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Introduction
ethyl ethyl ketone [1] (MEK)
(CAS No.: 78-93-3), is a
flammable, colourless liquid
with a sharp, sweet butterscotch odour
reminiscent of acetone. It is soluble in
four parts water and miscible with alcohol, ether, acetone, and benzene. It is
lighter than water and may be expected
to float while rapidly dissolving .
It is unsymmetrical or mixed aliphatic ketone. Its IUPAC name is
2-Butanone. Other names are: Methylacetone and Meetco.
MEK is the second link in the homologous series of aliphatic ketones
and next to acetone, the most important
commercially produced ketone.
DIVYESH ARORA
&
MOHIT SHARMA
Jaypee Institute of Engineering &
Technology
E-mail: divyesh_134@yahoo.co.in
Self-condensation
Aldol condensation of 2 moles of
MEK yields a hydroxyketone, which
readily dehydrates to an unsaturated
ketone:
O
II
CH3CCH2CH3 + H2O2
OH
I
CH3CCH2CH3
I
OOH
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Special Report
Table 2
How MEK is used in industries
Industry
Application
Adhesives manufacture
Electroplating
Cold-cleaning solvents
Electroplating
Laboratory chemicals
Solvents - extraction
Solvents
Metal degreasing
Solvents
Paint manufacture
Solvents
Paint stripping
Solvents
Paper coating
Solvents
Table 4
Applications of MEK by end-use
Sector
Share of
demand [%]
Coatings/solvents
58
Adhesives
11
Printing inks
8
Chemicals &
7
pharmaceuticals
Magnetic tapes
4
Lube oil dewaxing
2
Others
10
Total
100
Table 5
Major companies producing MEK[i]
Country / Company
Capacity
(ktpa)
USA
Shell
136
Exxon Mobil
135
Idemitsu Petrochem
135
Japan
Toren Chemical
70
Maruzen Petrochem
40
Brazil
Oxiteno
90
Germany
Sasol Solvents
65
Taiwan
Tasco Chemical
60
Taiwan Synthetic
15
France
Atofina
50
Romania
Petro Brazi
40
Thailand
Bangkok Synt.
20
South Korea
SK Corp.
15
vapor phase dehydrogenation of 2-butanol. The dehydrogenation of 2-butanol is an exothermic reaction (51 KJ/
Kg mol).
Chemical Weekly April 27, 2010
Special Report
Table 6
Imports of MEK into India [2007-08]
[Tons]
234 234
200
170 170
150
62
62
39
50
39
Other Asian
Countries
Japan
0
Middle East
Eastern Europe
& Africa
North America
Western Europe
100
2002
2007
490
500
400
400
300
213 220
200
180 193
129 133
36
47
25
28
17
Other Asian
Countries
14
Japan
100
Middle East
245 254
250
Eastern Europe
& Africa
2007
Western Europe
2002
296 296
North America
300
Import
672
2,036
1,467
3,286
39
1,087
45
Country
Taiwan
Japan
China
South Africa
Singapore
UK
Netherlands
Special Report
Table 7
Comparative study of all the processes
Catalytic dehydro- Liquid phase
genation
oxidation
Sec-Butyl
benzene hydro
peroxide
Raw material/(s)
Sec-Butyl alcohol
Butane
Butenes
Butenes
Sec-Butyl
benzene
Main products
MEK
Acetic acid
MEK
MEK
MEK
Chlorinated
butanone and nbutryaldehyde
By-products
Current status
88-90%
10-12%
Not accepted.
Not accepted
Uneconomical.
Catalysts
Copper, zinc or
bronze
Non-catalysed
PdCl2 / CuCl2
Palladium sulphate
& ferric sulphate
Zeolite beta
Conversion
Higher conversion
rate; 80-95%
Low conversion
95%
95%
Catalyst life
Several years
Small
Small
Selectivity
95%
86%
90%
Yield
Very high
Very low
High
High
Equivalent to
phenol
Energy consumption
Very low
Very low
High
Economical feasibility
Very high
Not known
Uneconomical
Process separation
Very simple
Not known as
process is
patented
Sec-Butylbenzene hydroperoxide
process
This process comprises the steps
of oxidizing sec-butylbenzene to obtain a reaction liquid containing secbutylbenzene hydroperoxide as the
main product, concentrating the reaction liquid by means of a distillation
column to obtain a bottom liquid containing sec-butylbenzene hydroperoxide as the main component from
the column bottom and decomposing
the bottom liquid to obtain phenol and
MEK.
Special Report
Super heaters
The liquid separated will be recycled and the dry alcohol (Stream 3)
will be fed to super heaters steam and
stream attains a temperature of 673K
(Stream 4). The combustion reaction of
hydrogen takes place in a furnace and
the hydrogen is taken from the absorption column. The heat of combustion of
hydrogen is very high so its heat is being utilized here.
Condenser
In the condenser about 80% MEK
and SBA are condensed (Stream 7),
which is sent for storage while the other
stream (Stream 8), which contains saturated non-condensable hydrogen along
with MEK and SBA at the temperature
of 358K.
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Special Report
Absorption column
The vapour is passed on to the
bottom of the packed bed absorption
column where MEK and SBA are absorbed in water. Absorption of MEK
is 98% and SBA is 96% in water. The
water (Stream 9) is recycled from the
extraction column and its rate is controlled to provide an aqueous effluent
containing 10% MEK.
Extraction column
The aqueous effluent (Stream 10)
from the absorber is pumped into an
extraction column where it is contacted with solvent 1,1,2-trichlorethane
(Stream 11) to extract MEK and SBA.
This solvent is selected because it has
the maximum partition coefficient
(3.44), in comparison to other solvents.
The raffinate comprises of mainly water, which is fed back to the absorption
column.
Solvent recovery column
The trichloroethane extract phase
(Stream 14) is pumped to a distillation
column for the separation of solvent.
Initially it is preheated to 371K. The
bottom product is solvent, i.e. 1,1,2-trichloroethane and the distillate from
this column (Stream 15) is MEK and
194