Formation of Cyclic Carbonates from CO2 and Epoxides Catalyzed by a Cobalt-Coordinated Conjugated Microporous Polymer

Article abstract of DOI:10.1002/cctc.201700386

An inexpensive and effective cobalt coordinated conjugated microporous polymer (Co-CMP-2) made up from cross-linked an ethanediamine-based salen ligand with 1,3,5-triethynylbenzene. Co-CMP-2 exhibited extremely high catalytic efficiency in the synthesis of cyclic carbonates from CO₂ and epoxides, which is superior to that of previously reported Co-CMP. Co-CMP-2 achieved a TOF of 23300 h^?1 for ethylene carbonate. Moreover, the catalyst can be reused more than 10 times without significant loss in activity.

Full text of DOI:10.1002/cctc.201700386

Accepted Article
Title: Formation of cyclic carbonates from CO2 and epoxides catalysed
by a cobalt coordinated conjugated microporous polymer
Authors: Jian Xiong, Ruixia Yang, Yong Xie, Nianyu Huang, Kun Zou,
and Weiqiao Deng
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ChemCatChem
10.1002/cctc.201700386
FULL PAPER
Formation of cyclic carbonates from CO and epoxides catalysed
2
by a cobalt coordinated conjugated microporous polymer
[ab]
[b]
[b]
[a]
[a]
[b]
Jian Xiong, Rui-Xia Yang, Yong Xie, Nian-Yu Huang, Kun Zou,* and Wei-Qiao Deng*
Abstract: A cheap and effective cobalt coordinated conjugated
microporous polymer (Co-CMP-2) was synthesized by the
ethanediamine-based salen ligand cross-linked with 1, 3, 5-
triethynylbenzene. Co-CMP-2 exhibited extremely high catalytic
coordinated CMPs have
a
superior performance to
corresponding homogeneous catalyst as heterogeneous
[
18]
catalysts
.
In this work, we extended the previous research and obtained
a cheaper but more effective cobalt coordinated conjuguated
microporous polymer (Co-CMP-2). This polymer was
synthesized by easily available ethylenediamine and 5-
Bromosalicylaldehyde. Moreover, its catalytic activity has been
efficiency in product of cyclic carbonates from CO
2
and epoxides,
which is superior to previous Co-CMP. The TOF of Co-CMP-2 could
-1
reach 23300 h for ethylene carbonate. Moreover, it can be reused
more than 10 times without significant loss in its catalytic activity.
significantly improved for the coupling reaction of CO
epoxides. For the reaction of propylene oxide and CO , the TON
of Co-CMP-2 is 236, which is higher than that of previous Co-
2
and
2
Introduction
[17]
CMP (201).
Moreover, the TOF of Co-CMP-2 can reach
-1
23300 h at mild conditions for ethylene carbonate, which is the
The CO
2
emission has attracted attention because it is widely
[19]
best among literature reports to the best of our knowledge.
This polymer still remains the significant recyclability for the
coupling reaction, remaining a yield of 96.2% after 10 times of
regeneration.
[
1]
considered as a primary factor to the changes in global climate.
[
2]
However CO
conversion of CO
strategy for reducing CO
2
itself is an excellent C
1
resource. Therefore, the
into useful chemicals became an important
2
[
3]
2
emission. One of these useful
chemicals is cyclic carbonate that has wide applications in
chemical industries. The cyclic carbonates were formed by the
Results and Discussion
cycloaddition reaction of CO
2
with epoxides. Up to now, plenty of
[
4]
catalyst systems for this reaction have been reported. For
To prepare Co-CMP-2, first we synthesized dibromo-
functionalized precursor monomers (Salen-Co) prepared by a
[
5]
[6]
[7]
instance, salen, metal salts, ionic liquids and porphyrin
[
8]
complexes were effective catalysts. However these catalysts
were homogeneous catalysts with difficulties to be separated.
[20]
complexation reaction of Salen and cobalt acetate (Co(OAc)2).
