- Ethyl acetoacetate
Chembox new
Name = Ethyl acetoacetate
ImageFile = Ethyl_acetoacetate.png
ImageFile1 = Ethyl_acetoacetate-3d.png
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
withfruit orrum 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 =ester s
OtherFunctn =Methyl acetoacetate Ethyl acetate Diethyl malonate
OtherCpds =Acetone Acetylacetone Diketene The
organic compound ethyl acetoacetate (EAA) is theethyl ester ofacetoacetic acid . It is asolvent , and is used as a chemical intermediate in the production of a wide variety of compounds, such asamino acid s,analgesic s,antibiotic s,antimalarial agent s,antipyrene andaminopyrene , andvitamin B1 ; and also in the manufacture ofdye s,ink s,lacquer s,perfume s,plastic s, andyellow paint pigment s. Alone, it is used as aflavoring forfood .Preparation
Ethyl acetoacetate may be prepared via the
Claisen condensation ofethyl 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 todiethyl malonate in theMalonic ester synthesis or theKnoevenagel condensation . The protons alpha tocarbonyl group s are easily deprotonated and then the carbanion formed can undergonucleophilic substitution . A subsequentthermal decarboxylation is also possible.Analysis
Ethyl acetoacetate is an
ester of a β-keto carbonic acid and therefore has a strongKeto-enol tautomerism . The enolate forms purple complexes with iron(III) salts:See also
*
Fructone , the ethylene glycol ketal of ethyl acetoacetate, an aroma compoundReferences
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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См. также в других словарях:
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