Catalysis Communications 125 (2019) 21–25

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Catalysis Communications
journal homepage: www.elsevier.com/locate/catcom

Short communication

Preparation of mesoporous mordenite for the hydroisomerization of n- T

hexane
⁎
Xinqing Lu, Yuping Guo, Chunhui Xu, Rui Ma , Xue Wang, Ningwei Wang, Yanghe Fu,
⁎
Weidong Zhu
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Institute of Physical Chemistry, Zhejiang Normal University, 321004 Jinhua, PR China

A R T I C LE I N FO A B S T R A C T

Keywords: A mesoporous mordenite (MOR) zeolite was prepared from a commercially available MOR sample by a se-
Mesoporous zeolite quential acid-alkaline-acid post-treatment. The latter was used as support of Pt to prepare a bifunctional Pt/H-
Bifunctional catalyst MOR catalyst for the hydroisomerization of n-hexane. The results showed that the available mesopores in the
Mordenite catalyst shorten the diffusion length of reactants and of the produced branched hexanes inside the micropores. In
Desilication
addition, the dispersion of supported Pt in the zeolite was increased and an enhancement in the conversion of n-
Hydroisomerization
hexane and at the same time the reduction of the non-selective cracking of hexane isomers and of the formation
of coke (catalyst deactivation) was observed.

1. Introduction sites in zeolites could be enhanced by introducing mesopores in the

The hydroisomerization of n-paraffins into isoparaffins plays an
important role in improving the quality of gasoline by increasing the
octane number. The commercial process consists of (de)hydrogenation
on metallic Pt and skeletal isomerization on acid sites typically cata-
lyzed by bifunctional Pt/H-MOR catalysts, which is generally accom-
panied with cracking reactions [1]. The balance between (de)hydro-
genation and skeletal isomerization plays a determinant role on the
activity and selectivity for branched products in this isomerization
process [2,3]. Additionally, the product selectivity is significantly af-
fected by the proximity between metallic Pt and acid sites [4,5]. MOR
has two types of channels, 12-membered-ring channels with an opening
size of 0.65 nm × 0.70 nm, and 8-membered-ring channels with an
opening size of 0.26 nm × 0.57 nm. Therefore, in general, MOR is re-
garded as one-dimensional pore system, because the 8-membered-ring
channels are too small for most molecules to enter, inducing one-di-
mensional diffusion, i.e., molecules cannot overtake each other in the
channels so a molecule located at the pore mouth blocks the entrance or
escape of other molecules [6,7]. Hence, the molecular transport in the
micropores is strongly hindered by this one-dimensional diffusion in
comparison with the 2-D or 3-D pore systems [6–8]. Additionally, the
lodgment of extra-framework species in the MOR channels can sig-
nificantly restrict the accessibility to adsorbate and/or reactant mole-
cules [7].
It has been repeatedly demonstrated that the accessibility of the acid
zeolite pore structure by either direct syntheses with soft and hard
templates [9,10] or post-treatments with acid [11], alkaline [12] and
NH4F [13]. Alkaline-derived desilication has been used as an efficient
strategy for the generation of mesopores in zeolite secondary crystals
[14–21]. However, the Si/Al molar ratios in zeolites should be in an
optimal range with the purpose to preserve the zeolite's crystallinity
and acidity [22–24]. If these ratios become too low, no mesoporosity is
formed, while if these ratios become too high, then excessive silicon
dissolution results in the collapse of the zeolite structure. Acid treat-
ment was used to increase the Si/Al ratio of MOR into its optimal range
via dealumination, making mesopores successfully formed by an alka-
line treatment [23]. van Laak et al. [24] found an improved reactivity
in the liquid-phase alkylation of benzene with propylene to cumene
over the mesoporous MOR catalyst prepared by a sequential acid-al-
kaline-acid post-treatment. A similar strategy was also applied for
preparing a mesoporous MOR-type titanosilicate that showed re-
markably improved catalytic properties in the hydroxylation of toluene
and the ammoximation of cyclohexanone [25]. Most recently, Pastvova
et al. [26] applied a sequential acid-alkaline-acid post-treatment to
generate the mesoporosity in MOR and then used this mesoporous
zeolite as a support to prepare a Pt/H-MOR catalyst for the hydro-
isomerization of n-hexane, showing a significantly improved catalytic
activity due to the simultaneous enhancement of the accessibility of the
acid sites and of molecular transport. However, less work dealt with the
effects of the introduced mesopores on the dispersion of Pt in the zeolite

