Gourt Home::Gourt :: Ethyl acetate
| General | |
|---|---|
| Systematic name | |
| Other names | acetic acid ethyl ester, ethyl ethanoate, acetic ester, ester of ethanoland acetic acid |
| Molecular formula | C4H8O2 |
| SMILES | CC(=O)OCC |
| Molar mass | 88.11 g/mol |
| Appearance | Clear, colorless liquid |
| CAS number | * |
| Properties | |
| Density and phase | 0.897 g/cm3, liquid |
| Solubility in water | 8.3 g/100 ml (20 °C) |
| Solubility in ethanol, acetone, diethyl ether, benzene | Miscible |
| Melting point | −83.6 °C (189.55 K) |
| Boiling point | 77.1 °C (350.25 K) |
| Critical temperature | 250.11 °C (523.26 K) |
| Viscosity | 0.426 cP at 25 °C |
| Structure | |
| Dipole moment | 1.78 D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | Flammable (F), Irritant (Xi) |
| NFPA 704 | |
| R-phrases | , , , |
| S-phrases | , , |
| Flash point | −4 °C |
| RTECS number | AH5425000 |
| Supplementary data page | |
| Structure and properties | n, εr, etc. |
| Thermodynamic data | Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related carboxylate esters | Methyl acetate Butyl acetate |
| Related compounds | Acetic acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Chemical infobox | |
Ethyl acetate, also known as acetic acid ethyl ester, ethyl ethanoate, acetic ether or acetic ester, is a clear, flammable liquid with a characteristic, not unpleasant smell like certain glues or nail polish removers. Ethyl acetate is an ester. Although present in all wines, it may be considered a contaminant if present at too high concentrations. This typically happens when wine is exposed to air for a prolonged period. 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.
Properties
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. The refractive index of ethyl acetate is 1.370.
Other uses
Ethyl acetate is a very effective poison for use in insect collecting and study (entomology). In a jar charged with ethyl acetate, the vapors will kill the collected (usually adult) insect quickly without destroying it. It also keeps the insect soft enough to allow proper mounting suitable for a collection. Ethyl acetate is also present in confectionery, perfumes, and fruits. This is because ethyl acetate can produce a fruity smell as can most esters. It is also present in nail varnishes and nail varnish removers, which is the smell ethyl acetate has naturally. Ethyl acetate is used in some methods of the decaffeination of coffee beans and tea leaves. When present at too high concentration in wine, it is regarded as an off-flavour, also called "VA" (volatile acidity).
Chemistry
Ethyl acetate is a hydrogen bond acceptor, but not a donor. 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
"Ethyl acetate"