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CAS NO.: 105-45-3
EC/LIST NO.: 203-299-8
Methyl acetoacetate is used as a chemical reagent used in the synthesis of pharmaceuticals.
Methyl acetoacetate participates in the Biginelli reaction, forming molecules including dihydropyrimidinones.
Methyl acetoacetate (MAA) is used for the synthesis of alpha-substituted aceto- acetic esters and cyclic compounds, e.g. pyrazole, pyrimidine and coumarin derivatives.
Methyl acetoacetate acid, also known as 3-oxo-butanoate or methyl acetylacetate, belongs to the class of organic compounds known as beta-keto acids and derivatives.
These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.
Methyl acetoacetate acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Methyl acetoacetate acid is a citrus, fresh, and fruity tasting compound
Methyl acetoacetate is a chemical reagent used in the synthesis of pharmaceuticals.
Methyl acetoacetate participates in the Biginelli reaction, forming molecules including dihydropyrimidinones.
Methyl acetoacetate (MAA) is a starting material for the syntheses of alpha-substituted aceto- acetic esters and cyclic compounds, e.g. pyrazole, pyrimidine and coumarin derivatives.
3-Oxobutanoic Acid Methyl Ester is a chemical reagent used in the synthesis of pharmaceuticals.
Methyl acetoacetate participates in the Biginelli reaction, forming molecules including dihydropyrimidinones
Methyl acetoacetate is produced by a reaction of Methyl acetoacetate with sodium methoxide.
A clear colorless liquid.
Flash point 158°F.
Denser than water and slightly soluble in water.
Vapors heavier than air.
Methyl acetoacetate is an ester.
Esters react 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.
Heat is also generated by the interaction of esters with caustic solutions.
Flammable hydrogen is generated by mixing esters with alkali metals and hydrides
Chemical recovery of methyl acetoacetate from the amoxicillin plant's waste stream was investigated.
In process of amoxicillin production for activation of amoxicillin molecule, hydrolysis takes place at final stage.
As a result methyl acetoacetate is formed.
Liquid-liquid extraction was employed for the recovery of methyl acetoacetate from the waste stream.
Diluted alkaline solution was used as an extractive agent for the chemical extraction process.
Extraction was carried out while the pH was adjusted to 9.5 by addition of alkaline solution.
The extraction was repeated in three consecutive stages to enhance the process yield.
Finally, distillation was carried out to remove the volatile compounds residues.
Samples were taken from each stage of separation for GC analysis.
The recovered methyl acetoacetate with purity of 93 % and yield of 75 % was obtained from extraction and distillation processes.
Boiling point : 170 °C (1013 hPa)
Density : 1.076 g/cm3
Explosion limit : 1.3 - 14.2 %(V)
Flash point : 70 °C
Ignition temperature : 260 °C
Melting Point : -80 °C
pH value : 3.8 (863 g/l, H₂O, 20 °C)
Vapor pressure : 1 hPa (20 °C)
Solubility : 863 g/l
Methyl acetoacetate is a beta-diketone (1,3-diketone) which two ketones are separated only by one carbon.
The beta-ketone is stable as a conjugated enol rather than alpha-diketone due to the delocalization which makes the counterion more stable and less likely to regain the proton.
Ascorbic acid is an example of enol compound. Enol compounds form complexes with many transition metal ions.
These compounds are readily soluble in organic solvents.
They are widely used as chelating agents, ligands, and catalyst precursors.
Methyl acetoacetate and its esters contain active methylene groups which have relatively acidic alpha-protons due to H atom adjacent to two carbonyl groups.
The reactivity of its methylene group provide the sequence of reactions of alkylation, hydrolysis of the esters and decarboxylation resulting in substituted ketones.
The methylene group can be reacted to form amino-carbonyl compounds. Acetoacetates are important aliphatic parts adjoining azo dyes and pigments.
Acetoacetic acid is unstable and decompose to acetone and carbon dioxide at room temperature.
