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Applied Catalysis A: General 336 (2008) 23–28

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Hydroisomerization of long-chain n-alkanes on bifunctional Pt/zeolite

catalysts: Effect of the zeolite structure on the product selectivity
and on the reaction mechanism
A. Soualah a,b, J.L. Lemberton a,*, L. Pinard a, M. Chater b, P. Magnoux a, K. Moljord c
a
Laboratoire de Catalyse en Chimie Organique, Université de Poitiers, UMR CNRS 6503, Faculté des Sciences,
40 Avenue du Recteur Pineau, 86022 Poitiers Cedex, France
b
Laboratoire d’Etudes Physico-Chimiques des Matériaux et Application à l’Environnement (LEPCMAE),
Université des Sciences et de la Technologie Houari Boumediène (USTHB), Faculté de Chimie, B.P. 32 El Alia, 16111 Alger, Algeria
c
Statoil Research Center, 7005 Trondheim, Norway
Received 5 July 2007; received in revised form 26 September 2007; accepted 26 September 2007
Available online 2 October 2007

Abstract
The transformation of n-decane, n-tetradecane and n-hexadecane was carried out in a fixed-bed reactor at 220 8C under a 30 bar total pressure
on bifunctional Pt-exchanged HBEA, HMCM-22 and HZSM-5 zeolite catalysts. The activities of the catalysts and especially the reaction scheme
depended strongly on the zeolite structure. Whatever the reactant, monobranched isomers were the only primary reaction products on PtHBEA,
while cracking was the main reaction observed on HMCM-22 and HZSM-5 with n-tetradecane and n-hexadecane. This was explained in terms of
diffusion of the reaction intermediates inside the zeolites porosities: rapid diffusion inside the large channels of the HBEA zeolite, improved by the
small size of the crystallites, blocking of the reaction intermediates inside the porosity of HMCM-22 and HZSM-5 yielding extensive cracking.
# 2007 Elsevier B.V. All rights reserved.
Keywords: Hydroisomerization; n-Alkanes; Platinum; Zeolites; Bifunctional catalysts

1. Introduction basically platinum or palladium [4–7]. Zeolites like mordenite,

The hydroisomerization of heavy linear alkanes is of a great
interest in petroleum industry. Indeed, the transformation of
long chain n-alkanes into branched alkanes allows to increase
the octane number of gasoline and to improve the low
temperature performances of diesel or lubricating oils [1–3].
However, while a selective isomerization of light n-alkanes is
easy to perform, that of heavy n-alkanes is much more difficult
to obtain, the cracking of long chain alkanes being very rapid.
Thus, the catalytic systems used for the transformation of long
chain alkanes must have a very high selectivity for isomeriza-
tion rather than for cracking.
Hydroisomerization catalysts will be bifunctional, associat-
ing a hydro-dehydrogenating function with an acidic one. The
hydro-dehydrogenating function is provided by a noble metal,
* Corresponding author.
E-mail address: jean.louis.lemberton@univ-poitiers.fr (J.L. Lemberton).
ZSM-5, Y and Beta (BEA) have been widely used as the acidic
function [5,8–13]. The selectivity of a bifunctional catalyst for
isomerization is expected to depend on the balance between the
two catalytic functions, i.e. the density and the strength of the
Brönsted acid sites (H+) and the amount and the dispersion of
the metal [10,14–16]. When the hydrogenating function is
highly active, the activity and the selectivity of the bifunctional
catalyst will depend only on the acidic function in the absence
of diffusional limitations. A decrease in acidity would decrease
cracking [17,18], but also the global activity since the acidic
step is rate-limiting.
On the other hand, in the case of zeolites, the pore structure
of the zeolite can also modify the activity and the selectivity of
the bifunctional catalyst [19,20]. For example, Pt or Pd-
exchanged medium-pore size zeolites like ZSM-22 [21], ZSM-
23 [22] and SAPO-11 [23–25] had high selectivities for
isomerization, because their channels are too small to allow the
formation of multibranched isomers, which are very sensitive to
cracking.

