Benzotriazolium ionic liquid immobilized on periodic mesoporous organosilica as an effective reusable catalyst for chemical fixation of CO2into cyclic carbonates

Article abstract of DOI:10.5562/CCA3668

A type of dichloro(dimethoxyethane)nickel anionic benzotriazolium ionic liquid-functionalized periodic mesoporous organosilicas were synthesized and tested as effective and practical heterogeneous catalysts in the cycloaddition of CO2 with epoxides. The catalyst PMO?ILC4H10O2NiCl3(1.0) showed brilliant catalytic activity for the synthesis of cyclic carbonates with high yields and selectivities under solvent- and cocatalyst-free conditions. We also found that the catalytic activity could be significantly influenced by the hydroxyl groups sites of periodic mesoporous organosilica and the active sites (hydroxyl groups/ dichloro(dimethoxyethane)nickel anion) of the benzotriazoliumcation ionic liquid, probably due to an intensification of intramolecular synergistic effect. The catalytic process displayed ease of recovery, excellent stability and recyclability for at least five runs without significant loss of its catalytic activity.

Full text of DOI:10.5562/CCA3668

O R I G I NA L S C I E N T I F I C P A P E R
Croat. Chem. Acta 2020, 93(2)
Published online: November 21, 2020
DOI: 10.5562/cca3668
Benzotriazolium Ionic Liquid Immobilized on
Periodic Mesoporous Organosilica as an Effective
Reusable Catalyst for Chemical Fixation of CO into
2
Cyclic Carbonates
Jing Rui Li, Yu Lin Hu*
College of Materials and Chemical Engineering, Key laboratory of inorganic nonmetallic crystalline and energy conversion materials, China Three Gorges University,
Yichang 443002, China
*
Corresponding author’s e-mail address: huyulinꢀ9ꢁꢂ@ꢀꢃꢄ.com
RECEIVED: June 27, 2020
REVISED: October 22, 2020
ACCEPTED: October 24, 2020
Abstract: A type of dichloro(dimethoxyethane)nickel anionic benzotriazolium ionic liquid-functionalized periodic mesoporous organosilicas
were synthesized and tested as effective and practical heterogeneous catalysts in the cycloaddition of CO with epoxides. The catalyst
PMO@ILC NiCl (ꢀ.ꢅ) showed brilliant catalytic activity for the synthesis of cyclic carbonates with high yields and selectivities under
2
4 10
H O
2
3
solvent- and cocatalyst-free conditions. We also found that the catalytic activity could be significantly influenced by the hydroxyl groups sites
of periodic mesoporous organosilica and the active sites (hydroxyl groups/ dichloro(dimethoxyethane)nickel anion) of the benzotriazolium-
cation ionic liquid, probably due to an intensification of intramolecular synergistic effect. The catalytic process displayed ease of recovery,
excellent stability and recyclability for at least five runs without significant loss of its catalytic activity.
Keywords: immobilized ionic liquid, periodic mesoporous organosilica, recyclable catalyst, carbon dioxide, cyclic carbonates.
metal complexes,[16–19] organocatalysts,[20–22] MOFs,[23–25]
INTRODUCTION
MgO/TBAB/Bu
4
NBr,[26] Bp-Zn@MA,[27] H-MFeSN,[28] and
[
29–31]
HEMICAL transformation of carbon dioxide into valua-
ble intermediates has attracted broad attention, as
2
is an economical and nontoxic C1 building block in or-
others.
In spite of their potential utility, however,
C
most of them still have problems such as harsh reaction
conditions, use of expensive reagents, cumbersome
product isolation and catalyst reusability procedures. Thus,
the development of new catalytic systems for the
cycloaddition that are more sustainable, more efficient and
more environmentally friendly is still a challenging goal.
Ionic liquids (ILs) have attracted much attention
CO
[
1–3]
ganic synthesis.
the cycloaddition of CO
bonates, which can be widely used in fine chemicals and or-
One of the most attractive protocols is
2
and epoxides to afford cyclic car-
[4–6]
ganic reactions.
epoxides and carbon dioxide into cyclic carbonates can
proceed with alkali metal salts, quaternary ammonium
Generally, the transformation from
[
7,8]
because of the excellent properties and have meaningful
applications in many fields, such as catalysis, chemical con-
[9,10]
and phosphonium salts catalysts.
However, most of
[
32–34]
these systems often need solvents or homogeneous
additives, high pressures and temperatures. Recently,
considerable effort has been devoted to the development
of efficient catalytic systems for the synthesis of cyclic
version, etc.
liquids as catalysts for the transformation of CO
Studies involving the utilization of ionic
into cyclic
Although, these
2
[35–37]
carbonates have also been reported.
functionalized ILs catalysts are quite effective but their
practical applications are restricted by some defects in the
separation and recyclability. Hence, the development of
[
11]
[12]
carbonates such as nano-PDA/KI,
ZnI
2 3
/NEt ,
2 2 2 2 3
Cp TiCl /Al O -TBAI,
)/KI,[13] ZnCl
[14]
[15]
(
Zn-SBA-15/KI,
This work is licensed under a Creative Commons Attribution 4.0 International License.

