1708 Chem. Eng. Technol. 2007, 30, No.

12, 1708–1715

Canan Uraz1 Research Article

Süheyda Atalay1

1
Ege University, Faculty
of Engineering, Department
of Chemical Engineering,
Bornova-Izmir, Turkey.
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 labora-
tory scale fluidized bed reactor on six different types of catalysts, which have dif-
ferent compositions. Effects of temperature, flow rates of benzene and air and cat-
alyst 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 mol–1, 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 sup-
ported 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 com-
parison 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

1 Introduction drocarbons has become increasingly important. Phthalic

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-fur-
andione, cis-butenedionic anhydride, toxilic anhydride and
maleic acid anhydride. This multifunctional chemical inter-
mediate 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 an-
hydride function, MAN is a versatile intermediate for the pro-
duction 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 hy-
drocarbons in the gas phase. Benzene used to be the predomi-
nant starting material but in recent years oxidation of C4 hy-
– fluidized bed.
Correspondence: C. Uraz (canan.uraz@ege.edu.tr), Ege University,
Faculty of Engineering, Department of Chemical Engineering, 35100
Bornova-Izmir, Turkey.
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 devel-
opment stage: Fixed-bed process, fluidized-bed process, and
transport-bed process [3, 4]. Nowadays, technological ad-
vancements are directing us to use fluidized bed reactors since
they have some advantages over the fixed bed reactors. The ba-
sic 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 distri-
bution throughout the whole bed, a consequence of inten-
sive 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 immer-
sed heating or cooling surfaces due to intensive solids mix-
ing.
IV) Easy handling of solids due to liquid-like behavior of the
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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Chem. Eng. Technol. 2007, 30, No. 12, 1708–1715 Fluidized Bed Reactor 1709

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 sup-
ports 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 composi-
and superacidic catalysts can also be used in the oxidation pro- tions 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 for- 2.1.1 Catalyst 1
mation of reduced vanadium ions. The preparation methods
and conditions are the critical factors for the catalytic perfor- This catalyst is prepared by following the procedure in the pat-
mance and the structure of supported vanadium oxide. Impreg- ent 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 cata- by 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 (pre-
enough 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 cat- bath for 10–12 hour at 100 °C. After descending of the acid
ions in the secondary framework have been the subject of sev- from 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 [9–14]. 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 modi- 2.1.2 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 pre-
cursor with acid results in an agglomeration of catalyst Type of the carrier Cat. 1 Cat. 2 Cat. 3 Cat. 4 Cat. 5 Cat. 6
particles [15]. Another method to improve the attri- and % by weight
Silica 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
colloidal silica sol. However, this method results in a CompositionsV2O5 53.6 63.99 – 100 53.6 36.263
decreased selectivity to maleic anhydride as well [16]. of active
Overbeek developed a preparation procedure which ingredient,
was cheaper and much more controllable than the wt %
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 %).
In general, titania-supported catalysts are much more NiO 10.7 1.15 – – 6.25 –
active than their silica counterparts. However, silica- Na2O – 1.2 – – 6.25 –
supported catalysts are much more selective, resulting
in better overall yields [17]. Bi2O3 – 1.92 – – – –
The aim of this study is to prepare catalysts by fol- ZrO2 – – 92.83 – – –
lowing the recommendations in the literature, to char-
acterize and to test them to investigate the influences B2O3 – – – – 6.25 –
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.

© 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim http://www.cet-journal.com

