Synthesis of P123-Templated and DVB-Cross-linked Meso-macroporous Poly (ionic liquids) with High-Performance Alkylation

Article abstract of DOI:10.1002/aoc.5460

Meso-macroporous poly (ionic liquids) (MPILs) were successfully synthesized through a novel strategy with P123 (PEO₂₀PPO₇₀PEO₂₀) as the pore-forming agent and divinylbenzene as crosslinker. Then effects of reaction temperature and the molar ratio of ionic liquid to divinylbenzene (IL to DVB) were systematically investigated together with the morphology and structure of MPILs. It was found the MPILs owned a meso-macroporous channel-like structure, large surface area (up to 732 m²/g), large pore volume (1.42 cm³/g) and high thermal stability. Meanwhile, the Brunauer–Emmett–Teller surface of MPILs could be fabricated by adjusting the reaction temperature and especially the IL to DVB molar ratio. In the probe reaction of alkylation of styrene and o-xylene, a 100% conversion of styrene and 96.4% PXE yield was acquired, and this is more expert than common commercial liquid acid catalyst. This work might develop a novel way for synthesizing porous heterogeneous polymer catalysts in the future and owning a promising future applied in other acidic catalytic reactions.

Full text of DOI:10.1002/aoc.5460

Received: 2 September 2019
DOI: 10.1002/aoc.5460
Revised: 18 November 2019
Accepted: 26 November 2019
F U L L P A P E R
Synthesis of P123-Templated and DVB-Cross-linked Meso-
macroporous Poly (ionic liquids) with High-Performance
Alkylation
Xiao Sha
| Xiaoli Sheng | Yuming Zhou | Beibei Wang | Zhiying Zhu |
Qiang Liao | Yonghui Liu
School of Chemistry and Chemical
Engineering, Southeast University,
Jiangsu Optoelectronic Functional
Materials and Engineering Laboratory,
Nanjing, 211189, P. R. China
Meso-macroporous poly (ionic liquids) (MPILs) were successfully synthesized
through a novel strategy with P123 (PEO PPO PEO ) as the pore-forming
20
70
20
agent and divinylbenzene as crosslinker. Then effects of reaction temperature
and the molar ratio of ionic liquid to divinylbenzene (IL to DVB) were system-
atically investigated together with the morphology and structure of MPILs. It
was found the MPILs owned a meso-macroporous channel-like structure, large
Correspondence
Xiaoli Sheng and Yuming Zhou, School of
Chemistry and Chemical Engineering,
Southeast University, Jiangsu
Optoelectronic Functional Materials and
Engineering Laboratory, Nanjing 211189,
P. R. China.
2
3
surface area (up to 732 m /g), large pore volume (1.42 cm /g) and high thermal
stability. Meanwhile, the Brunauer–Emmett–Teller surface of MPILs could be
fabricated by adjusting the reaction temperature and especially the IL to DVB
molar ratio. In the probe reaction of alkylation of styrene and o-xylene, a 100%
conversion of styrene and 96.4% PXE yield was acquired, and this is more
expert than common commercial liquid acid catalyst. This work might develop
a novel way for synthesizing porous heterogeneous polymer catalysts in the
future and owning a promising future applied in other acidic catalytic
reactions.
Email: xlsheng@seu.edu.cn; ymzhou@
seu.edu.cn
Funding information
National Natural Science Foundation of
China, Grant/Award Numbers: 21376051,
2
1676056, 51673040; Qinglan Project of
Jiangsu Province, Grant/Award Number:
107040167
1
K E Y W O R D S
catalysis, meso-macroporous structure, P123, polymers, porous materials
[
9–13]
1
| INTRODUCTION
and application of PILs.
PILs materials have been
[
14–18]
[19–21]
broadly used in catalysis,
separation,
Moreover, PILs as
[
22–26]
[27,28]
Recently, ionic liquids under room-temperature have
attracted much attention on account of their distinct
properties, such as negligible vapor pressure, high ther-
mal stability, wide liquid range and excellent
membranes
and absorption.
a burgeoning interdisciplinary topic possess many advan-
tages, including functional designability and eco-
[
29]
friendliness.
[1–3]
solubility.
Recently poly (ionic liquids) (PILs) comb-
In addition to structural units of PILs, many research
groups and scholars have started to report porous PIL
materials. In other words, porous PILs with large surface
areas and pore volume can be designed and synthesized.
has prepared a highly-crosslinked nonporous PILs
xerogel with very high SO2 adsorption capacity
ing the advantages of ionic liquids and the macromolecu-
lar architecture become increasingly popular and create
fresh capabilities and functions.
materials have been prepared by introducing cationic or
anionic ionic liquid with functional groups into dynamic
macromolecular polymeric architectures, which can
greatly expanded the properties, structures, functionality
[4–8]
A variety of PIL
[
30]
Xia
−
1
(498 mgÁg ) through the photopolymerization of Gemini
[
31]
ionic liquid monomers. Wang
has prepared a novel
Appl Organometal Chem. 2020;e5460.
wileyonlinelibrary.com/journal/aoc
© 2020 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.5460