⁎
Corresponding authors.
E-mail addresses: mr@zjnu.cn (R. Ma), weidongzhu@zjnu.cn (W. Zhu).

https://doi.org/10.1016/j.catcom.2019.03.017
Received 16 January 2019; Received in revised form 18 March 2019; Accepted 19 March 2019
Available online 20 March 2019
1566-7367/ © 2019 Elsevier B.V. All rights reserved.
X. Lu, et al.
and its derived catalytic selectivity and stability.
In the present work, a rich mesoporosity was introduced into MOR
secondary crystals via a sequential acid-alkaline-acid post-treatment. A
comparative study was conducted on the catalytic properties of Pt/H-
MOR catalysts prepared using commercially available, acid post-
treated, and sequential acid-alkaline-acid post-treated MOR samples as
supports for the hydroisomerization of n-hexane in order to investigate
the effects of the introduced mesopores in MOR secondary crystals on
the derived catalytic activity, selectivity and stability.
2. Experimental
2.1. Catalyst preparation
2.1.1. Acid and alkaline post-treatments
The MOR zeolite with a Si/Al molar ratio of 10 in an ammonium
form was purchased from Zeolyst (CBV 21A), denoted as NH4-MOR-p.
The mesoporous MOR was obtained by a sequential acid-alkaline-acid
treatment, similar to the procedure described elsewhere [23,24]. The
as-received Zeolyst MOR was calcined at 773 K for 3 h with a heating
rate of 1 K min−1 to get a proton-form MOR, denoted as H-MOR-p.
Afterwards, H-MOR-p was treated with 3 M HNO3 aqueous solution
with a solid-to-liquid weight ratio of 1:10 (w/w) at 373 K for 1 h under
stirring. The acid-treated product was filtered, washed with hot-deio-
nized water until the pH of the filtrate became ~ 7. Then, the obtained
filter cake was dried at 383 K overnight and calcined at 773 K for 3 h
with a heating rate of 1 K min−1 to get a partially dealuminated MOR
(denoted as H-MOR-p-a). The alkaline treatment was carried out over
H-MOR-p-a in 0.2 M NaOH aqueous solution with a solid-to-liquid
weight ratio of 1:30 (w/w) under stirring at 343 K for 5 min. The solid-
liquid mixture was subsequently centrifuged and decanted of the liquid.
The alkaline-treated product was washed with hot deionized water until
the pH of the filtrate became ~ 7, and then dried at 383 K overnight and
calcined at 773 K for 3 h with a heating rate of 1 K min−1. The calcined
sample was ion-exchanged with 1 M NH4NO3 aqueous solution with a
solid-liquid weight ratio of 1:12 (w/w) at 353 K for 12 h. To ensure the
complete exchange of Na+, this procedure was repeated three times,
and the obtained solid sample was dried at 383 K overnight and cal-
cined at 773 K for 3 h with a heating rate of 1 K min−1 to get a proton-
form MOR (denoted as H-MOR-p-a-a). Finally, H-MOR-p-a-a was wa-
shed with 0.1 M HNO3 aqueous solution with a solid-liquid weight ratio
of 1:20 (w/w) at 323 K for 15 min under stirring, and the obtained solid
sample was then dried at 383 K overnight and calcined at 773 K for 3 h
with a heating rate of 1 K min−1 to get an acid-alkaline-acid treated
MOR (denoted as H-MOR-p-a-a-a). The flow diagram for the separate
synthesis steps, including sample designations for the as-received Zeo-
lyst MOR to the sequential acid-alkaline-acid post-treated MOR, is
presented in Scheme 1.
2.1.2. Pt/H-MOR preparation
Pt/H-MOR catalysts were prepared by the impregnation method as
follows: a proton-form MOR sample (1 g) was impregnated with a Pt
(NH3)4Cl2 aqueous solution (0.5 mg g−1) of 2.5 mL initially to become a
slurry, followed by dropwise addition of the remaining Pt(NH3)4Cl2
aqueous solution of 7.5 mL into the slurry under vigorous stirring at
308 K for 24 h. Then the final slurry was filtered, washed with hot-
deionized water until the complete removal of chloride ions and dried
at 383 K overnight. Subsequently, the dried sample (1 g) was loaded in
a tubular reactor (5 cm inner diameter) and heated in flowing oxygen at
the flow rate of 500 mL min−1 at 673 K for 2 h with a heating rate of
0.5 K min−1. The resultant catalysts with nominal loading of 0.5 wt% Pt
