Synthesis of chromene derivatives in the presence of mordenite zeolite/MIL-101 (Cr) metal–organic framework composite as catalyst

Article abstract of DOI:10.1002/aoc.4801

In the present study, the synthesis of mordenite zeolite/MIL-101(Cr) metal–organic framework (MOF) composite [MOR/MIL-101(Cr)] using the ship in a bottle method was suggested. The properties of prepared composite and individual MOF and MOR zeolite were ch

Full text of DOI:10.1002/aoc.4801

Received: 2 November 2018
DOI: 10.1002/aoc.4801
Revised: 20 December 2018
Accepted: 21 December 2018
F U L L P A P E R
Synthesis of chromene derivatives in the presence of
mordenite zeolite/MIL‐101 (Cr) metal–organic framework
composite as catalyst
Mohsen Fallah1 | Shabnam Sohrabnezhad2
| Masoumeh Abedini2
1 Department of Chemistry, University of
In the present study, the synthesis of mordenite zeolite/MIL‐101(Cr) metal–
organic framework (MOF) composite [MOR/MIL‐101(Cr)] using the ship in a
bottle method was suggested. The properties of prepared composite and indi-
vidual MOF and MOR zeolite were characterized by X‐ray diffraction (XRD),
scanning electron microscopy (SEM), transmission electron microscopy
(TEM), nitrogen adsorption–desorption measurement, and thermogravimetric
analysis (TGA). The XRD results indicated diffraction peaks for each com-
pound (MOR and MOF) in composite. The SEM and TEM images showed
the formation of plates MOR (with size of 2.5 × 3 μm) along with spherical par-
ticles MIL‐101. The Brunauer–Emmett–Teller results showed that the surface
area of the composite was smaller than individual MOF and MOR zeolite.
Based on TGA plots, the hybrid zeolite/MOF composite was more thermally
stable compared with the isolated MIL‐101(Cr). The composite was functional-
ized by post‐synthetic modification to obtain acid–base bifunctionality (H‐
MOR/MIL‐101‐ED) for the synthesis of chromene derivatives. The acidity from
framework Al‐O(H)‐Si sites in MOR and basicity from amine groups in MIL‐
101 were obtained by post‐synthetic modification.
Guilan, University Campus2, Rasht, Iran
2 Department of Chemistry, Faculty of
Science, University of Guilan, P.O. Box
1914, Rasht, Iran
Correspondence
Shabnam Sohrabnezhad, Department of
Chemistry, Faculty of Science, University
of Guilan, P.O. Box 1914, Rasht. Iran.
Email: sohrabnezhad@guilan.ac.ir
KEYWORDS
chromene derivatives, metal–organic framework, metal–organic framework composite, mordenite
zeolite
1 | INTRODUCTION
of metal clusters and organic ligands can be built into
MOFs, a wide structural diversity and highly designable
Zeolites and metal–organic frameworks (MOFs) with pore
size smaller than 100 nm are two important examples of
nanoporous materials being intensively studied for many
applications.[1–7] The structure of MOFs is constructed by
metal ions or clusters that act as lattice nodes and are held
in place by multidentate organic ligands. This new class of
nanoporous materials was first discovered by Bernard
Hoskins and Richard Robson in 1989.[8] Until now, a num-
ber of conventional[9] and novel synthesis methods have
been developed for preparing of MOFs. Because a range
pore sizes and shapes in MOFs are expected, which endow
MOFs with tunable cavity architectures and properties.[10]
The diversity of MOF structures creates a variety of func-
tionalities and potential applications for the as‐synthesized
MOFs. Additionally, the components in MOFs, either
metal clusters or organic linkers, can be further modified
to bring in new functionalities. The framework of MOFs
can be functionalized through pre ‐ or post‐synthetic mod-
ification of metal clusters and/or organic ligands.[11] As
nanoporous materials, MOFs break the limitation of the
Appl Organometal Chem. 2019;e4801.
wileyonlinelibrary.com/journal/aoc
© 2019 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.4801

