Methyl acetate
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Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox headerbarTemplate:Chembox Lethal amounts (set)Template:Chembox setHeaderTemplate:Chembox setDatarowTemplate:Chembox setDatarowTemplate:Chembox setDatarowTemplate:Chembox SDSTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Chembox Footer| Template:Longitem | Template:Unbulleted list |
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| Template:Longitem | Template:Chembox Elements/molecular formula |
| Molar mass | Template:Chem molar mass |
| Appearance | Colorless liquid |
| Odor | Fragrant, fruity[2] |
| Density | 0.932 g cm−3 |
| Melting point | Template:Chembox CalcTemperatures |
| Boiling point | Template:Chembox CalcTemperatures |
| Vapor pressure | 173 mmHg (20°C)[2] |
| Template:Longitem | -42.60·10−6 cm3/mol |
| Template:Longitem | 1.361 |
| NFPA 704 (fire diamond) | Template:NFPA 704 diamond |
| Flash point | Template:Chembox CalcTemperatures |
| Explosive limits | 3.1%-16%[2] |
| Template:Longitem | Methyl formate Ethyl acetate Ethyl formate Methyl fluoroacetate |
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Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent, being less toxic and less soluble in water. Methyl acetate has a solubility 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 acids. Methyl acetate is not regulated as a volatile organic compound in the USA.[4][5]
Preparation and reactions
Methyl acetate is produced industrially via the carbonylation of methanol as a byproduct of the production of acetic acid.[6] Methyl acetate also arises by esterification of acetic acid with methanol in the presence of strong acids such as sulfuric acid; this production process is famousScript error: No such module "Unsubst". because of Eastman Kodak's intensified process using a reactive distillation.
Reactions
In the presence of strong bases such as sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid it is hydrolyzed 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 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. It is classified as a hard base and is a base in the ECW model with EB =1.63 and CB = 0.95.
Applications
A major use of methyl acetate is as a volatile low toxicity solvent in glues, paints, and nail polish removers.
Acetic anhydride is produced by carbonylation of methyl acetate in a process that was inspired by the Monsanto acetic acid synthesis.[7]
See also
References
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- ↑ Merck Index, 12th Edition, 6089.
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- ↑ Hosea Cheung, Robin S. Tanke, G. Paul Torrence “Acetic Acid” in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. Script error: No such module "CS1 identifiers".
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