2
(not final pg. №)
J. R. LI and Y. L. HU: Benzotriazolium Ionic Liquid Immobilized …
4 10 2 3
was only bulk ionic liquid of ILC H O NiCl or ILCl and PMO
support catalysts (Table 1, entries 6–8). Therefore,
PMO@ILC NiCl (1.0) is thought to the suitable cata-
4
H
10
O
2
3
lyst for the reaction. Then, the effect of catalyst dosage on
the cycloaddition was examined. The yield of propylene
carbonate increased with the catalyst amount of the cata-
lyst was increased from 5 mg to 20 mg (Table 1, entries 4,
1
0-12), while a further increase in the catalyst amount did
not gave more product (Table 1, entries 13 and 14). There-
fore, the best result was obtained with 20 mg catalyst.
The effect of the reaction temperature on the
Scheme ꢀ. Catalytic synthesis cyclic carbonates from CO
and epoxides with PMO@ILC NiCl
2
4
H
10
O
2
3
.
cycloaddition
PMO@ILC
was
NiCl
studied
over
the
catalyst
4
H
10
O
2
3
(1.0), and the results are revealed in
easy recovery and recyclable ionic liquid-based heteroge-
neous catalysts are always in demand. Immobilization of
Ionic liquids onto porous solid supports to explore hetero-
geneous supported ILs has gained comprehensive atten-
Figure 1. As shown in the figure, the yield and selectivity of
propylene carbonate were significantly increased with the
increase of reaction temperature. While, the temperature
was further increased from 110°C to 130°C, the yield and
selectivity of propylene carbonate showed a slight
decrease. The reason may be that the overly high
temperatures can increase the occurrence of side reactions
of isomerization and ring opening of propylene oxide,
which was determined by GC analysis. These results
indicated that the suitable temperature was 110 °C. The
[38–41]
tion.
Among these soild supports, periodic
mesoporous organosilicas (PMOs) have attracted increas-
ing attention because of their combined advantages of
large specific surface areas, tunable pore sizes, uniform
distribution of functional groups, chemical and thermal sta-
bilities, as well as highly ordered mesostructure proper-
[
42–50]
ties.
As part of our ongoing interest in the
development of efficient and environmentally friendly cat-
alytic systems, herein, we intend to perform immobilization
of benzotriazolium ionic liquid onto periodic mesoporous
organosilica to design multifunctional immobilized ionic liq-
2
Table 1. Catalyst screening for CO cycloaddition to
propylene oxide.
(
a)
Catalyst / Time / Yield / Selectivity /
Entry
Catalyst
PMO@ILC
(
b)
(b)
uids. The obtained PMO@ILC
ionic liquid concentration have been employed as hetero-
geneous and recyclable catalysts in the cycloaddition of CO
4
H
10
O
2
NiCl
3
with different
mg
h
%
%
4 10
H
1
2
3
4
5
20
5
5ꢇ.ꢅ
8ꢂ.ꢆ
9ꢄ.ꢈ
9ꢈ.ꢀ
9ꢈ.ꢄ
99.ꢅ
99.ꢆ
99.ꢄ
99.7
99.4
O
2
NiCl (ꢅ.ꢆ)
PMO@ILC
NiCl (ꢅ.6)
PMO@ILC
NiCl (ꢅ.ꢁ)
PMO@ILC
NiCl (ꢀ.ꢅ)
PMO@ILC
NiCl (ꢀ.ꢂ)
NiCl
3
2
4 10
H
20
20
20
5
with epoxides under cocatalyst- and solvent-free condi-
tions (Scheme 1). Additionally, the recyclability and reusa-
bility of the catalyst was also investigated.
O
2
3
H
4 10
3.ꢈ
3.ꢈ
3.ꢈ
O
2
3
H
4 10
O
2
3
RESULTS AND DISCUSSION
H
4 10
20
O
2
3
The catalytic activities of PMO@ILC
tested in the model reaction of CO
propylene oxide to produce propylene carbonate. As shown
in Table 1, the efficiency of PMO@ILC NiCl with
different ionic liquid concentration was screened. The
immobilized ILs catalysts include PMO@ILC NiCl (0.4),
PMO@ILC NiCl (0.6), PMO@ILC NiCl (0.8),
PMO@ILC NiCl (1.0), and PMO@ILC NiCl (1.2)
4 10
H O
2
NiCl
3
(x) were
20(c)
6
7
8
9
ILC
4
H
10
O
2
3
12
12
12
24
89.ꢈ
46.7
24
9ꢆ.ꢈ
9ꢀ.ꢄ
93.1
0
2
cycloaddition with
ILCl
20(c)
20(c)
–
PMO
H O
4 10 2
3
–
0
H O
4 10 2
3
PMO@ILC
NiCl
PMO@ILC
NiCl (ꢀ.ꢅ)
PMO@ILC
NiCl (ꢀ.ꢅ)
PMO@ILC
NiCl (ꢀ.ꢅ)
PMO@ILC
NiCl (ꢀ.ꢅ)
4
H
(ꢀ.ꢅ)
4 10
H
10
1
0
5
6
4ꢄ.ꢇ
8ꢄ.ꢂ
9ꢂ.ꢀ
9ꢈ.ꢅ
9ꢆ.ꢇ
99.4
99.3
99.4
99.3
99.1
O
2
3
4
H
10
O
2
3
4
H
10
O
2
3
4
H
10
O
2
3
4
H
10
O
2
3
11
10
15
25
30
4
O
2
3
could significantly enhance the catalytic activity of cycload-
dition (Table 1, entries 1–5), and PMO@ILC NiCl (1.0)
showed the highest catalytic activity with 95.1 % yield and
9.7 % selectivity (Table 1, entry 4). It was found that the
H
4 10
1
2
3
3.ꢈ
3.ꢈ
3.ꢈ
4
H
10
O
2
3
O
2
3
H
4 10
1
O
2
3
9
H
4 10
reaction did not accomplished in the absence of catalyst,
even the reaction time was prolonged to 24 h (Table 1, en-
try 9). For comparison, it was also observed that the
cycloaddition could not be carried out successfully if there
14
O
2
3
(a) Reaction conditions: propylene oxide (10 mmol), CO (ꢀ.ꢅ MPa), catalyst,
2
1
10 °C.
Determined by using GC;
(c) Reaction temperature is 150 °C.
(b)
Croat. Chem. Acta 2020, 93(2)
DOI: 10.5562/cca3668

