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CAS NO.: 141-97-9
EC/LIST NO.: 205-516-1
The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid.
Ethyl acetoacetate is a colorless liquid.
Ethyl acetoacetate is widely used as a chemical intermediate in the production of a wide variety of compounds.
Ethyl acetoacetate is used as a flavoring for food.
Ethyl acetoacetate is produced industrially by treatment of diketene with ethanol.
The preparation of ethyl acetoacetate is a classic laboratory procedure.
Ethyl acetoacetate is prepared via the Claisen condensation of Ethyl acetoacetate.
Two moles of Ethyl acetoacetate condense to form one mole each of ethyl acetoacetate and ethanol.
Ethyl acetoacetate is diprotic:
CH3C(O)CH2CO2Et + NaH → CH3C(O)CH(Na)CO2Et + H2
CH3C(O)CH(Na)CO2Et + BuLi → LiCH2C(O)CH(Na)CO2Et + BuH
Ethyl acetoacetate is subject to keto-enol tautomerism.
In the neat liquid at 33 °C, the enol consists of 15% of the total.
Ethyl acetoacetic acid is a building block in organic synthesis since the protons alpha to carbonyl groups are acidic, and the resulting carbanion undergoes nucleophilic substitution.
Ethyl acetoacetate is often used in the acetoacetic ester synthesis similar to diethyl malonate in the malonic ester synthesis or the Knoevenagel condensation.
A subsequent thermal decarboxylation is also possible.
The dianion of ethylacetoacetate is also a useful building block, except that the electrophile adds to the terminal carbon.
The strategy can be depicted in the following simplified form:
LiCH2C(O)CH(Na)CO2Et + RX → RCH2C(O)CH(Na)CO2Et + LiX
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 transesterifies to give benzyl acetoacetate via a mechanism involving acetylketene.
Ethyl (and other) acetoacetates nitrosate readily with equimolar sodium nitrite in acetic acid, to afford the corresponding oximinoacetoacetate esters.
A dissolving-zinc reduction of these in acetic acid in the presence of ketoesters or beta-diketones constitute the Knorr pyrrole synthesis, useful for the preparation of porphyrins.
Ethyl acetoacetate (CH3COCH2COOC2H5), also called acetoacetic ester, an ester widely used as an intermediate in the synthesis of many varieties of organic chemical compounds.
Industrially it is employed in the manufacture of synthetic drugs and dyes.
The ester is produced chiefly by self-condensation of Ethyl acetoacetate, brought about by sodium metal.
Ethyl acetoacetate readily forms sodium derivatives that can be alkylated and dialkylated.
The resulting esters may be converted to ketones or carboxylic acids.
Ethyl acetoacetate readily enters into condensation reactions, and it has been employed in the synthesis of pyridines, quinolines, furans, pyrazoles, pyrroles, and purines.
The pure ester is a colourless, fragrant liquid that boils with slight decomposition at 180.4 °C (356.7 °F).
Density : 1.03 g/cm3 (20 °C)
Explosion limit : 1.0 - 54 %(V)
Flash point : 73.5 °C
Ignition temperature : 350 °C
Melting Point : -53.3 °C
pH value : 4.0 (110 g/l, H₂O, 20 °C)
Vapor pressure : 0.26 hPa (20 °C)
Solubility : 130.3 g/l
Ethyl acetoacetate is used as an intermediate in organic synthesis and as a co-promoter for unsaturated polyester resins.
Ethyl acetoacetate is widely used in the production of dyes, inks, perfumes, plastics and flavoring agents.
Ethyl acetoacetate is an important starting material for the syntheses of alpha-substituted acetoacetic esters and cyclic compounds like pyrazole, pyrimidine and coumarin derivatives.
Ethyl acetoacetate acts as an intermediate in the synthesis of vitamins and pharmaceuticals.
Ethyl acetoacetate finds application as a formaldehyde scavenger.
Ethyl acetoacetate is a solvent with a boiling point of 77°C.
The vapor pressure at room temperature 97 hPa.
Ethyl acetoacetate has the chemical formula C4H8O2.
Ethyl acetoacetate can be easily solved in acetone, and alcohols, but fairly bad in water (80g per Liter).
Ethyl Acetoacetate (EAA) is a colorless liquid with a fruity odor that is used as a chemical intermediate.
Ethyl acetoacetate is used by consumers and professional workers.
Ethyl acetoacetate can be used in the manufacture of dyes, inks, lacquers, coatings, perfumes, plastics, and yellow paint pigments.
Ethyl acetoacetate is used as a low color-generating copromoter for unsaturated polyester resins.
Because of the fruity odor and the lack of color Ethyl acetoacetate can be used as a solvent in fragrances or a flavoring for food.
