Ethylacetoacetat

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H227：Combustible liquid

  H303：May be harmfulif swallowed

  H319：Verursacht schwere Augenreizung.

• Sicherheit

  P210：Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.

  P264：Nach Gebrauch gründlich waschen.

  P264：Nach Gebrauch gründlich waschen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

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

  P337+P313：Bei anhaltender Augenreizung: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

  P370+P378：Bei Brand: zum Löschen verwenden.

  P403+P235：An einem gut belüfteten Ort aufbewahren. Kühl halten.

  P501：Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Ethyl acetoacetate Chemische Eigenschaften,Einsatz,Produktion Methoden

• ERSCHEINUNGSBILD

  FARBLOSE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH.

• PHYSIKALISCHE GEFAHREN

  Die Dämpfe sind schwerer als Luft.

• CHEMISCHE GEFAHREN

  Reagiert mit starken Oxidationsmitteln.

• ARBEITSPLATZGRENZWERTE

  TLV nicht festgelegt.
  MAK: IIb (MAK nicht festgelegt, aber Informationen vorhanden). (DFG 2008).
  

• AUFNAHMEWEGE

  Aufnahme in den Körper durch Inhalation.

• INHALATIONSGEFAHREN

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

• WIRKUNGEN BEI KURZZEITEXPOSITION

  WIRKUNGEN BEI KURZZEITEXPOSITION:
  Die Substanz reizt die Augen, die Haut und die Atemwege.

• LECKAGE

  Ausgelaufene Flüssigkeit möglichst in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. Reste mit viel Wasser wegspülen.

• R-Sätze Betriebsanweisung:

  R36:Reizt die Augen.

• S-Sätze Betriebsanweisung:

  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S24/25:Berührung mit den Augen und der Haut vermeiden.

• Beschreibung

  The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine and amino pyrine, and vitamin B₁; as well as the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments. Alone, it is used as a flavoring for food.

• Chemische Eigenschaften

  Ethyl 3-Oxobutanoate is a colorless liquid with a fruity, ethereal, sweet odor reminiscent of green apples. It is used to create fresh, fruity top notes in feminine fine fragrances. Ethyl acetoacetate occurs in flavors of natural materials such as coffee, strawberries, and yellow passion fruits.

• Chemische Eigenschaften

  Ethyl acetoacetate has a characteristic ether-like, fruity, pleasant, refreshing odor.

• Occurrence

  Naturally occurring in strawberry, coffee, sherry, passion fruit juice (yellow), babaco fruit (Carica pentagona Heilborn) and bread.

• Verwenden

  Ethyl acetoacetate is used as an intermediate in organic synthesis and as a co-promoter for unsaturated polyester resins. It is widely used in the production of dyes, inks, perfumes, plastics and flavoring agents. It is an important starting material for the syntheses of alpha-substituted acetoacetic esters and cyclic compounds like pyrazole, pyrimidine and coumarin derivatives. It acts as an intermediate in the synthesis of vitamins and pharmaceuticals. It finds application as a formaldehyde scavenger.

• Verwenden

  Ethyl acetoacetate (EAA) is used as starting material for the syntheses of alpha-substituted acetoacetic esters and cyclic compounds, e.g. pyrazole, pyrimidine and coumarin derivatives as well as intermediate for vitamins and pharmaceuticals. Product Data Sheet

• synthetische

  Ethyl acetoacetate is produced industrially by treatment of diketene with ethanol.
  The preparation of ethyl acetoacetate is a classic laboratory procedure . It is prepared via the Claisen condensation of ethyl acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol.

• Vorbereitung Methode

  Ethyl acetoacetate is manufactured through a reaction of high-purity ethyl acetate with sodium, followed by neutralization with sulfuric acid.

• Definition

  This compound is a tautomer at room temperature consisting of about 93% keto form and 7% enol form.

• Aroma threshold values

  Detection: 520 ppb. Aroma characteristics at 10%: sweet fruity apple, fermented, slightly fusel-like and rummy, fruity banana with tropical nuances.

• Taste threshold values

  Taste characteristics at 100 ppm: fruity banana, apple and white grape with slightly green estry and tropical nuances.Taste characteristics at 300 ppm: estery, fatty, fruity and tutti-frutti

• Synthesis Reference(s)

  The Journal of Organic Chemistry, 58, p. 793, 1993 DOI: 10.1021/jo00055a046

• Allgemeine Beschreibung

  A colorless liquid with a fruity odor. Flash point 185°F. Boiling point 365°F. May cause adverse health effects if ingested or inhaled. May irritate to skin, eyes and mucous membranes. Used in organic synthesis and in lacquers and paints.

• Air & Water Reaktionen

  Flammable.

• Reaktivität anzeigen

  Ethyl acetoacetate, a beta-keto ester, is more reactive than many esters. Undergoes an exothermic cleavage reaction in the presence of concentrated base. Reacts with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Mixing with 2,2,2-tris(bromomethyl)ethanol and zinc led to an explosion [US Patent 3 578 619, Crotonaldehyde may rapidly polymerize with Ethyl acetoacetate (Soriano, D.S. et al. 1988. Journal of Chemical Education 65:637.).1971].

• Hazard

  Toxic by ingestion and inhalation; irritant to skin and eyes.

• Health Hazard

  Liquid may cause mild irritation of eyes.

• Flammability and Explosibility

  Non flammable

• Chemische Reaktivität

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

• Chemische Reaktivität

  Ethyl acetoacetate is subject to Keto - enol tautomerism. Ethyl acetoacetate is often used in the acetoacetic ester synthesis similar to diethyl malonate in the malonic ester synthesis or the Knoevenagel condensation. The protons alpha to carbonyl groups are acidic, and the resulting carbanion can undergo nucleophilic substitution. A subsequent thermal decarboxylation is also possible.Similar to the behavior of acetylacetone, the enolate of ethyl acetoacetate can also serve as a bidentate ligand. For example, it forms purple coordination complexes with iron (III) salts :
  Ethyl acetoacetate can also be reduced to ethyl 3-hydroxy butyrate.

• Sicherheitsprofil

  eye irritant. Combustible liquid when exposed to heat or flame; can react with oxidzing materials. Explosive reaction when heated with Zn + tribromoneopentyl alcohol or 2,2,2 tris(bromomethy1)ethanol. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.

• Synthese

  Ethyl acetoacetate is a mixture of two tautomer forms: the enolic and the ketonic; the liquid ester at equilibrium contains approximately 70% of the enolic form. It is prepared by Claisen condensation of ethyl acetate in the presence of sodium ethylate; also by reacting diketene with ethanol in the presence of sulfuric acid or triethylamine and sodium acetate, with or without solvent.

• läuterung methode

  Shake the ester with small amounts of saturated aqueous NaHCO3 (until no further effervescence), then with water. Dry it with MgSO4 or CaCl2 and distil it under reduced pressure. [Beilstein 3 IV 1528.]

Ethyl acetoacetate Upstream-Materialien And Downstream Produkte

Ethylacetoacetat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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