A simple matrine derivative for the facile syntheses of mesoporous zeolites ITQ-37 and ITQ-43

Article abstract of DOI:10.1039/c8cc08196d

ITQ-37 and ITQ-43 possessing mesoporous structures have aroused great interest because of their promising applications involving large molecules. However, it is challenging to synthesize these zeolites. Herein, MAS-ITQ-37 and MAS-ITQ-43 with enhanced Si/Ge ratios of 1.7 and 3.0 have been synthesized by using a simple matrine-derived organic structure-directing agent.

Full text of DOI:10.1039/c8cc08196d

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A Simple Matrine Derivative for the Facile Syntheses of
Mesoporous Zeolites ITQ-37 and ITQ-43
Chuanqi Zhang,a Xu Li,d Xinzhu Li,a Jibo Hu,a Liangkui Zhu,c Yan Li,c Jiuxing Jiang,*a Zhendong
Received 00th January 20xx,
Accepted 00th January 20xx
Wang*b and Weimin Yang*b
DOI: 10.1039/x0xx00000x
www.rsc.org/
ITQ-37 and ITQ-43 possessing mesoporous structures have aroused
great interests because of their promising application involving
large molecules. However, it is challenging to synthesize these
zeolites. Herein, MAS-ITQ-37 and MAS-ITQ-43 with enhanced Si/Ge
ratio of 1.7 and 3.0 have been synthesized by using a simple
matrine-derived organic structure-directing agent.
because of their unique mesoporous range pore sizes, but also
because they are promising candidates for enantio-selective and
shape-selective catalysis involving large substrates. Initially, ITQ-37
and ITQ-43 were synthesized by using two different bulky OSDAs, as
shown in Fig. 1a, b. Subsequently, other achiral OSDAs were tested
14
as effective alternatives to prepare ITQ-37 (Fig. 1c, d).13,
Nevertheless, the above-mentioned OSDAs are extremely expensive
or synthesized in very harsh conditions (concentrated sulfuric and
acetic acid medium for tmbiBr3).13 Additionally, no alternative OSDA
has been reported for the preparation of ITQ-43. The facile syntheses
of such crystalline mesoporous zeolites using cost-effective and
sustainable OSDAs are highly desirable for large-scale practical
applications.
Extra-large pore (>12 ring) and mesoporous (>2 nm) zeolites have
attracted great attentions because of their potential applications in
separation of large molecules, biomass processing and the cracking
of heavy-oil fractions.1, 2 Great efforts have been made by academic
and industrial laboratories, and about 20 extra-large pore zeolite
types were prepared up to now. One of the most effective synthetic
strategy for obtaining extra-large pore and mesoporous zeolites is
the utilization of the pre-designed organic structure-directing agents
(OSDAs).3, 4 By this means, a number of germanosilicates with extra-
large pore structures, such as IM-12,5 ITQ-33,6 ITQ-40,7 ITQ-44,8 ITQ-
54,9 and NUD-110 have been successfully synthesized by the
combination of bulky OSDAs, fluoride anions as well as Ge
substitution. Notably, heretofore, only two crystalline zeolites with
definite mesoporous structures, including ITQ-3711 and ITQ-4312,
have been successfully prepared by Corma’s group.
Encouragingly, simple quaternary ammonium cations as single
OSDAs have been utilized for the syntheses of some extra-large pore
zeolites in recent years. For instance, Sun and co-workers
synthesized the PKU-12 with the same structure of cloverite (-CLO,
3D, 20-ring) using a simple quaternary ammonium cation.15 In
addition, three related extra-large pore zeolites ITQ-33 (ITT, 3D, 18 ×
10 × 10-ring), ITQ-44 (IRR, 3D, 18 × 12 × 12-ring), and NUD-1 (3D, 18
× 12 × 10-ring) have been prepared by using very simple and cheap
OSDAs such as TEAOH, TPAOH and TBAOH.16 Nevertheless, these
synthesis examples are still few in number, and the majority of extra-
large pore zeolites were synthesized by expensive OSDAs, which
required complicated synthesis procedures in general.17-20
ITQ-37 possesses the largest 3D 30-ring chiral mesoporous
structure and ITQ-43 has 3D 28 × 12 × 12-ring hierarchical meso-
microporous structure. They are the landmark zeolites not only
On the other hand, the huge pool of natural products with
polycyclic skeletons are appropriate candidates for preparing novel
OSDAs.21, 22 Quinolizidine alkaloids, including matrine, sophoramine,
a. MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of
Chemistry, Sun Yat-sen University, Guangzhou 510275, P.R. China. Email:
jiangjiux@mail.sysu.edu.cn
sparteine and sophoridine, with unique molecular skeletons are easy
b. State Key Laboratory of Green Chemical Engineering and Industrial Catalysis,
Sinopec Shanghai Research Institute of Petrochemical Technology, Shanghai
201208, P. R. China. Email: wangzd.sshy@sinopec.com,
24
to modify to obtain suitable OSDAs.23,
Several specific zeolite
structures have been synthesized using such OSDAs. Notably, the
alkylated sparteine derivatives have been utilized for preparing large
pore and extra-large pore zeolites.25-27 Very recently, we have
yangwm.sshy@sinopec.com
c. State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin
University, Changchun, 130012, P. R. China.