Aacetoacetate is one of ketone bodies which are the end-products of rapid or excessive fatty acid breakdown in the human body.
Methyl acetoacetate has a reactive hydrogen atom on the carbon alpha to both carbonyl groups.
Methyl acetoacetate undergoes Knoevenagel condensation reaction as a reactant to forms a large class of target products including amino acids, drugs, colorants, lacquers, perfumes, and plastics.
Alone, it is used as a flavoring agent and a solvent.
Knoevenagel condensation is a nucleophilic addition of a reactive hydrogen atom at 1,3-diketone compounds to a carbonyl group, followed by an dehydration reaction.
1,3-Diketone compounds (beta-ketones) include malonic acid, diethyl malonate, Meldrum's acid, and acetoacetic acid derivatives.
Methyl acetoacetate’s fast evaporation range suggest its use in formulated products such as fast dry industrial maintenance coatings, air-dry automotive refinish paints, aerosol coatings, quick dry adhesives, aerospace coatings and spray applied furniture coatings.
For example, furniture coatings are often acrylic or nitrocellulose based lacquers containing a blend of fast and slow evaporation solvents.
In such a system, the fast evaporation rate of Methyl acetoacetate can be balanced with a slower evaporation “tail” solvent to maintain the desired overall drying rate.
Of course, the formulator must also be cognizant of flash point and blush resistance limitations when reformulating with Methyl acetoacetate.
Melting point : -80 °C (lit.)
Boiling point : 169-170 °C/70 mmHg (lit.)
density : 1.076 g/mL at 25 °C (lit.)
vapor density : 4 (vs air)
vapor pressure : 1 hPa (20 °C)
refractive index : n20/D 1.419(lit.)
Fp : 158 °F
storage temp. :2-8°C
solubility : 460 g/L (20°C)
pka : 10.67±0.46(Predicted)
form : Liquid
color : APHA: ≤20
PH : 3.8 (863g/l, H2O, 20℃)
explosive limit : 1.3-14.2%(V)
Water Solubility : 460 g/L (20 ºC)
Methyl acetoacetate is a fast evaporating, low odor, active solvent that can be used with a wide variety of coating and ink resins.
Because of its fast evaporation rate, Methyl acetoacetate is useful as a fast evaporating component in high-low solvent systems and other applications where rapid solvent release and fast touch dry time are required.
Methyl acetoacetate is an active solvent for the following resins: cellulose acetate butyrate, nitrocellulose, vinyl copolymers, acrylics, epoxies, polyamides, phenolics, alkyds and polyesters.
carboxylate ester with a chemical name Methyl acetoacetate.
Methyl acetoacetate is also called Methyl ethanoate or Methylacetat or Methyl ester of acetic acid.
Methyl acetoacetate is an acetate ester which results from the condensation of acetic acid and methanol.
Methyl acetoacetate is a clear liquid which has no colour and has a fragrant fruity odour.
Methyl acetoacetate is moderately toxic and vapours are heavier than air.
Methyl acetoacetate is commonly found in apple and various other fruits such as bananas, grapes, etc.
As it is an ester it can be synthesized in an esterification reaction by reacting acetic acid with methanol in the presence of sulfuric acid.
Methyl acetoacetate is used as a food additive to enhance the flavour of food.
Used in the manufacturing of artificial leather.
Used for the biodegradation of organic materials.
Used as a flavoring agent brandy, rum, and whiskey.
Used as a plasticizer.
Used to manufacture Lubricants.
Used in paint removers.
Industrially Methyl acetoacetate is obtained by the carbonylation of methanol as a byproduct of the synthesis of acetic acid.
Methyl acetoacetate can also be produced by esterification of acetic acid with methanol along with sulfuric acid (strong acid).
A significant application of Methyl acetoacetate in nail polish removers, glues, and paints is as a volatile low toxicity solvent.
Acetic anhydride is generated by Methyl acetoacetate carbonylation in a method that was inspired by the synthesis of Monsanto acetic acid.
