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Ethyl acetate
From Wikipedia, the free encyclopedia
| Ethyl acetate | |
|---|---|
  |
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| General | |
| IUPAC name | Ethyl acetate |
| Systematic name | Ethyl ethanoate |
| Other names | ethyl ester, ethyl acetate, acetic ester, ester of ethanol |
| Molecular formula | C4H8O2 |
| SMILES | CC(=O)OCC |
| Molar mass | 88.12 g/mol |
| Appearance | colorless liquid |
| CAS number | [141-78-6] |
| 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 |
3
1
0
|
| R-phrases | R11, R36, R66, R67 |
| S-phrases | S16, S26, S33 |
| Flash point | −4 °C |
| RTECS number | AH5425000 |
| Supplementary data page | |
| Structure and properties |
n = 1.3720 |
| 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, ethanol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Ethyl acetate is the organic compound with the formula CH3CH2OC(O)CH3. This colorless liquid has a characteristic, not unpleasant smell like certain glues or nail polish removers, in which it is used. As the ester derived from ethanol and acetic acid, EtOAc, as it is commonly abbreviated, is manufactured on a large scale for use as a solvent.
Contents |
Ethyl acetate is a moderately polar solvent that has the advantages of being volatile, relatively non-toxic, and non-hygroscopic. It is a weak hydrogen bond acceptor, and is not a donor due to the lack of an acidic proton (one directly bonded to an electronegative atom such as fluorine, oxygen, or nitrogen). Ethyl acetate can dissolve up to 3% water and has a solubility of 8% in water at room temperature. At elevated temperature its solubility in water is higher. It is unstable in the presence of strong aqueous bases and acids.
Ethyl acetate is widely employed as a solvent for nail varnishes and nail varnish removers. Industrially it is used to decaffeinate coffee beans and tea leaves.[citation needed] In chemistry, it is often mixed with a non-polar solvent such as hexanes as a chromatography solvent. It is also used as a solvent for extractions. It is rarely used as a reaction mixture due to the weakness of the ester linkage — it hydrolyzes in the presence of strong acids and bases to give acetic acid and ethanol.
Ethyl acetate is also present in confectionery, perfumes, and fruits because it evaporates at a fast rate, leaving but the scent of the perfume on the skin. It also confers a fruity smell, as do most esters. It is also used in paints as a activator or hardener.
Ethyl acetate is present in wines. It may be considered a contaminant at too high concentrations, as typically occurs when wine is exposed to air for a prolonged period. When present at too high concentration in wine, it is regarded as an off-flavour.
In the field of entomology, ethyl acetate is an effective poison for use in insect collecting and study. In a killing jar charged with ethyl acetate, the vapors will kill the collected (usually adult) insect quickly without destroying it. Because it is not hygroscopic, ethyl acetate also keeps the insect soft enough to allow proper mounting suitable for a collection.
Ethyl acetate is synthesized via an esterification reaction from acetic acid and ethanol, typically in the presence of an acid catalyst such as sulfuric acid.
- CH3CH2OH + CH3COOH → CH3COOCH2CH3 + H2O
Because the reaction is reversible and produces an equilibrium, the yield is low unless water is removed. In the laboratory, the ethyl acetate product can be isolated from water using a Dean-Stark apparatus.