0926-860X/$ – see front matter # 2007 Elsevier B.V. All rights reserved.
doi:10.1016/j.apcata.2007.09.038
24 A. Soualah et al. / Applied Catalysis A: General 336 (2008) 23–28

Several authors [26,27] used a mixture of zeolites having Table 2

Global activities and turnover frequencies (TOF) of the Pt-zeolite catalysts for
different pore sizes (ZSM-22 and Y) and observed a synergic
the transformation of n-C10, n-C14 and n-C16
effect on both the activity and the selectivity for isomerization.
Another approach could be to use a single zeolite possessing Catalysts nPt =nHþ a Activity TOF (h1)
(mmol h1 g1)
different pore sizes, which is the case of the MCM-22 [28].
Indeed, this zeolite has two independent internal pore systems: n-C10 n-C14 n-C16 n-C10 n-C14 n-C16
large cages, and narrow sinusoidal channels. The hydroisome- PtHBEA 0.09 18.3 14.6 14.2 41.2 32.9 32.0
rization of C6 to C10 n-alkanes was already studied on MCM-22 PtHMCM-22 0.06 7.0 6.6 2.2 11.9 11.2 3.7
[29–32], but no systematic studies of the hydroisomerization of PtHZSM-5 0.08 7.0 6.1 3.1 15.4 13.4 6.8
higher n-alkanes were carried out on this zeolite, nor compared Activities were measured at a 10 wt.% n-alkane conversion.
with other zeolites. a
Number of accessible Pt atoms/total number of Brönsted acidic sites.
That is why we examined in this work the catalytic
properties of three different Pt-exchanged zeolites, namely reactor under the following conditions: temperature = 220 8C,
HMCM-22, HBEA (large straight channels), and HZSM-5 total pressure = 30 bar, H2/n-alkane molar ratio = 20, weight
(narrow straight channels) for the hydroisomerization of n-C10, hourly space velocity (WHSV) = 2–100 h1. WHSV was
n-C14 and n-C16 alkanes. changed by modifying the catalyst weight and/or the flow
rates in order to obtain different conversion values. Before use,
2. Experimental the catalysts were reduced in situ under hydrogen flow at
450 8C during 6 h.
2.1. Catalysts While n-C10 could be used alone, it appeared necessary to
dilute n-C14 and n-C16 in a solvent to avoid on-line analysis
The protonic HBEA zeolite was obtained from PQ Corpora- problems. n-Hexane (Aldrich, >99.9% purity), which was
tion. MCM-22 and ZSM-5 were synthesized under their NH4 unreactive under our reaction conditions, was chosen as the
form according to [33,34], respectively. The NH4 zeolite samples solvent. The compositions of the feeds were 20 mol.% n-C14–
were calcined under dry air flow to transform into the protonic 80 mol.% n-hexane, and 10 mol.% n-C16–90 mol.% n-hexane.
form. The characteristics of the 3 zeolites (framework Si/Al ratio, The reaction products were analyzed on-line by gas liquid
crystallite size, specific surface area, pore volume) are reported in chromatography (Varian 3400) on a 50 m CPSil-5 capillary
Table 1, together with their Brönsted acidity. This latter was column from Chrompack, hydrogen being the carrier gas
measured by adsorption of pyridine followed by infrared (15 psi). The temperature programming was: from 45 to 85 8C
spectroscopy of adsorbed pyridine. The concentration of the (5 8C min1) for n-C10, from 45 to 170 8C (5 8C min1) then
Brönsted acidic sites was determined from the absorbance from 170 to 180 8C (2 8C min1) for n-C14 and n-C16.
surface area of the 1545 cm1 band (PyH+) and the extinction
coefficient determined previously [35]. The total number of 3. Results
acidic sites was expressed as the number of Brönsted acid sites
able to retain pyridine at 150 8C. The strongest acidic sites were 3.1. Activities
those able to retain pyridine at 450 8C.
All the catalysts contained 1 wt.% platinum, introduced into All the catalysts exhibited a very stable activity for each n-
the zeolite through ion exchange by [Pt(NH3)4)]2+ in competition alkane transformation. These activities, measured at n-alkane
with NH4+ (NH4+/[Pt(NH3)4)]2+ = 100), followed by calcination conversions lower than 10%, are presented in Table 2. On all the
under dry air flow at 450 8C for 4h. The dispersion of platinum, catalysts, the reactivity of the n-alkane decreased when the
measured using toluene hydrogenation [36], was 80% on HBEA, chain length increased. This decrease was very significant for n-
65% on MCM-22 and 70% on ZSM-5. C16 on PtHMCM-22 and PtHZSM-5, while n-C16 had the same
reactivity as that of n-C14 on PtHBEA. Whatever the n-alkane,
2.2. n-Alkanes transformation PtHBEA was the most active catalyst. PtHMCM-22 and
PtHZSM-5 exhibited similar activities.
The transformation of n-C10, n-C14 and n-C16, (Aldrich, The nPt =nHþ ratios (ratio between the number of accessible
>99.9% purity) was carried out in a fixed bed stainless steel Pt atoms and the total number of protonic sites) were 0.06 on
Table 1
Characteristics of the zeolites
Zeolite Framework Crystallite Specific surface Pore volume (cm3 g1) Brönsted acidic sites (mmol g1)
Si/Al ratio size (nm) area (m2 g1)
Micro Meso Totala Strongb
HBEA 11 20 640 0.21 0.51 0.444 0.142
HMCM-22 17 100–150 575 0.22 0.26 0.589 0.451
HZSM-5 25 150–300 415 0.16 0.03 0.456 0.259
a
Number of pyridine molecules retained on the zeolite after desorption at 150 8C.
b
Number of pyridine molecules retained on the zeolite after desorption at 450 8C.
 A. Soualah et al. / Applied Catalysis A: General 336 (2008) 23–28 25