1710 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 opera-
tion is carried out by slow evaporation with continuous stir-
ring of the solution. Finally, the catalyst is calcined at approxi-
mately 400 °C for 4 hours in a furnace.
2.1.3 Catalyst 3
Zr(OH)4 is impregnated with molybdic acid (H2MoO4) dis-
solved 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 Sat-
suma 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.
Figure 1. Schematic representation of the experimental setup.
© 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chem. Eng. Technol. 2007, 30, No. 12, 1708–1715
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 porce-
lain 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 oxa-
lic 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 phos-
phate is dissolved in water. Solutions A, B, C, D and E are
mixed together and poured on to the silica gel previously pre-
pared. 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 105–110 °C and heated until it becomes a fairly free flowing
powder (usually 5–7 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 mix-
ture is put into an Erlenmeyer flask. For samples containing
vanadia, the desired amount of V2O5 is dissolved in the solu-
tion 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 distri-
bution 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 ex-
plained as follows:
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Chem. Eng. Technol. 2007, 30, No. 12, 1708–1715
2.2.1 Air Supply Section
Air stream used as reactant is obtained from the dry air cylin-
der. 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 sili-
ca gel column to remove any water. Before the air is mixed
with benzene, it is heated to 150–200 °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 sec-
tion. 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 temper-
ature controller connected to an iron-constantan type Cole-
Palmer probe thermocouple. The powers of the heaters and
geometrical parameters of the reactor are listed in Tab. 2.
Figure 2. Schematic representation of the reactor.
© 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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 (HD×DGD×DD) 56 × 30 × 15 mm
2.2.4 Cooler
A cooler is placed to cool the hot gas mixture leaving the reac-
tor. 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 de-
sired flow rate. The time and the liquid level in
the measuring cylinder are recorded.
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1712 C. Uraz et al. Chem. Eng. Technol. 2007, 30, No. 12, 1708–1715

– The low rate of air is adjusted by the valve on the calibrated 4 Results and Discussion
rotameter and sent to the preheater and then the reactor.
– The effluent passes through the cooler, and then it goes In this study, by using six different type of catalysts, selective
through the traps. Flow rate of exit gas and CO2 % are mea- oxidation of benzene to MAN was studied in a fluidized bed
sured at specified time intervals. The uncondensed gas is reactor. During the experiments, effects of temperature, type
purged to the atmosphere. of catalyst, space-time, and benzene/air mole ratio on the reac-
– At the end of the experiment (after 2 hours), the pump is tion were investigated. Operating conditions are given in
switched off. Tab. 3.
– The preheater and reactor are cooled down. Air is passed for
a while and then it is stopped Table 3. Operating conditions in the experiments.
– The product mixture, which is obtained at each experiment
collected in the traps, are washed with 2 mL acetone and Parameter Range
then analyzed with a Hewlett Packard 5890 Series II Gas
Reactor temperature, TR (°C) 325–400
Chromatograph with flame ionization detector and HP inte-
–1
grator. Space time (W/FB0), (g s mole ) 11.28 · 105–31.9 · 105
Catalyst amount, (g) 13–94

3 Evaluation of the Experiments Benzene/air ratio, (mole/mole) 0.0109–0.0477

Catalyst/benzene ratio, (w/w) 2.46–17.83
The conversion of benzene is calculated considering the two
possible main reactions that take place in the reactor.
The experiments were performed by using six different types
C6 H6 …g† ‡ 4:5 O2 …g†→C4 H2 O3 …g† ‡ 2 CO2 …g† ‡ 2 H2 O…g† of catalysts. Although 1st, 2nd and 4th catalysts show good per-
C6 H6 …g† ‡ 7:5 O2 …g†→6 CO2 …g† ‡ 3 H2 O…g† formance, unfortunately no conversion of benzene to MAN
could be obtained by using 3rd, 5th and 6th catalysts.
Condensed components in the exiting gas stream are ana- If the experiments performed in the temperature range of
lyzed by GC. The weight percent of MAN is calculated with 325–400 °C and at nearly constant space-time values are com-
the help of the GC analysis. At the end of the each experiment, pared, it can be seen from Fig. 3 that conversion of benzene to
products collected in the traps are weighed. Moles of MAN MAN increases with increasing temperature for the catalysts
and total benzene fed into the reactor are calculated. Then supported by silica gel and titanium oxide. However low con-
conversion of benzene for reaction 1 (x1) is calculated by using versions are obtained on catalyst 2 supported by alumina. This
the following equation: catalyst is also not sensitive to temperature.
  If the experiments that are carried out at constant tempera-
consumed benzene in reaction1 ture (T = 400 °C) and at constant space-time values (W/
x1 ˆ (1)
Benzene Fed FB0 = 16.28 × 105 g s mol–1) are investigated, it is seen from
Since the total flow rate of exit gas and CO2 % are measured Fig. 4 that conversion increases with increasing air flow rate.
during the experiments, moles of CO2 is calculated. Conver- But catalyst 2 shows the same insensitive behavior. Catalyst 2
sion of benzene for reaction 2 is calculated using following is also not sensitive to change in air flow rate.
equation: If the experiments at changing temperature (325–390 °C)
  and at two different space-time values (7.99 × 105–
consumed benzene in reaction2
x2 ˆ (2)
Benzene Fed
Total conversion of benzene (xT) is calculated by using fol-
lowing equation:
 