Consumers can use Ethyl acetoacetate in air care products, cleaning and furnishing products, laundry and dish washing products, and more.
Ethyl acetoacetate is an organic compound that is the ethyl ester of acetoacetate.
The chemical formula of this compound is C6H10O3 or CH3COOCH2COOC2H5.
This compound is present as a colourless liquid with a fruity fragrance that is used as a food flavouring.
Ethyl acetoacetate is also used as a chemical intermediate for the production of various types of chemical compounds.
This compound is also used industrially in the production of synthetic dyes and drugs.
Ethyl acetoacetate is industry produced compound.
The ethyl acetoacetate structure is produced using the treatment of ethanol with diketene.
The production of this compound in the laboratory is a very well-known procedure.
This is done by using the process of Claisen condensation of Ethyl acetoacetate.
The reaction produces one molecule of ethyl acetoacetate and one molecule of ethanol from the condensation of two molecules of Ethyl acetoacetate.
CH3COOCH2COOC2H5 is a primary part of acetoacetate ester synthesis.
Now that you have a brief understanding of this compound and its production.
Let’s now learn about acetoacetate ester synthesis.
systematically known as ethyl 3-oxobutanoate
the Claisen condensation product from ethyl ethanoate (i.e. Ethyl acetoacetate) CH3CO2CH2CH3
an example of an active methylene compound
has a relatively acidic a-proton, pKa = 11, so the enolate is readily formed with ethoxide, EtO-
can be readily substituted then hydrolysed and decarboxylated to give a substituted ketone.
Alkylation of an active methylene enolate
Hydrolysis of an ester to a carboxylic acid
Decarboxylation of a b-ketoacid
This process is the equivalent of taking R-Xand substituting X with CH3C(=O)CH2-
In effect, the acyl group of the ester has been used to activate the ketone enolate towards alkylation and has then been removed.
Ethyl acetoacetate is a solvent used in many contexts, including printing inks, varnishes and car care chemicals, and in the manufacture of plastics and rubber.
In the food industry, Ethyl acetoacetate is used in the manufacture of flavourings and in the pharmaceutical industry as an extraction solvent in the production of pharmaceuticals.
Ethyl acetoacetate is also a common component of cosmetics and nail polish remover.
Ethyl acetoacetate is considered to be one of the least environmentally harmful of organic solvents.
Ethyl acetoacetate is very effective while it is easily broken down in both air and water.
The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid.
Ethyl acetoacetate 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 aminopyrine, 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.
Ethyl acetoacetate is an ester of ethanol and acetic acid.
Ethyl acetoacetate is typically manufactured for use as a solvent on a large scale.
Ethyl acetoacetate is a moderately polar, clear, colorless liquid solvent with a light fruity odor.
Ethyl acetoacetate, also known as ethyl ethanoate, is a widely used solvent in organic synthesis that is highly miscible with common organic solvents.
Ethyl acetoacetate is cost-effective, highly effective and is easily broken in both air and water simultaneously.
Ethyl acetoacetate can be mixed with non-polar solvents and is also used for extractions.
Ethyl acetoacetate is used to extract not only within the pharmaceutical industry and for industrial purposes but also in the food and beverage industry.
Ethyl acetoacetate has a sweet smell that is used to bring a fruity flavor to candy, baked goods, gum, etc.
Ethyl acetoacetate is also used to extract tobacco from cigarettes, decaffeinate tea leaves, and decaffeinate coffee.
The process to decaffeinate coffee can take up to ten hours, the green coffee beans are rinsed with an Ethyl acetoacetate solution to remove caffeine from them.
Immersing the green coffee beans in water softens the beans and dissolves the caffeine.
Ethyl acetoacetate is added to the water and the caffeine binds to the chemical due to the water holding all the caffeine instead of the coffee beans holding the caffeine.
When the water is heated, the Ethyl acetoacetate steams off, taking the caffeine with it.
Ethyl acetoacetate can also be found in wine.
Ethyl acetoacetate is also common ester in wines, helping to give wines a fruity flavor.
Ethyl acetoacetate is used as an artificial flavor in ice creams and cakes.
The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid.
Ethyl acetoacetate 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 aminopyrine, and vitamin B1; as well as producing paints, inks, varnishes, perfumes, plastics and yellow paint pigments.
Ethyl acetoacetate is used alone as a flavoring for food.
The chemical formula is CH3CO · CH2 COOC 2H 5.
A colorless liquid with an odor.
Melting point -43 to -45 °C, boiling point 181 °C Soluble in water, easily soluble in organic solvent.
There is a tautomeric equilibrium between the keto type and the enol type.
Used for various organic synthesis raw materials.
Synthesis is accomplished by reacting Ethyl acetoacetate with sodium metal or the like.
Ethyl acetoacetate (EAA) is a beta-ketone ester containing carbon (C), hydrogen (H), and oxygen (O) with the empirical formula C6H10O3.
