Ethyl acetate is an organic compound (C4H8O2) used primarily as a solvent in various industries, including the decaffeination of tea and coffee. It is a colorless liquid with a fruity odor, has low toxicity, and can cause irritation upon overexposure. Production methods include Fischer esterification, Tishchenko reaction, and dehydrogenation of ethanol, each with unique advantages and byproducts.

1. Ethyl Acetate
Submitted by,
Rajasekaran E
Final year- Bachelor of Technology,
Department of Pharmaceutical Technology,
University college of Engineering- BIT Campus,
Anna University,
Tiruchirappalli-24

2. Ethyl Acetate
• Ethyl acetate is a organic compound with the formula
CH3–COO–CH2–CH3, simplified to C4H8O2.
• Ethyl acetate is the ester of ethanol and acetic acid.
• This is a colourless liquid has a characteristic sweet
smell (similar to peer drops).
• They are manufactured in large quantities for use as a
solvent.
• They are also used in glues, nail polish removers, and in
decaffeinating tea /coffee.

3. For your knowledge
 Caffeine is a CNS stimulant of Methyl xanthine class present in tea
and coffee.
 Removal of caffeine from the tea leaves,coco,coffee bean,etc. Is
known as decaffeinating process.
 In this process the unroasted beans are soaked in the ethyl acetate and
washed.
 Decaffeinated drinks should contain 1- 2•/• of original caffeine.

4. Properties
• It is also called as ethyl ethanoate, Acetic ester, acetic ether.
• commonly abbreviated EtOAc, ETAC or EA.
• Lethal dose & concentration:.
 LD 50- 11.3 g/kg (in rat).
 LC 50- 16000 pm (in rat for 6 hed).
• General properties:
 Chemical formula - C4H8O2
 Malar mass- 88.106 g/mol
 Appearance- colourless
 Odour- fruity smell

5.  The LD50 for rats is 5620 mg/kg, indicating low toxicity,
though there is little risk of toxicity.
 Overexposure to ethyl acetate may cause irritation of the eyes,
nose, and throat.
 Severe overexposure may cause weakness, drowsiness, and
unconsciousness.
 Ethyl acetate is an irritant of the conjunctiva and mucous
membrane of the respiratory tract. Which causes temporary
opacity and eruption of skin.
 At higher concentrations (20,000 to 43,000 ppm (2.0–4.3%))
there may be pulmonary edema with hemorrhages, symptoms
of central nervous system depression, secondary anemia and
liver damage.

6.  Flammable (F),I.
 Irritant (Xi).
 Flash point - −4 °C (25 °F; 269 K).
 Explosive limits- 2.0–11.5%
Hazards properties

7. Manufacturing methods
of Ethyl acetate

8. Production techniques
Fisher esterification process.
Tishchenko reaction.
Dehydrogenation of ethanol.

9. Fischer esterification
This is a special type of esterification by refluxing a carboxylic acid
and an alcohol in presence of an acid catalyst.
Manufacture of ethylacetate is done by refluxing ethanol and acetic
acid.

11.  Maximum yield obtained from this reaction is 65
percent.
 Equilibrium can be shifted to right by removal of
water.
 One of the easiest technique for dedicated
production.
 Initially in all the chemical industry this technique
is used.

12. Tishchenko reaction
 Ethyl acetate can also be prepared by tishchenko
reaction. Which is similar to that of cannizaro
reaction.
 In Tishchenko reaction disproportion of an aldehyde
in the presence of an alkoxide happens to form a ester
product.
 Aluminium/sodium alkoxide as catalyst is used.

13.  This reaction is similar to that of the cannizaro reaction.
 Were parallel oxidation and reduction happens.
 Oxidation product is carboxylic acid.
 Reduction product is alcohol.
(When the reaction is continued to prolong it gives ester).

14. Dehydrogenation of
ethanol
• A specialized industrial route entails the catalytic
dehydrogenation of ethanol.
• This method is more cost effective than the
esterification.
• because this is applied with surplus ethanol in a chemical
plant.
• Typically, dehydrogenation is conducted with copper at
an elevated temperature but below 250 °C.

15. • The copper may have its surface area
increased by depositing it on zinc, zeolite,
typically ZSM-5.
• Which promotes growth of flakes.
• Traces of rare-earth and alkali metals are
beneficial to the process.

16.  Some of the possible side reactions

18. Byproducts of the dehydrogenation include
 diethyl ether, which is thought to arise primarily due to
aluminum sites in the catalyst,
 acetaldehyde and its aldol products, higher esters, and
ketones.
Hence separation of such kinds of mixtures are very tedious
process. Because,
 ethanol forms an azeotrope with water, as does ethyl
acetate with ethanol and water.
 azeotropes are broken by pressure swing distillation or
membrane distillation.

19. For your knowledge
 An azeotrope is a mixture of two or more liquids whose proportions
cannot be altered or changed by simple distillation.
 This happens because when an azeotrope is boiled, the vapour has
the same proportions of constituents as the unboiled mixture.
 Because their composition is unchanged by distillation, azeotropes
are also called constant boiling point mixtures.

20. Pressure swing distillation:
Pressure-swing distillation is a method for
separating a pressure-sensitive azeotrope that
utiltizes 2 columns operated in sequence at 2
different pressures.

21. Distillate D1 is sent to Column T-2 as feed F2 .
Nearly pure B is obtained from bottom of T-2, and
the distillate D2 is recycled to Column T-1

22. Membrane distillation
 Membrane distillation (MD) is a thermally driven separation process
in which separation is driven by phase change.
 A hydrophobic membrane presents a barrier for the liquid phase,
allowing the vapour phase (e.g. water vapour) to pass through the
membrane's pores.
 The driving force of the process is a partial vapour pressure
difference commonly triggered by a temperature difference.

24. Uses of ethyl acetate
 Ethyl acetate is used primarily as a solvent and diluent,
being favored because of its low cost, low toxicity, and
agreeable odor.
 it is commonly used to clean circuit boards and in some
nail varnish removers.
 Coffee beans and tea leaves are decaffeinated with this
solvent.
 Ethyl acetate is present in confectionery, perfumes, and
fruits.
 In perfumes, it evaporates quickly, leaving only the scent
of the perfume on the skin.

25.  Ethyl acetate is the most common ester in wine, being generated
during the fermentation.
 The aroma of ethyl acetate is most vivid in younger wines.
 Excessive amounts of ethyl acetate are considered a wine fault.
 In the field of entomology, ethyl acetate is an effective asphyxiant
for use in insect collecting and study

26. Laboratory uses
 In the laboratory, mixtures containing ethyl acetate are
commonly used in column chromatography and extractions.
 Ethyl acetate is rarely selected as a reaction solvent because
it is prone to hydrolysis and transesterification.
 Ethyl acetate is fairly volatile at room temperature and has a
boiling point of 77 °C (171 °F).Hence, it can be removed
from a sample by heating in a hot water bath and providing
ventilation with compressed air.

27. Thank you
for
your patience.
~நன்றி
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