Ethyl acetate

From Plastics Wiki, free encyclopedia

(Redirected from ETAC)

Ethyl acetate
Image:Ethyl acetate2.png
General
Systematic name	Ethyl acetate
Other names	acetic acid ethyl ester</br> ethyl ethanoate</br> acetic ester
Molecular formula	C₄H₈O₂
SMILES	CC(=O)OCC
Molar mass	88.11 g/mol
Appearance	Clear, 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,</br> acetone, diethyl ether,</br> 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	Template:Nfpa
R-phrases	R11, R36, R66, R67
S-phrases	S16, S26, Template:S33
Flash point	−4 °C
RTECS number	AH5425000
Supplementary data page
Structure and properties	n, ε_r, 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) Infobox disclaimer and references

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. From the chemical point of view it is an ester with formula: 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.

1 Properties
- 1.1 Other uses
2 Chemistry
3 See also
4 External links

[edit]

Properties

Esters generally are not very soluble in water, they are quite volatile as they cannot 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. The refractive index of Ethyl acetate is 1.370.

[edit]

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 confectionary, 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.

[edit]

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 an elevated temperature.