Methyl acetate
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| Names | |
|---|---|
| IUPAC name
Methyl acetate
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| Systematic IUPAC name
Methyl ethanoate | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.001.078 |
CompTox Dashboard (EPA)
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| Properties | |
| C3H6O2 | |
| Molar mass | 74.08 g/mol |
| Density | 0.932 g/cm³ |
| Melting point | −98 °C (−144 °F; 175 K) |
| Boiling point | 56.9 °C (134.4 °F; 330.0 K) |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Flash point | -9 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methyl acetate, 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 acetate has characteristics very similar to its analog ethyl acetate. Methyl acetate is used as a solvent in glues, paints, and nail polish removers, in chemical reactions, and for extractions. Methyl acetate is a non-polar (lipophilic) to weakly polar (hydrophilic) aprotic solvent. 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 acids. Methyl acetate is VOC exempt.[2]
Chemistry
Methyl acetate is an ester that is synthesized from acetic acid and methanol in the presence of strong acids such as sulfuric acid in an esterification reaction. 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.
Applications
Acetic anhydride is produced by carbonylation of methyl acetate in a process that was inspired by the Monsanto acetic acid synthesis.[3]
See also
References
- ^ Merck Index, 12th Edition, 6089.
- ^ Zeno, W. Wicks, JR, Frank N. Jones, S. Peter Pappas, and Douglas A. Wicks. Organic Coatings Hoboken, New Jersey: Wiley, 2007. ISBN# 978-0-471-69806-7
- ^ Zoeller, J. R.; Agreda, V. H.; Cook, S. L.; Lafferty, N. L.; Polichnowski, S. W.; Pond, D. M. (1992). "Eastman Chemical Company Acetic Anhydride Process". Catalysis Today. 13: 73–91. doi:10.1016/0920-5861(92)80188-S.
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