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Oxidation of Benzene to Maleic Anhydride in a

Fluidized Bed Reactor
Article in Chemical Engineering & Technology December 2007
DOI: 10.1002/ceat.200700249

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Chem. Eng. Technol. 2007, 30, No. 12, 17081715

1708

Canan Uraz1
Sheyda Atalay1
1

Ege University, Faculty

of Engineering, Department
of Chemical Engineering,
Bornova-Izmir, Turkey.

Research Article

Oxidation of Benzene to Maleic Anhydride

in a Fluidized Bed Reactor
In this project, the selective oxidation of benzene to maleic anhydride (MAN)
was studied. Gas phase catalytic oxidation of benzene was carried out in a laboratory scale fluidized bed reactor on six different types of catalysts, which have different compositions. Effects of temperature, flow rates of benzene and air and catalyst type on the reaction selectivity were investigated at atmospheric pressure.
The experiments were performed over a temperature range of 325 to 400 C, a
space-time (W/FA0) range from 11.28 105 to 31.9 105 g s mol1, and benzene/
air mole ratio changes between 0.0109 and 0.0477. It was seen that conversion of
benzene to MAN increased with increasing temperature for the catalysts supported by silica gel, aluminum oxide and titanium oxide. From the results it was
found that conversion increased with increasing flow rate of air. When the comparison of the catalysts were made, it could be said that catalysts supported by
silica gel showed higher MAN conversions. So it can be concluded that catalysts
supported by silica gel were more suitable catalysts for benzene oxidation to
MAN in a fluidized bed reactor.
Keywords: Benzene, Fluidized Bed Reactor, Maleic Anhydride, Oxidation
Received: July 2, 2007; accepted: October 4, 2007
DOI: 10.1002/ceat.200700249

Introduction

Oxidation of organic compounds such as benzene in the vapor

phase is an industrially important reaction since the products
such as maleic anhydride, phthalic anhydride are very valuable
intermediates. Maleic anhydride (MAN) is also called 2,5-furandione, cis-butenedionic anhydride, toxilic anhydride and
maleic acid anhydride. This multifunctional chemical intermediate finds applications in almost any field of industrial
chemistry. The principal use of MAN is in the manufacture of
alkyd and unsaturated polyester (UPE) resins, surface coatings,
plasticizers, lubricating oil additives, agricultural chemicals,
textile chemicals, paper reinforcement, food additives and
pharmaceuticals. Furthermore, due to its double bond and anhydride function, MAN is a versatile intermediate for the production of co-polymers of MAN and, for example, ethylene
glycol and vinyl monomer. Recently, potential new uses of
MAN have been found in its conversion to 1,4-butanediol and
the manufacturing of tetrahydrofuran (THF) [1, 2].
MAN is produced industrially by oxidation of suitable hydrocarbons in the gas phase. Benzene used to be the predominant starting material but in recent years oxidation of C4 hy-

Correspondence: C. Uraz (canan.uraz@ege.edu.tr), Ege University,

Faculty of Engineering, Department of Chemical Engineering, 35100
Bornova-Izmir, Turkey.

2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

drocarbons has become increasingly important. Phthalic

anhydride production might account for 2 % of the total MAN
production. In the oxidation of C4 hydrocarbons, there are
three types of process have been developed or are in the development stage: Fixed-bed process, fluidized-bed process, and
transport-bed process [3, 4]. Nowadays, technological advancements are directing us to use fluidized bed reactors since
they have some advantages over the fixed bed reactors. The basic advantages of gas fluidized beds are:
I) It is difficult to prevent a temperature profile in the radial
direction of the catalyst bed for fixed bed reactors. Hot
spot formation affects catalyst life. This risk is prevented
by using a fluidized bed system. It is easy to operate and
control fluidized bed reactors. Uniform temperature distribution throughout the whole bed, a consequence of intensive solids mixing, prevents hot spot formation even in the
presence of highly exothermic reactions.
II) Good heat and mass transfer between gas and particles,
owing to small particle sizes.
III) High heat transfer coefficients between bed and immersed heating or cooling surfaces due to intensive solids mixing.
IV) Easy handling of solids due to liquid-like behavior of the
fluidized bed.
V) The product yield is higher in a fluidized bed reactor. And
in fixed bed reactor systems, the increase in the n-butene/
air mixtures over a certain ratio causes explosions [5].

