International Journal of Hydrogen Energy 31 (2006) 1348 – 1356

www.elsevier.com/locate/ijhydene

Development of dehydrogenation catalyst for hydrogen generation in

organic chemical hydride method
Yoshimi Okada∗ , Eiji Sasaki, Eiji Watanabe, Shinji Hyodo, Hiroaki Nishijima
R&D Center, Chiyoda Corporation, Moriya-cho 3-13, Kanagawa-ku Yokohama 221-0022, Japan

Accepted 10 November 2005

Available online 4 January 2006

Abstract
The utilization of the organic chemical hydride method (OCH method) for hydrogen storage and transportation using hydro-
genation and dehydrogenation chemical reactions with aromatic compounds has been investigated since the 1980s. This method
provides for both high gravimetric and volumetric hydrogen densities, and the potential risk is very small due to the storage and
transportation in the liquid state under ambient pressure. It also has the advantage that hydrogen storage and transportation is
carried out as a conventional petrochemical product. However, this method has not been technically established because the de-
hydrogenation catalyst does not have a sufficient stability and performance. We have developed a dehydrogenation catalyst using
a simple fixed-bed reactor that has a high stability and sufficient performance. This catalyst can generate hydrogen from methyl-
cyclohexane (MCH: 99.9%) with a conversion > 95%, toluene selectivity > 99.9%, hydrogen generation rate > 1000 Nm3 /h/m3
cat under the reasonable conditions of 593 K, ambient pressure, LHSV:2.0/h and co-feed hydrogen 5–20 mol% in the feed. The
estimated production cost at a hydrogen station for fuel cell vehicle (FCV) is around 64.7
/Nm3 H2 (59 /Nm3 H2 ). Two pos-
sible applications of this method are introduced. One is the utilization of low-grade hydrogen including impurities. The other is
a future vision of the global hydrogen energy chain.
䉷 2005 International Association for Hydrogen Energy. Published by Elsevier Ltd. All rights reserved.

Keywords: Dehydrogenation catalyst; Organic chemical hydrides; OCH method; Hydrogen station; Low-grade hydrogen; Global hydrogen
energy chain

1. Introduction chemical hydrides, which means hydrogenated aro-

A system that has a low potential risk for hydro-
gen storage and transportation is needed to be estab-
lished, since hydrogen has an explosive combustion rate
and very high combustion temperature. Various meth-
ods have already been investigated, for example, liq-
uid hydrogen (4 K, −253 ◦ C), compressed hydrogen
(35–70 MPa), metal hydrides, inorganic chemical hy-
drides, however, there is no conclusive result. Organic
∗ Corresponding author. Tel.: +81 45 441 9145;
fax: +81 45 441 9728.
E-mail address: yookada@ykh.chiyoda.co.jp (Y. Okada).
0360-3199/$30.00 䉷 2005 International Association for Hydrogen Energy. Published by Elsevier Ltd. All rights reserved.
doi:10.1016/j.ijhydene.2005.11.014
matic compounds by a chemical reaction, have a very
high efficiency for hydrogen storage [1,2], and some
of them attained the goal of the US Department of
Energy (DOE) hydrogen program or US cars program.
This method had been investigated by the Euro-Quebec
Hydrogen project in the 1980s as the MCH method [3,4]
using methylcyclohexane (MCH), and compared to am-
monia method and liquefied hydrogen (LH2 ) method.
In this project, LH2 was selected, because Canadian
hydropower can be utilized as the liquefaction energy
source. The MCH method had another problem such
that it was not technically established, since there is
no dehydrogenation catalyst having sufficient stability
 Y. Okada et al. / International Journal of Hydrogen Energy 31 (2006) 1348 – 1356 1349