and the various zeolite treated samples (see Section 2.1.1) are named as
Pt/H-MOR-p, Pt/H-MOR-p-a, and Pt/H-MOR-p-a-a-a.
22
Catalysis Communications 125 (2019) 21–25
2.2. Catalyst characterization
The powder X-ray diffraction (XRD) patterns of the solid catalysts
prepared were recorded by a Philips PW3040/60 powder dif-
fractometer using Ni-filtered Cu Kα radiation (λ = 0.1541 nm) in the
range of 5–50° with a scanning rate of 2° min−1. The zeolite crystal
morphology was examined by a Hitachi S-4800 scanning electron mi-
croscope (SEM). Transmission electron microscopy (TEM) for Pt par-
ticle size and mesoporosity characterization was carried out on a JEOL
JEM-2100 microscope after the sample was deposited onto a holey
carbon foil supported on a copper grid. The textural properties of the
samples were determined by N2 adsorption-desorption at 77 K using a
Micromeritics ASAP 2020 instrument after the samples were degassed
in vacuum at 573 K for 6 h. The specific surface area of the investigated
samples was calculated using the Brunauer-Emmett-Teller (BET)
method in the relative pressure range of p/p0 = 0.05–0.35. The mi-
cropore volume and the external specific surface area were determined
by the t-plot method, and the total pore volume was determined by
converting the amount adsorbed at a relative pressure of 0.995 to the
volume of liquid nitrogen. The mesopore volume was computed by
subtracting the volume of micropores from the total pore volume.
The bulk Si/Al ratio and the amount of Pt loading in the catalyst
were determined by inductively coupled plasma-atomic emission
spectrometry (ICP-AES) on a Thermo IRIS Intrepid II XSP after the
samples were dissolved in liquated NaOH. The 27Al MAS NMR spectra
were collected on a Varian VNMRS-400 MB NMR spectrometer. The
spectra were collected at a frequency of 104.18 MHz, a spinning rate of
9.0 kHz and a recycling delay of 4 s. KAl(SO4)2·12H2O was used as re-
ference for chemical shift.
The amount of the acid sites was determined by temperature-pro-
grammed desorption of NH3 (NH3-TPD) on a Micromeritics AutoChem
II 2920 instrument equipped with a thermal conductivity detector
(TCD). Typically, 80 mg of the sample was pretreated in flowing helium
(25 mL min−1) at 823 K for 1 h. The adsorption of NH3 was carried out
at 393 K for 15 min, and then weakly chemisorbed NH3 was purged by
flowing helium (25 mL min−1) at the same temperature for 30 min. To
ensure the complete removal of weakly chemisorbed NH3, the purging
process was repeated three times. The NH3-TPD profile was then re-
corded from 393 to 973 K with a heating rate of 15 K min−1 using He as
carrier gas. The signal of desorbed NH3 was measured by TCD detector.
2.3. Hydroisomerization of n-hexane
The hydroisomerization of n-hexane was carried out in a fixed-bed
reactor (6 mm inner diameter) at 1 atm pressure. 0.2 g of Pt/H-MOR
catalyst was loaded into the reactor and in-situ activated in 80 vol% H2
/20 vol% N2 gas mixture at 673 K for 2 h (total flow rate of
10 mL min−1). After the reactor temperature was reduced to the reac-
tion temperature of 513 K, n-hexane was introduced into the reactor by
a high-pressure constant flow pump. The weight hourly space velocity
(WHSV) of n-hexane and the H2/n-hexane molar ratio for all the ex-
periments conducted were maintained at 2 h−1 and 6, respectively. The
reaction products were analyzed by a gas chromatograph (Agilent
6820) equipped with a 50 m OV-101 capillary column and a flame io-
nization detector (FID).
3. Results and discussion
3.1. Catalyst characterization
As shown in Fig. S1 (ESI), all the investigated catalysts showed the
powder XRD characteristic patterns of MOR, indicating that the crystal
structures are well preserved after the different post-treatments of the
zeolite applied. Both Pt/H-MOR-p and Pt/H-MOR-p-a show a type-I N2
adsorption-desorption isotherm (Fig. S2A), which is a characteristic of
microporosity. The acid-derived dealumination makes the micropore
X. Lu, et al. Catalysis Communications 125 (2019) 21–25