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FALLAH ET AL.
small pore sizes of zeolites. They can be used for a number
of potential applications, including gas separation, storage
and heterogeneous catalysis.[12,13] MOFs as catalysts can
be synthesized or functionalized with active sites, includ-
ing unsaturated metal sites or functional groups on
organic linkers.
for the promotion of the reactions that need the use of an
acidic or basic catalyst to speed up. Here in, we wish to
extend the application of this catalyst for the synthesis
of chromene derivatives via one‐pot condensation of alde-
hydes with resorcinol and malononitrile. MOR has spe-
cial importance over other 12‐membered ring zeolites
because of its one‐dimensional pore structure and high
activity. These properties make MOR important in many
industrial applications.[22] MIL‐101(Cr)[2] is a three‐
dimensional chromium terephthalate‐based porous mate-
rial with the empirical formula [Cr3(O)‐X (bdc)3(H2O)2]
(bdc = benzene‐1,4‐dicarboxylate, X = OH or F). MIL‐
101(Cr) has two types of inner cages with diameters of
29 Å and 34 Å, and pore aperture window diameters of
up to 16 Å with a high surface area [Brunauer–Emmett–
Teller (BET) surface area of 4000 m2 g−1].[2]
Zeolites are crystalline microporous aluminosilicates,
widely used as heterogeneous catalysts, adsorbents and
ion‐exchange materials in petrochemical and fine chemi-
cal industries. Hydrothermal synthesis is the conventional
method used for generating zeolite materials. The required
synthesis temperature and pressure depend on the zeolite
type. Most commercial zeolites are synthesized at 90–
100°C, but some dense zeolites need higher crystallization
temperatures (up to 350°C). The optimal pH range for zeo-
lite synthesis is 11–13,[14] which can be modulated by the
addition of OH− guest molecules. The zeolite acidity in H
+‐form zeolites originates from framework Al species.[15]
As porous materials, zeolite and MOF share common
characteristics of high surface areas and uniform micro-
pores, but they differ in thermal/mechanical stability
and structural flexibility.[16] The integration of MOF and
zeolites into composite particles is expected to produce
useful hybrid nanoporous materials where inorganic zeo-
lite and organic MOF components impart the advantages
of high thermal, mechanical and structural stability of
zeolites and specific functionality and high flexibility of
MOFs. MOF‐based composites are generally formed by
physical or chemical mixing of MOFs with inorganic
and/or organic substrates. MOF‐based composite mem-
branes such as ZIF‐8/Matrimid have been synthesized
for direct uses in gas and liquid separations.[17]
Silica@MOF core‐shell composite spheres were prepared
by the seeded growth method and were used as stationary
phases for chromatographic separation.[18] Zhu et al.
reported synthesis of ZSM‐5 zeolite@ UiO‐66 MOF core‐
shell composites by solvothermal growth of MOF on the
surface of zeolite support, and demonstrated an applica-
tion of this material as a bifunctional acid–base catalyst
in two‐step cascade reactions.[19] MOF [MIL (Fe)]–graph-
ite oxide composites were used for ammonia adsorp-
tion.[20] The loaded metal oxides or insolubilized
materials into the MOFs pores are other composites that
were prepared using post‐synthesis methods, such as the
impregnation method.[21]
2 | EXPERIMENTAL
2.1 | Materials
Ditopic terephthalic acid (H2BDC), chromium nitrate [Cr
(NO3)3·9H2O] and dimethylformamide (DMF) were pur-
chased from Fluka and Merck (Darmstadt, Germany). Sil-
ica gel (Fisher, 28–200 mesh) and sodium aluminate were
used in the synthesis of MOR. Hydrochloric acid and
sodium hydroxide were applied for a variation of the pH
of sample solutions. 4‐Nitrobenzaldehyde, resorcinol
and malononitrile were used for catalytic reaction. All
materials were from Merck.
2.2 | Synthesis of MIL‐101(Cr) and MOR
zeolite
The synthesis procedure for MOR zeolite was as reported
in our previous paper.[23] The chemical composition of
the MOR gel was 6Na2O:5Al2O3:30SiO2:780H2O. Cr‐
based MOF (MIL‐101) was synthesized by the hydrother-
mal method based on the published recipe with a slight
modification.[24] A small‐scale synthesis of MIL‐101 (Cr)
includes a solution containing Cr (NO3)3·9H2O (1.6 mg,
1.0 mmol), nitric acid 67% (0.65 mL, 1.0 mmol) and
ditopic terephthalic acid (H2BDC; 0.65 mg, 1.0 mmol) in
20 mL H2O. The mixture was stirred for 90 min, and after
that was transferred to a stainless‐steel autoclave that was
heated for 8 hr at 200°C and cooled afterwards slowly to
room temperature. The content of the autoclave was
turquoise‐colored. The solid product was centrifuged,
after that DMF (5 mL) was added to the solid product,
which was then placed in a hot (80°C) ultrasonic bath
and sonicated for 45 min. Centrifugation was again per-
formed to separate MIL‐101 and DMF. The precipitate
In this article, we will consider the ship in a bottle
(SIB) method for the synthesis of mordenite zeolite
(MOR)/MIL‐101(Cr) MOF composite. The synthesized
composite was modified by post‐synthetic modification
to obtain acid–base bifunctionality (H‐MOR/MIL‐101‐
ED) for the synthesis of chromene derivatives. On the
basis of the structure of (H‐MOR/MIL‐101‐ED), we antic-
ipated that this reagent can be used as an efficient catalyst