performance. The dehydrogenation of cycloalkanes 2.2. Equilibrium conversion

needs around 570 K for sufficient equilibrium conver-
sion. Since the conventional catalyst needed more than
670 K with a fix-bed reactor, there is a remarkable coke
deposition on the catalyst surface, which was the cause
of the catalyst deactivation [5–8]. Saito et al. reported
that a thin liquid film in the superheated state could
generate hydrogen at 483 K without any equilibrium
restriction [9]. Pez and Cooper et al. proposed using
decalin or polycyclic aromatic hydrocarbons as liquid
hydrides to lower the dehydrogenation temperature
[10,11].
We have developed a dehydrogenation catalyst that
can be utilized in a conventional fixed bed reactor for
the hydrogen storage and transportation method us-
ing an organic chemical hydride, for example MCH,
cyclohexane, decalin, etc., and we called this method
the fixed bed “organic chemical hydrides method (OCH
method)”. The hydrogen station system for FCV when
using the developed catalyst has been designed to es-
timate the production cost by the OCH method. Two
possible uses of this method are introduced. One is
Fig. 1 shows the temperature dependence of the equi-
librium conversion for dehydrogenation of Eqs. (1)–(3).
The dehydrogenation of decalin easily occurs compared
to cyclohexane and MCH. MCH which has a side chain
is also easier to be dehydrogenated, than cyclohexane.
The order of the required temperature for the same equi-
librium conversion is decalin < MCH < cyclohexane.
The equilibrium conversion for the dehydrogenation of
MCH increases at around 473 K and attains 99% at
593 K.
2.3. Hydrogen storage efficiency
Fig. 2 shows the hydrogen storage efficiency of vari-
ous methods [13]. The target of the DOE hydrogen plan
100
Decalin
80
Equilibrium Conversion (%)

Methyl cyclohexane
the application of the method to low-grade hydrogen
including an impurity by selective hydrogenation. The
other is the global hydrogen transportation scheme in 60
the future.
40

2. Reactions of OCH method Cyclohexane

20
2.1. Hydrogenation and dehydrogenation equation Pressure : 0.1 × 106 Pa

CH3 CH3 0
- 3H2 373 423 473 523 573 623 673
(1)

H=205kJ/mol Temperature (K)
+ 3H2
Fig. 1. Temperature dependence on equilibrium conversion of
- 3H2 dehydrogenation for typical organic chemical hydrides.

H=206kJ/mol (2)
+ 3H2

- 5H2 200

H=332kJ/mol
Volmetric content (kg-H2/m3)

