Acetonitril Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
FARBLOSE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH.
PHYSIKALISCHE GEFAHREN
Die Dämpfe mischen sich leicht mit Luft. Bildung explosionsfähiger Gemische.
CHEMISCHE GEFAHREN
Zersetzung beim Verbrennen unter Bildung giftiger Rauche mit Cyanwasserstoffund Stickstoffoxiden. Reagiert mitwasserhaltigen Säurenund Basen unter Bildung giftiger Rauche. Reagiert mit starken Oxidationsmitteln. Feuer- und Explosionsgefahr. Greift einige Kunststoff-, Gummi- und Beschichtungsarten an.
ARBEITSPLATZGRENZWERTE
TLV: 20 ppm (als TWA) Hautresorption Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); (ACGIH 2005).
MAK: 20 ppm 34 mg/m?Spitzenbegrenzung: überschreitungsfaktor II(2); Hautresorption; Schwangerschaft: Gruppe C; (DFG 2005).
EG Arbeitsplatz-Richtgrenzwerte: 70 mg/m? 40 ppm (als TWA); Hautresorption; (EG 2006)
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation der Dämpfe, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20 °C kann schnell eine gesundheitsschädliche Kontamination der Luft eintreten.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz reizt die Augen, die Haut und die Atmungsorgane. Möglich sind Auswirkungen auf die Zellatmung (Hemmung) mit nachfolgenden Krämpfenund Atemversagen. Exposition weit über den Arbeitsplatzgrenzwerten kann zum Tod führen. Die Auswirkungen treten u.U. verzögert ein. ärztliche Beobachtung notwendig.
LECKAGE
Belüftung. Zündquellen entfernen. Ausgelaufene Flüssigkeit in abdichtbaren Behältern sammeln. Reste mit trockenem Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. NICHT in die Kanalisation spülen. Persönliche Schutzausrüstung: Vollschutzanzug mit umgebungsluftunabhängigem Atemschutzgerät.
R-Sätze Betriebsanweisung:
R11:Leichtentzündlich.
R36:Reizt die Augen.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R10:Entzündlich.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R41:Gefahr ernster Augenschäden.
R24:Giftig bei Berührung mit der Haut.
R20/22:Gesundheitsschädlich beim Einatmen und Verschlucken.
S-Sätze Betriebsanweisung:
S16:Von Zündquellen fernhalten - Nicht rauchen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S27:Beschmutzte, getränkte Kleidung sofort ausziehen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Aussehen Eigenschaften
CH3CN, Ethannitril, Methylcyanid.
Gefahren für Mensch und Umwelt
Gefährliche Reaktionen mit Oxidationsmitteln (u.a. Perchloraten, Perchlorsäure, Salpetersäure, Oleum), Säuren( u.a. konz. Schwefelsäure), Cyanopropylnitrat, in dampf-/gasförmigen Zustand mit Wasser, explosionsfähig in dampf-/gasförmigen Zustand mit Luft.
Verschlucken führt zu Übelkeit und Erbrechen. Nach Resorption großer Mengen, die auch über die Haut möglich ist, erfolgt im Körper eine relativ langsame Abspaltung von Blausäure aus der Verbindung. Unter diesen Umständen kann es zu Atemnot und innerer Erstickung kommen. Giftig beim Einatmen,Verschlucken und Berührung mit der Haut.
Giftwirkung auf Fische und Plankton. Trinkwassergefährdend bereits bei Auslaufen geringer Mengen in den Untergrund.
Schutzmaßnahmen und Verhaltensregeln
Lagerung: dicht verschlossen, kühl, an gut belüfteten Ort, von Zündquellen entfernt, nicht in die Nähe von brennbaren Stoffen. Maßnahmen gegen elektrostatische Aufladung treffen.
bei Auftreten von Dämpfen/Aerosolen. Filter A
Laborschutzbrille
Berührung mit der Haut vermeiden
Verhalten im Gefahrfall
Mit Rotisorb aufnehmen. Der Entsorgung zuführen. Mit Wasser nachreinigen
Wasserstrahl, Schaum, Kohlendioxid, Pulver
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: 15 Minuten bei gespreizten Lidern unter fließendem Wasser mit Augendusche ausspülen. Augenarzt konsultieren!
