Essigsäureanhydrid Produkt Beschreibung

Acetic anhydride Struktur
108-24-7
  • CAS-Nr.108-24-7
  • Bezeichnung:Essigsäureanhydrid
  • Englisch Name:Acetic anhydride
  • Synonyma:Eissigsureanhydrid;Essigsäureanhydrid;Acetylanhydrid;Ethans?ureanhydrid;Acetyloxid
    AC2O;acetic;(CH3CO)2O;acetylether;Acetyl ether;ACETYL OXIDE;ACETIC OXIDE;Acetanhydrid;Acetanhydride;Acetyl acetate
  • CBNumber:CB2852742
  • Summenformel:C4H6O3
  • Molgewicht:102.08864
  • MOL-Datei:108-24-7.mol
Essigsäureanhydrid physikalisch-chemischer Eigenschaften
  • Schmelzpunkt: :-73.1 °C
  • Siedepunkt: :140 °C
  • Dichte :1.087
  • Dampfdichte :3.5 (vs air)
  • Dampfdruck :10 mm Hg ( 36 °C)
  • Brechungsindex :n20/D 1.390(lit.)
  • Flammpunkt: :130 °F
  • storage temp.  :Store at RT.
  • Löslichkeit :Miscible with ether, chloroform and benzene.
  • Aggregatzustand :Liquid
  • Farbe :Colorless
  • Wichte :1.082
  • PH :3 (10g/l, H2O, 20°C)
  • Geruch (Odor) :Very strong; pungent; vinegar-like characteristic odor.
  • Explosionsgrenze :2.0-10.2%(V)
  • Wasserlöslichkeit :REACTS
  • Sensitive  :Moisture Sensitive
  • Merck  :14,56
  • BRN  :385737
  • Expositionsgrenzwerte :NIOSH REL: ceiling 5 ppm (20 mg/m3), IDLH 200 ppm; OSHA PEL: 5 ppm; ACGIH TLV: ceiling 5 ppm.
  • Stabilität: :Stability Flammable. Incompatible with strong oxidizing agents, water, strong bases, alcohols.
  • CAS Datenbank :108-24-7(CAS DataBase Reference)
  • NIST chemische Informationen :Acetic acid anhydride(108-24-7)
  • EPA chemische Informationen :Acetic acid, anhydride(108-24-7)
Sicherheit

Acetic anhydride Chemische Eigenschaften,Einsatz,Produktion Methoden

  • ERSCHEINUNGSBILD FARBLOSE FLüSSIGKEIT MIT STECHENDEM GERUCH.
  • CHEMISCHE GEFAHREN Zersetzung beim Verbrennen unter Bildung giftiger Gase und giftiger Rauche einschließlich Essigsäurerauche. Reagiert sehr heftig mit Alkoholen, Aminen, Oxidationsmitteln, starken Basen und Wasser. Greift viele Metalle in Gegenwart von Wasser an, oder auch im trockenen Zustand.
  • ARBEITSPLATZGRENZWERTE TLV: 5 ppm (als TWA) (ACGIH 2006).
    MAK: 5 ppm; 21 mg/m? Spitzenbegrenzung: überschreitungsfaktor I (1); Schwangerschaft: Gruppe D (DFG 2006).
  • AUFNAHMEWEGE Aufnahme in den Körper durch Inhalation der Dämpfe und durch Verschlucken.
  • INHALATIONSGEFAHREN Beim Verdampfen bei 20°C kann schnell eine gesundheitsschädliche Kontamination der Luft eintreten.
  • WIRKUNGEN BEI KURZZEITEXPOSITION WIRKUNGEN BEI KURZZEITEXPOSITION:
    Tränenreizend. Der Stoff ist ätzend auf die Augen, die Haut und die Atemwege. ätzend beim Verschlucken. Inhalation des Stoffes kann zu asthmaähnlichen Reaktionen führen.
  • WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION Inhalation des Stoffes kann asthmaähnliche Reaktionen auslösen (RADS).
