10/10/2014 Engineers Guide: Cumene Peroxidation Process for Phenol Production

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Cumene Peroxidation Process for Phenol Production
C
6
H
5
CH (CH
3
) + O
2
C
6
H
5
C (CH
3
)
2
OOH
C
6
H
5
C (CH
3
)
2
OOH + H
2
SO
4
C
6
H
5
OH + CH
3
COCH
3
(Cumeneperoxide) (Phenol) (Acetone)
Material Requirements:
The raw materials those are required for the manufacture of phenol involves following materials.
Cumene
Air
Sulfuric acid
Sodium hydroxide
Final product: Phenol
Co-product: Acetone
A Short Process Description for Phenol Manufacturing:
The cumene peroxidation process for the manufacture of phenol involves the liquid phase air oxidation of cumene to cumene peroxide, which in turn is
decomposed to phenol and acetone by the action of acid.
The cumene (isopropyl benzene) may be manufactured by either liquid or vapor phase alkylation of benzene with propylene. In the liquid phase the
alkylation catalyst is usually sulfuric acid; in the vapor phase it is phosphoric acid absorbed on a carrier. Purified cumene is mixed with purified recycle
cumene and fed to the oxidation vessel along with a dilute soda ash solution, in order to maintain the pH between 6.0 and8.0, the mixture is contacted
with air and held at 110 and 115C until 20 to 25% of the cumene is converted to the cumene peroxide. Yields of cumene peroxide may be improved
by operating at lower temperature (100 to 110C) and accepting lower conversions. In one modified process sequence of three to four reactors is
operated at successively lower temperature.
The crude mixture from the oxidizer is concentrated to about 80% cumene peroxide and fed to a reactor in which the cumene peroxide is cleaved to
phenol and acetone. The reaction is usually carried out under conditions of mild temperature (70 to 80C) and pressure, and in the presence of a small
amount of sulfuric acid.Numerous non oxidizing inorganic acids, e.g. sulphuric dioxide are used. The cleavage mechanism is an example of a 1, 2 shift
from carbon to oxygen.
It is highly undesirable that such 1, 2 cleavages occur during the oxidation stage because phenols are potent inhibitors of free radical oxidation.
Therefore, it is essential that no acidic materials interfere with the oxidation process.
The resulting product mixture consists following compositions of the products
COMPOUND (wt %) %COMPOSITION
Phenol 14
Cumene 76
Acetone 8
Acetophenone 0.4
methyl styrene 1.6
Reactions Involved in Cumene Peroxidation Process:
10/10/2014 Engineers Guide: Cumene Peroxidation Process for Phenol Production
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The products are separated by distillation. Acetone is removed overhead in the first column and further purified by distillation. The bottoms from this
column are then vacuum distilled to send unreacted cumene and by product a methyl styrene overhead. If this impure cumene were recycled as such,
the methyl styrene must be purified. This can be done by catalytic hydrogenation of the methyl styrene to cumene, to by careful fractionation. In the
latter case a methyl styrene is available as a by product. The bottoms from the vacuum still are further distilled to separate acetophenone and cumene
from phenol .phenol is the overhead product obtained with a yield of 90 to 92%.
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