J. R. LI and Y. L. HU: Benzotriazolium Ionic Liquid Immobilized …
(not final pg. №) 3
effects of initial pressure on the cycloaddition was also
studied (Figure 2). As shown in the figure, the yield and
selectivity of propylene carbonate were strengthened
gradually with the CO
.2 MPa to 1.0 MPa. However, the yield and selectivity of
propylene carbonate showed a visible decrease when CO
pressure was above 1.0 MPa. The reason may be that too
high CO pressure retard the interaction of propylene
oxide, CO and PMO@ILC NiCl (1.0), which reduced
the concentration of propylene oxide and lead to low yields
2
pressure was increased from
0
2
2
2
4
H
10
O
2
3
[
13–16]
and selectivities.
pressure was 1.0 MPa.
The stability and reusability are important properties
for the designed catalyst PMO@ILC NiCl (1.0), which
It can be observed that the proper
4
H
10
O
2
3
was evaluated in the cycloaddition of propylene oxide with
Figure 3. Reusability test of catalyst for synthesis of
propylene carbonate.
Figure ꢀ. The effect of the reaction temperature on
the cycloaddition. Reaction conditions: propylene oxide
Figure 4. FT-IR spectra of fresh and reusable catalyst.
(ꢀꢅ mmol), PMO@ILC
4 10 2 3 2
H O NiCl (ꢀ.ꢅ) (ꢂꢅ mg), CO
pressure (ꢀ.ꢅ MPa), ꢄ.ꢈ h.
Figure 5. Hot filtration test and leaching effect of
PMO@ILC
carbonate. Reaction conditions: propylene oxide (10 mmol),
CO (ꢀ.ꢅ MPa) at 110 °C with catalyst (a) and catalyst
removal (b) after 2 h.
4 10 2 3
H O NiCl (ꢀ.ꢅ) for synthesis of propylene
Figure ꢂ. The effect of the CO
tion. Reaction conditions: propylene oxide (ꢀꢅ mmol),
PMO@ILC NiCl (ꢀ.ꢅ) (ꢂꢅ mg), ꢀꢀꢅ °C, ꢄ.ꢈ h.
2
pressure on the cycloaddi-
2
H O
4 10 2
3
DOI: 10.5562/cca3668
Croat. Chem. Acta 2020, 93(2)