  • LECKAGE Persönliche Schutzausrüstung: Atemschutzfilter für saure Gase. Chemikalienschutzanzug. Gesichtsschutz benutzen. Fachmann zu Rate ziehen! Belüftung. Ausgelaufene Flüssigkeit möglichst in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen.
  • R-Sätze Betriebsanweisung: R11:Leichtentzündlich.
    R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
    R37/38:Reizt die Atmungsorgane und die Haut.
    R41:Gefahr ernster Augenschäden.
    R34:Verursacht Verätzungen.
    R20/21:Gesundheitsschädlich beim Einatmen und bei Berührung mit der Haut.
    R10:Entzündlich.
    R20/22:Gesundheitsschädlich beim Einatmen und Verschlucken.
    R19:Kann explosionsfähige Peroxide bilden.
  • S-Sätze Betriebsanweisung: S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
    S39:Schutzbrille/Gesichtsschutz 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.
    S33:Maßnahmen gegen elektrostatische Aufladungen treffen.
    S16:Von Zündquellen fernhalten - Nicht rauchen.
  • Beschreibung Acetic anhydride is a colourless liquid and appreciably soluble in water. It is of ethanoic acid smell. Acetic acid anhydride is flammable, moisture sensitive, and incompatible with strong oxidising agents, water, strong bases, alcohols, metals, reducing agents, amines, ammonia, nitrates, nitric acid, permanganates, phenols, sodium hydroxide, hydrogen peroxide, chromium trioxide, potassium hydroxide, perchloric acid, and ethanol. Acetic anhydride is mainly used for the acetylation of cellulose to cellulose acetate for photographic film and other applications. Upon burning, acetic anhydride decomposes and produces toxic gases and toxic fumes including acetic acid fumes. It attacks many metals with or without the presence of water.
  • Chemische Eigenschaften Colorless liquid
  • Chemische Eigenschaften Acetic anhydride is a combustible, colorless, strongly refractive, liquid which has a strongly irritating odor.
  • Chemische Eigenschaften Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolatable acid anhydride and is a widely used reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, formed by its reaction with the moisture in the air.
    Formic anhydride is an even simpler acid anhydride, but it spontaneously decomposes, especially once removed from solution.
  • Chemische Eigenschaften An esterification agent used in the preparation of modified starch and for acetylation of acetylated monoglycerides. It has a strong acetic odor.
  • Physikalische Eigenschaften Colorless, very mobile liquid with a very strong, acetic acid-like odor. Experimentally determined detection and recognition odor threshold concentrations were <600 μg/m3 (<140 ppbv) and 1.5 mg/m3 (360 ppbv), respectively (Hellman and Small, 1974).
  • Occurrence Reported found in watercress (Nasturtium officinale r. br.).
  • Verwenden Acetic Anhydride is an esterifier for food starch; also used in combi- nation with adipic anhydride.
  • Verwenden Preparation of anhydrous acetic acid in nonaqueous titrimetry.
  • Verwenden manufacture of acetyl compounds, cellulose acetates. As acetulizer and solvent in examining wool fat, glycerol, fatty and volatile oils, resins; detection of rosin. Widely used in organic syntheses, e.g., as dehydrating agent in nitrations, sulfonations and other reactions where removal of water is necessary.
  • Verwenden Acetic anhydride is an important solvent and acetylation agent. It is used for the manufacture of acetylcellulose, acetylsalicylic acid, acetanilide, nitrofurane, sulfonamides, vitamin B6 etc. Product Data Sheet
  • Definition ChEBI: An cyclic carboxylic anhydride of acetic acid.