After removing impurities, we produced the Co-CMP-2 (Scheme
[
9]
Other metal oxides immobilized catalyst as heterogeneous
catalysts also have been claimed but suffering the problem of
low catalytic activities. It remains
3 4
1) catalysed by Pd(PPh ) and CuI with 1, 3, 5-triethynylbenzene
in toluene under reflux. The synthesis details are given in the
Supplementary Information. Like other CMPs, the polymer, Co-
CMP-2, was also completely insoluble in any organic solvents
and exhibited high thermal stabilities, of which pyrolysis
temperature is about 300℃ shown in Figure S1.
[
10]
a
challenge
for the
development of the synthesis of cyclic carbonate in
heterogeneous catalyst at mild conditions.
Conjugated microporous polymers (CMPs) discovered by
[
11]
Cooper group are of great interest because they have lots of
excellent properties. These CMPs can be tailored for various
[
12]
[11,13]
applications
superhydrophobic
including
catalysis,
gas
sensors
sorption,
[
14]
[15]
separations,
and
[
16]
supercapacitors. In recent years, several metal functionalized
CMPs were reported to have the combination of various
properties together such as the combination of gas sorption and
catalytic activity. In this field, we developed a cobalt/aluminium
functionalized CMPs which can capture CO
2 2
and convert CO
into cyclic carbonates at room temperature and atmospheric
[
17]
pressure.
2
Because of high CO capture ability, the metal
Scheme 1. Synthesis of Co-CMP-2
[
a]
Jian Xiong, Nian-Yu Huang, Kun Zou*
Hubei Key Laboratory of Natural Products Research and
Development, College of Biology and Pharmacy, China Three
Gorges University
Yichang 443002, P. R. China.
E-mail: kzou@ctgu.edu.cn
Jian Xiong, Rui-Xia Yang, Yong Xie, Wei-Qiao Deng*
State Key Laboratory of Molecular Reaction Dynamics, Dalian
National Laboratory for Clean Energy, Dalian Institute of Chemical
Physics, Chinese Academy of Sciences, Dalian 116023, China.
E-mail: dengwq@dicp.ac.cn
Scanning electron microscopy (SEM) and high-resolution
transmission electron microscopy (HR-TEM) were used to
record the morphological structure of Co-CMP-2. The SEM
images shown in Figure 1 a and b reveal that the Co-CMP-2
network morphologically consists of submicron spheres with
porous features and it can be also observed from the HR-TEM
pictures (Figure 1 c and d) that the Co-CMP-2 show finely
ordered micropores with roughly 0.5 nm in diameter. According
to these images, the polymer was featureless at those length
scales.
[
b]
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the document.((Please delete this text if not appropriate))
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Figure 2.CO
98K
2
-adsorption and desorption isotherm for polymer Co-CMP-2 at
2
Figure 1. SEM images of Co-CMP-2 with different scan bars of 5µm (a) and
CO
volumetric methods. As given in Figure 2, Co-CMP-2 shows a
good CO adsorption quantity of 64.6 mg/g, much higher than
reported CMPs . The CO
CMPs were 59.4 mg/g, 36.1 mg/g and 55.4 mg/g under the
same condition, although they have higher surface area than
that of Co-CMP-2. The excellent uptake capacity is ascribed to
the good porosity of Co-CMP-2. On the other hand, the metal
centres distributing in the CMP-2 network can function as active
2
adsorption was measured at 298K and 1bar using
1µm (b); HR-TEM images of Co-CMP-2 with different scan bars of 10nm (c)
and 5nm (d).
2
[
21]
2
uptakes of the tetrahedrally linked
Moreover, nitrogen sorption isotherms were measured to
investigate the porosity of Co-CMP-2 and the results are further
demonstrated that the Co-CMP-2 network is porous. As
summarized in Table 1, the Co-CMP-2 shows a high Brunauer-
2
Emmett-Teller (BET) surface area of 475 m /g and total pore
3
volume of 0.918cm /g. According to IUPAC classification, Co-
sites to attract CO
2
molecule, facilitating to the CO
2
adsorption.