Nach Einatmen: Frischluft, ggf. Atemspende oder Gerätebeatmung.
Nach Verschlucken: Sofort Kochsalzlösung (1 Eßl./Glas) trinken und erbrechen lassen!
Bei Unwohlsein ärztlichen Rat einholen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als Sonderabfall (halogenfreies Lösungsmittelgemisch) entsorgen, zuständige Stellen: Hubland-Herr Riepl:8884711, Klinikum-Herr Uhl:2015557.
Beschreibung
Acetonitrile is a liquid with an etherlike odor. It is a highly
polar, volatile solvent used in many different industrial applications.
It is widely used in the pharmaceutical, photographic,
chemical, and analytical industries. It is useful as an industrial
solvent for the separation of olefins, polymers, spinning fibers,
and plastics. Other uses include the extraction and refining of
copper and by-product ammonium sulfate; used for dyeing
textiles and in coating compositions; used as a stabilizer for
chlorinated solvents; manufacture of perfumes and cosmetics;
and as a general reagent in a wide variety of chemical processes.
Chemische Eigenschaften
Acetonitrile (methyl cyanide), CH3CN, is a colorless liquid with a sweet, ethereal odor. It is completely miscible with water and its high dielectric strength and dipole moment make it an excellent solvent for both inorganic and organic compounds including polymers. it is commonly applied to the development and manufacturing of cosmetics, pharmaceutical and agricultural products.Acetonitrile has been banned in cosmetic products in the European Economic Area (EEA) since early 2000 and acetone and ethyl are often preferred as safer for domestic use.
Physikalische Eigenschaften
Colorless liquid with an ether-like or pungent odor of vinegar. A detection odor threshold
concentration of 1,950 mg/m
3 (1,161 ppm
v) was experimentally determined by Dravnieks (1974).
An odor threshold concentration of 13 ppm
v was reported by Nagata and Takeuchi (1990).
Verwenden
Acetonitrile is the simplest organic nitrile. It is a by-product of the manufacture of acrylonitrile, and acetonitrile has, in fact, replaced acrylonitrile. Acetonitrile has a number of uses, primarily as an extraction solvent for butadiene; as a chemical interme- diate in pesticide manufacturing; as a solvent for both inorganic and organic compounds; to remove tars, phenols, and coloring matter from petroleum hydrocarbons not soluble in acetonitrile; in the production of acrylic fi bers; in pharmaceuticals, perfumes, nitrile rubber, and acrylonitrile-butadiene-styrene (ABS) resins; in high-performance liquid and gas chro- matographic analysis; and in extraction and refi ning of copper. It is used as a starting material for the produc- tion of acetophenone, alpha-naphthalenacetic acid, thiamine, and acetamidine.
Application
Acetonitrile is used as a solvent for polymers, spinning fibers, casting and molding plastics, and HPLC analyses; for extraction of butadiene and other olefins from hydrocarbon streams; in dyeing and coating textiles; and as a stabilizer for chlorinated solvents. It occurs in coal tar and forms as a by-product when acrylonitrile is made. Although acetonitrile is one of the more stable nitriles, it undergoes typical nitrile reactions and is used to produce many types of nitrogencontaining compounds.Acetonitrile also is used as a catalyst and as an ingredient in transitionmetal complex catalysts.
Definition
ChEBI: Acetonitrile is a nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group. It has a role as a polar aprotic solvent and an EC 3.5.1.4 (amidase) inhibitor. It is an aliphatic nitrile and a volatile organic compound.
Vorbereitung Methode
Acetonitrile is mainly prepared by dehydration of acetamide (CH
3CONH
2) with
glacial acetic acid (Turner 1950) or by reacting acetic acid with ammonia at
400-500°C in the presence of a dehydration catalyst (Anon 1978).
Allgemeine Beschreibung
A colorless limpid liquid with an aromatic odor. Flash point 42°F. Density 0.783 c / cm3. Toxic by skin absorption. Less dense than water. Vapors are denser than air.
Air & Water Reaktionen
Highly flammable. Water soluble.
