Ethylacetoacetat 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 B
1; 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.
Occurrence
Naturally occurring in strawberry, coffee, sherry, passion fruit juice (yellow), babaco fruit (Carica pentagona
Heilborn) and bread.
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.
Definition
This compound is a tautomer at room temperature
consisting of about 93% keto form and 7% enol
form.
Vorbereitung Methode
Ethyl acetoacetate is manufactured through a reaction of
high-purity ethyl acetate with sodium, followed by neutralization
with sulfuric acid.
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.
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.
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.]
Ethylacetoacetat Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
3-CHLORO-4-METHYL-7-HYDROXYCOUNMARIN
Ethyl 2-hydroxy-4-methyl-5-pyrimidinecarboxylate
3,3'-Dimethyl-1,1'-diphenyl-4,4'-bi-5-pyrazolon
4-CHLORO-2,6-DIMETHYL-NICOTINIC ACID
ETHYL 2,4-DIMETHYLQUINOLINE-3-CARBOXYLATE
Disperse Yellow H-4GL
ETHYL 2-ACETYL-3-OXO-HEXANOATE
1-(6-CHLORO-2-HYDROXY-4-PHENYL-QUINOLIN-3-YL)-ETHANONE
Ethyl-3-hydroxybutyrat
5-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLIC ACID
PHENOXYACETIC ACID
5,7-Dihydroxy-4-methyl-2-benzopyron
4-HYDROXY-2-METHYLQUINOLINE
ETHYL 4-CHLORO-2,6-DIMETHYLPYRIDINE-3-CARBOXYLATE
7-(Acetyloxy)-4-methyl-2-benzopyron
Ethyl-3,4-dihydro-6-methyl-2H-pyran-5-carboxylat
Kalium-N-phenylglycinat
TIADINIL
ETHYL 5-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLATE
6-Bromhexan-2-on
Pentoxifyllin
6-TERT-BUTYL-4-METHYLCOUMARIN
Hymecromon
ETHYL 2-(HYDROXYIMINO)-3-OXOBUTANOATE
Cloricromene
2,4-DIMETHYLQUINOLINE-3-CARBOXYLIC ACID
Acetoacetic Acid
Ethyl-3-anilinocrotonat
(5-METHYL-1-PHENYL-1H-PYRAZOL-4-YL)METHANOL
5,7-Dihydroxy-2-phenyl-4H-benzo[b]pyran-4-on
4,7-DIMETHYLCOUMARIN
3-Ethyl-4-methyl-3-pyrrolin-2-one
4-Chloro-6-methyl-2-(methylthio)pyrimidine
2-Amino-6-methylpyrimidin-4-ol
4-Methylcumarin
1,3-Dimethyl-5-hydroxypyrazole
6-Methyl-2-(methylthio)pyrimidin-4-ol
7,8-Dihydroxy-4-methyl-2-benzopyron
3-METHYL-5-PHENYL-4-ISOXAZOLECARBOXYLIC ACID
Ethyl-2-[2-(diethylamino)ethyl]acetoacetat