CMP-2 gave rise to type І isotherms (Figure S2), indicating that
the material consisted of both micropores and mesopores. Metal
2
Table 2.Cycloaddition of CO with ethylene oxide
(
Co) content distributed in the polymer network is determined by
inductively coupled plasmaoptical emission spectroscopy (ICP-
OES) and 6.15 wt% of Co is detected, less than the theoretical
value of 10.07 wt%. FT-IR result with characteristic peaks at
-1
around 3425cm , attributed to the O-H vibrations, indicated the
existence of the Salen units in the Co-CMP-2 framework without
Co-coordinated (Figure S4). The solid-state NMR data of Co-
CMP-2 is in Supplementary Figure S3.
[
a]
-1
Entry
Co-CMP-2
mol%)
TBAB(mmol)
Yields (%)
TOF(h )
(
[
[
[
c]
b]
b]
1
2
3
4
5
6
0
0.9
0.9
0.9
0.9
0.9
0.9
18.6
99.2
88.5
81.8
63.2
58.4
10.35
990
0.1
Table 1.Physical properties for Co-CMP-2.
Parameter
value
475
0.05
0.01
0.005
0.0025
1710
8180
12600
23300
2
[a]
[b]
[b]
[b]
[b]
S
V
BET (m /g)
3
tot (cm /g)
0.918
10.07
6.15
[
c]
Mcalc (wt%)
[
d]
Reaction conditions: EO (50mmol, 2.2g), 100℃, 3.0 MPa initial CO
2
pressure,
MICP (wt%)
1h, 40mL autoclave. [a] Yields of isolated product obtained after column
[
e]
CO
2
uptake (mg/g)
64.6
chromatography. [b] TOF = mol of EC produced per mol of Co catalytic center
-
per hour. [c] TOF = mol of EC produced per mol of Br per hour.
[
a] Brunauer-Emmett-Teller (BET) surface area was calculated in the
pressure range of (p/p ) 0.05−0.3; [b] Total pore volume was measured at
p/p = 0.99; [c] Data was calculated based on 100% reaction of salen unit;
d] Data was obtained by inductively coupled plasma-optical emission
0
0
2
Co-CMP-2 was used as solid catalyst for CO transformation
[
spectroscopy (ICP-OES); [e] Volumetric CO
isotherms were measured for Co-CMP-2 at 298 K.
2
-adsorption-desorption
in this work. The Co-CMP-2 exhibits exceptional catalytic activity
towards the cycloaddition of CO2 and ethylene oxide with n-
tetrabutylammonium bromide (TBAB) as co-catalyst. Using 0.1
mol% of Co-CMP-2 and 0.9 mmol of TBAB, a yield of 99.2%
-1
was achieved with a TOF=990 h (entry 2, Table 2). However,
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the reaction catalysed by the co-catalyst TBAB only gave a yield
Bromosalicylaldehyde materials, the CO-CMP-2 catalyst can be
used as a promising candidate in industrial application.
-1
of 18.6% with a TOF=10.35 h (entry 1, Table 2) in the absence
of Co-CMP-2. The results indicate that the Co-CMP-2 polymer
2
exhibited high catalytic activity for CO transform. With the use
of reduced amounts of Co-CMP-2 (entry 3-6, Table 2),
considerable yields could still be achieved. Especially, when the
amount of Co-CMP-2 reduced to just 0.0025 mol% of the
ethylene oxide , an extremely high TOF up to 23300 h per mole
of Co loading can be obtained, indicating that the Co-CMP-2 has
Conclusions
In conclusion, the Co-CMP-2 polymer can not only capture CO
but also transform CO with high efficiency under atmospheric
pressure and room temperature. A significantly high TOF was
achieved for the cycloaddition of CO and ethylene oxide.
Besides, the low cost of the Co-CMP-2 is also favourable for the
2
-1
2
an superior catalytic ability for the CO
Table 2).