Reaktivität anzeigen
Acetonitrile decomposes when heated to produce deadly toxic hydrogen cyanide gas and oxides of nitrogen. Strongly reactive [Hawley]. May react vigorously with strong oxidizing reagents, sulfuric acid, chlorosulfonic acid, sulfur trioxide, perchlorates, nitrating reagents, and nitric acid. [Sax, 9th ed., 1996, p. 20]. Potentially explosive in contact with nitrogen-fluorine compounds (e.g., tetrafluorourea) [Fraser, G. W. et al., Chem. Comm., 1966, p. 532].
Health Hazard
Acetonitrile liquid or vapor is irritating to the skin, eyes, and respiratory tract. Acetonitrile
has only a modest toxicity, but it can be metabolized in the body to hydrogen cyanide
and thiocyanate. Acetonitrile causes delayed symptoms of poisoning (several hours after
the exposure) that include, but are not limited to, salivation, nausea, vomiting, anxiety,
confusion, hyperpnea, dyspnea, respiratory distress, disturbed pulse rate, unconscious-
ness, convulsions, and coma. Cases of acetonitrile poisoning in humans (or, more strictly,
of cyanide poisoning after exposure to acetonitrile) are rare but not unknown, by inha-
lation, ingestion, and (possibly) by skin absorption. Repeated exposure to acetonitrile
may cause headache, anorexia, dizziness, weakness, and macular, papular, or vesicular
dermatitis.
Flammability and Explosibility
Acetonitrile is a flammable liquid (NFPA rating = 3), and its vapor can travel a
considerable distance to an ignition source and "flash back." Acetonitrile vapor
forms explosive mixtures with air at concentrations of 4 to 16% (by volume).
Hazardous gases produced in a fire include hydrogen cyanide, carbon monoxide,
carbon dioxide, and oxides of nitrogen. Carbon dioxide or dry chemical
extinguishers should be used for acetonitrile fires.
Industrielle Verwendung
Acetonitrile is used as a solvent both in industry and in the laboratory, as a
rodenticide, and in the denaturation of alcohol. Because of both its solvent
properties and volatility, it is useful for extracting vegetable and animal oils and
dissolving hydrocarbons, oils, and greases. Acetonitrile is used for the purification
of acetylene and artificial textile fibers, and as an antioxidant for rubber (Dequidt
et al 1974). It has also been used to extract herbicide residues from soils (Smith
1980), to remove tars and other compounds from petroleum hydrocarbons, and to
extract fatty acids from vegetable and fish liver oil. Acetonitrile is now a standard
solvent component in reversed-phase high-performance liquid chromatography. It
is the starting point for the syntheses of a number of organic compounds such as
carboxylic acids and various nitrogen derivatives (Smiley 1981).
Sicherheitsprofil
Poison by ingestion and intraperitoneal routes. Moderately toxic by several routes. An experimental teratogen. Other experimental reproductive effects. A skin and severe eye irritant. Human systemic effects by ingestion: convulsions, nausea or vomiting, and metabolic acidosis. Human respiratory system effects by inhalation. Mutation data reported. Dangerous fire hazard when exposed to heat, flame, or oxidizers. Explosion Hazard: See also CYANIDE and NITRILES. When heated to decomposition it emits highly toxic fumes of CNand NOx,. Potentially explosive reaction with lanthanide perchlorates and nitrogen-fluorine compounds. Exothermic reaction with sulfuric acid at 53°C. Will react with water, steam, acids to produce toxic and flammable vapors. Incompatible with oleum, chlorosulfonic acid, perchlorates, nitrating agents, inchum, dinitrogen tetraoxide, N-fluoro compounds (e.g., perfluorourea + acetonitrile), HNO3, so3. To fight fire, use foam, Con, dry chemical
mögliche Exposition
Acetonitrile is used as an extractant for animal and vegetable oils, as a solvent; particularly in the pharmaceutical industry, and as a chemical intermediate in pesticide manufacture; making batteries and rubber products. It is present in cigarette smoke
Carcinogenicity
Under the conditions of these 2-
year inhalation studies by NTP, there was equivocal evidence
of carcinogenic activity of acetonitrile in male F344/N rats
based on marginally increased incidences of hepatocellular
adenoma and carcinoma. There was no evidence of carcinogenic
activity of acetonitrile in female F344/N rats exposed
to 100, 200, or 400 ppm. There was no evidence of carcinogenic
activity of acetonitrile in male or female B6C3F1 mice
exposed to 50, 100, or 200 ppm. Exposure to acetonitrile by
inhalation resulted in increased incidences of hepatic basophilic
foci in male rats and of squamous hyperplasia of the
forestomach in male and female mice.