(3) Organic
+ 5H2 100 Decalin
DOE Hydrogen plan Chemical
Hydride
Eqs. (1)–(3) show the hydrogenation and dehydro- MCH
LH2
50 Cyclohexane
genation of typical organic chemical hydrides. In all
ed
cases, hydrogenation is an exothermic reaction and de- Metal hydride
anc
d advd
hydrogenation is an endothermic reaction. The heat of 20 ta n sse
ren pre
reaction is around 70 kJ/mol H2 . The hydrogenation Cur com
processes of these aromatic compounds have been 10
commercialized [12], while the dehydrogenation pro- 5
0.5 1 2 5 10 20
cess for aromatic hydride does not exist, since these Gravimetric content (wt%)
aromatic compounds are industrially produced from
crude oil by a separation process. Fig. 2. Hydrogen storage efficiency of various storage systems.
1350
Number of pH swing operation (-)
1
2
3
is 6.5 wt% and 62.0 kg H2 /m3 . Decalin has an efficiency
of 7.2 wt% and 64.9 kg H2 /m3 . These values meet the
targets of the DOE hydrogen plan. MCH has 6.1 wt%
and 47.0 kg H2 /m3 and cyclohexane has 7.1 wt%
and 55.5 kg H2 /m3 . Although the pressure vessel for
75 MPa is under development to raise the pressure for
compressed hydrogen from 35 MPa, organic chemi-
cal hydrides have a higher volumetric content than
those of compressed hydrogen in spite of the ambient
pressure.
3. Development of dehydrogenation catalyst
3.1. Concept of catalyst design
Since the conventional dehydrogenation catalysts re-
quired a reaction temperature greater than 670 K, the
catalyst deactivation was remarkable due to coke de-
position in this temperature range. The coking reac-
tion is started from cleavage of the C–C bond of the
aromatic ring by protolytic cracking or -scission, and
these cracking reactions occurred on the acid site of
the catalyst surface [14]. -Alumina, which is com-
monly used as a catalyst carrier, has acid sites on its
surface. Additionally, there is the possibility of cleav-
age reactions occurring on the platinum surface. From
the above consideration, the keys of this catalyst de-
velopment were to lower the reaction temperature by
Y. Okada et al. / International Journal of Hydrogen Energy 31 (2006) 1348 – 1356
Acid side (Dissolution) Alkali side (Precipitation)
pH
Water NaAlO2 alkaline solution
H2SO4 Acidic solution
NaAlO2 alkaline solution
H2SO4 Acidic solution
NaAlO2 alkaline solution
Fig. 3. Principle of pH swing method.
increasing the catalytic activity and to reduce sites on
the catalyst at which the cleavage reaction occurs.
As a result, an attempt was made to raise the cat-
alytic activity by increasing the dispersibility of the plat-
inum metal by using a pore controlled -alumina carrier
and optimization of the pH value for impregnation of
chloroplatinic acid. Furthermore, impregnation of the
alkali metal species was investigated for masking the
acid sites.
3.2. Unimodal porous alumina carrier
The pH swing method to control the pore distribution
of the alumina carrier [15] was developed by the Chiy-
oda Corporation more than 20 years ago. The method is
commercially available to produce alumina carrier for
the desulfurization catalysts. Fig. 3 shows the principles
of the pH swing method. Generally, alumina is made
by the calcination of boehmite gel precipitated by alka-
line conditions. In the pH swing method, the pH value
of the precipitated slurry solution is reduced by acid to
dissolve the fine particles among the various precipi-
tated sizes of the boehmite particles. After this disso-
lution, the aluminum source and alkaline solution are
thrown into the slurry again to grow the particles. The
remaining particles then grow larger, and fine particles
are generated again. By this pH swing operation, the
boehmite particle size meets a certain range. A large
pore is formed by calcination of the large boehmite
 Y. Okada et al. / International Journal of Hydrogen Energy 31 (2006) 1348 – 1356
0.5
Incremental Volume (ml/g-dLogD)
0.4
0.3
0.2
0.1
0
1 10 100
Pore Diameter (nm)
Fig. 4. Pore distribution of pore controlled alumina and non-
controlled alumina.
particles. Typically, the pore size is controlled by the
number of pH swing operations. Fig. 4 shows the pore
distributions of alumina by the pH swing method and
the non-controlled alumina carrier.
The pore size controlling method was originally de-
veloped for improving the diffusion for large molecule
like heavy oil in the catalyst pores. Recently, the pore
controlling alumina has a good dispersibility for metal
impregnation. The preparation of the long-life dehy-
drogenation catalyst for isobutane using the unimodal
alumina carrier has been reported [16–18]. During this
development of the dehydrogenation catalyst for chem-
ical hydrides, this alumina carrier is used for increas-
ing the dispersibility of the platinum metal and alkaline
metal species.
3.3. Experimental
3.3.1. Catalyst preparation
The -alumina carrier was prepared by the pH swing
method using the system of consisting sulfuric acid and
sodium aluminate aqueous solution. A boehmite suspen-
sion slurry (pH 10) was obtained by adding a sodium
aluminate solution (1.35 mol/l, 390 cm3 ) to a hot and
dilute sulfuric acid solution (11.6 wt%, 150 cm3 and
water 10l) that was being agitated. The sulfuric acid
solution (11.6 wt%, 150 cm3 ) was added to the slurry
solution after 5 min (pH 3.5). The sodium aluminate so-
lution (1.35 mol/l, 390 cm3 ) was then added to the slurry
solution after 5 min again (pH 10). This pH swing op-
eration in which the acid and alkaline solutions were
alternately added was repeated 3 times, and the final
1351
Table 1
Physical properties of -alumina carrier
Average pore diameter (nm) 11.9
B.E.T surface area (m2 /g) 240
Pore volume (cm3 /g) 0.713
suspension was filtered and washed to produce a cake,
which was subjected to an extrusion. This extrusion was
dried at 393 K (120 ◦ C) for 3 h and calcined at 773 K
(500 ◦ C) for 3 h. In the above preparation, if the purity
of the sodium aluminate is low, the aqueous solution is
brown colored. That solution should be filtered before
use. Table 1 shows the physical properties of the pre-
pared alumina carrier. The catalyst was prepared by a
1000 simple impregnation method. Pt (0.6 wt%) was impreg-
nated with a chloroplatinic acid solution. However, the
pH value was adjusted at 2.0 before immersion. After
immersion, the water is removed using an evaporator,
dried at 393 K, and calcined at 673 K (400 ◦ C) for 3 h.
K (0.1 wt%) was impregnated with a potassium nitrate
solution. After drying, it was directly reduced by hy-
drogen stream at 673 K for 15 h without calcination.
3.3.2. Reaction test
MCH was selected as the organic chemical hydride
for the reaction tests, because methane formation due
to scission of the side chain is a good index for the
catalytic selectivity. MCH (Wako, 99.9%) was evap-
orated to eliminate the heavy impurities. The catalyst
(10 cm3 ) was charged to the stainless-steel tube re-
actor (ID 12.6 mm) which has a thermocouple tube
located at the center of the cross section. Beads of -
alumina (1 mm, 10 cm3 ) were placed in the pre-heat
zone before the catalyst bed in the reactor. The tem-
perature was raised to 593 K under a hydrogen stream
(GHSV = 8.0/h, 80 cm3 /h) and MCH was fed to the
reactor (LHSV = 2.0/h, GHSV = 350/h). The reaction
temperature was controlled at the outer skin of the re-
actor that corresponds to the center of the catalyst bed.
The amount of co-feed hydrogen was reduced step-
by-step from 80 to 40 cm3 /h at 1300 h and from 40 to
20 cm3 /h at 1800 h.
3.4. Results
Fig. 5 shows the reaction test results after approx-
imately 3000 h. The developed catalyst provided a
stable MCH conversion of 95%, toluene selectivity
> 99.9%, and the hydrogen generation rate is greater
than 1000 Nm3 /m3 cat/h after 3000 h. The formation
of methane and benzene is the main side reaction
with a selectivity of around 0.02%. Although several
1352 Y. Okada et al. / International Journal of Hydrogen Energy 31 (2006) 1348 – 1356

