Ethyl acetate

Ethyl acetate

Names
IUPAC name Ethyl acetate
Systematic IUPAC name Ethyl acetate
Identifiers
Properties
Chemical formula	C4H8O2 CH3COOCH2CH3
Molar mass	88.106 g/mol
Appearance	Colorless liquid
Odor	Fruity, pear-like
Density	0.902 g/ml
Melting point	−83.6 °C (−118.5 °F; 189.6 K)
Boiling point	78.1 °C (172.6 °F; 351.2 K)
Solubility in water	8.3g/100ml
Solubility	Miscible with acetone, alcohols, benzene, chloroform, diethyl ether, ethanol, toluene, xylene
Vapor pressure	92.3 mmHg (20 °C)
Acidity (pKa)	25
Hazards
Safety data sheet	Sigma-Aldrich
Flash point	−4 °C (25 °F; 269 K)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	11,300 mg/kg (rat, oral)
LC50 (Median concentration)	16,000 ppm (rat, 6 h) 12,295 ppm (mouse, 2 h) 1600 ppm (rat, 8 h)
Related compounds
Related compounds	Ethyl formate Methyl acetate Propyl acetate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Ethyl acetate or ethyl ethanoate is the organic compound with the chemical formula CH₃-COO-CH₂-CH₃. The acetate ester of ethanol, ethyl acetate is a safe and common laboratory and domestic solvent with a distinctive odor.

Properties

Chemical

Ethyl acetate, like many other carboxylate esters, is prone to hydrolysis accelerated by basic conditions. Because ethyl acetate is cheap and easy to come by in some locations, it is sometimes intentionally hydrolyzed using sodium hydroxide into its component species: acetic acid and ethanol. The acetic acid produced reacts with the sodium hydroxide to form sodium acetate, effectively providing two useful and easily separable reagents. Because of it's polar yet aprotic nature, ethyl acetate is a commonly used solvent in chromatography.

Physical

Ethyl acetate is a clear, colorless, mobile liquid at room temperature. As with other carboxylate esters, ethyl acetate has an ethereal, fruity smell, reminiscent to that of pears. Its chief use as a solvent comes from its ability to dissolve many water-insoluble substances, such as glues and lacquers, and it is often used as a substitute for another popular solvent in hardware stores, methyl ethyl ketone.

Availability

Ethyl acetate can often be found in hardware stores either in pure form as a solvent (sometimes labelled as MEK substitute) or as a component of mixed solvents, which may or may not allow its extraction via fractional distillation. Many acetone-free nail polish removers often contain it as well, usually mixed with alcohol, water, glycerol and other long chain esters. Some types of paint thinners and polyurethane solvents contain a mixture of ethyl acetate and methyl acetate, usually in a 1:1 ratio. Both solvents can be extracted by using fractional distillation.

In some countries, the sale of pure or lab-grade ethyl acetate may be monitored, due to its use in the production of phenylacetone or purification of various drugs, though this route has not been used in decades by meth cooks, who have largely switched to the pseudoephedrine reduction route.

Preparation

Ethyl acetate is most often prepared by the Fischer esterification between ethanol and glacial acetic acid. Using anhydrous reagents and sulfuric acid as a catalyst and drying agent results in a roughly 65% yield. As with most such syntheses, this esterification is conducted under reflux and is benefited by the removal of water by some means, such as excess sulfuric acid or a desiccant. The ethyl acetate formed is difficult to remove from any remaining ethanol, though one way to do so is by dumping the products of the reaction into water, in which ethyl acetate is not highly soluble, forming a layer on top which can be separated off physically. The crude ethyl acetate is then washed with sodium bicarbonate solution to remove residual acids and gently distilled over a desiccant such as calcium chloride.

Projects

• Caffeine extraction
• Ethyl acetoacetate synthesis

Handling

Safety

Ethyl acetate is flammable as well as being a mild skin irritant, but is relatively nontoxic to humans.

Storage

Ethyl acetate can be stored relatively indefinitely, but may degrade over time in the presence of substantial water or bases.

Disposal

Ethyl acetate does not have any special requirements for disposal, but it may be a better idea to recover it via distillation or hydrolyze it to useful ethanol and acetic acid instead.

References

Relevant Sciencemadness threads

• Ethyl Acetate?