Stoffwechsel
Acetonitrile metabolism in dogs was demonstrated by Lang (1894), who reported that about 20% of the nitrile administered was converted to thio-cyanate in the urine, while guinea pigs metabolized acetonitrile to a greater extent (50% of dose excreted as thiocyanate). When the animals were pre-treated with ethanol, acetonitrile metabolism was induced (Tanii and Hashimoto 1986). In rats, acetone was found to potentiate acetonitrile toxicity and elevate cyanide concentrations in the blood (Freeman and Hays 1985). Baumann et al (1933) found that rabbits injected with acetonitrile excreted 27-35% of the dose as thiocyanate, while in thyroidectomized rabbits, the excretion decreased significantly (3-5% of the dose). Thiocyanate excretion was increased notably upon feeding dessicated thyroid to these animals. Hunt (1923) found that powdered sheep thyroid protected mice against acetonitrile toxicity. However, the role played by the thyroid in the detoxication of cyanide to thiocyanate is unclear. It has been suggested that the thyroid may have a role in the microsomal cleavage of cyanide from acetonitrile other than its direct effect on sulphation of cyanide to thiocyanate.
Lager
Acetonitrile should be
used only in areas free of ignition sources, and quantities greater than 1 liter should
be stored in tightly sealed metal containers in areas separate from oxidizers.
Versand/Shipping
UN1648 Acetonitrile, Hazard Class: 3; Labels: 3-Flammable liquid
Inkompatibilitäten
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, chlorosulfonic acid, oleum, epoxides. May accumulate static electrical charges, and may cause ignition of its vapors. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids
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 nitrogen oxide removal from effluent gases by scrubbers or incinerators
Acetonitril Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
2-THENOYLACETONITRILE
CIS-2-AMINOCYCLOHEXANOL HYDROCHLORIDE
METHYL 3-((PYRROLIDIN-1-YL)METHYL)BENZOATE
1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex
1-(1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-4-YL)-2,2,2-TRIFLUOROETHANONE
BIS(DIISOPROPYLAMINO)CHLOROPHOSPHINE
4-Methyl-3-nitroanisol
2-Amino-5-chlorbenzonitril
(E)-METHYL 3-(4-BROMOPHENYL)ACRYLATE
Chloroneb
Isopropylsulfonylchlorid
2,2,2-TRIFLUORO-1-(3-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOL-4-YL)ETHANONE
2-Hydroxy-5-bromopyridine
6-CHLORO-[1,2,4]TRIAZOLO[4,3-B]PYRIDAZINE
1-Phenylimidazole
3-AMINO-1-PHENYL-PROPAN-1-OL
Naphthalin-1-sulfonylchlorid
Chinolin-2-carbonitril
6-(BOC-AMINO)-HEXYL BROMIDE
Boron trifluoride acetonitrile complex
Palladium(II)di(4-oxopent-2-en-2-oat)
Methyl 3-(morpholinomethyl)benzoate ,98%
(Z)-Tetradec-9-enol
1-Boc-piperazine acetate
[1,2-Bis(diphenylphosphino)ethane]dichloropalladium(II)
Dichloro[(1,2,5,6-?)-cycloocta-1,5-dien]palladium
1-BENZYL-2-IMIDAZOLECARBOXYLIC ACID
Benzoylacetonitril
Dimethyl-(2-oxopropyl)phosphonat
4-(2-Hydroxyethoxy)benzaldehyde
Piperidin-1-propylamin
1-PIPERIDINEPENTANOL
6-Brom-1H-purin
Hexadecyltrimethylammoniumhydroxid
5-BROMO-2-(PYRROLIDIN-1-YL)PYRIMIDINE
N-Cyano etrhl ethyl midxite
Bis(acetonitril)dichloropalladium
4-Aminobutan-2-ol
5-(TRIFLUOROMETHYL)-1-PHENYL-1H-PYRAZOLE
[[2,2',2''-Nitrilotris[ethanolato]](3-)-N,O,O',O'']bor