Scheme 1. Flow diagram of the different post-treatment steps, starting from the commercial zeolite.

Table 1
Textural properties and chemical composition of the catalysts investigated.
Catalysts SBET (m2 g−1) Vmicroa (cm3 g−1) Sexta (m2 g−1) Vtotal (p/p0 = 0.995) (cm3 g−1) Vmesob (cm3 g−1) Si/Alc Pt loadedc (wt%)

Pt/H-MOR-p 419 0.17 39 0.25 0.08 10 0.45

Pt/H-MOR-p-a 452 0.18 61 0.27 0.09 28 0.43
Pt/H-MOR-p-a-a-a 492 0.17 126 0.46 0.29 15 0.46

a
Determined from the measured N2 adsorption-desorption isotherms at 77 K using the t-plot method.
b
Vmeso = Vtotal–Vmicro.
c
Determined by the ICP-AES analysis.

volume and the external specific surface area sharply from

Fig. 1. NH3-TPD profiles of Pt/H-MOR-p (a), Pt/H-MOR-p-a (b), and Pt/H-
MOR-p-a-a-a (c).
volume and the specific surface area slightly increased from
0.17 cm3 g−1 and 419 m2 g−1 for Pt/H-MOR-p to 0.18 cm3 g−1 and 452
m2 g−1 for Pt/H-MOR-p-a, respectively (Table 1) due to the enlarge-
ment in the micropore size after the removal of Al in the framework
[24,25]. Moreover, the Si/Al molar ratio is increased from 10 for Pt/H-
MOR-p to 28 for Pt/H-MOR-p-a, where the latter is in the optimum
range of Si/Al molar ratio in the zeolite for the subsequent alkaline
post-treatment [24]. A further alkaline-acid post-treatment changes the
isotherm to the combined one of type-I and type-IV with a well pro-
nounced hysteresis loop. The latter indicates the generation of meso-
pores in the zeolite crystals (Fig. S2A). As shown in Table 1, the se-
quential acid-alkaline-acid post-treatment increases the mesopore
0.08 cm3 g−1 and 39 m2 g−1 for Pt/H-MOR-p to 0.29 cm3 g−1 and 126
m2 g−1 for Pt/H-MOR-p-a-a-a, respectively, while the micropore vo-
lume almost remains unchanged. Hence, these results confirm the va-
lidity of the sequential acid-alkaline-acid post-treatment as an effective
method to create mesoporosity in MOR crystals, while the micro-
porosity is preserved. Furthermore, the pore size distribution profiles
determined by the Barrett-Joyner-Halenda (BJH) method from the ad-
sorption branch, shown in Fig. S2B, indicate that Pt/H-MOR-p-a-a-a
possesses mesoporosity centered at ca. 10 nm, while Pt/H-MOR-p and
Pt/H-MOR-p-a are purely microporous. Additionally, the Si/Al molar
ratio is decreased from 28 for Pt/H-MOR-p-a to 15 for Pt/H-MOR-p-a-a-
a, respectively, due to the desilication (Table 1).
To elucidate the effects of dealumination and desilication of zeolites
on their acidity, 27Al MAS NMR spectra and NH3-TPD profiles were
measured. In the 27Al MAS NMR spectra (Fig. S3), Pt/H-MOR-p shows
only a resonance at 58 ppm ascribed to tetrahedral Al, the so-called
framework Al species. The dealumination can develop extra-framework
Al species showing a new resonance at 0 ppm in the spectrum of Pt/H-
MOR-p-a, while these extra-framework Al species can be effectively
removed by the alkaline-acid post-treatment, as the resonance at 0 ppm
in the spectrum of Pt/H-MOR-p-a-a-a is almost absent.
Fig. 1 shows the NH3-TPD profiles recorded after removing the
weakly chemisorbed NH3 species on the investigated catalysts. The low-
temperature (400–525 K) and high-temperature (525–973 K) deso-
rption peaks are ascribed to the desorption of NH3 from the weak and
strong acid sites of MOR, respectively [26,27]. As shown in Fig. 1, the
strong acid sites, which are mainly considered as the catalytic sites in
the hydroisomerization, have been well preserved during the deal-
umination and desilication post-treatments. Compared to the high-
temperature desorption peak, the low-temperature peak was more ob-
viously affected by the variation of the Si/Al ratio (Table 1 and Fig. 1).

