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Jubilant
Jubilant
Sagar Arora
2011CH10110
Group-2
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ETHYL ACETATE
Produced via the Fischer Esterification of Ethanol and Acetic Acid
FISCHER ESTERIFICATION
KETTLE REACTOR
Most of the reaction takes place
inside the kettle. The vapour
stream (A) which leaves from
the top of the kettle already
consists of 80% ester by weight.
A constant level is maintained in
the kettle(usually 70% of the
total capacity) by adjusting the
feed stream (C).
The feed consists of ethanol
and acetic acid with the
concentration of the alcohol
slightly higher than the acid,
along with the catalyst, PTSA.
Acetate
%
----
Ethanol
%
Acid %
Total
(kg/hr)
55
45
4700
A(Kettle
to Vapour
Column)
80
11
22100
D(Reflux
from
Vapor
Column)
78
12
10
19400
B(Kettle
to Liquid
Column)
15
50
35
25000
E(Reflux
from
Liquid
Column)
10
53
37
23000
Ethanol
(Kg/hr)
Acid
(Kg/hr)
Total
(Kg/hr)
----
2585
2115
4700
A(Kettle
to Vapour
Column)
17680
2431
1989
22100
D(Reflux
from
Vapor
Column)
15142
2328
1940
19400
B(Kettle
to Liquid
Column)
3750
12500
8750
25000
C (Feed)
Acetate
(Kg/hr)
E(Reflux
2300
12200
8500
23000
from
Liquid
Column)
By calculations, it was found that:
Ethyl Acetate produced in kettle=3988 kg/hr (Total capacity of the plant=4220 kg/hr)
Ethanol consumed in kettle=2182 kg/hr
Acid consumed in kettle=1816 kg/hr
System
I. Back to feed
J. To Storage Tank
Acid
(Kg/hr)
Total
(Kg/hr)
C(Feed)
--
2585
2115
4700
I(Back to
feed)
720
56
24
800
J(To
Storage
Tank)
3500
--
--
3500
C. Feed
System
I. Back to feed
Total mass exiting the system is less than the mass entering. This is accounted by a
primer tank that stores material at around 400 kg/hr and is drained at regular
intervals.
J. To Storage Tank
OVERALL DATA
Ethanol consumed in the whole process= 2585-56 =2529 kg/hr
Acetic acid consumed in the whole process= 2115-24=2091 kg/hr
Ethyl acetate formed in the whole process= 3500+720=4220 kg/hr
OR
101.2 MT/day
ACETIC ANHYDRIDE
Acetic anhydride is an organic compound with the formula (CHCO)O. This
colorless liquid has a characteristic very pungent, penetrating, vinegar-like
smell.
Acetic anhydride is prepared commercially by KETENE PROCESS.
Ketene or Ethanone is a very reactive organic compound that is formed by
dehydrating the hot vapours of acetic acid in a furnace.
CH3COOH
CH2=CO + H2O
THE FURNACE
Vapours of Acetic Acid are decomposed to form Ketene in the presence of TEP under 750 deg
Celsius.
B(To chillers)
A(96% Acetic Acid)
Furnace
Acetic Acid Water
Ketene
Total
A(In)
3483.89
145.16
-----
3629.05
B(Out)
1045.17
876.78
1707.1
3629.05
Ketene
Total
96
B(Out)
28.8
24.16
-----
100
47.04
100
SEPARATOR
The product of the furnace is sent to the Separator after passing
through a series of coolers and brine water chillers. The product
stream exiting the separator contains almost 100% Ketene.
B(From Chillers)
Separator
Ketene
1707.1
Total
B(In)
1045.17
876.78
3629.05
C(Out)
----
----
1707.1
1707.1
D(Out)
1045.17
876.78
----
1921.95
Ketene
Total
B(In)
28.8
24.16
47.04
100
C(Out)
----
----
100
100
D(Out)
54.38
45.62
----
100
ABSORPTION TOWER
C(From Separator)
E(99.8% Acid)
Absorption Tower
F(To Distillation)
The Ketene gas from the separator is made to flow against a liquid stream of
almost pure acetic acid for the following reaction to take place.
CH3COOH + CH2=CO
Acetic
Water
Acid
CH3CO-O-OCCH3
Ketene
Acetic
Total
Anhydrid
e
E(In)
2893.58
5.8
-----
C(In)
----
----
1707.1
F(Out)
454.85
Acetic
Acid
5.80
Water
---Ketene
E(In)
99.8
0.2
C(In)
----
----
----100
-----
2899.37
1707.1
4145.83
4606.48
Acetic
Total
Anhydrid
e
-----
100
100
DISTILLATION
COLUMN
This is usually the final stage of the process as it ends up in giving us 99.5%
Acetic Anhydride as the final product. Anhydride being the least volatile in the
mixture, is collected at the bottom.
However, if more purity is desired, further stages like separating using a third
liquid can be used(Liquid-Liquid Equilibrium), although it is not often practised.
G(Top Product)
F(From Absorber)
Distillation Column
H(Bottom Product)
Acetic
Acid
Water
F(In)
454.85
5.80
G(Out)
434.02
5.8
H(Out)
20.833
Acetic
Acid
---Water
F(In)
9.87
0.13
G(Out)
98.67
1.33
Ketene
-----
Acetic
Total
Anhydrid
e
4145.83
4606.48
---
---
439.81
---Ketene
4145.83
4166.67
Acetic
Total
Anhydrid
e
-------
90
100
---
100
OVERALL DATA
Total Acetic Acid entered=
Total Acid recovered=
6377kg/hr
1464kg/hr
4913kg/hr
4146 kg/hr
or
99.5
MT/day
Q/A
1) Which catalyst is used in the Fischer Esterification and why?
2) Why tertiary alcohols are not suitable for use in Fischer Esterification?
3)Why is a reflux of vapour used in the kettle reactor in the production of Ethyl
Acetate?
4) Which catalyst is used in the production of Acetic Anhydride?
Q/A
1) Which catalyst is used in the Fischer Esterification and why?
Ans- PTSA(p-Toluenesulfonic acid),because it acts as a dehydrating agent by providing a hydronium ion.
2) Why tertiary alcohols are not suitable for use in Fischer Esterification?
Ans- Tertiary alcohols are prone to elimination, leading to the formation of an alkene.
3)Why is a reflux of vapour used in the kettle reactor in the production of Ethyl
Acetate?
Ans- To prevent the loss of volatile compounds.
4) Which catalyst is used in the production of Acetic Anhydride?
Ans- TEP (Tri Ethyl Phosphate)
5) Why is Acetic Anhydride chemically stable despite the dipole-dipole repulsion
between the two carbonyl oxygens?
Ans- Due to the resonance stabilization by pi system linkage through the central oxygen.
THANK YOU