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Fluidized Bed Reactor

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The most widely used catalysts in the production of MAN

2 Experimental Section
include vanadium pentaoxide (V2O5), molybdenum trioxide
(MoO3) and sodium oxide (Na2O). Catalysts proposed in the
2.1 Catalyst Preparation
literature have difficult production processes and expensive supports such as aluminium, magnesium, zirconium, beryllium
In this study, six different types of catalysts were prepared to
and titanium. It is seen that the catalysts supported by silica gel
investigate the oxidation of benzene to MAN. The composiand superacidic catalysts can also be used in the oxidation protions of them are given in Tab. 1.
cesses [6, 7]. The catalytic performances are sometimes affected
by the crystal phase of the titania support, anastase and rutile,
because of differences in the dispersion of vanadia and the for2.1.1 Catalyst 1
mation of reduced vanadium ions. The preparation methods
and conditions are the critical factors for the catalytic perforThis catalyst is prepared by following the procedure in the patmance and the structure of supported vanadium oxide. Impregent by R. Marg [18]. Silica-gel is initially treated with 72 mL
nation, flash hydrolysis, chemical vapor deposition, grafting
HCl, 14.4 mL HNO3 and 57.6 mL H2O in porcelain basin.
and chemical liquid deposition are preparation methods [8].
Secondly, V2O5 slurried with water and kept at around 80 C
Polyoxometalates (POMs) are finding increasing use as cataby heating on a hot plate. Powdered oxalic acid is added to the
lysts for the selective oxidation of several alkanes, aldehydes
slurry in a small quantity (solution A). Ammonium molybdate
and acids. POMs are the most active and selective systems for
is dissolved in water (solution B) and nickel nitrate is dissolved
oxidation reactions; however, yields achieved are not high
in water (solution C). A 36 mL mixture of this solutions (preenough to justify a commercial exploitation of the reaction. In
pared by mixing of solutions A, B, and C) is kept on the sand
general, POMs having diavelent/trivalent transition metal catbath for 1012 hour at 100 C. After descending of the acid
ions in the secondary framework have been the subject of sevfrom solution, water is drained off and the gel is dried in an
eral recent investigations, since the presence of these elements
oven. The gel is then spread out in silica trays and left in a
may considerably affect catalytic performance [914].
muffle furnace. The temperature is gradually raised to 700 C
The catalyst generally used for the selective oxidation of
in 5 hours and maintained at this temperature for 2 hours.
benzene to MAN consists of vanadium-phosphorus-oxide
(VPO). The most important catalytic component in benzene
oxidation is V2O5. A catalyst for this purpose is usually modi2.1.2 Catalyst 2
fied by addition of MoO3. To improve the performance of the
catalyst, V2O5 and MoO3 have been combined with oxidized
The second catalyst is prepared based on a receipt cited in the
forms of one or more metal oxides. These complex mixtures of
literature [19]. Concentrated HCl, ammonium paramolybdate
oxides may be used as such in the form of powder, grains or
and ammonium metavanadate are mixed perfectly stirred for a
agglomerates. In a fluidized bed, where the catalyst particles
few minutes. The following solutions are prepared separately;
will continuously collide with each other and with the reactor
first, a solution of 0.79 parts trisodium phosphate in 3.59 parts
internals, the catalyst must have a high attrition resistance.
water; second, a solution of 0.64 parts bismuth nitrate in 1.28
Suciu et al. who, have been developing various methods to
enhance this attrition resistance of a VPO catalyst, for
Table 1. Compositions of the catalysts.
instance, have found that treatment of the catalyst precursor with acid results in an agglomeration of catalyst
Type of the carrier
Cat. 1
Cat. 2 Cat. 3 Cat. 4
Cat. 5
Cat. 6
and % by weight
particles [15]. Another method to improve the attriSilica gel Al2O3 No
Titanium
Silica gel No
tion resistance of VPO catalysts is the incorporation of
(72)
(83.3) carrier oxide (91.34) (72)
carrier
silica into the fluidized-bed catalyst by addition of a
CompositionsV2O5
53.6
63.99
100
53.6
36.263
colloidal silica sol. However, this method results in a
of active
decreased selectivity to maleic anhydride as well [16].
ingredient,
Overbeek developed a preparation procedure which
wt %
was cheaper and much more controllable than the
preparation procedures of VPO catalyst. However, the
MoO3
35.7
30.82 7.17

21.44
54.34
newly developed supported VPO catalysts did not
P2O5

0.92

6.25

show reasonable catalytic performance (yield <20 %).