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SHA ET AL.
acidic poly(4-vinylpyridine) supported ionic liquid for
effectively catalyzing the anthranilamide
cyclocondensation with aldehydes under ultrasound
exposure. Thus, the channel structure and surface area of
PILs are controllable via appropriate reaction conditions
and reaction system.
The alkylation of o-xylene and styrene is a significant
industrial Friedel-Crafts reaction, the research has last
for a very long time for the product Phenylxylylethane
under normal temperature. Then transferred the mix-
ture into a 100 ml Teflon lined stainless steel autoclave
for 24 hr reaction at 100 C. The yellowish solids were
ꢀ
collected by filtration and the solid was washed with
ꢀ
ethanol for three times and dried at 60 C under vac-
uum condition. Finally, the soft template was removed
by extraction in HCl solution (ethanol: concentrated
aqueous HCl(36–38%) =150 ml: 1 ml). The final prod-
ucts were named MPIL-T(p), where T is the reaction
temperature and p is the IL to DVB molar ratio.
Acidic mesoporous PILs were synthesized by impregna-
(PXE) exhibits a great range of application, such as the
pressure-sensitive record materials, a heating medium,
[36]
an
materials.
electric-insulating
oil
and
other
applied
tion method according to a reported approach
with
[32–34]
H SO , AlCl and HF are commonly used
slight modification. Meanwhile, alkylation of o-xylene
and styrene was conducted as a detective reaction to
investigate the activity.
2
4
3
[
9]
as the catalyst of the reaction. However, these tradi-
tional catalysts are difficult to separate and always show
a low active performance in recycle reactions, which
make them high-cost catalysts. In order to overcome
these drawbacks, it is important and urgent to discover
an environment-friendly heterogeneous solid catalysts for
this Friedel-Crafts reaction.
2.2 | Characterization of catalysts
The surface areas and pore size distributions of catalysts
were investigated by the Fourier transform infrared (FT-
IR, FTIR-6700), scanning electron microscopy (SEM, FEI
Inspect F50) and transmission electron microscopy
In this work, a series of meso-macroporous poly
(ionic liquids) (MPILs) were designed and synthesized by
a free radical copolymerization method with P123 as a
soft template and DVB as crosslinker, then by solvent
extraction process to remove the P123 template. The
effects of reaction temperature and the molar ratio of
ionic liquid to divinylbenzene (IL to DVB) on the struc-
ture and catalyst performance were studied in detail.
Later, counter anions were easily tuned through the
anion exchange which can improve the catalysis property
of the MPILs where the Keggin-structured phospho-
tungstic anion could be exchanged and highly dispersed
onto the channel surfaces of the catalyst. Meanwhile,
alkylation of o-xylene and styrene was adopted as a detec-
tive reaction to investigate the activity property of the
prepared catalyst.
(TEM, JEOL, JEM-2100). The N adsorption/desorption
2
isotherms were recorded on an ASAP 2020 apparatus
(Micromertics USA). And the specific surface area and
pore size distributions were performed using Brunauer–
Emmett–Teller (BET) and Barrett–Joyner–Halenda (BJH)
model, respectively. a Rigaku ThermoPlus TG8120 sys-
ꢀ
−1
tem was used under a rate of 10 C min in air to exe-
cute Thermo Gravimetric Analysis (TGA) and a Thermo
ESCALAB 250 X-ray photoelectron spectroscope (XPS)
with Al Kα radiation.
2.3 | Determination of alkylation
catalyst activity
2
| EXPERIMENTAL
The alkylation of o-xylene and styrene was used to evalu-
ate the catalytic performance of the prepared products.
The target product is 1,2-diphenylethane (PXE) which
can be used in pressure-sensitive record materials, a
heating medium and used as an electric-insulating oil.
Through a typical procedure, 30 g o-xylene, 4 g styrene,
and catalyst (x wt%, where x represents relative to the
weight of the whole reaction system) were blended in a
2
.1 | Preparation of catalyst
[35]
In analogy to a method from Gao.,
the MPILs were
synthesized through free radical copolymerization of
-butyl-3-vinylimidazolium bromide (ionic liquid) with
1
DVB (80.0%w) by using an amphiphilic soft template
P123. In a typical procedure, 3.0 g of P123 template
was dissolved in 30 ml of tetrahydrofuran (THF) to
form a clear homogenous P123 solution, and then
ꢀ
250 ml flask. Then, we heated the mixture to 120 C in
an oil bath with continued magnetic stirring for 3 hr
under common pressure. And after the procedure, cata-
lyst sample was recycled through vacuum filter procedure
2
.31 g of the ionic liquid and appropriate amount of
ꢀ
DVB were added under stirring for more than 3 hr.
After that, 3%w azodiisobutyronitrile (AIBN) was
added to the mixture under vigorous stirring for 3 hr
and dry at 60 C for 12 hr. The catalyst performance of
the samples were detected by gas chromatograph, GC
9890A.

