Acetophenon

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H302：Gesundheitsschädlich bei Verschlucken.

  H319：Verursacht schwere Augenreizung.

• Sicherheit

  P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

Acetophenone Chemische Eigenschaften,Einsatz,Produktion Methoden

• ERSCHEINUNGSBILD

  FARBLOSE FLüSSIGKEIT ODER WEISSE KRISTALLE MIT CHARAKTERISTISCHEM GERUCH.

• ARBEITSPLATZGRENZWERTE

  TLV: 10 ppm (als TWA); (ACGIH 2005).
  MAK nicht festgelegt (DFG 2005).
  

• 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:
  Die Substanz reizt die Augen. Möglich sind Auswirkungen auf das Zentralnervensystem. Exposition gegenüber hohen Konzentrationen kann zu Bewusstlosigkeit führen.

• WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION

  Die Flüssigkeit entfettet die Haut.

• LECKAGE

  Ausgelaufene Flüssigkeit möglichst in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. Persönliche Schutzausrüstung: Atemschutzgerät, A/P2-Filter für organische Dämpfe und schädlichen Staub.

• R-Sätze Betriebsanweisung:

  R22:Gesundheitsschädlich beim Verschlucken.
  R36:Reizt die Augen.
  R63:Kann das Kind im Mutterleib möglicherweise schädigen.
  R43:Sensibilisierung durch Hautkontakt möglich.
  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
  R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
  R45:Kann Krebs erzeugen.
  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.
  S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
  S24/25:Berührung mit den Augen und der Haut vermeiden.
  S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
  S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
  S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
  S16:Von Zündquellen fernhalten - Nicht rauchen.
  S7:Behälter dicht geschlossen halten.

• Aussehen Eigenschaften

  C8H8O; Methylphenylketon, Acetylbenzol. Farblose Flüssigkeit mit charakteristischem Geruch.

• Gefahren für Mensch und Umwelt

  Gesundheitsschädlich beim Verschlucken. Reizt die Augen. Resorption führt zur Narkose.
  Nicht mit starken Oxidationsmitteln, Laugen und Säuren in Berührung bringen.
  LD₅₀ (oral, Ratte): 815 mg/kg

• Schutzmaßnahmen und Verhaltensregeln

  Geeignete Schutzhandschuhe als kurzzeitiger Spritzschutz.

• Verhalten im Gefahrfall

  Mit flüssigkeitsbindendem Material, z.B. Rench Rapid aufnehmen. Der Entsorgung zuführen. Nachreinigen.
  Kohlendioxid, Pulver, Schaum.
  Brennbar. Im Brandfall kann Kohlenmonoxid entstehen.

• Erste Hilfe

  Nach Hautkontakt: Mit reichlich Wasser abspülen.
  Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 10 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
  Nach Einatmen: Frischluft.
  Nach Verschlucken: Reichlich Wasser trinken lassen. Erbrechen auslösen. Arzt hinzuziehen.
  Nach Kleidungskontakt: Kontaminierte Kleidung entfernen.
  Ersthelfer: siehe gesonderten Anschlag

• Sachgerechte Entsorgung

  Als halogenfreie, organische Lösemittelabfälle.

• Beschreibung

  Acetophenone is the simplest aromatic ketone and is a clear liquid/crystal and very slightly soluble in water with a sweet pungent taste and odour resembling oranges. It is used as a polymerisation catalyst for the manufacture of olefins. Acetophenone is used in perfumery as a fragrance ingredient in soaps, detergents, creams, lotions, and perfumes; as a flavouring agent in foods, non-alcoholic beverages, and tobacco; as a specialty solvent for plastics and resins; as a catalyst for the polymerisation of olefins; and as a photosensitiser in organic syntheses. Acetophenone is a raw material for the synthesis of some pharmaceuticals and is also listed as an approved excipient by the U.S. FDA. Acetophenone occurs naturally in many foods such as apple, apricot, banana, and beef. Acetophenone has been detected in ambient air and drinking water; exposure of the general public may occur through the inhalation of contaminated air or the consumption of contaminated water. It is highly flammable and will get easily ignited by heat, sparks, or flames, and the vapours may form explosive mixtures with air.