100.00
99.99

Toluene Selectivity (%)

99.98
99.97
99.96
99.95
99.94
99.93
99.92
99.91 Co-feed H2: 20% Co-feed H2: 10% Co-feed H2: 5%
99.90
0 500 1000 1500 2000 2500 3000 3500

100
95
MCH Conversion (%)

90
85
80 Catalyst : K(0.1)-Pt(0.6)/Al2O3
75 Reaction condition
70 Temp. : 593K (320°C)
65 Press. : 0.1MPa
LHSV : 2.0h-1
60 Co-Feed H2 : 20, 10, 5%
55
50
0 500 1000 1500 2000 2500 3000 3500
Hours on Stream (h)

Fig. 5. Influence of Co-feed H2 to MCH conversion and toluene selectivity.

100.000
H2purity in (H2+CH4) (%)

Catalyst : K(0.1)-Pt(0.6)/Al2O3
Reaction condition
99.999
Press. : 0.1MPa
LHSV : 2.0h-1
99.998 Co-Feed H2 : 5%

99.997

99.996

99.995
523 533 543 553 563 573 583 593 603 613 623

100
MCH conversion (%)

90
80 Catalyst : K(0.1)-Pt(0.6)/Al2O3
Reaction condition
70 Press. : 0.1MPa
LHSV : 2.0h-1
60
Co-Feed H2 : 5%
50
523 533 543 553 563 573 583 593 603 613 623
Reaction temperature

Fig. 6. Temperature dependence of MCH conversion and H2 purity in H2 and CH4 .

compounds due to the ring cleavage reaction were also tion rate of H2 and CH4 at 3100 h on stream after the
detected, the total amount is around 0.005%. The se- run shown in Fig. 5. It is considered that the devel-
lectivity of toluene has been greater than 99.9% after oped catalyst can produce hydrogen with more than a
reducing the co-feed hydrogen to 20 cm3 /h. 99.99% purity with the removal of components except
Fig. 6 shows the temperature dependence of the MCH for H2 and CH4 using a vapor adsorbent column. Since
conversion and H2 purity calculated from the genera- methane is an inert gas for an electrochemical reaction
 Y. Okada et al. / International Journal of Hydrogen Energy 31 (2006) 1348 – 1356 1353