FALLAH ET AL.
3 of 9
was transferred to a beaker, and it was stirred with 10 mL
of water at 80°C for 2 hr. After separation by centrifuga-
tion, the washing procedure using ethanol was repeated.
The final product was obtained by centrifugation and
dried in an oven (95°C) for 2 hr.
101(Cr) MOF to the synthesis mixture of MOR zeolite.
The starting materials required for preparing MOR gel
with composition of 6Na2O:Al2O3:30SiO2:780H2O were
added in the following order: double‐deionized water,
sodium hydroxide, sodium aluminate and silica gel. The
resulting mixture was stirred for 1 hr in the presence of
0.15 g MIL‐101(Cr) MOF, and then transferred to
Teflon‐lined stainless‐steel autoclaves. Crystallization
was carried out under hydrothermal conditions at 170°C
for 24 hr. After the autoclave was quenched in cold water,
the solid products were filtered, washed with water and
dried at 110°C overnight. The prepared sample was called
MOR/MIL‐101SIB.
2.3 | Synthesis of MOR/MIL‐101 (Cr)
composite via the ship in a bottle method
The synthesis of MOR/MIL‐101 (Cr) composite via the
SIB method was performed by the addition of MIL‐
2.4 | Incorporation of amine (‐NH2)
groups and acid exchange activation into
MOR/MIL‐101 composite
Modification of composite by ‐NH2 and acid groups was
SCHEME
1
(H‐MOR/MIL‐101‐ED) catalyzed synthesis of
chromene derivatives
performed based on the published recipe with a slight
FIGURE 1 Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) Images of MIL‐101 and MOR zeolite