  • Vorbereitung Methode Acetic anhydride is produced by carbonylation of methyl acetate :
    CH3CO2CH3 + CO → (CH3CO)2O
    This process involves the conversion of methyl acetate to methyl iodide and an acetate salt. Carbonylation of the methyl iodide in turn affords acetyl iodide, which reacts with acetate salts or acetic acid to give the product. Rhodium iodide and lithium iodide are employed as catalysts. Because acetic anhydride is not stable in water, the conversion is conducted under anhydrous conditions. In contrast, the Monsanto acetic acid process, which also involves a rhodium catalyzed carbonylation of methyl iodide, is at least partially aqueous.
    To a decreasing extent, acetic anhydride is also prepared by the reaction of ethenone (ketene) with acetic acid at 45–55 °C and low pressure (0.05–0.2 bar).
    H2C= C= O + CH3COOH → (CH3CO)2O (ΔH = ?63 kJ/mol)
    Ketene is generated by dehydrating acetic acid at 700–750 °C in the presence of triethyl phosphate as a catalyst or (in Switzerland and the CIS) by the thermolysis of acetone at 600–700 °C in the presence of carbon disulfide as a catalyst.
    CH3COOH H2C= C= O + H2O (ΔH = +147 kJ/mol)
    CH3COCH3 → H2C= C= O + CH4
    The route from acetic acid to acetic anhydride via ketene was developed by Wacker Chemie in 1922, when the demand for acetic anhydride increased due to the production of cellulose acetate.
    Due to its low cost, acetic anhydride is purchased, not prepared, for use in research laboratories.
  • Application As indicated by its organic chemistry, Ac2O is mainly used for acetylations leading to commercially significant materials. Its largest application is for the conversion of cellulose to cellulose acetate, which is a component of photographic film and other coated materials. Similarly it is used in the production of aspirin (acetylsalicylic acid), which is prepared by the acetylation of salicylic acid.It is also used as a wood preservative via autoclave impregnation to make a longer lasting timber.
    In starch industry, acetic anydride is a common acetylation compound, used for the production of modified starches
    Because of its use for the synthesis of heroin by the diacetylation of morphine, acetic anhydride is listed as a U.S. DEA List II precursor, and restricted in many other countries.
  • Reaktionen introduction of acetyl groups to organic substrates . In these conversions, acetic anhydride is viewed as a source of CH3CO+. Alcohols and amines are readily acetylated. For example, the reaction of acetic anhydride with ethanol yields ethyl acetate:
    (CH3CO)2O + CH3CH2OH → CH3CO2CH2CH3 + CH3COOH
    Often a base such as pyridine is added to function as catalyst. In specialized applications, Lewis acidic scandium salts have also proven effective catalysts.
    Aromatic rings are acetylated, usually in the presence of an acid catalyst. Illustrative is the conversion of benzene to aceto phenone:
    (CH3CO)2O + C6H6 → CH3COC6H5 + CH3CO2H
    Ferrocene can be acetylated as well:
    Cp2Fe + (CH3CO)2O → CpFe(C5H4COCH3).
  • Aroma threshold values Detection: 490 ppb; Recognition: 1.5 ppm
  • Allgemeine Beschreibung A clear colorless liquid with a strong odor of vinegar. Flash point 129°F. Corrosive to metals and tissue. Density 9.0 lb /gal. Used to make fibers, plastics, pharmaceuticals, dyes, and explosives.
  • Air & Water Reaktionen Flammable. Reacts violently with water to generate acetic acid . This reaction is heightened by the presence of mineral acids (nitric, perchloric, sulfuric acid, etc.) [Chem. Eng. News 25, 3458].
  • Reaktivität anzeigen Acetic anhydride reacts violently on contact with water, steam, methanol, ethanol, glycerol and boric acid. Reaction with water is particularly dangerous in presence with mineral acids (e.g., nitric, perchloric, chromic, sulfuric acid) [Chem. Eng. News 25, 3458]. Potentially explosive reactions with oxidizing reagents such as barium peroxide, chromium trioxide, chromic acid, hypochlorous acid, nitric acid, perchloric acid, peroxyacetic acid, potassium permanganate, hydrogen peroxide. [Sax, 9th ed., 1996, p. 15]. Reacts violently with metal nitrates used as nitrating agents [Davey W. et al., Chem. & Ind., 1948, p. 814].