Toluene Selectivity (%) 100.0

99.9

99.8 Co-feed H2: 20% 10% 5%

99.7 Catalyst : K(0.1)-Pt(0.6)/Al2O3

Condition : 593K (320), 0.1MPa, LHSV=2.0h-1
99.6
Co-feed H2 infeed (mol%)=20%, 10%, 5%
99.5
0 500 1000 1500 2000 2500 3000 3500 4000 4500 5000 5500 6000 6500

100
95
90
MCH Conversion (%)

85
80
75 Catalyst Performance
70 MCH conv. : 95% Hydrogen generation Rate
65
Tolueneselec. : 99.9% 1000Ncc/h/cc-cat (90g-H2/h/L-cat)
60
55
50
0 500 1000 1500 2000 2500 3000 3500 4000 4500 5000 5500 6000 6500
Hours on Stream

Fig. 7. Result of catalyst life performance test.

Vapor High
Low Adsorber Compres.
Compres. H2
Dehydrogenation Unit
MCH
Dispenser FCV
H2
Toluene Heat
Electricity

Co-generation System
Fuel Exhaust

H2 Storage System

Fig. 8. Concept of hydrogen station.

in a fuel cell, it is considered that the purity of 99.99% the next step, we plan to investigate the influence of
will be sufficient for the hydrogen specification in fuel impurities in the hydrogenation product on the life of
cells. the dehydrogenation catalyst.
The run in Fig. 5 was continued as the catalyst
life performance test after the experimental shown in
4. Hydrogen station
Fig. 6. Fig. 7 showed that the catalyst performance
is very stable after more than 6000 h without regen- 4.1. Concept of hydrogen station design
eration. It is considered that 5% of the co-feed H2 is
sufficient for the pure MCH feed. Based on these re- The hydrogen station using this catalyst has been de-
sults, the developed catlayst has a sufficient stability signed to estimate the hydrogen production cost by the
for the OCH method using the pure MCH feed. As OCH method. Fig. 8 shows the concept of the station.
1354 Y. Okada et al. / International Journal of Hydrogen Energy 31 (2006) 1348 – 1356

Table 2 relative production cost of compressed H2 and LH2 . The

Design base of hydrogen station for FCV cost is the total sum of the raw hydrogen, processing
Service capacity of FCV 100 cars for hydrogenation, transportation and station cost. When
H2 supply capacity 3500 Nm3 /day the LH2 production cost is taken at 100 pts, compressed
269 Nm3 /h H2 is around 80 pts and the OCH method is around
Service hours 13 hours/day 70 pts.
Service days 365 days/year

5. Possibilities of application of OCH method

The feature of this station is to effectively utilize the
heat and electricity using a co-generation system. The
system supplies all the energy for the station using the
exhaust heat and electricity. The fuel of the system is
diesel oil or kerosene. The reactor design, system de-
sign, and equipment selection to estimate the fixed cap-
ital have been completed. Table 2 shows the design base
of the station.
4.2. Production cost
The hydrogen production cost from this station design
was estimated. The raw hydrogen cost is considered to
be 8
/Nm3 H2 (7.2 /Nm3 H2 ). The transportation cost
is based on a 100 km round trip. The production cost
of hydrogen from this station using the OCH method
is estimated to be 64.7
/Nm3 H2 (59 /Nm3 H2 ). This
price is equal to 725
/kg H2 (6.6 $/Nm3 H2 , 110
/$).
Since FCV can be driven for 500 km with 5 kg H2 ,
the fuel consumption cost by the OCH method is es-
timated to be 7.3
/km (6.6 /km). Fig. 9 shows the
5.1. Utilization of low-grade hydrogen sources from
the industrial complex area
The hydrogenation process using pure hydrogen has
been commercialized as cyclohexane or decalin pro-
duction. If a low-grade hydrogen such as coke oven
gas (COG) from an iron-manufacturing plant, or bleed
gas from a refinery or petrochemical plant is able to
be utilized, the hydrogen energy source could be ex-
tended. Fig. 10 shows the applied scheme for the utiliza-
tion of these hydrogen sources. In the case of a certain
domestic complex, there is the possibility of produc-
ing 7.2 × 108 Nm3 H2 /year from the complex in Japan.
This amount corresponds to the yearly consumption by
580,000 FCV cars. However, the utilization of waste
plastic or residual oil as an alternative energy source
will be required, since COG or such a bleed gas in-
cluding H2 is consumed as fuel in these plants. The
economical removal process for impurities or a selec-
tive hydrogenation catalyst would also be needed, since
these hydrogen sources contain CO or S.