Fig. 1. Distribution (mol.%) of the cracking products formed on the platinum–zeolite catalysts at a 20 wt.% n-C10, n-C14 or n-C16 conversion.

PtHMCM-22, 0.08 on PtHZSM-5 and 0.09 on PtHBEA 3.2. Reaction products

(Table 2). Consequently, these values are much greater than
0.03 which indicates that the acidic step of the reaction is rate-
limiting [37]. Table 2 also presents the turnover frequencies
(TOF), i.e. the activities per protonic site. It can be seen that
the TOF values measured on PtHBEA are much higher than
those measured on PtHMCM-22 and PtHZSM-5. The TOF
values measured on PtHMCM-22 are lower than those
measured for PtHZSM-5, although both catalysts have the
same activity.
On all the catalysts, the n-alkanes transformed into
isomerization products I (monobranched isomers M and
multibranched isomers B) and into cracking products C.
Monobranched isomers M were mainly methylnonanes in
the case of n-C10, methyltridecanes in the case of n-C14 and
methylpentadecanes in the case of n-C16. Ethyl-branched
isomers were formed in very small amounts, propyl-branched
isomers were not observed.

Fig. 2. Transformation of n-C10, n-C14 and n-C16 on the platinum-zeolite catalysts: yields in monobranched isomers M, in multibranched isomers B, and in cracking
products C as a function of n-alkane conversion.
26 A. Soualah et al. / Applied Catalysis A: General 336 (2008) 23–28
Multibranched isomers were not formally identified, except
in the case of n-C10: they were mainly dimethyloctanes; 3-
methyl 4-ethylheptane and a small amount of 3,4,5-trimethy-
heptane were also formed, 2,3-dimethyloctane was hardly
observed. On all the catalysts, the distribution of the multi-
branched isomers formed from n-C10 did not depend on the
conversion.
Cracking products were C1 to C9, C1 to C13 or C1 to C15
molecules (Fig. 1). Let us consider the Cnx and Cx products
formed through cracking of a Cn n-alkane, for example C4 and
C12 in the case of n-C16 transformation. In the case of n-C10, only
very small amounts of C9 were formed, and the C1/C9 molar ratio
was always very different from unity while the other molar ratios
were close to 1. C5, C4 and C6 were the main products formed on
PtHBEA and PtHMCM-22. On PtHZSM-5, a minimum was
observed for C5, and a maximum for C3 and C7 or C4 and C6.
With n-C14 and n-C16, none of the molar ratios was equal to 1.
With n-C14, the main C products were C4–C6 on PtHBEA, C4 and
C10 on PtHMCM-22, and C3 and C4 on PtHZSM-5. With n-C16, a
maximum of C4 was obtained on the three catalysts. Lastly,
significant amounts of C13 and C15 were formed on PtHBEA.
Whatever the n-alkane, the iso/n ratios of the cracking
products were very high on PtHBEA (from 3 to 5). They were
ranging between 2 and 3 on PtMCM-22, and were around 0.5 on
PtHZSM-5.
3.3. Selectivities
Fig. 2 shows the distributions of M, B and C products formed
from n-C10, n-C14 and n-C16 on the three catalysts, as a function
of the n-alkane conversion. Different reaction schemes could be
observed, depending on the catalyst and on the length of the n-
alkane.
3.3.1. PtHBEA
n-C10: M isomers were primary reaction products, B isomers
and cracking products C were secondary reaction products.
n-C14 and n-C16: M, B and C were all apparent primary
reaction products, M isomers being the main products formed
initially.
3.3.2. PtHMCM-22
n-C10: M, B and C were all apparent primary reaction
products; cracking was more rapid than the formation of B
isomers.
Fig. 3. Transformation of n-C10, n-C14 and n-C16 on the platinum-zeolite catalysts: yields in isomerization as a function of n-alkane conversion.
