There are four types of manufacturing process of cumene.

1. Liquid phase alkylation using Phosphoric acid.

2. Liquid phase alkylation using Aluminium chloride.
3. Q-Max process.
4. CD-Cumene process.

D.1 LIQUID PHASE ALKYLATION USING PHOSPHORIC ACID

D.1.1 INTRODUCTION
SPA (Solid phosphoric acid) remains a viable catalyst for cumene
syenthesis. In recent years , producers have been given increasing incentives for
better cumene product quality of the phenol, acetone, and especially alpha-methyl
styrene produced from the downstream phenol units.
D.1.2 PROCESS DESCRIPTION
Propylene-propane feedstock from refinery off gases from a naphtha steam
cracking plant and recycle benzene is mixed with benzene are charged upflow into
fixed bed reactor, which operates at 3-4 MPa and at 200-260 C and pumped at 25
atms. Into the top of a reactor packed stage wise with H3PO4 impregnated catalyst.
The SPA catalyst provides an essentially complete conversion of propylene on a
one pass basis. The temperature is maintained at approximately 250oC by adding
cold propane at each stage to absorb heat of reaction.
The reactor effluent is depropanized and the propane split into quench or
product streams. The propanized bottoms are separated into benzene, cumene,and
polycumenes in the remaining two stills. A typical reactor effluent stream contain
94.8 wt% cumene and 3.1 wt% diisopropylbenzene (DIPB). The remaining 2.1% is
primarily heavy aromatics. This high yield of cumene is achieved without
transalkylation of DIPB is the key advantage of SPA catalyst process. The cumene
product is 99.9 wt% pure. The heave aromatics which have research octane no
(RON) of about 109 can be either used as high octane gasoline blending
components or combined with additional benzene and sent to transalkylation
section of the plant where DIPB is converted to cumene. The overall yield of
cumene for this process based on benzene and propylene is typically 97-98 wt% if
transalkylation is included or 94-96 wt% without transalkylation
D.1.4 PROCESS FLOW DIAGRAM

Figure 4.1.4.a Liquid phase alkylation using phosphoric acid

D.2 LIQUID PHASE ALKYLATION USING AlCl3 [2]
D.2.1 INTRODUCTION
Aluminium chloride is a preferred alkylating agent for the production of
cumene. Basically the design is same to that described for other processes, having
pretreatment section if required, a reactor section and a distillation section. The
reaction conditions, including arrangement for the feeding catalyst and recycle of
polyalkylbenzenes for dealkylation are however quite different.
D.2.2 PROCESS DESCRIPTION-
If feed treatment is required depending on the quality of feedstock,
propylene is dried in a regenerative absorptive drier and fed to de-ethanizer where
c2 compounds are distilled. The bottoms pass to a propylene column where c4s and
heavier are removed in the base stream. Liquid propylene in the overheads is
vaporized and fed to the reactor. Fresh benzene contains too much water for
immediate addition to the reactors, is mixed with recycle benzene and fed to
column. After condensation, benzene and water separate in a decanter. Benzene
from the base contains less than 10ppm water.
The reaction section usually consists of two or more brick lined vessels
partitioned into reaction and settling zones with downstream separators and wash
drums. All the reactants and recycle streams are introduced into the reaction zone.
Since agitation is required, propylene vapours are admitted at the base where
catalyst complex, which is insoluble in a hydrocarbon, tends to settle. The complex
is hereby lifted and mixed intimately with the reactants. Aluminium chloride is
added to the top of the reactor and the promoter usually HCl or isopropyl enters
with the reactant. The promoter is essential for stabilizing the catalyst complex, for
only a stable complex will catalyze the reaction. In addition to the gaseous feed to
distribute the catalyst complex, there may be provided a pump to recirculate settled
complex to the top of the reaction zone and a compressor to recycle propane. The
distillation section consist of ethylbenzene unit have been constructed where the
catalyst complex is prepared in a separate vessel. Care has to be taken with the
reactor off gases which in addition to benzene and other light hydrocarbons contains
HCl. The benzene is recovered in an absorber containing recycling PAB and the
HCl is scrubbed out of the off- gas in two towers, one containing water and the
other containing caustic
soda solution. The residual gas can be compressed and used as fuel. The material
heavier than cumene is not disposed of as fuel, is returned to the reactors for
transalkylation after removing the heaviest polyalkylbenzenes. The later operation
is conducted in a small column under high vacuum.
4.2.3 PROCESS FLOW DIAGRAM

Fig 4.2.3.a Liqid phase alkylation using Aluminium Chloride

D.3 Q-MAX PROCESS

D.3.1 INTRODUCTION

The Q- Max process is based on liquid phase process. The Q-Max process
produces nearly equilibrium levels of cumene between 85 to 95 mole% and DIPB
between 5 and 15 mole%. The Q-Max process had selected most promising catalyst
based on beta zeolite for cumene production.