23
X. Lu, et al.
The concentration of weak acid sites is in the order: Pt/H-MOR-p > Pt/
H-MOR-p-a-a-a > Pt/H-MOR-p-a, which is in accordance with the Al
amount in the zeolite. Additionally, the presence of a shoulder peak at
higher temperatures in the Pt/H-MOR-p-a indicates that the acid
strength is increased after dealumination due to the formation of extra-
framework Al species acting as Lewis acid sites [28].
As shown in Table 1, the Pt amounts in all the catalysts, determined
by the ICP-AES analysis, are within their nominal values of 0.5 wt%,
indicating the efficiency of the impregnation method applied for pre-
paring the catalysts. The SEM image of H-MOR-p shows that MOR
particles are aggregates of nanocrystals (Fig. S4a), while TEM images
reveal the mesoporosity in Pt/H-MOR-p-a-a-a and the distribution of
platinum oxide particle size in all catalysts (Figs. S4b-d). Pt/H-MOR-p
and Pt/H-MOR-p-a both show opaque crystals with some dark spots,
corresponding to the presence of platinum oxide particles located on
the surface of the MOR crystals (Figs. S3b and c). In contrast, the TEM
image of Pt/H-MOR-p-a-a-a shows many white spots with a diameter of
ca. 10 nm (Fig. S4d), indicating the presence of mesopores in the MOR
crystals, which is in accordance with the N2 adsorption-desorption
characterization results (Fig. S2). Moreover, the created mesopores are
indeed embedded in the crystals as shown in the TEM images of Fig. S5.
The mean diameter of platinum oxide particles decreases from ca.
3.2 nm in Pt/H-MOR-p and ca. 3.0 nm in Pt/H-MOR-p-a to ca. 1.8 nm in
Pt/H-MOR-p-a-a-a, implying that the presence of mesopores in the
zeolite enhanced the dispersion of Pt.
3.2. Hydroisomerization of n-hexane
The catalytic hydroisomerization of n-hexane consists of the dehy-
drogenation of n-hexane to n-hexene on metallic Pt, the skeletal iso-
merization of n-hexene to monobranched methylpentenes and di-
branched dimethylbutenes on acid sites, and the hydrogenation of the
branched alkene intermediates to the corresponding branched alkanes
on metallic Pt [26]. In addition, the hydroisomerization of n-hexane to
isohexane is usually accompanied with the cracking reaction and coke
formation [1]. As shown in Figs. 2 and 3, Pt/H-MOR-p-a possesses a
higher conversion of n-hexane and a higher yield of hexane branched
isomers than Pt/H-MOR-p in the initial reaction stage. The available
Lewis acid sites due to the formation of extra-framework Al species in
Pt/H-MOR-p-a have a promoting effect on the rates of the hydro-
isomerization, cracking and coking that leads to catalyst deactivation
[28]. Therefore, although the initial conversion of n-hexane is enhanced
over Pt/H-MOR-p-a in comparison with that over Pt/H-MOR-p, the
catalytic activity will be rapidly dropped due to coke formation on the
Fig. 2. Comparative results on the hydroisomerization of n-hexane over Pt/H-
MOR-p (a), Pt/H-MOR-p-a (b) and Pt/H-MOR-p-a-a-a (c). Reaction conditions:
WHSV (n-hexane) = 2 h−1, H2/n-hexane molar ratio = 6:1, and T = 513 K.
24
Catalysis Communications 125 (2019) 21–25
Fig. 3. Distribution of products and the yield of total branched hexanes in the
hydroisomerization of n-hexane over Pt/H-MOR-p (a), Pt/H-MOR-p-a (b) and
Pt/H-MOR-p-a-a-a (c) in the first 60 min of reaction. The reaction conditions are
the same as those presented in Fig. 2. Others stands for C1-C5 products from the
cracking reaction.