n-C14 and n-C16: cracking was the main reaction observed;
B isomers were formed only at high conversion in the case of n-
C14 and not observed in the case of n-C16.
3.3.3. PtHZSM-5
n-C10, n-C14 and n-C16: M isomers and C products were
apparent primary reaction products. With n-C10, the main
reaction products were M isomers, while they were cracking
products C with n-C14 and n-C16. B isomers were hardly
observed.
In Fig. 3 are plotted the yields in isomerization (M + B) as a
function of the n-alkane conversion on the three catalysts. It can
be seen that PtHBEA was the most selective catalyst for
isomerization, whatever the n-alkane. However this selectivity
decreased when the length of the n-alkane increased. At a
80 wt.% n-alkane conversion, the selectivity of PtHBEA for
isomerization was close to 70% with n-C10, 40% with n-C14 and
only 35% with n-C16. PtHMCM-22 and PtHZSM-5 had rather
similar selectivities, which also decreased when the length of
the n-alkane increased.
4. Discussion
4.1. Activities
Whatever the zeolite, the activity of the Pt-zeolite catalysts
for n-alkane conversion decreases when the n-alkane length
increases (Table 2). This result was already observed by others
on small pores zeolite-based catalysts [38], whereas the
opposite was observed on large pores zeolite-based catalysts or
on amorphous silica-alumina catalysts [39,40]. On the other
hand, the decreasing order in activity, whatever the n-alkane, is
PtHBEA  PtMCM-22 ffi PtHZSM-5. This result cannot be
related to the protonic acidity of the zeolite, since the most
numerous and the strongest acidic sites are present on
PtHMCM-22 (Table 1). Similarly, PtHBEA is much more
active than PtZSM-5, while they have the same total amount of
protonic sites, these latter being even stronger on PtHZSM-5.
The TOF values (Table 2), which correspond to the number of
molecules transformed per acidic site (in fact the number of
olefinic intermediates formed on the metallic sites which react
on the protonic sites) follow the decreasing order:
PtHBEA  PtHZSM-5 > PtMCM-22. This indicates that the
protonic sites on PtHBEA are better fed with olefinic
intermediates than the protonic sites on PtHZSM-5 and
 A. Soualah et al. / Applied Catalysis A: General 336 (2008) 23–28
especially on PtHMCM-22. Since the amount and the
dispersion of platinum are similar on the three catalysts, the
only explanation for these first results is an effect of the porosity
of the zeolites.
Indeed, the three zeolites used in the present work have very
different pore systems [41]:
 BEA has straight channels (7.6 Å  6.4 Å) interconnected
through sinusoidal channels (diameter 5.6 Å). The channels
intersections generate 12–13 Å cavities [42].
 MCM-22 has two independent pore systems, both
accessible through 10 membered-rings openings. The
first one, tridimensional, consists of large supercages
(18.2 Å  7.1 Å  7.1 Å) interconnected by straight chan-
nels (5.5 Å  4.0 Å). The second one, bidimensional,
consists of interconnected sinusoidal channels (diameter
5.0 Å  4.0 Å). External pockets (7.1 Å  7.0 Å), corre-
sponding to half supercages, are located on the external
surface.
 ZSM-5 has straight channels (5.6 Å  5.6 Å) interconnected
through sinusoidal channels (5.5 Å  5.6 Å). The channels
intersections generate 8.5 Å cavities.
As a consequence, the acidic sites in the large pore system of
BEA would be much more accessible to the n-alkane than the
acidic sites in MCM-22 and ZSM-5. The fact that the TOF
values are smaller on PtHMCM-22 than on PtHZSM-5 suggest
