Ethyl acetoacetate

Ethyl acetoacetate

Chembox new
Name = Ethyl acetoacetate
ImageFile = Ethyl_acetoacetate.png ImageName = Ethyl acetoacetate
ImageFile1 = Ethyl_acetoacetate-3d.png IUPACName = Ethyl 3-oxobutanoate
OtherNames = Acetoacetic acid ethyl ester
Ethyl acetylacetate
3-Oxobutanoic acid ethyl ester
Section1 = Chembox Identifiers
SMILES = CC(=O)CC(=O)OCC
CASNo = 141-97-9
RTECS = AK5250000
Section2 = Chembox Properties
Formula = C6H10O3
MolarMass = 130.14 g/mol
Appearance = Colourless liquid
with fruit or rum odour
Density = 1.021 g/cm3, liquid
Solubility = 2.86 g/100 ml (20 °C)
MeltingPt = -45 °C (228 K)
BoilingPt = 180.8 °C (454.0 K)
pKa = 10.68 (in H2O)
14.2 (in DMSO)
Viscosity =
Section3 = Chembox Structure
Dipole =
Section7 = Chembox Hazards
ExternalMSDS =
EUClass = not listed
NFPA-H = 2
NFPA-F = 2
NFPA-R =
FlashPt = 70 °C
Section8 = Chembox Related
Function = esters
OtherFunctn = Methyl acetoacetate
Ethyl acetate
Diethyl malonate
OtherCpds = Acetone
Acetylacetone
Diketene

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

Preparation

Ethyl acetoacetate may be prepared via the Claisen condensation of ethyl acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol.


Another method is to use acetyl ketene and ethanol. They directly form ethyl acetoacetate, and the yield is good, so this method is widely used in industry, but acetyl ketene is very dangerous.Fact|date=January 2008

Chemistry

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 easily deprotonated and then the carbanion formed can undergo nucleophilic substitution. A subsequent thermal decarboxylation is also possible.

Analysis

Ethyl acetoacetate is an ester of a β-keto carbonic acid and therefore has a strong Keto-enol tautomerism. The enolate forms purple complexes with iron(III) salts:

See also

* Fructone, the ethylene glycol ketal of ethyl acetoacetate, an aroma compound

References

External links

* [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc10/icsc1024.htm International Chemical Safety Card 1024]
* [http://www.inchem.org/documents/icsc/icsc/eics1024.htm Inchem properties database]


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