Ethyl acetoacetate can be prepared by condensing Ethyl acetoacetate with sodium acetate with Claisen or by some modification of this process.
Ethyl acetoacetate finds many important applications both commercially and scientifically. The food industry uses it in a variety of ways and is used as an intermediate in medicines, as well as polishes, paints and other surface preparations.
At the research level, the ester is an important reagent in organic synthesis and ligand chemistry.
Ethyl acetoacetate gives a pleasant, fruity aroma.
This makes it a popular synthetic for use in chemically modified flavoring and fragrance applications, as is the case with fructone.
Also, food manufacturers use the substance in resinous and polymeric coatings.
Such coatings can be used on food contact surfaces on equipment or surfaces, or to a limited extent on the food itself.
Ethyl acetoacetate can be used in non-food surface coatings or textiles as an accelerator in the curing process.
About 1-3 weight percent EAA is added to the unsaturated polyester resin, called a promoter or co-promoter.
In other products, EAA may be added as a solvent, a stabilizer or a catalyst.
More extensively modified, acetoacetic acid derivatives find application in paints, pigments and agrochemicals.
Acetoacetoxyethyl methacrylate is used in copolymerization to reduce viscosity in adhesives.
Ethyl acetoacetate (CH 3 COCH 2 COOC 2 H 5 ), also called acetoacetic ester, is an ester widely used as an intermediate in the synthesis of many kinds of organic chemistry compounds.
Ethyl acetoacetatet is used industrially in the production of synthetic drugs and dyes.
The ester is mainly produced by the self-condensation of Ethyl acetoacetate brought about by sodium metal.
Ethyl acetoacetate already forms sodium derivatives that can be alkylated and dialkylated.
The resulting esters can be converted to ketones or carboxylic acids.
Ethyl acetoacetate readily undergoes condensation reactions and has been used in the synthesis of pyridines, quinolines, furans, pyrazoles, pyrroles, and purines.
The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid.
ethyl acetoacetate is mainly used as a chemical intermediate in the manufacture of a wide variety of amino acids, analgesics, antibiotics, anti-malarial agents, antipyrine and amino pyrine, and vitamin B compounds 1 ; as well as the manufacture of paints, inks, varnishes, perfumes, plastics and yellow paint pigments.
ethyl acetoacetate is used alone as a sweetener to dishes.
Ethyl acetoacetate has a characteristic ether-like, fruity, pleasant, refreshing odour.
Ethyl 3-Oxobutanoate is a colorless liquid with a fruity, ethereal, sweet odor reminiscent of green apples.
ethyl acetoacetate is used to create fresh, fruity top notes in feminine fragrances.
Ethyl acetoacetate is found in the flavors of natural materials such as coffee, strawberries and yellow passion fruit.
ethyl acetoacetate occurs naturally in strawberries, coffee, sherry, passion fruit juice (yellow), babaco fruit (Carica pentagona Heilborn), and bread.
Ethyl acetoacetate (EAA) is used as a starting material for the synthesis of alpha-substituted acetoacetic esters and cyclic compounds, for example pyrazole, pyrimidine and coumarin derivatives, as well as intermediate for vitamins and pharmaceuticals.
This compound is a tautomer consisting of approximately 93% keto form and 7% enol form at room temperature.
Ethyl acetoacetate is produced by the reaction of high purity ethyl acetate with sodium followed by neutralization with sulfuric acid.
Ethyl acetoacetate is produced industrially by treating dikethene with ethanol.
Preparation of ethyl acetoacetate is a classic laboratory procedure.
ethyl acetoacetate is prepared by Claisen condensation of ethyl acetate.
Two moles of ethyl acetate condense to form one mole of ethyl acetoacetate and ethanol.
Appearance : White crystalline powder
Ethyl acetoacetate, %≥ : 99.0
Acidity(acetate), %≤ : 0.1
Moisture,%≤ : 0.1
Ethyl acetate solution test : through tests
Density P20, g/cm3 : 1.020-1.030
IUPAC NAME :
1-Ethoxybuate-1,3-Dione
1-Ethoxybutane-1,3-dione
1-ethoxybutane-1,3-dione
acetoacetic acid ethyl ester
Acetoacetic ester, EAA, Acetoacetic acid ethyl ester
EAA
ETHYL 3-OXOBUTANOATE
Ethyl 3-oxobutanoate
SYNONYMS:
Ethyl acetoacetate
141-97-9
205-516-1
3-Oxobutanoate d'éthyle
3-Oxobutanoic acid, ethyl ester
acetoacetic acid ethyl ester
ACETOACETIC ESTER
Butanoic acid, 3-oxo-, ethyl ester
EAA
Ethyl 3-oxobutanoate