NiO
10.7
1.15

6.25

In general, titania-supported catalysts are much more

active than their silica counterparts. However, silicaNa2O

1.2

6.25

supported catalysts are much more selective, resulting

Bi2O3

1.92

in better overall yields [17].

The aim of this study is to prepare catalysts by folZrO2

92.83

lowing the recommendations in the literature, to charB2O3

6.25

acterize and to test them to investigate the influences

of parameters such as catalyst type, temperature, space
H3PO4

4.625
time and benzene/air mol ratio on the oxidation of
KNO3

4.772
benzene in a laboratory scale fluidized bed reactor.

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C. Uraz et al.

parts water; and third, 0.71 parts nickel nitrate in 2.27 parts
H2O. These three solutions are then added to the hydrochloric
solution, and the mixed solution is stirred. 100 g of aluminum
oxide is added to this solution as support. The coating operation is carried out by slow evaporation with continuous stirring of the solution. Finally, the catalyst is calcined at approximately 400 C for 4 hours in a furnace.

2.1.3 Catalyst 3
Zr(OH)4 is impregnated with molybdic acid (H2MoO4) dissolved in 3.56 mL of ammonium hydroxide (25 %) and
26.7 mL of water followed by evaporating the water at room
temperature, drying and calcining in air. The formulation and
preparation technique of superacidic catalyst are proposed by
K. Arata [20].

2.1.4 Catalyst 4
V2O5/TiO2 catalyst is prepared by impregnation of TiO2 with
a NH4VO3 solution according to the method described by Satsuma et al. [8]. NH4VO3 is dissolved in oxalic acid solution.
After addition of TiO2, the solution is evaporated with stirring
until it becomes a pasty cake or a powder. The solid thus
obtained is dried at 110 C and calcined at 500 C for 7 h.

2.1.5 Catalyst 5
Catalyst 5 is prepared like Catalyst 1. The carrier is same as the
first catalyst but the active ingredients are different. A molar
ratio between V2O5, and MoO3 in 2.72 g silica gel is treated
with 200 mL HCl, 40 mL HNO3 and 360 mL H2O in a porcelain basin.
Solution A: 15 g V2O5 is slurried with 150 mL water and
kept at around 80 C by heating on a hot plate. Powdered oxalic acid (41.82 g) is added to the slurry in a small quantity with
stirring until the V2O5 is completely dissolved, giving a deep
blue solution. Solution B: 7.28 g of ammonia molybdate is
dissolved in 72 mL of hot water. Solution C: 6.153 g of nickel
nitrate is dissolved in water. Solution D: 4.793 g of sodium
borate is dissolved in water. Solution E: 20.35 g sodium phosphate is dissolved in water. Solutions A, B, C, D and E are
mixed together and poured on to the silica gel previously prepared. The mixture is kept heated on a sand bath at around
100 C with frequent stirring. When the mixture dries to a
fairly loose powder, it is transferred to an air oven maintained
at 105110 C and heated until it becomes a fairly free flowing
powder (usually 57 h). Lastly, the impregnated silica gel is
transferred into a muffle furnace. The temperature is gradually
raised to 500 C in around 5 h and maintained at this level for
2 h.