  • Health Hazard Liquid is volatile and causes little irritation on uncovered skin. However, causes severe burns when clothing is wet with the chemical or if it enters gloves or shoes. Causes skin and eye burns and irritation of respiratory tract. Nausea and vomiting may develop after exposure.
  • Brandgefahr Flash Point (°F): 136 ℃; 120 ℃; Flammable Limits in Air (%): 2.7 - 10.0; Fire Extinguishing Agents: Water spray, dry chemical, alcohol foam, or carbon dioxide; Fire Extinguishing Agents Not To Be Used: Water and foam react, but heat liberated is not enough to create a hazard. Dry chemical forced below the surface can cause foaming and boiling; Special Hazards of Combustion Products: Irritating vapors generated upon heating; Behavior in Fire: Not pertinent; Ignition Temperature (°F): 600; Electrical Hazard: Not pertinent; Burning Rate: 3.3 mm/min.
  • Chemische Reaktivität Reactivity with Water: Reacts slowly with water, but considerable heat is liberated when contacted with spray water; Reactivity with Common Materials: Corrodes iron, steel and other metals; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Dilute with water and use sodium bicarbonate solution to rinse; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
  • Sicherheitsprofil Moderately toxic by inhalation, ingestion, and skin contact. A skin and severe eye irritant. A flammable liquid. A fire and explosion hazard when exposed to heat or flame. Potentially explosive reactions with barium peroxide, boric acid, chromium trioxide, 1,3diphenyltriazene, hydrochloric acid + water, hypochlorous acid, nitric acid, perchloric acid + water, peroxyacetic acid, potassium permanganate, tetrafluoroboric acid, 4toluenesulfonic acid + water, and acetic acid + water. Reactions with ethanol + sodium hydrogen sulfate, and hydrogen peroxide form explosive products. Reactions with ammonium nitrate + hexamethylenetetrammonium acetate + nitric acid form as products the military explosives RDX and HMX. Reacts violently with N-tert-butyl-phthalimic acid + tetrafluoroboric acid, chromic acid, glycerol + phosphoryl chloride, and metal nitrates (e.g., copper or sodium nitrates). Incompatible with 2-aminoethanol, aniline, chlorosulfonic acid, (CrOs + acetic acid), ethylene-diamine, ethyleneimine, glycerol, oleum, HF, permanganates, NaOH, Na2O2, H2SO4, water, N2O2, (glycerol + phosphoryl chloride). When heated to decomposition it emits toxic fumes; can react vigorously with oxidizing materials, wdl react violently on contact with water or steam. Used in production of drugs of abuse. To fight fire, use CO2, dry chemical, water mist, alcohol foam. See also ANHYDRIDES.