• Chemische Eigenschaften

  Acetophenone is a colorless, oily liquid with a sweet, floral odor.It is a naturally occurring component of a large number of foods and essential oils.
  Acetophenone can be hydrogenated catalytically to 1-phenylethanol. It is obtained as a by-product in the Hock phenol synthesis and is purified from the high-boiling residue by distillation. The quantities obtained from this source satisfy the present demand.
  Acetophenone is used for perfuming detergents and industrial products and is an intermediate in the synthesis of other fragrance materials.

• Chemische Eigenschaften

  Acetophenone has a characteristic sweet, pungent and strong medicinal odor with a bitter, aromatic cherry branch taste. It is useful in flavors of grape, cherry and tobacco

• Occurrence

  Reported found in cocoa, beef, raspberry, peas, and concord grape

• Verwenden

  Acetophenone is a reagent used in the production of fragrances and resin polymers.

• Verwenden

  Acetophenone is used in perfumery, as aphotosensitizer in organic synthesis, and asa catalyst in olefin polymerization.In perfumery to impart an orange-blossom-like odor; in organic syntheses, especially. as photosensitizer.

• Definition

  ChEBI: Acetophenone is a methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group. It has a role as a photosensitizing agent, an animal metabolite and a xenobiotic.

• Vorbereitung Methode

  Most methyl phenyl ketone originates from the Hock process for the production of phenol from isopropylbenzene (→Phenol); it is isolated from the residue of this process. In addition, acetophenone can be obtained as a main product by selective decomposition of cumene hydroperoxide in the presence of copper catalysts at 100℃:
  
  A second possibility is the oxidation of ethylbenzene with air or oxygen at 130℃ and 0.5 MPa. Catalysts used include cobalt salts or manganese salts of naphthenic or fatty acids. Conversion of ethylbenzene is limited to ca. 25 % to minimize the byproducts 1-phenylethanol and benzoic acid. A third method is the Friedel – Crafts acetylation of benzene with acetic anhydride, but this is not of industrial importance.

• synthetische

  From benzene and acetylchloride in the presence of aluminum chloride or by catalytic oxidation of ethyl benzene; also prepared by fractional distillation and crystallization from the essential oil of Stirlingia latifolia.

• Aroma threshold values

  Detection: 170 ppb; Recognition: 2.9 ppm

• Taste threshold values

  Taste characteristics at 10 ppm: sweet, nutty, benzaldehyde with musty, fruity notes

• Synthesis Reference(s)

  Canadian Journal of Chemistry, 56, p. 2269, 1978 DOI: 10.1139/v78-373
  Chemical and Pharmaceutical Bulletin, 31, p. 4209, 1983 DOI: 10.1248/cpb.31.4209

• Allgemeine Beschreibung

  Acetophenone appears as a colorless liquid with a sweet pungent taste and odor resembling the odor of oranges. Freezes under cool conditions. Slightly soluble in water and denser than water. Hence sinks in water. Vapor heavier than air. A mild irritant to skin and eyes. Vapors can be narcotic in high concentrations. Used as a flavoring, solvent, and polymerization catalyst.

• Air & Water Reaktionen

  Slightly soluble in water.

• Reaktivität anzeigen

  Acetophenone reacts with many acids and bases liberating heat and flammable gases (e.g., H2). Reacts with many oxidizing agents. Reacts with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. The amount of heat in these reactions may be sufficient to start a fire in the unreacted portion. Incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides.

• Health Hazard

  Acetophenone is an irritant, mutagen, and amildly toxic compound. In rabbits 0.77 mgproduced severe eye irritation, but the actionon skin was mild. In mice, subcutaneousadministration of this compound producedsleep; a dose of 330 mg/kg was lethal.
  LD50 value, intraperitoneal (mice): 200mg/kg
  No symptoms of severe toxicity, nor its carcinogenicityin humans, has been reported..