d. School of Chemical Engineering & Light Industry, Guangdong University of
Technology, Guangzhou 510006, P. R. China.
discovered
a new germanosilicate zeolite SYSU-3 with an
unprecedented 3D 24 × 8 × 8-ring channel system using a sophoridine
based OSDA.28 It is meaningful to prepare specific extra-large pore
and mesoporous zeolites by using simple natural product derivatives.
†Electronic Supplementary Information (ESI†) available: Detailed synthetic
procedures of the OSDA and the zeolites, the characterization such as SEM images,
TG curves, chemical analysis and solid-state NMR. CCDC 182267. For ESI† and
crystallographic data in CIF or other electronic format See DOI: 10.1039/x0xx00000x
This journal is © The Royal Society of Chemistry 20xx
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Tab 1. Survey of zeolites synthesis using MeMAS as the OSDA.
View Article Online
DOI: 10.1039/C8CC08196D
IV
IV
◦
OSDA/T =0.3, F/T =0.3, 160 C2 days
Si/Ge=1
Si/Ge=2
Si/Ge=5
ITQ- 37+ITQ- 43
ITQ- 43
III IV
ITQ- 37+GeO2
ITQ- 37
T /T =0
H20/TIV=1.5
IV
ITQ- 43+GeO2 ITQ- 37+ITQ- 43
Al/T =0.025
IV
ITQ- 37+GeO2
ITQ- 37
ITQ- 37+ITQ- 43
B/T =0.025
III IV
ITQ- 37+GeO2 ITQ- 37+ITQ- 43 ITQ- 37+ITQ- 43
ITQ- 43+GeO2 ITQ- 43 ITQ- 43
ITQ- 37+GeO2 ITQ- 37+ITQ- 43 ITQ- 37+ITQ- 43
T /T =0
20/TIV =3.0
IV
H
Al/T =0.025
IV
B/T =0.025
at 160◦C for 2 days. When Si/Ge ratio is 1, a dense phase always
accompanies the formation of MAS-ITQ-37 and MAS-ITQ-43. The
decrease of germanium content, with a Si/Ge ratio of 2, facilitates
the generations of pure phases of these two zeolites. In addition, the
content of water has an important impact on the crystallization
progress, MAS-ITQ-37 and MAS-ITQ-43 with high crystallinity can be
obtained when the H2O/T ratios are 1.5-3.0, further increasing the
water content leads to the decrease of crystallinity and the
emergence of dense phase. The MAS-ITQ-37 and MAS-ITQ-43, as
competitive phases, are obtained in many cases, and the pure phase
of MAS-ITQ-37 can be made in concentrated gel condition (H2O/T =
1.5), while the addition of small amount of aluminum induces the
crystallization of pure phase of MAS-ITQ-43, indicating that the Al
atoms plays important role in the phase selectivity of the
crystallization. It was noteworthy that the MeMAS has specific
structure-directing effect for the formation of mesoporous
structures MAS-ITQ-37 and MAS-ITQ-43, no other zeolite by-
products were observed. Additionally, in the case of MAS-ITQ-37, it
required shorter crystallization time using MeMAS than that of tmbi
(15 to 45 days).13
Fig. 1 OSDAs used for the syntheses of ITQ-37 and ITQ-43 and the
synthesis of N-methylmatrinium (MeMAS).
Herein, we demonstrate for the first time the facile syntheses of
mesoporous zeolites ITQ-37 and ITQ-43 (denoted as MAS-ITQ-37 and
MAS-ITQ-43) by using
a simply modified martine derivative.
Remarkably, these materials exhibit record-high N2 adsorption BET
surface area (978.9 m2/g for MAS-ITQ-37 and 923.7 m2/g for MAS-
ITQ-43) among the as-made zeolites. Additionally, we have studied
the influence of synthetic factors and characterized the as-
synthesized materials by XRD, ICP, CHN, TG, SEM, MAS-NMR and N2
adsorption.
