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Ethyl acetate

Ethyl acetate
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Ethyl acetate
Systematic IUPAC name
Ethyl ethanoate
Other names
Acetic ester
Acetic ether
Ethyl ester of acetic acid
Identifiers
141-78-6 YesY
3D model (Jmol) Interactive image
506104
ChEBI CHEBI:27750 YesY
ChEMBL ChEMBL14152 YesY
ChemSpider 8525 YesY
ECHA InfoCard 100.005.001
E number E1504 (additional chemicals)
26306
KEGG D02319 YesY
PubChem 8857
RTECS number AH5425000
UNII 76845O8NMZ YesY
Properties
C4H8O2
Molar mass 88.11 g·mol−1
Appearance Colorless liquid
Odor ether-like, fruity
Density 0.902 g/cm3
Melting point −83.6 °C (−118.5 °F; 189.6 K)
Boiling point 77.1 °C (170.8 °F; 350.2 K)
8.3 g/100 mL (at 20 °C)
Solubility in ethanol,
acetone, diethyl ether,
benzene 		Miscible
Vapor pressure 73 mmHg (9.7 kPa) at 20 °C
Acidity (pKa) 25
−54.10×10−6 cm3/mol
1.3720
Viscosity 426 μPa s (0.426 cP) at 25 °C
Structure
1.78 D
Hazards
Main hazards Flammable (F),
Irritant (Xi)
Safety data sheet See: data page
R-phrases R11, R36, R66, R67
S-phrases S16, S26, S33
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −4 °C (25 °F; 269 K)
Explosive limits 2.0–11.5%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 11.3 g/kg, rat
16,000 ppm (rat, 6 h)
12,295 ppm (mouse, 2 h)
1600 ppm (rat, 8 h)
21 ppm (guinea pig, 1 h)
12,330 ppm (mouse, 3 h)
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 400 ppm (1400 m3)
REL (Recommended)
 TWA 400 ppm (1400 mg/m3)
IDLH (Immediate danger)
 2000 ppm
Related compounds
Methyl acetate,
Propyl acetate,
Butyl acetate
Related compounds
 Acetic acid,
ethanol
Supplementary data page
Refractive index (n),
Dielectric constant (εr), etc.
Thermodynamic
data
 Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Ethyl acetate (systematically ethyl ethanoate, commonly abbreviated EtOAc or EA) is the organic compound with the formula CH3–COO–CH2–CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, decaffeinating tea and coffee, and cigarettes (see list of additives in cigarettes). Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent. The combined annual production in 1985 of Japan, North America, and Europe was about 400,000 tonnes. In 2004, an estimated 1.3 million tonnes were produced worldwide.

Ethyl acetate is synthesized in industry mainly via the classic Fischer esterification reaction of ethanol and acetic acid. This mixture converts to the ester in about 65% yield at room temperature:

The reaction can be accelerated by acid catalysis and the equilibrium can be shifted to the right by removal of water. It is also prepared in industry using the Tishchenko reaction, by combining two equivalents of acetaldehyde in the presence of an alkoxide catalyst:

Silicotungstic acid is used to manufacture ethyl acetate by the alkylation of acetic acid by ethylene:


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