University of Baghdad

College of engineering
Chemical engineering department

Lab. of .1

Organic chemistry
Name of experiment .2

Ethyl acetate preparation

Class /B2

Name the students

Doha shaker mahmood

Date of experiment:2021/5/19
Date of submit: 2021/5/29

Written by: Doha shaker

Name of the lecturer: Maryam lbrhim

Name of experiment
Ethyl acetate preparation

Aim of the experiment

preparation of ethyl acetate by fischer
esterification

Introduction
Ethyl acetate also known as ethyl
ethanoate, is an esteric organic
compound that is a colorless and
flammable liquid, with a fruit-like odor,
chemical formula: C2H500CCH,
molecular weight 88.11, density of
0.898 g / cm3, melting point-83
Celsius degree, boiling point 77
degrees Celsius. It breaks down slowly
by moisture and is water absorbable.
It is soluble in water, alcohol, acetone,
chloroform and ether. It should be
kept in a cool, dry place and away
from heat and flame sources. Heavy
exposure causes burning in the eyes,
nose and throat. And anesthesia in
the body and inflammation of the
skin. Ethyl acetate is used as a solvent
in the manufacture of decaffeinated
tea or coffee, and this substance is
also used in the manufacture of colors
and inks used to mark fruits or
vegetables. This substance is also
included in flavorings, perfumes,
paints, artificial leather and others.
Industry 9 9 Ethyl acetate is produced
in industry mainly by the classic
Fisher's esterification reaction of
ethanol and acetic acid.
CH3CO2CH2CH3 + CH3CO2H +
CH3CH2OH H20

Tools used in the experiment

Materials and substances used in the
experiment:

1-Ethanol
2-Glacial acetic acid
3- H2SO4 conc.
4- 30% Na2CO3 sol.
5-CaCL2 solution
6-Anhydrous CaCl, or MgSO4

Procedure:
1. Add (25 ml) of ethanol and (25 ml)
of glacial acetic acid in a (150 ml)
distillation flask
2. Add cautiously (5 ml) of
concentrated H2SO4.
3. Boil under reflux for 30 minutes,
then distill.
4. Collect 2/3 the volume of the
mixture and transfer to a separating
funnel.
5. Add (12 ml) of 30% Na2CO3 shake
well, let stand and discard the lower
aqueous layer, then add (12 ml)
solution of CaCl2 shake well, let stand
and discard the lower aqueous layer.
6. Transfer into conical flask, add (3
grams) of anhydrous CaCl2 or MgSO4
for drying, shake well the solution
leave over night.
7. Filter and distill. Collect the fraction
boiling point 74- 79. determine the%
yield of ethyl acetate on the basis of
either alcohol or acid.
Safety and hazard

Protective equipment is important

when handling any toxic substance.
The following should be worn when
using ethyl acetate: long breathable
shoes, long rubber gloves, synthetic
aprons, overalls, chemical safety
glasses, face shield, management,
exposure to ethyl acetate, exposure to
ethanol, may be in the form of vapor
(inhalation), skin / body contact, or
ingestion. They are all dangerous and
need to be managed appropriately to
ensure that no further damage occurs
while trying to take care of exposure:
Inhalation- If exposed to ethyl fumes,
move to a well-ventilated area to
access fresh air. Contact emergency
medical personnel for more
assistance. Skin Contact- If ethanol
comes into contact with your relatives,
wash the area gently with warm soapy
water.If skin irritation persists, seek
medical help for further treatment. In
contact with eyes- if ethyl splashes
into your eyes, find a flush station and
wash eyes for at least 15 minutes. Call
emergency medical personnel.
Ingestion- Lie down and call
emergency medical personnel right
away. Don't induce vomiting as it can
cause more damage. Don't drink
anything else. Safe storage of ethyl. If
you need to store it, make sure the
tubes and container are not
susceptible to the corrosion that the
ethyl can cause. The most
recommended containers are stainless
steel when storing ethanol. Cabinets
need secondary containment, to be
fireproof and impact resistant
Advantages of the Fisher esterification
mechanism

Compared to other methods of

esterification, the primary benefits of
the Fisher ester are based on its
relative simplicity. When acid-
sensitive functional groups are not a
concern, clear acidic conditions may
be used; Sulfuric acid can be used.
Weaker acids can be used in swaps for
longer reaction times. Since the
reagents used are "straightforward",
in terms of product waste and reagent
spoilage, there is less environmental
impact. Compared to the synthesis of
ester through acyl chloride, the
chemicals used and the by-products
emitted are non-toxic to the
environment. A basic laboratory
setup can also be used to perform the
reaction without the need for strict
safety measures or access to less
common combination reagents.

Defects of the Fisher esterification

mechanism

Their thermodynamic reversibility and

relatively slow reaction speed
accelerate the defects of the Fisher
esterification pathways, often on a
scale from several hours to years,
depending on the reaction conditions.
If other functional groups are
susceptible to the strong acid,
alternative solutions may be
inappropriate, in which case other
catalytic acids may be selected. The
substance may be distilled instead of
water if the product ester has a lower
boiling point than water or the
primary reagents are. Esterification by
Fisher is not the best method for
generating phenolic esters. Alcohols
are not the biggest nucleophiles lover,
and under these strong acidic
conditions, where a significant portion
of the OH groups is in the form of an
acid-conjugate, this would be
especially true. Another disadvantage
of the Fisher ester is that in the
presence of strong acids, the triple
alcohols undergo rapid dehydration.
In these methods they can be used to
prepare the desired ester, such as the
high reaction to chlorides of acids and
carboxyl salts, alternate cases
discussed above

https://pubchem.ncbi.nlm.nih.gov/co
mpound/8857

https://pubchem.ncbi.nlm.nih.gov/co
mpound/8857