As shown in Fig. 2, the powder XRD patterns of the MAS-ITQ-37
and MAS-ITQ-43 are consistent with the simulated ones based on the
reported crystallographic data, indicating the good crystallization
and pure phase of the as-synthesized samples. The SEM images
shows spherical morphology with crystals around 100-200 nm in
diameter for the MAS-ITQ-37 (Fig. S1, ESI†), and the MAS-ITQ-43
exhibits uniform crossed sheet-like morphology with a width of
For the structure of matrine, the carbonyl group can be easily
reduced with LiAlH4, methylation of the corresponding reduced
product gives the N-methylmatrinium (MeMAS), as pictured in Fig.
1e. A pure phase of MAS-ITQ-37 can be prepared with a gel
composition of Si/Ge=2, SDA/T=0.3, NH4F/T=0.3, H2O/T=1.5 (T=Si+Ge)
at 160◦C for 2 days. The addition of a small amount of aluminium
source in the same gel leads to the pure phase MAS-ITQ-43 with a
molar composition of Si/Ge=2, Al/T=0.025, SDA/T=0.3, NH4F/T=0.3,
H2O/T=3. The detailed synthetic procedures of the OSDA and the
zeolites were provided in Electronic Supporting Information.
Previous literatures reported OSDAs used in the syntheses of ITQ-
37 and ITQ-43 zeolites are either costly or synthesized in harsh
conditions. In this work, the highly crystalline MAS-ITQ-37 and MAS-
ITQ-43 have been obtained by using the simple MeMAS in the similar
reaction conditions. The detailed influence of synthetic factors, such
as the ratios of Si/Ge, Si/F, gel concentration, crystallization
temperature as well as heteroatoms have been investigated. As
shown in Tab 1, the MAS-ITQ-37 and MAS-ITQ-43 can be prepared
with the gel molar compositions of Si/Ge=x, SDA/T=0.3, NH4F/T=0.3,
H2O/T=y (x=5, 2, 1; y=1.5, 3.0) when the crystallization is performed
around 1.5-2.0 m and a thickness of 300-400 nm. The solid-state 13
C
NMR spectrum of MAS-ITQ-43 is in well agreement with the liquid
13C NMR of MeMAS, proving that the OSDA remains intact in the
structure. While the resonance around 105 ppm indicates that some
OSDAs decomposed during the crystallization process for MAS-ITQ-
37 (Fig. S2, ESI†).28, 29 Additionally, compared to that of the liquid, the
broaden peaks for both zeolites result from the restraint of mobility
of OSDA within the framework in zeolites. MAS-ITQ-37 and MAS-ITQ-
43 were obtained in fluoride synthesis media, thus the 19F MAS NMR
were studied to confirm the locations of fluoride ions. As seen in Fig.
S3 (ESI†), the presence of resonance bands at -9.5 ppm for MAS-ITQ-
37 and -8.5 ppm for MAS-ITQ-43 indicate that the fluoride ions are
located in the germanium-rich double-4-rings for both zeolites, and
the band at -123.5 ppm for MAS-ITQ-37 and MAS-ITQ-43 may
attribute to the mobile fluoride ions in the channels and cavities to
balance the charge of the zeolite structures.15 Interestingly, MAS-
ITQ-37 and MAS-ITQ-43 could be obtained at the almost same
2 | J. Name., 2012, 00, 1-3
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synthesis condition, the introduction of a small amount of aluminium
source lead to the formation of pure phase of MAS-ITQ-43. Although
Al element cannot be detected by ICP technique, the 27Al MAS-NMR
spectrum of the MAS-ITQ-43 shows strong bond at 52.3 ppm,
indicating that tetrahedrally coordinated Al were introduced into the
framework (Fig. S4, ESI†).
View Article Online
DOI: 10.1039/C8CC08196D
ICP analyses of the samples synthesized from gels with Si/Ge= 2
show Si: Ge molar ratios of 1.4 for MAS-ITQ-37 and 1.7 for MAS-ITQ-
43, respectively. CHN analyses of MAS-ITQ-37 and MAS-ITQ-43 give
the C/N ratios of 8.5 and 8.4, respectively, which are close to that of
the MeMAS (8.0), seen in Tab S1 (ESI†). As pictured in Fig. S5 (ESI†),
the TG curves of MAS-ITQ-37 and MAS-ITQ-43 show two weight
losses. The first weight loss of 8.0% for MAS-ITQ-37 and 2.5% for
MAS-ITQ-43 from 25 to 200◦C may attribute to the removal of guest
H2O molecules. The second weight loss of ca. 23.6 and 29.1% in the
region of 250-800◦C correspond to the removal of the remaining
guest molecules for MAS-ITQ-37 and MAS-ITQ-43, respectively.