• Brandgefahr

  Combustible liquid; flash point (closed cup) 82°C (180°F); vapor pressure 1 torr at 37°C (98.6°F); vapor density 4.1 (air = 1); autoignition temperature 570°C (1058°F); fire-extinguishing agent: dry chemical, foam, or CO2; water may cause frothing, but it can be used to flush and dilute the spill. Its reaction with strong oxidizers may be violent.

• Flammability and Explosibility

  Not classified

• Sicherheitsprofil

  Poison by intraperitoneal and subcutaneous routesModerately toxic by ingestion. A skin and severe eye irritant. Mutation data reported. Narcotic in high concentration. A hypnotic. Flammable liquid. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes. See also IGTONES

• mögliche Exposition

  Acetophenone is used as a solvent and in perfume manufacture to impact a pleasant jasmine or orange-blossom odor. It is used as a catalyst in olefin polymerization and as a flavorant in tobacco. It is also used in the synthesis of pharmaceuticals

• Carcinogenicity

  No carcinogenicity studies were identified for acetophenone. The U.S. EPA has classified acetophenone as a Category D, not classifiable as to human carcinogenicity.

• Environmental Fate

  It is unclear what mechanism is responsible for the central nervous system depression observed following high doses of acetophenone. In vitro evaluations have demonstrated that acetophenone suppresses voltage-gated ion channels in olfactory receptor cells and retinal neurons; however, it is unclear if this is related to any of the observed toxicity in animal studies.

• Stoffwechsel

  At one time, acetophenone was used as a hypnotic. Its conversion to benzoic acid and methylphenylcarbinol in dogs and rabbits was observed by a number of early workers. Small amounts are also excreted as mandelic acid. In the rabbit about half the dose is excreted as methylphenylcarbinyl glucuronide and about 20 % as hippuric acid. It is probable that the ketone is first asymmetrically reduced to the carbinol, which is the precursor of benzoic and mandelic acids.

• Solubility in organics

  miscible with ethyl alcohol, essential oils and perfume chemicals. Sp.Gr. = 1.033.

• Versand/Shipping

  UN1993 Flammable liquids, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, Technical Name Required.

• läuterung methode

  Dry it by fractional distillation or by standing with anhydrous CaSO4 or CaCl2 for several days, followed by fractional distillation under reduced pressure (from P2O5, optional), and careful, slow and repeated partial crystallisations from the liquid at 0o excluding light and moisture. It can also be crystallised at low temperatures from isopentane. Distillation can be followed by purification using gas-liquid chromatography [Earls & Jones J Chem Soc, Faraday Trans 1 71 2186 1975.] [Beilstein 7 H 271, 7 IV 619.] § A commercial polystyrene supported version is available — scavenger resin (for diol substrates).

• Toxicity evaluation

  The production and use of acetophenone as a specialty solvent and fragrance and flavor additive may result in environmental releases to the air, water, and soil. Acetophenone is slightly soluble in water and freely soluble in alcohol, chloroform, fatty oils, and glycerol. The vapor pressure at 25 °C is 0.4 mmHg, the Henry’s law constant is estimated to be 1.04×105 atmm3 mol^-1, and the octanol/water partition coefficient (log Kow) is 1.58.
  If released to the soil, acetophenone is expected to have high mobility, with volatilization from moist soils. If released to the water, volatilization is anticipated from the surface and acetophenone is not anticipated to adsorb to sediment. The potential for bioconcentration in aquatic organisms is predicted to be low. If released to the atmosphere, the half-life is anticipated to be 6 days, with degradation occurring by reaction with photochemically produced hydroxyl radicals.

• Inkompatibilitäten

  May form explosive mixture with air. See flash point, above. Reacts violently with strong oxidizers, many acids, bases, amines, amides, and inorganic hydroxides; alkali metals; hydrides, and nitrides. Reacts with reducing agents; alkali metals; hydrides, nitrides. Contact with all preceding materials release heat and flammable gases, including hydrogen; the heat may be sufficient enough to result in fire. Incompatible with aldehydes, aliphatic amines, alkanolamines, cyanides, isocyanates, organic acids, peroxides; perchloric acid. May attack plastics, and some rubbers and coatings

• 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, preferably with a flammable solvent

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