Total consumed benzene
xT ˆ (3)
Benzene Fed
Selectivity is the ratio of benzene conversion for reaction 1
versus for reaction 2. Total selectivity is also the ratio of ben-
zene conversion for reaction 1 and total conversion. Their
equations are:
 
x
Selectivity ˆ 1
x2 (4)

 
x1
Total Selectivity ˆ (5) Figure 3. Temperature vs. conversion for nearly constant W/
xT FB0 = 18.38 g s molB–1 and benzene/air mole ratio is in the
range of 0.0109–0.0477.

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Chem. Eng. Technol. 2007, 30, No. 12, 1708–1715 Fluidized Bed Reactor 1713

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

1 atm.

Methods Catalyst 4 Catalyst 6

Fresh Exper. Fresh Exper.
2
BET A (m /g) 6.283 2.049 124.8 117.9
3
Vm (cm /g) 1.444 0.980 28.69 27.10
2
LANG- A (m /g) 9.122 2.783 175.9 165.3
MUIR
Vm (cm3/g) 2.099 0.997 40.45 37.99

13.69 × 105 g s mol–1) with Catalyst 3 are evaluated, it is found

Figure 4. Benzene/air mole ratio vs. conversion at 400 °C and
W/FB0 = 16.28 · 105 g s molB–1.
Figure 5. The result of IR spectroscopy of Catalyst 3.
that satisfactory results could not be obtained. When the reac-
tor 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 cm–1 and 3450 cm–1. So Catalyst 3 was not tested further.
To understand if there is any loss in the activity of the cata-
lysts 1, 4 and 6, fresh and experienced catalysts were character-
ized. When the results of IR spectroscopy of fresh and experi-
enced 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 volu-
metric adsorption instrument (OMNISORP 100 CX). The ad-
sorption isotherms of the fresh and the experienced Catalyst 4
are shown in Figs. 8 and 9. The results of the analyses are pre-
sented in Tab. 4. Additionally, adsorption volume of experi-
enced catalyst is almost 1⁄2 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 cata-
lyst, pore sizes are more uniform than in the experienced cata-
lyst.
Catalyst 6 is a V2O5 doped Keggin type polyoxometalate cat-
alyst. This type of catalyst was tested over a broad range of op-
erating 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.

© 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim http://www.cet-journal.com

1714 C. Uraz et al. Chem. Eng. Technol. 2007, 30, No. 12, 1708–1715

Figure 8. The adsorption isotherms of fresh Catalyst 4. 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. Figure 13. Pore size distribution of experienced Catalyst 6.

© 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim http://www.cet-journal.com

Chem. Eng. Technol. 2007, 30, No. 12, 1708–1715 Fluidized Bed Reactor 1715

MAN could be obtained. Pore size distribution of the experi- V [mL] volume
enced and the fresh catalysts are shown in Figs. 12 and 13. It is Vm [cm3/g] volume of catalyst
seen from Figs. 12 and 13 that pore size distribution of both X [%] conversion
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. References
When the comparison of all catalysts is made, it can be said
that Catalyst 1 had higher performance than the other cata- [1] Kirk-Othmer, Encyclopedia of Chemical Process and Design
lysts. In the experiments carried out over Catalyst 1, the high- Vol.14, Marcel Dekker, New York 1977.
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