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FALLAH ET AL.
modification.[19] The incorporation of amine groups in
the composites was performed in a 50‐mL flask equipped
with a reflux condenser and heated in a temperature‐
controlled oil bath under atmospheric pressure and mag-
netic stirring conditions; 50 μL ethylenediamine was
added to 30 mL anhydrous toluene in the flask, and 0.5
g MOR/MIL‐101 composites was added to the solution
sequentially. The mixture was refluxed at 110°C for 12
hr. The particles were collected by centrifugation and
washed with ethanol three times. The particles were then
dried in conventional oven at 70°C.
Analyzer, Model TESCAN MIRA II. The SEM operated at
30 kV. Chemical analysis of the samples was performed
by energy‐dispersive X‐ray analysis (EDX) joined with a
Philips XL30 SEM. The specific surface area and pore
diameter were measured using a BET Analyzer, Model
BEL SORP mini II. The thermogravimetric analysis
(TGA) was conducted using a TGA/DSC Instruments
LINSIES STP PT‐1000 with a heating rate of 5°C per
min under air atmosphere.
The acid exchange was performed in a 50‐mL flask
equipped with a reflux condenser and heated in a
temperature‐controlled oil bath under atmospheric pres-
sure and magnetic stirring; 0.5 g ‐NH2‐modified
MOR/MIL‐101 composites was added to 50 mL 0.1 mol
L−1 HCl ethanol solution. The mixture was refluxed at
90°C for a total of 6 hr. The acid‐exchanged particles were
washed with water and ethanol repeatedly. The sample
was then dried at 100°C in a vacuum oven. The sample
was denoted as H‐MOR/MIL‐101‐ED after this step.
3 | RESULTS AND DISCUSSION
3.1 | Characterization of composite
The morphological characteristics of MOR, MIL‐101 and
synthesized composite can be shown by SEM and TEM
images (Figure 1). The SEM image of MOR zeolite
revealed the presence of aggregates of thin plate‐shaped
crystals with varying geometry. The thickness of the
plates is less than 100 nm. The SEM image of MIL‐101
(Cr) indicated clearly small crystal particles. The crystal
size is less than 500 nm, and MIL‐101(Cr) MOF exhibited
regularly octahedral shape. The TEM images of MOR and
2.5 | Catalytic reaction for the synthesis of
chromene derivatives
A mixture of aldehyde (1.0 mmol), malononitrile (1.2
mmol), resorcinol (1.0 mmol) and H‐MOR/MIL‐101‐ED
(5 mg) in H2O was stirred at 80°C. The progress of the
reaction was monitored by thin‐layer chromatography.
After completion of the reaction, evaporation of water
and ethanol (5 mL) was added to the mixture. Then the
solid catalyst was obtained through simple filtering. After
evaporation of solvent, the solid product was recrystal-
lized from ethanol to afford pure product in good to high
yields (Scheme 1).
2.6 | Characterizations
The powder X‐ray diffraction (XRD) patterns of the sam-
ples were recorded using an X‐ray diffractometer (XRD
Philips, Model PW 1730) with Cu Kα radiation (λ =
1.545 Å) under conditions of 45 kV and 30 mA, at a step
size of 2θ = 0.05°. The XRD patterns were recorded
between 2° and 70° 2θ at a scanning speed of 0.5° per
min. All samples were analyzed in random orientation.
The transmission electron microscopies (TEM) were
recorded with a Zeiss‐EM10C, working at a 100 kV accel-
erating voltage. Samples for TEM were prepared by dis-
persing the powdered sample in acetone by sonication,
and then drip‐drying on a copper grid coated with carbon
film. Samples were sonicated for 15 min. The scanning
electron microscopy (SEM) was conducted with a FESEM
FIGURE 2 X‐ray diffraction (XRD) patterns of samples

FALLAH ET AL.
5 of 9
MIL‐101 were in agreement with their SEM images.
Based on the TEM image of MOR, the size of the smooth
plate was ~1.2 × 3 μm.
solution, respectively.[23,24] These kinds of SEM images
were observed by Liu et al.[27]
The TEM image and EDX results of the composite are
exhibited in Figure 3c and d, respectively. The TEM
image of MOR/MIL‐101SIB indicated aggregation of
MIL‐101 MOF that was located over the surface area of
MOR zeolite. This image was in agreement with SEM
images. The EDX result of the composite (Figure 3d) indi-
cated all elements (Al, Si, O, Cr, C and Si) in the compos-
ite and elemental analysis were in agreement with SEM
images.
The XRD profiles of the MOR/MIL‐101 composite,
MOR and MIL‐101 samples are shown in Figure 2. The
composite showed all the peaks that had been ascribed
to individual MIL‐101(Cr) MOF and MOR zeolite, in its
XRD pattern. The XRD pattern of composite was
matched quite well with patterns that were given in arti-
cles,[25,26] which allowed identifying the product as MOR
zeolite and MIL‐101 MOF, respectively.
The SEM image of MOR/MIL‐101SIB indicated
smooth plates MOR with overall size of 2.5 × 3 μm
(Figure 3a and b), and spherical particles MIL‐101 that
diffused in mordenite plates. In this method, formation
of plates MOR is observed in the presence of MIL‐101.
The octahedral MIL‐101 is not observed in the SEM
image of the MOR/MIL‐101SIB sample. Probably, the
morphology of pre‐synthesized MIL‐101 MOF changes
during the hydrothermal treatment in a basic aqueous
solution, because mordenite and MIL‐101(Cr) are hydro-
thermally synthesized in basic and acidic aqueous
The nitrogen sorption isotherms of the synthesized
materials [MOR, MIL‐101 (Cr)] and composites at 77 K
and 1 bar are observed in Figure 4. The MIL‐101(Cr)
and MOR samples showed a Type I isotherm with uptake
at P/P0 ~ 0.2 that is characteristic of microporous mate-
rials.[24] The pore volumes and surface areas of the
MOR zeolite according to the Si/Al value (Si/Al = 6)
and MIL‐101 (Cr) are listed in Table 1. MIL‐101(Cr) and
MOR had BET surface areas of 2583 and 450 m2 g−1
respectively. The total pore volumes of MIL‐101 and
MOR zeolite were obtained as 3.45 and 0.16 cm3 g−1
,
,
FIGURE 3 (a), (b) Scanning electron microscopy (SEM) images of MOR/MIL‐101 composite with different magnification. (c)
Transmission electron microscopy (TEM) image and (d) energy‐dispersive X‐ray analysis (EDX) result of MOR/MIL‐101(Cr) composite