2.1.6 Catalyst 6
Keggin-type polyoxometalate catalyst is prepared based on the
study by Etienne et al. [9]. It is prepared by dissolving MoO3,
H3PO4, KNO3 in water to obtain an equiatomic ratio between
K and P, and a ratio between Mo and P equal to 12. This mixture is put into an Erlenmeyer flask. For samples containing
vanadia, the desired amount of V2O5 is dissolved in the solution before addition of nitric acid. Samples containing an
amount of vanadia between 0 and 1.5 atoms for each Keggin
formula, PMo12O40 can be prepared. For this catalyst, the V/P
ratio is selected as 0.5. HNO3 is then added to this mixture to
reach a pH lower than 1.0. A magnetic stirrer is used for this
purpose. When the pH value is equal to 0.97 and no change is
obtained, stirring is stopped. The sample obtained at the end
is filtered. Then it is dried at 100 C for 8 h, and calcined at
120 C for 12 h, at 140 C for 12 h and at 180 C for 12 h. The
final temperature of calcination (350 C) is reached in 6 h, and
maintained for 6 h. After all the catalysts are prepared, sieve
analysis is performed in order to achieve a uniform size distribution of 150 lm.

2.2

Apparatus

The schematic diagram of experimental set-up used is shown

in Fig. 1. The parts of the experimental set-up can be explained as follows:

Figure 1. Schematic representation of the experimental setup.

2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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Chem. Eng. Technol. 2007, 30, No. 12, 17081715

2.2.1 Air Supply Section

Air stream used as reactant is obtained from the dry air cylinder. A valve and a rotameter are used to adjust the flow rate of
the dry air stream. First, the air stream is passed through a silica gel column to remove any water. Before the air is mixed
with benzene, it is heated to 150200 C by passing it through
the electric preheater.

2.2.2 Benzene Supply Section

The main reactant, benzene, is fed by using a Cole Palmer
Masterflex C/L pump, which is designed to pump the fluid
with peristaltic action. A special Viton plastic tube is used for
transferring benzene from the reservoir to the connection section. Before entering the reactor it is vaporized in the preheater
and mixed with heated air.

2.2.3 Reactor
A fluidized bed reactor with a 25.4 mm (1) inside diameter
and 420 mm length is used for the reaction (see Fig. 2). It was
made of AISI-316 SS. The catalyst is placed into the reactor
and two 300 mesh sieves are placed at the bottom and at the
exit of the reactor to support and to prevent the escape of the
powder catalyst. An electrical heater wound around the reactor
is used for heating. Glass wool is used insulating the reactor.
The reaction temperature is controlled through a PID temperature controller connected to an iron-constantan type ColePalmer probe thermocouple. The powers of the heaters and
geometrical parameters of the reactor are listed in Tab. 2.

Fluidized Bed Reactor

1711

Table 2. The powers of heaters and geometrical parameters of

the reactor.
Reactor material

AISI 316 SS

Heater power supply

250 W

Preheater power supply

300 W

HR

420 mm

DR

25.4 mm

hR

355 mm

Volume of reactor

206 cm3

Catalyst particle diameter

150 lm

Gas distributor dimensions (HDDGDDD)

56 30 15 mm

2.2.4 Cooler
A cooler is placed to cool the hot gas mixture leaving the reactor. The gas contains MAN, unreacted benzene, by-products
and excess air. The cooler is a shell and tube type apparatus
and contains 14 tubes of 8 mm diameter and 500 mm length.
Tap water is circulated through the shell side of the cooler.

2.2.5 Absorber Columns/Traps

The cooled stream leaving the cooler is passed through two
traps. One of these traps is filled with ice-salt mixture and the
other is cooled with a circulating water-alcohol mixture. Traps
are connected in series. The collected products are weighted
and analyzed by using the gas chromatograph.

2.3

Experimental Procedure

One of the most important design parameter in a

fluidized bed reactor is the minimum fluidization
velocity [21]. It was calculated theoretically and
the experiments have been carried out at the air
flow rates higher than the value that will satisfy the
minimum fluidization. Experiments are performed
according to the following procedure:
Before start the experiment, the sieved catalyst is
charged into the reactor and leakage control is
performed. Then catalyst is kept in a 350 C air
stream in two hours.
The temperature of the reactor and preheater
are set to the desired value.
Circulation of the cooling fluid (tap water) is
started.
Benzene is charged into a graduated cylinder.
After the temperature attains the desired value,
benzene is supplied into the air stream at a desired flow rate. The time and the liquid level in
the measuring cylinder are recorded.
Figure 2. Schematic representation of the reactor.

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C. Uraz et al.