4
(not final pg. №)
J. R. LI and Y. L. HU: Benzotriazolium Ionic Liquid Immobilized …
CO
2
under optimized conditions (Figure 3). The catalyst
Table 2. Formation of cyclic carbonates from diverse
(
a)
could be easily recovered by simple filtration, and then re-
used directly in the following runs. The results demon-
strated that the catalyst can be recycled for five
consecutive runs without significant loss in catalytic activ-
ity. In addition, FT-IR spectra for the recovered catalyst af-
ter five runs was similar to that of fresh catalyst, indicating
that its characteristic framework did not change signifi-
cantly during the reaction (Figure 4). Furthermore, a hot fil-
tration test confirmed that the reaction follows a
heterogeneous pathway and no obvious active species
leaching was present in the catalytic process (Figure 5).
These results clearly illustrating the excellent stability and
recyclability of the designed catalyst.
epoxides and CO
2
.
Time / Yield / Selectivity /
Entry Epoxide
Product
(b)
(b)
h
%
%
O
O
1
O
O
O
O
3.ꢈ
95.ꢀ
99.7
O
O
O
2
3.ꢈ
3.ꢈ
9ꢆ.ꢄ
9ꢂ.ꢁ
99.3
99.5
O
O
3
O
O
O
O
O
4
5
OCH3
3.ꢈ
5.ꢅ
9ꢇ.ꢃ
8ꢆ.ꢅ
99.4
99.ꢂ
OCH
O
3
O
O
The versatility of the catalyst PMO@ILC
4 10 2 3
H O NiCl (1.0)
O
for the cycloaddition of CO with different substituted
2
epoxide substrates were studied under the optimal
reaction conditions, and corresponding results were
detailed in Table 2. The CO cycloaddition with different
2
O
O
O
O
6
7
C
l
3.ꢈ
4.ꢅ
9ꢅ.ꢅ
89.ꢈ
99.ꢀ
Cl
O
terminal epoxides containing electron withdrawing and
electron donating groups exhibited good to excellent
yields. All the terminal cyclic carbonates were obtained
with good to high yields (84.0 %~97.6 %) and excellent se-
lectivity (> 99 %) within the reaction time of less than 5 h.
However, the reaction of cyclohexene oxide requires a
longer time of 5 h to obtain a good yield (Table 2, entry 5),
which may be ascribed to the steric hindrance obstructed
the nucleophilic attack of anion.
O
O
99.ꢄ
O
(
a)
b)
Reaction conditions: propylene oxide (10 mmol), CO
PMO@ILC NiCl (ꢀ.ꢅ) (ꢂꢅ mg), 110 °C.
Determined by using GC.
2
(ꢀ.ꢅ MPa),
4
H
10
O
2
3
(
through the coordination of active nickel anion and
hydroxyl sites of PMO@ILC NiCl (1.0) and the oxygen
4
H
10
O
2
3
of epoxide, resulting in the polarization of C–O bond, so as
On the basis of the above results and those
previously reported works,[12–15,18–21] a possible mechanism
is proposed in Scheme 2. First, epoxide could be activated
to form the intermediate i, together with the adsorption
and activation of CO
2
by the benzotriazolium cation to form
carbonate species. Meanwhile, the nucleophilic attack of
Scheme ꢂ. Proposed possible reaction mechanism for the synthesis of cyclic carbonates.
Croat. Chem. Acta 2020, 93(2)
DOI: 10.5562/cca3668

J. R. LI and Y. L. HU: Benzotriazolium Ionic Liquid Immobilized …
(not final pg. №) 5
anion on the less sterically hindered carbon atom of
epoxide generates the intermediate ii. Then, there is
nucleophilic attack of the oxygen anion (ii) on the C atom
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iii. Finally, cyclic carbonate is formed by subsequent
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CONCLUSION
6
In conclusion, this work demonstrates the synthesis of a
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O
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with excellent stability is a reusable catalyst that can be
recycled for five consecutive times without significant
loss of activity. These discoveries suggests that
2
to epoxides. The catalytic results
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