D.3.2 PROCESS DESCRIPTION

A Q-max unit consists of an alkylation reactor, a distillation section, and a
transalkylation reactor. Both reactors are fixed bed. The alkylation reactor is
divided into four catalyst beds contained in a single reactor vessel. Propylene and a
mixture of fresh and recycle benzene are charged to the alkylation reactor, where
the propylene reacts to completion to form mainly cumene. Effluent from the
alkylation reactor is sent to the depropanized column, which removes the propane
that entered the unit with the propylene feed, along with any excess water which
may have accompanied the feeds. The Depropanizer column bottoms is sent to the
benzene column where benzene is collected overhead and recycled. Benzene
column bottom is sent to the cumene column where cumene product is recovered
overhead. The bottom from the cumene column, containing mostly
diisopropylbenzene is sent to the DIPB column where DIPB is recovered and
recycled to the transalkylation reactor. The bottoms from the DIPB column consist
of a small stream of heavy aromatic by-product which are normally used as high
octane gasoline blending component.
The catalyst in both the alkylation and transalkylation reactors is
regenerable. The typical design cycle length between regenerations is 2years, but
the unit can be designed for somewhat longer cycles if desired. Ultimate catalyst
life is at least three cycle. Mild operating conditions and a corrosion free process
environment permit the use of carbon steel construction and conventional process
equipment.
D.3.3 PROCESS FLOW DIAGRAM

Figure4.3.3.a : Q-Max process

D.4 CD CUMENE PROCESS

D.4.1 INTRODUCTION

The CD- Cumene process produces ultra high purity cumene using a
proprietary zeolite catalyst that is non corrosive and environmentally friendly.

D.4.2 PROCESS DESCRIPTION

Cumene is formed by the catalytic alkylation of benzene with propylene.
CD-cumene process uses a proprietary zeolite catalyst. The catalyst is non corrosive
and environmentally friendly. This modern process features higher product yields,
with a much lower capital investment, than the environmentally outdated acid-
based processes.
The unique catalytic distillation column combines reaction and fractionation
in a single unit operation. The alkylation reaction takes place isothermally and at
low temperature. Reaction products are continuously removed from the reaction
zones by distillation. These factors limit the formation of by-product impurities,
enhance product purity and yields, and result in expected reactor run lengths in
excess of two years. Low operating temperatures result in lower equipment design
and operating pressures, which help to decrease capital investment, improve safety
of operations, and minimizing fugitive emissions. All waste heat, including the heat
of reaction, is recovered for improved energy efficiency.
The CD-cumene technology can process chemical or refinery grade
propylene. It can also use dilute propylene streams with purity as low as 10mol
percent, provided the content of other olefins and related impurities are within
specification.
Except for the CDTech process, which combines catalytic reaction and
distillation in a single column, all zeolite-based processes consist of essentially the
same flowsheet configuration. The alkylation reaction is carried out in fixed-bed
reactors at temperatures below those used in SPA-based processes. When
refinerygrade propylene is used as a feedstock, the effluent from alkylation is sent
to a depropanizer column that removes propane overhead. A separate
transalkylation reactor converts recycled PIPB and benzene to additional cumene.
The bottoms of the depropanizer are then mixed with the transalkylation reactor
effluent and fed to a series of three distillation columns. Benzene, product cumene,
and PIPB are respectively separated in the overhead of each column, with PIPB and
benzene recycled to the reaction system. A small stream of heavy aromatics is
separated in the bottoms of the PIPB column. Like the AlCl3 catalyst, zeolites are
sufficiently active to transalkylate PIPB back to cumene. Overall selectivity of
benzene to cumene is quite high, varying from 99.7% to almost stoichiometric,
depending on the nature of the zeolite employed. Product purities as high as 99.97%
can be obtained, with B/P feed ratios between 3 and 5. A particular advantage of
the zeolite catalysts is that they are regenerable and can be used for several cycles.
Therefore, the waste disposal problems associated with SPA and AlCl3 catalysts are
greatly reduced. In addition, carbon steel can be used as the material of construction
throughout the plant because of the mild operating conditions and the absence of
highly corrosive compounds. One limitation of the zeolite technology is potential
poisoning of the catalyst by contaminants in the feed.
Depending on feedstock quality, guard beds or additional feed pretreatment
may thus be required. If refinerygrade propylene is used, for example, its sulfur
content must be closely controlled.
 D.4.3 PROCESS FLOW DIAGRAM

E.1 Advantages
E.1.1 Liquid Phase Alkylation Using Phosphoric Acid
a) The SPA catalyst provides an essentially complete conversion of
propylene on a one pass basis.
b) Cumene product 99.9 wt% pure.
c) By product removal is relatively simple.
E.1.2 Liquid Phase Alkylation Using Aluminium Chloride (AlCl3)
a) Propane in propylene feed is recovered as liquid petroleum gas (LPG)
b) By product removal is relatively simple.
c) PAB may be recycled to the reactor as aluminium chloride has ability
to transalkylated PAB in presence of benzene.
E.1.3 Q-Max Process
a) The catalyst in the both alkylation and Transalkylation reactor are
regenerable.
b) The expected catalyst cycle is 2-4 years and the catalyst should not
need replacement for at least 3 cycles.
c) The Q-Max requires minimum pretreatment of feeds, which further
minimizes the capital costs.
5.1.4 CD- Cumene Process
 a) High selectivity and lower by product formation. High product yield;
reduced plot area.
b) Lower maintenance cost.
c) Decrease capital investment; improve safety and operability;
applicable to conversion of existing cumene plants.
d) Reduces utilities and operating cost; recover all waste heat and heat of
reactions.
e) Catalytic reaction and distillation is done in single column.
E.2 Disadvantages
E.2.1 Liquid Phase Alkylation Using Phosphoric Acid
a) Cumene yield is limited to 95% because of the oligomerization of
propylene and the formation of heavy alykalate by-products.
b) The process requires a relatively high benzene propylene molar feed
ratio on the order of 7/1 to maintain cumene yield.
c) The catalyst is not regenerable and must be disposed at the end of each
short catalyst cycle.
E.2.2 Liquid Phase Alkylation Using Aluminium Chloride (AlCl3)
a) Feed pretreatment is required.
b) The presence of HCL in and around the reaction area can be
troublesome; its treatment is the major disadvantage of this process.