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FALLAH ET AL.
FIGURE 5 Thermogravimetric analysis (TGA) plots of MIL‐
101(Cr) and MOR/MIL‐101(Cr) composite
and the MIL‐101(Cr) can be stable up to 400°C; The sec-
ond one from 400°C to 600°C should result from the
decomposition of the framework (87.7%) due to the pres-
ence of the nitro‐group. This means that there are more
degradable species in MIL‐101(Cr) that could be mainly
attributed to the existence of the nitro‐group in MIL‐
101. The TGA plots in Figure 5 showed that MOR/MIL‐
101 composite became more thermally stable compared
with the isolated MIL‐101(Cr). This enhancement can
be attributed to the incorporation of the MOR, which is
a crystalline aluminosilicate material with high thermal
stability and only starts to decompose at relatively higher
temperatures.[22] Based on SEM and TEM images,
MOR/MIL‐101SIB composite consists of a strong interac-
tion between MIL‐101 and MOR zeolite, and this interac-
tion was visible in SEM images. On the one hand, one of
the disadvantages of mesoporous materials such as MIL‐
101 MOF is low thermal stability,[23] then, MIL‐101
MOF as a mesoporous material with inner cages diame-
ters of 29 Å and 34 Å has lower thermal stability than
MOR zeolite.
FIGURE 4 N2‐sorption isotherms plots of MIL‐101(Cr), MOR
and hybrid composite
TABLE 1 Physical properties of MIL‐101(Cr), MOR and MOR/
MIL‐101 composite
Pore
BET surface
area (m2 g−1
Pore volume
(cm3 g−1
)
diameter
(nm)
Sample
)
MOR
450
2583
440
0.16
3.45
0.99
0.65
5.3
MIL‐101 (Cr)
MOR/MIL‐
1.11
101SIB
BET, Brunauer–Emmett–Teller.
respectively. These results were in agreement with other
articles.[24,28] The presence of a hysteresis over the higher
P/P0 region of the composite (MOR/MIL‐101SIB) is an
indication that some mesoporosity had been developed,
indicating structural modifications that were induced by
the presence of the MIL‐101. Additionally, the surface
area of MOR/MIl‐101SIB (440 m2 g−1) was similar to pure
MOR (450 m2 g−1), but the pore volume (0.99 cm3 g−1) of
the MOR/MIL‐101SIB composite was greater than that of
the pure MOR sample (0.16 cm3 g−1; Table 1). This obser-
vation can be ascribed to the formation of additional
mesoporous in the resulting hybrid composite.
3.2 | Study of the preparation of
chromene derivatives by modified
composite
In order to confirm the crystallinity of the MOR/MIL‐101
composite after treatment with ethylenediamine (ED)
and HCl, XRD were employed. The XRD pattern of H‐
MOR/MIL‐101‐ED composite is shown in Figure 2. The
composite consists of diffraction peaks from both MIL‐
101 and MOR, indicating the presence of both phases in
the composite material. In addition, the crystalline phases
were well preserved after the addition of ED and HCl.On
the basis of the information obtained from the above‐
mentioned studies and the structure of (H‐MOR/MIL‐
101‐ED), we anticipated that this reagent can be used as
Further, it can be observed from the TGA that MIL‐
101(Cr) showed two weight losses (Figure 5): the first
one before 150°C could be attributed to the removal of
the solvent water or methanol trapped within the pores

