Catal Surv Asia (2008) 12:1–5
DOI 10.1007/s10563-007-9023-3
The Omega Process for Propylene Production by Olefin
Interconversion
Takashi Tsunoda Æ Mitsuhiro Sekiguchi
Published online: 12 February 2008
Ó Springer Science+Business Media, LLC 2008
1 Introduction
Asahi Kasei Chemicals Corporation has developed and
commercialized a novel process (OMEGA process) for the
production of propylene from the hydrocarbons containing
olefins at high concentration.
The first commercial plant with the capacity of 50,000 t/
y of propylene, which uses C4 raffinate from the ethylene
plant as feedstock, has been started in June 2006 in
Mizushima Works of Asahi Kasei Chemicals and keeping
its stable operation since then.
Asahi Kasei Chemicals has already developed and
commercialized the new aromatics production process
from olefinic light hydrocarbons (ALPHA process).1,2 The
OMEGA process has been achieved by combining the
development of a propylene selective and stable catalyst
with the process know-how of the ALPHA process. The
OMEGA process is the first commercial process of pro-
pylene production by olefin interconversion.
The outlines of the OMEGA process are introduced
hereinafter.
T. Tsunoda (&)
Planning & Control Department, Mizushima Works,
Asahi Kasei Chemicals Corporation, Ushio-Dori,
Kurashiki-shi, Okayama 712-8633, Japan
e-mail: t.tsunoda@hs.cias.osakafu-u.ac.jp
M. Sekiguchi
Chemical Technology Laboratory,
Asahi Kasei Chemicals Corporation Shionasu, Kojima,
Kurashiki-shi, Okayama 711-8510, Japan
2 Outlines of Process
2.1 Process Scheme
OMEGA process consists of (a) the reaction section, (b) the
purification section, and (c) the regeneration section. The
schematic flow diagram of OMEGA process is shown in
Fig. 1.
The reactor system consists of a pair of swing reactors,
which are single stage adiabatic fixed bed reactors. The
reaction conditions are normally selected from the range
described as follows depending on the feed composition:
the reaction temperature, 530–600 °C; the reaction pres-
sure, 1–5 atmospheric pressure. The OMEGA catalyst is our
proprietary zeolite type catalyst, which has high propylene
selectivity and good tolerance of catalyst deactivation.
The reactor effluent is separated into C3 and lighter
fraction and C4 and heavier fraction by a depropanizer col-
umn. In Asahi’s case, C3 and lighter fraction is fed to the
purification section of existing ethylene plant to recover
propylene and ethylene. However, it is also possible by
adding deethanizer column to produce propylene in the
OMEGA process, and then only propylene can also be
produced by recycling C2 and lighter fraction to the reactor.
On the other hand, a part of C4 and heavier fraction is
recycled to the reactor, and the remainder is used for feed-
stock of cracker or the above-mentioned ALPHA process.
The catalyst activity can be restored by burning coke on
catalyst under the controlled oxygen content to maintain the
burning temperature within safety range. The regeneration is
operated with a conventional inert-air system keeping the
temperature around 500 °C. The switching of reactors is fully
1
ECN Process Review, April 7 (1994).
2
Petrotech, 19 (8), and 651 (1996).
123
2 T. Tsunoda, M. Sekiguchi

C2 Recycle

Propylene

REACTORS C3
To Ethylene Plant
Purification section

DISTILLATION
HEAT COLUMN
HEATERS EXCHANGERS

CATALYST
TALYST
REGENERATION
N

Feed C4
To plant* or Cracker

Recycle

Fig. 1 Simplified process flow of the OMEGA process

computer controlled aiming to minimize the disturbance in
operation and the labor requirement and to maximize safety
during regeneration. The catalyst regeneration is also fully
computerized as the reactor swing operation.
2.2 The Feature of OMEGA Process
butene in these conditions is estimated to be about 75%.
Figure 3 indicates in the conversion range less than about
75% butene conversion that side-reaction (aromatization of
the C6 and heavier olefins) is inhibited, and olefin inter-
conversion reactions advance selectively. In other words,
the main challenges in the propylene production process by
olefin interconversion are:

Figure 2 shows the olefin interconversion reaction scheme (1) to inhibit the aromatization and perform interconver-
in the case of using butene as a starting raw material. sion of olefins selectively.
Butene is converted to propylene by dimerization and (2) to control the olefin conversion rate in the reasonable
catalytic cracking (olefin interconversion). Olefin dimer- range below the equilibrium conversion rate.
ization reactions and olefin cracking reactions are (3) to maintain the reaction temperature as high as
reversible, so it is hardly dependent on the feed olefin possible, in order to improve the propylene yield.
composition and feed olefin isomer, and the product Therefore it was essential to develop the catalyst that
composition is mainly determined by reaction conditions. combines high propylene selectivity with durability against
Figure 3 shows the results of the model experiment with deterioration by coking and the dealumination of zeolite.
the OMEGA catalyst by using 1-butene as a raw material. We have solved this essential subject by the development
The equilibrium conversion rate of interconversion of of unique catalyst.

