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Ethyl acetate (systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula CH 3 CO 2 CH 2 CH 3, simplified to C 4 H 8 O 2.This flammable, colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, and the decaffeination process of tea and coffee.
At large scale, ethyl acetoacetate is industrially produced by treatment of diketene with ethanol. [2] The small scale preparation of ethyl acetoacetate is a classic laboratory procedure. [3] It involves Claisen condensation of ethyl acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol. [4]
Structure Type IUPAC name Boiling point (°C) [3] 1-pentanol or normal amyl alcohol primary Pentan-1-ol: 138.5 2-methyl-1-butanol or active amyl alcohol primary 2-Methylbutan-1-ol: 128.7 3-methyl-1-butanol or isoamyl alcohol or isopentyl alcohol primary 3-Methylbutan-1-ol: 131.2 2,2-dimethyl-1-propanol or neopentyl alcohol primary 2,2 ...
The typical reaction is conducted at temperatures and pressures designed to be as hot as possible while still keeping the butane a liquid. Typical reaction conditions are 150 °C (302 °F) and 55 atm. [41] Side-products may also form, including butanone, ethyl acetate, formic acid, and propionic acid. These side-products are also commercially ...
Sodium ethoxide, also referred to as sodium ethanolate, is the ionic, organic compound with the formula CH 3 CH 2 ONa, C 2 H 5 O Na, or NaOEt (Et = ethyl). It is a white solid, although impure samples appear yellow or brown. It dissolves in polar solvents such as ethanol. It is commonly used as a strong base. [2]
The conversion of methyl acetate back into its components, by an acid, is a first-order reaction with respect to the ester. The reaction of methyl acetate and a base, for example sodium hydroxide, is a second-order reaction with respect to both reactants. Methyl acetate is a Lewis base that forms 1:1 adducts with a variety of Lewis acids.
Acetoacetic esters are used for the acetoacetylation reaction, which is widely used in the production of arylide yellows and diarylide dyes. [3] Although the esters can be used in this reaction, diketene also reacts with alcohols and amines to the corresponding acetoacetic acid derivatives in a process called acetoacetylation .
A second synthesis involves the base-catalyzed condensation (e.g., by sodium ethoxide CH 3 CH 2 O − Na +) of acetone and ethyl acetate, followed by acidification of the sodium acetylacetonate (e.g., by hydrogen chloride HCl): [11]