  • Chemical Synthesis It may be synthesized from diacetyl by partial reduction with zinc and acid or may be derived from fermentation
  • mögliche Exposition Acetic anhydride is used as an acetylating agent or as a solvent in the manufacture of cellulose acetate, acetanilide, aspirin, synthetic fibers, plastics, explosives, resins, perfumes, and flavorings; and it is used in the textile dyeing industry. It is widely used as a pharmaceutical intermediate and as a pesticide intermediate
  • Enzyminhibitor This carboxylic anhydride (FW = 102.09 g/mol; CAS 108-24-7; M.P. = – 73°C; B.P. = 139°C) reacts with amino groups in peptides/proteins under slightly alkaline conditions. If the amino group is essential for biological or catalytic activity, its acetylation will often inhibit the modified peptide/protein. Tyrosyl residues are also acetylated; however, under alkaline condition, O-acetyltyrosyl residues hydrolyze readily. The latter can occasionally be trapped as the N-acetohydroxamate after reaction with neutral hydroxylamine. Acetic anhydride hydrolyzes slowly (t1/2 at 0°C = 50 min; t1/2 at 25°C = 4.5 min) to yield two molecules of acetic acid, the presence of which imparts a distinct odor. CAUTION: This liquid is a skin and eye irritant. Avoid breathing acetic anhydride vapor. In view of its relatively low flash point of 54°C, acetic anhydride is a combustible liquid requiring appropriate caution. Target(s): glucose dehydrogenase; citrate (si)-synthase; thrombin; carboxypeptidase A; chymotrypsin; acetoacetate decarboxylase; trypsin; crotoxin B; dendrotoxin I; cAMP-dependent protein kinase; Na+/K+- exchanging ATPase; collagenase; alkaline phosphatase; fructose-1,6-bisphosphatase; arylsulfatase; lysozyme; glutamine synthetase; glutamate dehydrogenase; hexokinase; phenylalanine ammonia-lyase; 3-oxoacid CoAtransferase, or 3-ketoacid CoA-transferase; aryl-acylamidase, but stimulated at low concentrations; butyrylcholinesterase, but stimulated at low concentrations; acetylcholinesterase; leukotriene-A4 hydrolase; endo-1,4-b-xylanase; ribonuclease T1; poly(3-hydroxyoctanoate) depolymerase; phospholipase A2; sterol O-acyltransferase, or cholesterol O-acyltransferase, or ACAT; and glycerol-3-phosphate O-acyltransferase.
  • Environmental Fate Chemical/Physical. Slowly dissolves in water forming acetic acid. In ethanol, ethyl acetate is formed (Windholz et al., 1983).
  • Versand/Shipping UN1715 Acetic anhydride, Hazard class: 8; Labels: 8-Corrosive material, 3-Flammable liquid.
  • läuterung methode Adequate purification can usually be achieved by fractional distillation through an efficient column. Acetic acid can be removed by prior refluxing with CaC2 or with coarse Mg filings at 80-90o for 5days, or by distillation from a large excess of quinoline (1% AcOH in quinoline) at 75mm pressure. Acetic anhydride can also be dried by standing with Na wire for up to a week, removing the Na and distilling it under vacuum. (Na reacts vigorously with acetic anhydride at 65-70o). Dippy & Evans [J Org Chem 15 451 1950] let the anhydride (500g) stand over P2O5 (50g) for 3hours, then decanted it and stood it with ignited K2CO3 for a further 3hours. The supernatant liquid was distilled and the fraction b 136-138o was further dried with P2O5 for 12hours, followed by shaking with ignited K2CO3, before two further distillations through a five-section Young and Thomas fractionating column. The final material distilled at 137.8-138.0o. It can also be purified by azeotropic distillation with toluene: the azeotrope boils at 100.6o. After removal of the remaining toluene, the anhydride is distilled [sample had a specific conductivity of 5 x 10-9 ohm-1cm -1]. [Beilstein 2 H 96, 2 I 39, 2 II 91, 2 III 134, 2 IV 94.] Rapid procedure: Shake with P2O5, separate, shake with dry K2CO3 and fractionally distil.
  • 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, epoxides, alcohols, chromic acid (violent reaction), amines, strong caustics; finely divided metals. Contact with water forms acetic acid and liberates a large amount of heat. Corrosive to iron, steel and other metals.
  • Waste disposal Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.
Acetic anhydride Upstream-Materialien And Downstream Produkte
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108-24-7, Acetic anhydride Verwandte Suche:
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  • Acetyl acetate
  • Acetyl anhydride
  • Acetyl ether
  • acetylanhydride
  • acetylether
  • Anhydrid kyseliny octove
  • Anhydride acetique
  • anhydrideacetique
  • anhydrideacetique(french)
  • anhydridkyselinyoctove
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  • Acetic Anhydride (Controlled Chemical)
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  • Cap A (acetic anhydride 12% in acetonitrile)
  • Acetic anhydride ;Acetic oxide;Acetyl oxide;Ethanoic anhydrde
  • Ethanoic anhydrde
  • acetic anhydrid
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