POLYMERS POROUS MATERIALS P123; MESO-MACROPOROUS STRUCTURE CATALYSIS
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3
3
| RESULTS AND DISCUSSION
.1 | Catalysts characterization
namely the channel size of MPIL-T(p) is between
0–50 nm. All the samples show a type-IV curve with a
2
wide capillary condensation step at p/p of 0.4–1.0, which
0
indicates the porous structure of the samples (Figure 1B).
In short, all the samples possess large specific surface
areas and pore diameters.
The porosity and physicochemical properties of MPIL-
T(p) are shown in Table 1 and Figure 1A-B. It can be
observed that the reaction temperature and the IL to
DVB molar ratio both significantly influence the BET
surface area and average pore size within the samples
The characteristic functional group of the samples
was evaluated through Fourier transform infrared spec-
trometry (FT-IR) (Figure 1C). Peaks at 1660, 1540 and
1460 cm− attributed to C=O, C=N stretching vibration,
and imidazole ring C-H deformation vibration, respec-
tively, suggest the imidazole ring structure has been
embedded in the meso-macroporous polymers. The FT-
IR spectrum of PW/MPIL-T(p) clearly shows the bands at
1
(Table 1). With the IL to DVB molar ratio rising from 1:1
to 1:3, the surface area of MPIL-100(p) increased from
2
3
33 to 732 m /g and pore volumes decreased gradually
which can be attributed to the addition ratio of cross-
linker of DVB. The effects of reaction temperature were
reflected in two ways, including micelle size of P123 and
the free radical copolymerization of IL and DVB. The two
factors led to the porosity difference of MPIL-T(1:2). Pore
size distribution of the samples is shown in Figure 1A, or
1082 cm− (P-O in the central tetrahedron), 980 cm
1
−1
−1
(terminal W=O), 896 and 812 cm (W–O–W), which are
associated with Keggin ions. Thermogravimetric
(TG) curve shows in Figure 1D. It is of great necessity to
evaluate the thermal and structural stability of the prod-
uct, all the synthesized products comprise three main
weight loss steps. In the first stage of the curve, it could
be observed that PW/MPIL-100(1:2) shows a consistent
thermogravimetric loss which can due to the combined
water within the samples and the miner weight loss of
the sample indicate the fact that PW/MPIL-100(1:2)
owing a perfect hydrophobic property which can conduce
to the detective alkylation reaction of o-xylene and sty-
TABLE 1 Physicochemical properties of the MPIL-T(p)
Pore
Average
Pore Size
(nm)
BET Surface
Volume
2
3
Sample
Area (m /g)
(cm /g)
MPIL-100(1:1) 333
MPIL-100(1:2) 589
MPIL-100(1:3) 732
0.43
1.03
1.42
1.16
1.01
1.31
1.52
7.53
9.01
9.7
ꢀ
rene. When the temperature is below 300 C, PW/MPIL-
MPIL-80(1:2)
MPIL-90(1:2)
618
527
9.22
9.71
9.84
10.05
100(1:2) can maintain high thermal stability.
The SEM image, TEM image, EDS elemental map-
ping, XRD patterns are shown in Figure 2. The
PW/MPIL-100(1:2) and MPIL-100(1:2) display a similar
MPIL-110(1:2) 665
MPIL-120(1:2) 615
FIGURE 1 N2adsorption-
desorption isotherms (A), pore size
distributions (B) and FT-IR spectra
(
C) of MPIL-T(p), TG curves (D) of
PW/MPIL-100(1:2)

