Ethyl acetate
From Biocrawler, the free encyclopedia.
| Ethyl acetate | |
|---|---|
| Chemical name | Acetic acid ethyl ester |
| Chemical formula | C4H8O2 |
| Molecular mass | 88.11 g/mol |
| Density | 0.895 g/ml |
| Melting point | -83.6 °C |
| Boiling point | 77.1 °C |
| CAS number | 141-78-6 |
| SMILES | O=C(C)OCC |
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Ethyl acetate, also known as acetic acid ethyl ester, ethyl ethanoate, or acetic ester, is a clear, flammable liquid with a characteristic, not unpleasant smell like certain glues or nail polish removers. It is an ester with the formula is: CH3COOCH2CH3. It may be formed (along with acetic acid) as a contaminant in wine that has been exposed to air. Ethyl acetate is used as a solvent in glues and nail polish removers, in chemical reactions, and for extractions. Ethyl acetate is a non-polar (lipophilic) to weakly polar (hydrophilic) aprotic solvent with an 8% solubility in water. Ethyl acetate is not stable in the presence of strong aqueous bases and acids.
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Properties
Esters generally are not very soluble in water, they are quite volatile as they connot undergo hydrogen bonding due to lack of -OH groups. Ethyl acetate can dissolve up to 3% water and has a solubility of 8% in water at room temperature. At elevated temperature its miscibility with water is much higher.
Chemistry
Ethyl acetate is an ester that is synthesized from acetic acid and ethanol in the presence of strong acids like sulfuric acid in an esterification reaction. The two reactants and the H2SO4 catalyst are heated under reflux for approx. 40 min.
CH3CH2OH + CH3COOH ⇋ CH3COOCH2CH3 + H2O
Because the reaction is reversible and produces an equilibrium, yield is low unless driven to the right by removal of water. The yield can also be increased by using an acid chloride, acetyl chloride (CH3COCl), instead of the carboxylic acid. This is usually performed in the presence of a base such as pyridine (to remove HCl) and since it does not result in an equilibrium more of the ester is produced. It is unstable in the presence of strong bases like sodium hydroxide or strong acids like hydrochloric acid, and it is hydrolyzed back into ethanol and acetic acid, especially at elevated temperature.
See also
External links
- Material safety data (MSD) (http://www.jtbaker.com/msds/englishhtml/e2850.htm) for ethyl acetate
- Ethyl Acetate: Molecule of the Month (http://www.chm.bris.ac.uk/motm/ethylacetate/ethylh.htm)nl:Ethylacetaat