Notably, the total weight loss values (up to 31.6%) are unusually high
for these two zeolites.
Fig 3. N2 adsorption–desorption isotherms at 77 K of calcined MAS-
ITQ-37 and MAS-ITQ-43.
unprecedented zeolite structures for germanosilicates.31-35 For these
purposes, we have increased the Si/Ge ratios in synthesis gels.
Fortunately, the MAS-ITQ-37 and MAS-ITQ-43 with enhanced ICP
Si/Ge ratios up to 1.7 and 3.0 (literature report the highest Si/Ge is
1.4 for ITQ-3711 and 2.2 for ITQ-4312) can be synthesized from gels
with Si/Ge= 6 and 10, respectively. As shown in Fig. S7 (ESI†), both
materials show high crystallinities and uniform morphologies. Highly
stable siliceous ITQ-43 and new materials are expected to be
prepared by isomorphous degermanation and ADOR method using
The gas adsorption properties of MAS-ITQ-37 and MAS-ITQ-43
were also studied. These samples were treated at 550 ◦C for 5 hours
under dry oxygen atmosphere. The N2 adsorption give the BET
surface area of 978.9 and 923.7 m2/g, and t-plot micropore volumes
of 0.363 and 0.345 cm3/g for the calcined MAS-ITQ-37 and MAS-ITQ-
43, respectively (Fig. 3 and Fig. S6 (ESI†)). Such record-high BET
surface areas may attribute to the high crystallization and more guest
molecules occluded in the frameworks.
It was well-known that the incorporation of large quantity of Ge MAS-ITQ-43 with an enhanced Si/Ge ratio, work along this line is
atoms into the framework limits the practical application of under way in our laboratory.
germanosilicates due to the hydrolysis of Ge-O bond. The
Interestingly, single crystal X-ray diffraction analysis reveals that
enhancement of Si/Ge ratios would not only improve their
the MeMAS maintains the origin conformation of matrine,
hydrothermal stability, but also provide the opportunity to obtain
confirming the rigidity of matrine-type alkaloids (Fig. S8 and Table S2
stable high-silica zeolites by post-synthesis treatment.30 In addition ,
ESI†). Furthermore, compared to the diquaternary ammonium
the ADOR (assembly-disassembly-organization-reassembly), a top-
cation N, N’-dimethylsophoridinium (Me2SOP), the MeMAS has only
down synthetic approach, opens up the possibilities to construct
one N-methyl group as the consequence of high steric hindrance
around the nitrogen of the tertiary amine group in matrine (Fig. S9,
ESI†). Me2SOP was able to direct the formation of SYSU-3,28 while
MeMAS lead to MAS-ITQ-37 and MAS-ITQ-43 in similar reaction
condition. It is intriguing that the minor structural difference
(diastereomer for matrine and sophoridine) gives rise to two distinct
OSDAs with different size, configuration and charge, which further
induces the different phase-selectivity of zeolites. These results
reveal that the structure of alkaloids play essential roles in the
formation of zeolite structures.
In conclusion, it is very easy to prepare MeMAS by modifying the
low-cost martrine. MeMAS is an efficient OSDA to prepare highly
crystalline MAS-ITQ-37 and MAS-ITQ-43 with record-high gas
adsorption performances in similar synthesis conditions. The specific
structure-directing effects of MeMAS for the formation of
mesoporous structures are probably due to its unique skeleton, rigid
configuration and proper thermal stability. The successful syntheses
of MAS-ITQ-37 and MAS-ITQ-43 demonstrate that it is a sustainable
Fig.2 XRD patterns of the as-synthesized MAS-ITQ-37 and MAS-ITQ-
and facile route to prepare specific extra-large pore and mesoporous
43, and the simulated XRD patterns of ITQ-37 and ITQ-43.
zeolites using alkaloid-based OSDAs. Also, they may be promising
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This research was supported by the Youth 1000 Talents Program
of China; the National Natural Science Foundation for Young
Scientists of China (Grant No.21601211, 21805316), the
Fundamental Research Funds for the Central Universities (Grant
No.16lgpy24) and Sinopec.
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DOI: 10.1039/C8CC08196D
Matrine extracted from sophora flavescens can be simply modified to afford a novel
OSDA for the syntheses of mesoporous zeolites.