4
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SHA ET AL.
FIGURE 2 SEM images of MPIL-
100(1:2) (A), PW/MPIL-100(1:2) (B);
TEM images of PW/MPIL-100(1:2); EDS
elemental mapping of PW/MPIL-
100(1:2) (D-F); XRD patterns (G)
morphology of sphere-like aggregation with a loose
porous structure (Figure 2A-B) which is a typical poly-
mer structure. It can be easily observed that the porous
structure of PW/MPIL-100(1:2 is different from that of
MPIL-100(1:2) which may due to the introduction of
Keggin structure and it was loaded in the mesoporous
channels of the catalysts successfully.
Table 2 listed the styrene conversion and PXE yield
with different catalyst precursors. As displayed in
Table 2, it can be observed that catalysts with different
precursors all exhibit a relative high PXE yield and distin-
guished selectivity. Among them, PW/MPIL-100(1:2) and
PW/MPIL-100(1:3) exhibit the 100% styrene conversion.
On the contrary, the catalyst activity of PW/MPIL-
100(1:1) was not corresponding with the styrene conver-
sion and PXE yield were 82.51% and 81.34%, respectively.
In Table 2, it can be find that the low surface and pore
volume construction of MPIL-100(1:1) was unfavorable
for the reaction. Therefore, the designed profitable struc-
ture is beneficial to the catalytic performance of catalyst.
3
−
PW O
2 40
through the ionic exchange step. Moreover,
1
the obvious meso-macroporous structure is evident on
the TEM image (Figure 2C). EDS elemental mapping
(Figure 2D-F) confirms the immobilization of high-
dispersity PW species, which is consistent with FT-IR of
PW/MPIL-100(1:2). Moreover, XPS of PW/MPIL-100(1:2)
(Figure S1) verifies the composition and valence states of
the elements, and XRD patterns reflect the amorphism of
ꢀ
the carbon skeleton on 2θ =15–25 .
XPS was performed to detect the surface chemical
composition of the material and analyze the valence
states of the elements in the PW/MPIL-100 (1:2). It can
be observed from the XPS wide scan spectrum (Figure 3)
that PW/MPIL-100 (1:2) was composed of C, N, O, P,
W. At about 284.2 eV, the C1s spectrum shown a signal
peak which was assigned to C-C bonds within the cata-
lyst. The N1 s spectrum can be observed in two peaks at
3.2 | Catalytic performance evaluation
Stability and reusability of the catalyst are vital for any
catalytic system. Also, the cycling performance of the cat-
alyst PW/MPIL-100(1:2) were summarized in Figure 4. In
this section, the catalysts with different ratio of DVB are
investigated through the target alkylation of o-xylene
with styrene. The specific reaction process is listed in the
experimental section. It can be observed that when the
p = 2, the catalyst perform a much better yield. Too little
or too much DVB both effect the property of the sample
and the reason of this phenomenon may attribute to the
polymerization of different functional groups during the
process which may block the active site of the catalyst. It
can be observed that only 13.5% reduction in the activity
4
00.1 eV and 401.2 eV respectively which corresponds to
N-C and N=C bond. A wide signal peak at about
d133.8 eV was displayed in the P2p spectrum which
5+
ascribe the existence of the oxidation state of P .
Besides, the W4f spectrum is deconvoluted into two sig-
nificant peaks at 35.1 eV (4f5/2) and 37.2 eV (4f7/2),
respectively, which are typically attributed to the W–O
6+
bond configuration and W in HPW of the W element.
Combining XPS spectrum of P2p and W4f, it can be veri-
fied that 12-tungstophosphoric acid exhibits a typical