The low rate of air is adjusted by the valve on the calibrated

rotameter and sent to the preheater and then the reactor.
The effluent passes through the cooler, and then it goes
through the traps. Flow rate of exit gas and CO2 % are measured at specified time intervals. The uncondensed gas is
purged to the atmosphere.
At the end of the experiment (after 2 hours), the pump is
switched off.
The preheater and reactor are cooled down. Air is passed for
a while and then it is stopped
The product mixture, which is obtained at each experiment
collected in the traps, are washed with 2 mL acetone and
then analyzed with a Hewlett Packard 5890 Series II Gas
Chromatograph with flame ionization detector and HP integrator.

Evaluation of the Experiments

Results and Discussion

In this study, by using six different type of catalysts, selective

oxidation of benzene to MAN was studied in a fluidized bed
reactor. During the experiments, effects of temperature, type
of catalyst, space-time, and benzene/air mole ratio on the reaction were investigated. Operating conditions are given in
Tab. 3.
Table 3. Operating conditions in the experiments.
Parameter

Range

Reactor temperature, TR (C)

325400
1

Space time (W/FB0), (g s mole )

11.28 10531.9 105

Catalyst amount, (g)

1394

Benzene/air ratio, (mole/mole)

0.01090.0477

Catalyst/benzene ratio, (w/w)

2.4617.83

The conversion of benzene is calculated considering the two

possible main reactions that take place in the reactor.
C6 H6 g 4:5 O2 gC4 H2 O3 g 2 CO2 g 2 H2 Og
C6 H6 g 7:5 O2 g6 CO2 g 3 H2 Og
Condensed components in the exiting gas stream are analyzed by GC. The weight percent of MAN is calculated with
the help of the GC analysis. At the end of the each experiment,
products collected in the traps are weighed. Moles of MAN
and total benzene fed into the reactor are calculated. Then
conversion of benzene for reaction 1 (x1) is calculated by using
the following equation:


consumed benzene in reaction1
(1)
x1
Benzene Fed
Since the total flow rate of exit gas and CO2 % are measured
during the experiments, moles of CO2 is calculated. Conversion of benzene for reaction 2 is calculated using following
equation:


consumed benzene in reaction2
x2
(2)
Benzene Fed

The experiments were performed by using six different types

of catalysts. Although 1st, 2nd and 4th catalysts show good performance, unfortunately no conversion of benzene to MAN
could be obtained by using 3rd, 5th and 6th catalysts.
If the experiments performed in the temperature range of
325400 C and at nearly constant space-time values are compared, it can be seen from Fig. 3 that conversion of benzene to
MAN increases with increasing temperature for the catalysts
supported by silica gel and titanium oxide. However low conversions are obtained on catalyst 2 supported by alumina. This
catalyst is also not sensitive to temperature.
If the experiments that are carried out at constant temperature (T = 400 C) and at constant space-time values (W/
FB0 = 16.28 105 g s mol1) are investigated, it is seen from
Fig. 4 that conversion increases with increasing air flow rate.
But catalyst 2 shows the same insensitive behavior. Catalyst 2
is also not sensitive to change in air flow rate.
If the experiments at changing temperature (325390 C)
and at two different space-time values (7.99 105

Total conversion of benzene (xT) is calculated by using following equation:



Total consumed benzene
xT
(3)
Benzene Fed
Selectivity is the ratio of benzene conversion for reaction 1
versus for reaction 2. Total selectivity is also the ratio of benzene conversion for reaction 1 and total conversion. Their
equations are:
 
x
Selectivity 1
x2
(4)

Total Selectivity

 
x1
xT

2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

(5)

Figure 3. Temperature vs. conversion for nearly constant W/

FB0 = 18.38 g s molB1 and benzene/air mole ratio is in the
range of 0.01090.0477.

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Fluidized Bed Reactor

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Table 4. The results of N2 adsorption on the catalysts. Pressure:

1 atm.
Methods

BET

LANGMUIR

Figure 4. Benzene/air mole ratio vs. conversion at 400 C and

W/FB0 = 16.28 105 g s molB1.

Figure 5. The result of IR spectroscopy of Catalyst 3.

Catalyst 4

Catalyst 6

Fresh

Exper.

Fresh

Exper.