Lewis acid sites (Fig. 2), and the cracking products are pronounced as
shown in Fig. 3. It is thus illustrated that Pt/H-MOR-p-a-a-a shows the
highest conversion of n-hexane and yield of hexane isomers, with a
stable activity and at the same time negligible cracking products
(Figs. 2 and 3). The enhanced catalytic activity must be related to the
introduction of mesoporosity with the preservation of the zeolite fra-
mework crystallinity, microporosity and acidity. The introduced me-
sopores in the MOR by the sequential acid-alkaline-acid post-treatment
can shorten the diffusion length of the reactants and of the produced
branched hexanes inside the micropores [26], affect the proximity be-
tween metallic Pt and acid sites [4,5], and enhance the dispersion of Pt
in the zeolite. All these factors eventually lead to the increase of con-
version of n-hexane and reduction of the non-selective cracking of
hexane isomers and the formation of coke. For all the investigated
catalysts, the product distributions almost remain unchanged with time
on stream (Fig. S6). Additionally, the selectivity for the branched iso-
mers for all the investigated catalysts follows the order: 2, 2-di-
methylbutane < 2, 3-dimethylbutane < 3-methylpentane < 2-methyl-
pentane, similar to the order of the molecular diameters of these hexane
isomers. Moreover, Pt/H-MOR-p-a-a-a provides almost the same se-
lectivity for the branched isomers as Pt/H-MOR-p, indicating that the
introduced mesopores do not alter the shape selectivity of Pt/H-MOR
catalysts. This observation agrees well with that most recently reported
[27].
4. Conclusions
The simple acid post-treatment applied over a commercial MOR
zeolite does not obviously introduce mesoporosity in the zeolite crystals
but it can significantly increase the Si/Al ratio due to partial deal-
umination that results in the formation of extra-framework Al species.
The prepared corresponding bifunctional Pt/H-MOR catalyst does not
show an improved catalytic activity in the hydroisomerization reaction
of n-hexane since the extra-framework Al species can enhance the for-
mation of cracking products and coke. These results may depend on the
specific MOR under investigation because other synthesis/post-treat-
ment procedures or commercial MOR may lead to different results re-
garding the acid leaching treatment. On the other hand, the sequential
acid-alkaline-acid post-treatment can introduce significant meso-
porosity in the MOR crystal structure. The prepared corresponding bi-
functional zeolite-supported Pt catalyst shows then an enhanced cata-
lytic activity with long-term stability, due to the facts that the available
mesopores in the zeolite catalyst can shorten the diffusion length of the
X. Lu, et al.
reactants and produced branched hexanes inside the micropores, and
enhance the dispersion of Pt in the zeolite. The latter contributes to the
enhancement of proximity of Pt and acid sites in the mesopores of
zeolite which is a very important aspect in the present catalytic reac-
tion.
Acknowledgements
The authors gratefully acknowledge the financial support from the
National Natural Science Foundation of China (20971109, 21036006,
21476214, and 21706239) and the Programme of Introducing Talents
of Discipline to Universities (D17008).
Appendix A. Supplementary data
Supplementary data to this article can be found online at https://
doi.org/10.1016/j.catcom.2019.03.017.
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