that the supercages of MCM-22 are not accessible to the
reactant, due to the small diameter of the straight channels. The
acidic sites in the narrow channels of ZSM-5 are also difficult to
reach for the reactant. This effect would become more
significant as the length of the n-alkane increases: the TOF
values dramatically decrease on PtHMCM-22 (TOF n-C16/TOF
n-C10 = 0.31) and PtHZSM-5 (TOF n-C16/TOF n-C10 = 0.44),
while they are almost constant on PtHBEA (TOF n-C16/TOF n-
C10 = 0.78). It must also be pointed out that the small crystallite
size of the BEA zeolite (0.02 mm) allows a better diffusion of
the n-alkanes in the zeolite channels.
4.2. Selectivities
On PtHBEA, whatever the n-alkane, monobranched isomers
M were always the main products formed initially (Fig. 2).
With n-C10, multibranched isomers B and cracking products
C were secondary reaction products, which indicates that the
bifunctional transformation of n-C10 occurs through a step-by-
step process as shown in Scheme 1.
The formation of the B isomers is made possible by the large
size of the BEA channels. The amounts of M and B isomers
decreased when the conversion of n-C10 increased, due to
cracking. Cracking products are formed mainly from the highly
reactive B isomers, as evidenced by the high iso/n ratios of the
C products (3–5). However, cracking remains limited, due to
Scheme 1.
27
Scheme 2.
the moderate acidity of the zeolite and very likely to the small
crystallite size which allows a rapid diffusion of B isomers out
of the zeolite.
With n-C14 and n-C16, B isomers and C products also appear
as primary reaction products, which would correspond to the
reaction Scheme 2.
However, B isomers cannot be formed directly from n-C14 or
n-C16, but only from the M isomers. Similarly, C products are
only apparent primary reaction products: as was the case with
n-C10, they are produced from the B isomers. This change in the
reaction scheme when compared to n-C10 transformation can be
explained by the increase in the n-alkane length which
increases the time-life of the reaction intermediates inside the
zeolite channels.
On PtHMCM-22, M isomers were the main products formed
initially from n-C10 (Fig. 2), but B isomers and C products were
also formed initially. Thus, the apparent reaction scheme would
be the same as Scheme 2. This would mean that n-C10 can
access to the zeolite supercages, but very likely to those located
near the external surface, which allows the diffusion of the B
isomers out of the zeolite. On the other hand, the iso/n ratio of
the cracking products is greater than 1 (2–3) which indicates
that they are formed mainly from B isomers, as was the case on
PtHBEA.
With n-C14 and n-C16, C products were the main products
formed initially; M isomers were also formed initially, B
isomers appeared only at high conversions (when observed).
The iso/n ratios of the C products are the same as in the case
with n-C10. These products are consequently mainly produced
from B isomers. Thus, the true reaction scheme would be that
shown in Scheme 1, with a very rapid transformation of B
isomers into C products. This means that the diffusion of the B
isomers inside the MCM-22 porosity is slow, which allows their
cracking.
On PtHZSM-5, M isomers and C products were both
primary reaction products, B isomers being observed only at
high conversions. The iso/n ratios of the C products were
always smaller than 1, which suggests that they were produced
from the M isomers. Consequently, the reaction scheme on
PtHZSM-5 would be as in Scheme 3.
