.

Anilin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Anilin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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62-53-3(Anilin)Verwandte Suche:


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