FALLAH ET AL.
7 of 9
TABLE 2 Preparation of chromene derivatives using (H‐MOR/
MIL‐101‐ED) as the catalyst
an efficient catalyst for the promotion of the reactions
that need the use of an acidic or basic catalyst to speed
up.[29–31] Herein, we wish to extend the application of this
catalyst for the synthesis of chromene derivatives via one‐
pot condensation of aldehydes with resorcinol and
malononitrile. In order to optimize the reaction condi-
tions, we carried out the reaction of 4‐nitrobenzaldehyde
(1 mmol), resorcinol (1 mmol) and malononitrile (1.2
mmol) in H2O as green solvent in the presence of the
new catalyst (Scheme 1). The obtained result showed that
the reaction using 5 mg of the catalyst in water at 80°C
proceeded with the highest yield in the shortest reaction
time (Table 2, entry 4). Then, to assess the efficiency of
(H‐MOR/MIL‐101‐ED) in the synthesis of chromene
m. p. (°C)
Time Yield
(min) (%)
Reported
[Ref.]
Entry Aldehyde
Found
1
2
3
4
5
6
7
4‐ClC6H4CHO
4‐MeC6H4CHO
16
12
90
85
87
90
83
85
80
156–159 161–162[29]
178–180 184–186[29]
106–108 112–114[29]
205–207 210–212[30]
163–165 169–170[29]
156–158 160–162[31]
248–250 252–254[30]
4‐MeOC6H4CHO 12
4‐NO2C6H4CHO
8
3‐NO2C6H4CHO 10
2‐NO2C6H4CHO 10
4‐HOC6H4CHO 20
SCHEME 2 Proposed mechanism for the synthesis of chromene derivatives in the presence of (H‐MOR/MIL‐101‐ED) as a catalyst
TABLE 3 Compared performance of various catalysts in synthesis of 2‐amino‐3‐cyano‐7‐hydroxy‐4‐(4‐chlorophenyl)‐4H‐chromene
Catalyst
Entry
Catalyst/condition
loading (mol%)
Time (min)
Yield (%)
Ref.
[3]
1
2
3
L‐Proline/EtOH, reflux
10
5 hr
30
98
88
76
[4]
[5]
Na2CO3/Grinding, 50°C
10 (10.5 mg)
0.37
MIL‐101(Cr)‐SO3
7 hr
H/H2O, 100°C
[1]
[6]
[2]
[7]
4
5
6
7
8
Saccharose/EtOH:H2O, reflux
20 (60 mg)
1.11 (30 mg)
25
50
88
80
95
90
90
Tungstic acid functionalized SBA‐15/H2O, 100°C
Potassium hydrogen phthalate/H2O, 50°C
Amino‐appended β‐cyclodextrin/H2O, r.t.
(H‐MOR/MIL‐101‐ED) /H2O, 80°C
15 hr
2.5 hr
5 hr
16
0.5
5 mg
This work

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FALLAH ET AL.
derivatives, a wide range of aromatic aldehydes contain-
ing electron‐withdrawing groups as well as electron‐
donating groups were easily subjected to the same reac-
tion under the optimal conditions. It has been observed
that this method is quite general, and all these reactions
occurred with good to excellent yields in very short times
(Table 2, entries 1–7).
ORCID
Shabnam Sohrabnezhad
9368-256X
https://orcid.org/0000-0002-
REFERENCES
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on the available literature for this reaction.[29] It seems
that (H‐MOR/MIL‐101‐ED) catalyzes the reaction by the
activation of the aldehyde and malononitrile. Firstly,
Knoevenagel product (I) was obtained from the conden-
sation of these activated compounds. Then the Michael
addition (II) occurred between the Knoevenagel product
and resorcinol, which is followed by intra‐molecular
cyclization to yield 2‐amino‐4H‐chromene derivatives
(Scheme 2).
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4 | CONCLUSIONS
The MOR/MIL‐101 composite was prepared using the
SIB method. In the SIB method, the octahedral shape
of MIl‐101 was converted to spherical particles, and a
strong interaction was observed between them. The
MOR/MOF composite was more thermally stable com-
pared with the isolated MIL‐101(Cr). The BET results
showed that the surface area of the new composite was
smaller than individual MOF and MOR zeolite. The
composite was functionalized by post‐synthetic modifica-
tion to obtain acid–base bifunctionality (H‐MOR/MIL‐
101‐ED) as an efficient solid catalyst for the simple
synthesis of 2‐amino‐3‐cyano‐4H‐chromene derivatives.
This procedure has several advantages, such as ease of
preparation and handling of the catalyst, simple experi-
mental procedure, high reaction rates and good yields
of the products.
[16] P. Jacobs, E. M. Flanigen, J. Jansen, H. van Bekkum, Introduction
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How to cite this article: Fallah M,
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