This means that the channels of the ZSM-5 zeolite are too
small to allow the formation of the B isomers. On the opposite,
Scheme 3.
28 A. Soualah et al. / Applied Catalysis A: General 336 (2008) 23–28
M isomers can be formed, but encounter some difficulties to References
leave the porosity, and undergo a significant cracking.
The situation is still worse with n-C14 and n-C16, cracking [1]
[2]
being the main reaction observed.
[3]
These changes in the reaction schemes, linked to the [4]
different porous systems of the three zeolites used, are clearly
responsible for the significant differences in the selectivities for [5]
isomerization (Fig. 3). PtHBEA is by far the most selective
[6]
catalyst, in particular when the length of the n-alkane increases.
[7]
Concerning the nature of the cracking products (Fig. 1), [8]
whatever the n-alkane, very significant amounts of C1, together [9]
with smaller amounts of C2 were observed on all the catalysts.
Traces of C8 and C9, C12 and C13, C14 and C15 were also formed [10]
[11]
from n-C10, n-C14 and n-C16, respectively. The formation of all
[12]
these products cannot be explained by a classical bifunctional [13]
mechanism which would imply the formation of very unstable [14]
primary carbocations. Thus, they are very likely produced
through hydrogenolysis on platinum. The great amount of C1 [15]
formed indicates that a multiple hydrogenolysis of the reactant
[16]
and of the other C products occurs on all the catalysts. [17]
In the case of n-C10, the other cracking products result on all [18]
the catalysts from a classical bifunctional mechanism: indeed, [19]
the Cnx/Cx ratios are close to unity. On PtHZSM-5, C3 and C7
[20]
together with C4 and C6 were favored compared to C5, which
means that cracking occurred mainly at the end of the chain, [21]
due to the small size of the channels.
On the opposite, none of the Cnx/Cx ratios was close to 1 in [22]
the case of n-C14 and n-C16. This indicates that the carbocations
formed from these n-alkanes were blocked inside the zeolite
[23]
porosity, allowing secondary cracking to occur. [24]
5. Conclusions [25]
[26]
On all the catalysts, n-C10, n-C14 and n-C16 transform through
two reactions: bifunctional hydroconversion yielding mono- [27]
branched isomers, multibranched isomers and cracking products,
and hydrogenolysis on platinum yielding mainly C1. The
activities of the catalysts, and especially their selectivity for [28]
isomerization, depend clearly on the structure of zeolite rather
[29]
than on their acidity. The large channels of HBEA zeolite,
together with the small size of the crystallites, allow a very rapid [30]
diffusion of the reactants. Moreover, this zeolite has a moderate [31]
acidity which limits cracking. Monobranched isomers are always
[32]
the main reaction products, whatever the length of the n-alkane.
This is not the case with PtHMCM-22 or PtHZSM-5 where [33]
cracking is the main reaction for n-C14 and n-C16. The reaction
intermediates are blocked inside the porosity of these zeolites [34]
where they can undergo, via successive carbocations, several [35]
[36]
reactions on the protonic sites: isomerization into monobranched
isomers, then into very reactive multibranched isomers which [37]
crack rapidly. As a consequence, the PtHBEA catalyst exhibits
the highest activity and the highest selectivity for isomerization. [38]
[39]
[40]
Acknowledgements
[41]
This work was supported by Statoil. A.S. thanks the [42]
Algerian and French governments for a grant.
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