Unlike Acetone, Methyl acetoacetate has a low odor that is ideal for use in furniture and automotive applications.
Methyl acetoacetate can also be used in cosmetics such as perfumes and removers of nail polishes, resulting in less damage to nails than acetone.
Methyl acetoacetate can be produced by subjecting methanol and acetic acid to esterification in the presence of an esterification catalyst and subsequently separating the products in the presence of an entrainer with the help of two distillation columns.
Methyl acetoacetate is a colorless transparent liquid with a fruit-like fragrance.
Methyl acetoacetate’s low-toxic, but it’s flammable with the boiling point at 57℃, melting point at -98.05℃ and density of 0.93.
Methyl acetoacetate’s usually used to replace acetone, butanone, ethyl acetate and cyclopentane.
Due to its low toxicity, Methyl acetoacetate can fufill the environmental requirements of coating, ink, resin and adhesive industries.
Methyl acetoacetate, also known as methyl ethanoate, is a carboxylated ester.
Some glues or nail polish removers have an odor reminiscent of the characteristic pleasant smell.
Although it is sometimes used as a lipophilic solvent, ethyl acetate is preferred as it is less toxic and less soluble in water.
Methyl acetoacetate is not stable in the presence of dilute acids or bases.
Methyl acetoacetate is a flammable liquid, characteristically reminiscent of the pleasant smell of some glues and nail polish removers.
Methyl acetoacetate is sometimes used as a solvent because it is weakly polar and lipophilic.
However, its close relative, ethyl acetate, is a much more widely used solvent because it is less toxic and less soluble in water.
Methyl acetoacetate has a solubility of about 25% in water at room temperature.
In high temperature water, its solubility is much higher.
Methyl acetoacetate is not stable in the presence of strong aqueous bases or aqueous acids.
Methyl acetoacetate is not considered a VOC.
Methyl acetoacetate is produced industrially by carbonylation of methanol as a byproduct of acetic acid production.
Methyl acetoacetate is also formed by esterification of methanol with acetic acid in the presence of strong acids such as sulfuric acid.
This production process, which Eastman Kodak accelerated using reactive distillation, is quite famous.
In the presence of strong bases such as sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid, it is hydrolyzed, especially at high temperature, to methanol and acetic acid in the initial state.
Converting Methyl acetoacetate back to its components with the aid of an acid is a first-order reaction with respect to the ester.
The reaction of Methyl acetoacetate and a base such as sodium hydroxide is a secondary reaction with respect to both reactants.
Since Methyl acetoacetate is a low-toxicity volatile solvent, it is mainly used in glues, paints and nail polish removers.
Methyl acetoacetate, also known as acetic acid methyl ester or methyl ethanoate, is a clear, flammable liquid with a characteristic, not unpleasant smell like certain glues or nail polish removers.
Methyl acetoacetate has characteristics very similar to its analog ethyl acetate.
Methyl acetoacetate is used as a solvent in glues and nail polish removers, in chemical reactions, and for extractions.
Methyl acetoacetate is a non-polar (lipophilic) to weakly polar (hydrophilic) aprotic solvent.
Methyl acetoacetate has a solubility of 25% in water at room temperature.
At elevated temperature its miscibility with water is much higher.
Methyl acetoacetate is not stable in the presence of strong aqueous bases or acids.
IUPAC NAME :
3-oxo-butanoic acid methyl ester
Acetoacetic acid methyl ester
Butanoic acid, 3-oxo-, methyl ester
MAA
Methyl 3-oxobutanoate
methyl 3-oxobutanoate
methyl 3-oxobutanoate
SYNONYMS:
3-OXBUTANOIC ACID METHYL ESTER;
3-OXOBUTANOIC ACID METHYL ESTER;
3-OXOBUTYRIC ACID METHYL ESTER;
ACETYL METHYL ACETATE;
ACETOACETIC ACID METHYL ESTER;
ACETOACETIC ESTER (METHYL);
ACM;
HYL ACETOACETATE