A (m /g)

6.283

2.049

124.8

117.9

Vm (cm /g)

1.444

0.980

28.69

27.10

A (m /g)

9.122

2.783

175.9

165.3

Vm (cm3/g)

2.099

0.997

40.45

37.99

13.69 105 g s mol1) with Catalyst 3 are evaluated, it is found

that satisfactory results could not be obtained. When the reactor was opened after the experiments, it was seen that the sieve
placed at the bottom of the reactor was affected by the super
acidic catalyst. When the results of IR spectroscopy of Catalyst
3 was investigated (see Fig. 5), carbonyl peaks were detected at
1700 cm1 and 3450 cm1. So Catalyst 3 was not tested further.
To understand if there is any loss in the activity of the catalysts 1, 4 and 6, fresh and experienced catalysts were characterized. When the results of IR spectroscopy of fresh and experienced Catalysts 1 were investigated (Figs. 6, 7), the same peaks
were detected for both catalysts. The surface areas of the fresh
and the experienced Catalyst 4 were investigated with a volumetric adsorption instrument (OMNISORP 100 CX). The adsorption isotherms of the fresh and the experienced Catalyst 4
are shown in Figs. 8 and 9. The results of the analyses are presented in Tab. 4. Additionally, adsorption volume of experienced catalyst is almost 12 of the fresh catalyst. At the same
time, the pore size distribution of the fresh and experienced
catalyst are obtained. As can be seen from Figs. 10 and 11,
pore size distribution occurred in a broad range. In fresh catalyst, pore sizes are more uniform than in the experienced catalyst.
Catalyst 6 is a V2O5 doped Keggin type polyoxometalate catalyst. This type of catalyst was tested over a broad range of operating variables; unfortunately no conversion of benzene to

Figure 6. The result of IR spectroscopy of fresh Catalyst 1.

Figure 7. The result of IR spectroscopy of experienced Catalyst 1.

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C. Uraz et al.

Figure 8. The adsorption isotherms of fresh Catalyst 4.

Chem. Eng. Technol. 2007, 30, No. 12, 17081715

Figure 11. Pore size distribution of experienced Catalyst 4.

Figure 9. The adsorption isotherms of experienced Catalyst 4.

Figure 12. Pore size distribution of fresh Catalyst 6.

Figure 10. Pore size distribution of fresh Catalyst 4.

2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Figure 13. Pore size distribution of experienced Catalyst 6.

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Chem. Eng. Technol. 2007, 30, No. 12, 17081715

MAN could be obtained. Pore size distribution of the experienced and the fresh catalysts are shown in Figs. 12 and 13. It is
seen from Figs. 12 and 13 that pore size distribution of both
catalysts are almost same. It is also easily seen from Tab. 4 that
adsorption volume of experienced catalyst is almost the same
as the fresh catalyst.
When the comparison of all catalysts is made, it can be said
that Catalyst 1 had higher performance than the other catalysts. In the experiments carried out over Catalyst 1, the highest MAN conversions were obtained. It can be concluded that
Catalyst 1 is a more suitable catalyst for benzene oxidation to
MAN in a fluidized bed reactor. The results also indicate that:
V2O5 and MoO3 are essential active components.
SiO2 as a support is more suitable than Al2O3 and titanium
oxide.

Symbols used
[m2/g]
[]
DD
[mm]
DR
[mm]
DGD
[mm]
F
[mol/s]
FB0
[mol/s]
G.C.
[]
hR
[mm]
HD
[mm]
HR
[mm]
MAN
[]
M, m, wt [g]
MW
[g/mol]
n
[mol]
P
[atm]
q
[g/mL]
S.S.
[]
t
[s]
T
[C]
TC
[]
W
[g]
W/FAO
[g s mol1]

A
C

surface area
constant
diameter of the gas distributor cap
inside diameter of the reactor
inside diameter of the gas distributor
flow rate
flow rate of benzene
gas chromatography
length of the reactor
length of the gas distributor
length of the reactor
maleic anhydride
mass
molecular mass
mole number
pressure
density
stainless steel
time
temperature
temperature controller
mass of catalyst
space-time

2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Fluidized Bed Reactor

V
Vm
X

[mL]
[cm3/g]
[%]

1715

volume
volume of catalyst
conversion

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