Fig. 2 Reaction pass of butene H2

H
C H2C CH3
H
conversion CH2
H3C C C
H3C CH2
+
C
C C CH3 H
H2C H H2
H
hexenes C CH2
CH2 CH2
H3C CH2 H2C
H2C H2C
+ +
H2 H2 H H2 H2 H
H 2C C H2C C H3C C C C H3C C CH3 H2C CH3
+
C CH3 C CH3 C C C CH3 C C C
H H H2 H H2 H2 H H

butenes octenes pentenes

CH2
H H2
C H
H3C C C CH3 H2C
H3C CH2 C C C
H2 H H2
heptenes

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Omega Process for Propylene Production
[ ]
[ ]
[ ]
Fig. 3 Results of model reaction by OMEGA catalyst using 1-butene
as a raw material (reaction conditions) 600 °C, 0.1 MPa
Figure 4 shows the typical yield of products in the
OMEGA process when the C4 raffinate-1 after butadiene
extraction is used for feedstock and a part of C4 and heavier
fraction is recycled.
The OMEGA process can convert about 54% of the feed
olefin to propylene, and can obtain the high propylene yield
and high propylene/ethylene product ratio, which cannot be
attained by a pyrolysis reaction.
Although the thermal cracking process requires much
energy since high temperature of 800–850 °C is needed
and the reaction is highly endothermic, the OMEGA pro-
cess is energy-saving and simple process since it can adopt
a low temperature condition and a single stage adiabatic
reactor because the heat of reaction is not very high.
2.3 The Feature of Catalyst
The proton free medium pore zeolite catalyst which we
have proprietary developed is used for this process.3 The
3
USP5,968,342.
3
Other C2 & Lighter 1.1 wt%
Ethylene 12.9 wt%
C4 raffinate
Propylene 46.6 wt%
87% Olefin
Propane 2.2 wt%
C4s 28.1 wt%
C5+ Gasoline 9.1 wt%
BTX 2.9 wt%
Fig. 4 Typical yield of OMEGA process using C4 raffinate-1 as
feedstock
protons of this zeolite are substituted by the Ia, IIa and Ib
group metal cations and the Ib group metal cations
function as the active sites. This catalyst has the following
features.
(a) The easiness of close catalytic activity control
To control the olefin conversion rate is very
important for the OMEGA process to obtain high
and stable propylene yields as mentioned above.
Since the activity for olefin interconversion reac-
tion is proportional to the quantity of Ib group
metal cations on the OMEGA catalyst, the olefin
conversion is controllable with easiness and suffi-
cient accuracy by controlling the amount of Ib
group metal cations on the catalyst.
(b) Hydrothermal stability
In the case of conventional proton type zeolites, the
Al–O bond of zeolite is hydrolyzed by the steam,
which is generated during the regeneration opera-
tion by burning and removing the coke, causing a
loss of activity sites and permanent degradation of
catalyst.
In this hydrolysis reaction, the proton in proton
type zeolite itself acts as a catalyst (refer to Fig. 5).
On the other hand, the OMEGA catalyst was not
deteriorated because of having eliminated the
protons. Hydrothermal stability of OMEGA cata-
lyst is clearly shown in Fig. 6.
(c) High propylene selectivity and low coke formation
Reflecting the difference in type of active sites, the
OMEGA catalyst has a high propylene selectivity
and a low selectivity to coke formation compared
with a conventional proton type zeolite (Figs. 7 and
8). Because there is little coke formation, a fixed-
bed reactor is able to be adopted in the OMEGA
process.
123
4 T. Tsunoda, M. Sekiguchi

Proton type catalyst Proton free type catalyst

H

H
O

O H O H O H O A O M O A

Si Al Si Al Si Al Si Al Si Al Si Al
O O O O O O O O O O
O O O O O O O O O O O O

AI (activity) loss A :Alkali metal or alkaline rare-earth metal

M :Group I B metal

O H OH O H
Al(OH)3
Si Al Si Si Al
O O OH HO O
O O O OH O O

Fig. 5 Structures of proton type and proton free type zeolite

Fig. 8 Results of accelerated aging test coke yield: H-ZSM-5 100%

(base) Asahi catalyst 63%
Fig. 6 Comparisons of hydrothermal stability

2.4 Experience in the Commercial Plant

The world first commercial plant for production of pro-

pylene by olefin interconversion has been started in June
2006. Figure 9 shows the general view of Asahi’s OMEGA
plant in Mizushima.
The followings are the outline of the plant:
(1) Feedstock: C4 raffinate-1 and -2 from the ethylene
plant.
(2) Capacity: 50,000 MT/Y of propylene.
(3) Location: Mizushima Works, Okayama, Japan.
Expected catalyst performance has been successfully
Fig. 7 Differences of propylene selectivity confirmed in the commercial plant.

As a result of the intensive research works on catalyst, a 3 Application of OMEGA Process

unique catalyst has successfully been developed.4
The OMEGA process uses the optimized catalyst of the The OMEGA process will be applied to the processing of
above category and demonstrates high propylene yields olefins containing fractions from ethylene complex or FCC
from high olefin content feedstocks for long time. unit in petroleum refinery to produce propylene. This
process can use various hydrocarbons because of no limi-
4
JP3,707,607 (USP6,307,117). tation of carbon number and isomer of olefins.

123
Omega Process for Propylene Production
Fig. 9 The general view of Asahi’s OMEGA plant in Mizushima
For ethylene complex, C4 raffinate-1 after the extraction
of butadiene or C4 raffinate-2 after further extraction of
i-butene for MTBE or MMA and C4/C5/C6 fraction after
5
the partial hydrogenation of diolefins are used as feedstock
for the OMEGA process.
For petroleum refinery, C4 fraction and light gasoline
fraction from FCC unit are used for the feedstock, espe-
cially the C4 fraction and the light naphtha from high
severity FCC unit, containing olefins at high concentration,
are more preferable.
4 Conclusion
(1) A novel catalyst having high selectivity for propylene
production and high durability made the unique pro-
cess (OMEGA Process) available for the production
of propylene from olefin rich hydrocarbons.
(2) The first commercial plant of the OMEGA Process
with the capacity of 50,000 MT/Y of propylene is in
stable operation since June 2006 using C4 raffinates
from ethylene plants.
(3) The OMEGA process is applicable to upgrade olefinic
fractions from ethylene plants or FCC units in
petroleum refineries to produce propylene.
123