Ethyl acetate

 

Ethyl Acetate

Chemical formula	CH3COOCH2CH3
OTP appearance	clear liquid
Molar Mass(g/mol)	88.11
Density(g/cc)	0.897
Melting Point(°C)	-83.6
Boiling Point(°C)	77.1
Solubility in water(g/L)	80.3
Water azeotrope(%v/v)	78.6
Water azeotrope bp(°C)	70.3
NFPA 704	3 1 0

Uses

Primary

• Excellent organic solvent
• Liquid/liquid extractions

Secondary

• Decaffeination

Natural occurrence

• May occur naturally whre ethanol is consumed by acetobacter

Hazards

• Extremely flammable

Production

Synthesis

Hypothetically simply mixing ethanol and acetic acid will produce ethyl acetate. In practice, particularly with water impurities, this reaction is too slow.

CH₃CH₂OH + CH₃COOH → CH₃CH₂OC(O)CH₃ + H₂O

esterification

In practice this is a "fischer esterification" where an acid and reflux distillation are used to hurry the process along

1. Combine stochiometric amounts of ethanol and acetic acid in a boiling flask
2. Add sulfuric acid catalyst/drying agent
3. Reflux for 1-2 hours to complete esterification

   CH₃CH₂OH + CH₃COOH

   {H₂SO₄

   →

   118°C}

   CH₃CH₂OC(O)CH₃ + H₂O

4. Fractional distillation

   < 77°C unknown, discard.

   77-83°C - ethyl acetate, retain

   83-330°C - primarily impure water, discard.

   335-340°C - sulfuric acid, recycle.