100
Row hydrogen cost Process cost
90
Transportation cost Station cost
80
Relative H2 supply cost (-)

70

60

50

40

30

20

10

0
Chemical hydride Compressed H2 Liquefied H2

Fig. 9. Comparison of H2 supply cost at hydrogen station by OCH method with compressed H2 and liquefied H2 (LH2 = 100).
 Y. Okada et al. / International Journal of Hydrogen Energy 31 (2006) 1348 – 1356 1355

Fig. 10. Applied scheme of OCH method to various hydrogen source from the complex.

Fig. 11. Future vision of global hydrogen energy chain.

5.2. Global vision of hydrogen energy chain by OCH
method
Fig. 11 shows the future vision of a global hydrogen
energy chain [19] using the OCH method. Hydrogen
production and hydrogenation to an organic chemical
hydride are processed near the gas fields. It is consid-
ered that this scheme realizes the utilization of hydro-
gen energy with a large reduction in the CO2 emission,
because the generated CO2 through the hydrogen pro-
duction process will be injected into the ground. The
chemical hydride is transported to the consumer coun-
tries by the usual sea-going chemical tankers, and it is
stored in tanks on land, the hydride is finally delivered
to the hydrogen station by chemical trucks. It is consid-
ered that this scheme has a low potential risk regarding
safety and a small loss of hydrogen through the trans-
portation, because the storage and transportation are car-
ried out in the liquid state under ambient pressure and
temperature. However, it is also considered that a ca-
pacity as large as an LNG plant will be needed to make
the scheme economically viable, so the popularization
of hydrogen energy use is expected.
6. Conclusion
A dehydrogenation catalyst, which has the high
performance of 95% of MCH conversion, and 99.9%
toluene selectivity at around 573 K has been developed.
1356 Y. Okada et al. / International Journal of Hydrogen Energy 31 (2006) 1348 – 1356
The catalyst shows an excellent stability of 6000 h
without regeneration in the life test using the pure
MCH feed. It is possible that the OCH method will be
established due to the catalyst development. However,
the catalyst life investigation using the feed of a hydro-
genation product and the total system test are needed
for it. The hydrogen station for the FCV was designed
using the co-generation system to supply all the energy
for the station, and the hydrogen production cost was
estimated to be 64.7
/Nm3 H2 (59 /Nm3 H2 ). The
applied scheme for utilization of low-grade hydrogen
from the complex was investigated. It was estimated
that a certain domestic complex has the possibility to
supply 7.2 × 108 Nm3 H2 /year of hydrogen. However,
the utilization of an alternative energy source, the eco-
nomical removal process or selective hydrogenation
catalyst will be needed, since the low-grade hydro-
gen contains CO or S. A future global vision of the
hydrogen energy chain by the OCH method was also
proposed. Hydrogen production and hydrogenation to
an organic chemical hydride are processed near the gas
fields. It is considered that this scheme will realize the
utilization of hydrogen energy with a large reduction in
the CO2 emission, because the generated CO2 through
the hydrogen production process will be injected into
the ground.
Acknowledgements
We gratefully acknowledge Dr. K. Fukuda (The
Institute of Applied Energy, JAPAN) for the various
discussions regarding the point of total utilization of hy-
drogen energy. We also gratefully acknowledge NEDO
(New Energy and Industrial Technology development
Organization), since the application scheme of Fig. 10
is a result of research supported by their funds.
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