POLYMERS POROUS MATERIALS P123; MESO-MACROPOROUS STRUCTURE CATALYSIS
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FIGURE 3 XPS wide scan spectra
of PW/MPIL-100(1:2) (A) and C1s, N1 s,
P2p and W4f of PW/MPIL-100(1:2) (BE)
TABLE 2 Yield of PXE and conversion of styrene in the
alkylation of o-xylene and styrene
Styrene Conversion
(%)
PXE Yield
(%)
Catalyst
PW/MPIL-100(1:1)
82.5
81.3
96.4
95.4
86.2
91.3
88.4
PW/MPIL-100(1:2) 100.0
PW/MPIL-100(1:3) 100.0
PW/MPIL-80(1:2)
PW/MPIL-90(1:2)
PW/MPIL-110(1:2)
87.5
92.6
90.2
FIGURE 4 Cycling performance test of PW/MPIL-100(1:2)
Reaction conditions: o-xylene: styrene = 7.5:1, reaction temperature = 393 K
reaction time = 1.0 hr, catalyst dosage 0.20 g
3.3 | Plausible mechanism of the catalyst
is observed after 4 runs for the catalyst PW/MPIL-
Figure 5 reveals the possible formation mechanism of
PW/MPIL-T(p), which is tentatively elucidated based on
the P123 and DVB interaction. As we all know, triblock
P123 molecules were introduced into mesoscale micelles
in aqueous systems through self-assemble method due to
the hydrophobic core and the hydrophilic head of
1
00(1:2). The catalyst PW/MPIL-100(1:2) was prepared
by anion exchange process, thus, it's easier to site the acid
sites because of the strong interaction between the active
composition and support. And the PXE yield reached
8
5.5% after 4 times.

6
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SHA ET AL.
FIGURE 5 Postulated
formation mechanism of the meso-
macroporous poly (acidic ionic
liquid)
amphiphilic molecules. The polymerization process con-
sists of three parts. Firstly, a uniform transparent P123
micelle solution is formed. The size of P123 micelles is
solution-dependent, which affects pore size and pore size
distribution of the synthetic polymer. Secondly, the dis-
persion process of IL and DVB is a critical intermediate
process. In the third stage of crosslinking polymerization
on micelle surface, P123 micelles are wrapped by cross-
linked polymerization products. Then the template P123
is removed by solvent extraction and catalyst PW/MPIL-
T(p) is prepared by anion exchange. The difference in the
physicochemical properties among samples may be
ascribed to the P123 micelle distinction caused by P123
aggregation at different temperatures and DVB dosages.
Meanwhile, there is also an interaction with P123 and
the physicochemical properties of MPILs are evidently
affected by the reaction temperature and the IL to DVB
molar ratio.
through exchanging with the acidic anions. The samples
were characterized by FT-IR, BET, TG, SEM, TEM, XRD
and XPS analysis techniques together with the catalyst
performance test, and the results proved that the catalyst
the can achieve the best conversion ratio(100%) and PXE
Yield(96.4%) Also, the catalyst contains abundant meso-
pores and presents great thermal stability and surface
area. The PW/MPIL-T(p) exhibited an excellent catalytic
activity in the alkylation of styrene with o-xylene. As a
heterogeneous catalyst, PW/MPIL-T(p) can be easily sep-
arated from the reaction solvent which can especially cut
the cost of the catalyst. In addition, from a potential
application perspective, the as-prepared showed a prom-
ising catalytic performance in alkylation of o-xylene and
styrene. Through this study, it may be possible to develop
some novel green and time-saving routes for reactions
such as Friedel-Crafts reaction, transesterification, esteri-
fication, cellulose hydrolysis reaction and so on under
heteropolyanion-loaded condition which may finally
greatly expanded the application of solid acidic catalytic
materials.
4
| CONCLUSION
Meso-macroporous poly (ionic liquid) materials were suc-
cessfully synthesized under free radical copolymerization
and anion change together with a templating approach
by using P123 as the soft template and cross-linking of
DVB. The channel construction and physicochemical
properties of MPIL-T(p) can be adjusted easily by control-
ling appropriate reaction temperature and the IL to DVB
molar ratio. The MPILs can be simply modified chemi-
cally, owing to the special properties of the IL-like struc-
ture units in the meso-macroporous polymer
frameworks. Thus, based on the structural properties,
heteropolyanion-loaded catalysts were synthesized
ACKNOWLEDGEMENTS
The authors are grateful to the financial supports of the
National Natural Science Foundation of China (Grant
No. 21676056, 21376051 and 51673040), “Six Talents Pin-
nacle Program” of Jiangsu Province of China (JNHB-
006), Qinglan Project of Jiangsu Province (1107040167).
CONFLICT OF INTEREST
There are no conflicts to declare.
ORCID
Xiao Sha https://orcid.org/0000-0002-7377-2293

POLYMERS POROUS MATERIALS P123; MESO-MACROPOROUS STRUCTURE CATALYSIS
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How to cite this article: Sha X, Sheng X, Zhou Y,
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High-Performance Alkylation. Appl Organometal
Chem. 2020;e5460. https://doi.org/10.1002/aoc.
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