Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

with the formula CH₃COOCH₃. It is a flammable liquid with a characteristically pleasant smell reminiscent of some

glue Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advantage ...

s and nail polish removers. Methyl acetate is occasionally used as a

solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

, being weakly polar and

lipophilic Lipophilicity (from Greek language, Greek λίπος "fat" and :wikt:φίλος, φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are c ...

, but its close relative

ethyl acetate Ethyl acetate commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula , simplified to . This flammable, colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, ...

is a more common solvent being less toxic and less soluble in water. Methyl acetate has a

solubility In chemistry, solubility is the ability of a chemical substance, substance, the solute, to form a solution (chemistry), solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form su ...

of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous

acid An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis ...

s. Methyl acetate is not regulated as a

volatile organic compound Volatile organic compounds (VOCs) are organic compounds that have a high vapor pressure at room temperature. They are common and exist in a variety of settings and products, not limited to Indoor mold, house mold, Upholstery, upholstered furnitur ...

in the USA.

Preparation and reactions

Methyl acetate is produced industrially via the

carbonylation In chemistry, carbonylation refers to reactions that introduce carbon monoxide (CO) into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemis ...

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

as a byproduct of the production of

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

. Methyl acetate also arises by

esterification In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

of acetic acid with methanol in the presence of strong acids such as

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...

; this production process is famous because of

Eastman Kodak The Eastman Kodak Company, referred to simply as Kodak (), is an American public company that produces various products related to its historic basis in film photography. The company is headquartered in Rochester, New York, and is incorporated i ...

's intensified process using a reactive distillation.

Reactions

In the presence of strong bases such as

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...

or strong acids such as

hydrochloric acid Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungency, pungent smell. It is classified as a acid strength, strong acid. It is ...

or sulfuric acid it is

hydrolyzed Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysi ...

back into methanol and acetic acid, especially at elevated temperature. The conversion of methyl acetate back into its components, by an acid, is a first-order reaction with respect to the

. The reaction of methyl acetate and a base, for example

, 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. It is classified as a hard base and is a base in the

ECW model In chemistry, the ECW model is a semi-quantitative model that describes and predicts the strength of Lewis acid–Lewis base interactions. Many chemical reactions can be described as acid–base reactions, so models for such interactions are of pot ...

with E_B =1.63 and C_B = 0.95.

Applications

A major use of methyl acetate is as a volatile low toxicity

in glues, paints, and nail polish removers.

Acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of c ...

is produced by

of methyl acetate in a process that was inspired by the Monsanto acetic acid synthesis.

References

{{Authority control Methyl esters Ester solvents Acetate esters Sweet-smelling chemicals

Preparation and reactions

Reactions

Applications

See also

References