2
transformation(entry 6,
2
To further demonstrate the superiority of Co-CMP-2, we next
carried out reactions to compare with previous Co-CMP (Table
real application. This work provides
heterogeneous catalyst and new strategy for CO
a
cost-effective
conversion.
2
3). As for ethylene carbonate, Co-CMP-2 gave excellent yield
(
99.1%) at the relatively high temperature(100 ℃ ) and CO
2
The work is supported by NSFC 21373202 and 21525315.
pressures (3MPa)(Entry 1, Table 3). For the reaction to produce
propylene carbonate, the TON of Co-CMP-2 exhibited 236 with
yield 98.7% (Entry 2, Table 3), which is better than that of
Experimental Section
[
17]
previous Co-CMP (TON 201 with yield 98.1%).
The procedure for the synthesis of Co-CMP-2: Salen-Co-OAc(scheme 1,
2
Table 3. Cycloaddition of CO with various epoxides.
0.6mmol), 1, 3, 5-triethynylbenzene (1.2mmol), copper(I) iodide (50 mg)
[
a]
and tetrakis-(triphenylphosphine) palladium(0) (100 mg) were dissolved
in a mixture of toluene (15 mL) and triethylamine (6 mL). The reaction
mixture was heated to 40℃ and stirred for 1 hour under an argon
atmosphere (to exclude oxygen and prevent any homocoupling of the
alkyne monomers). Next, the reaction mixture was heated to 80℃, stirred
for 72 hours, then cooled to room temperature. The insoluble precipitated
polymer was filtered and washed four times with dichloromethane,
methanol, water, and acetone to remove any unreacted monomers or
catalyst residues. Further purification of the polymer was carried out by
Soxhlet extraction with methanol and dichloromethane (volume ratio =
1:1) for 48 hours. The product was dried in a vacuum for 24 hours at
70 °C and isolated as a brown powder (yield: 79.6%).
Entry
Substrate
Product
T/℃
P/MPa
Yield /%
TON
TOF
h
[
d]
[e] -1
[
[
b]
c]
1
EO
PO
EC
PC
100
100
3.0
3.0
99.1
98.7
237
236
237
236
2
[
a] Yields of isolated product obtained after column chromatography. [b]
EO=ethylene oxide, EC=ethylene carbonate, reaction conditions: Co-CMP-
(100mg), EO (25mmol), co-catalyst (TBAB) 1.8mmol, 1h. [c] PO=propylene
oxide, PC=propylene carbonate, reaction conditions: Co-CMP-2(100mg), PO
25mmol), TBAB 1.8mmol, 1h. [d] TON = (moles of product)/(moles of metal in
2
(
the catalyst). [e] TOF = mol of product produced per mol of Co catalytic center
per hour.
The procedure for the synthesis of cyclic carbonates at room temperature
and atmospheric pressure (Propylene oxide as an example): A mixture of
Bu
vacuum tube reaction. Propylene oxide (25 mmol, 1.75 ml) was added to
the tube using a syringe, and CO (at atmospheric pressure) was
4
NBr (1.8 mmol, 600 mg) and Co-CMP-2 (100 mg) was placed in a
2
introduced. After being stirred for 48 hours at 25°C, the reaction mixture
was dissolved with ethyl acetate (30 ml), and the insoluble solid material
was filtered. Removing the solvent from the filtrate yielded a pale yellow
oily substance. Further purification of the crude product was carried out
by column chromatography (yield: 97.0%).
Keywords: carbon dioxide • cyclic carbonates• heterogeneous
catalysis • cost-effective • high-efficiency
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Entry for the Table of Contents (Please choose one layout)
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We developed a cobalt coordinated
conjugated microporous polymer (Co-
CMP-2), which is cheaper and more
effective than our previous Co-CMP.
The TOF of this polymer catalysing
Jian Xiong, Rui-Xia Yang,Yong Xie,
Nian-Yu Huang, Kun Zou,* and Wei-
Qiao Deng*
Page No. – Page No.
the cycloaddition reaction of CO
2
with
Formation of cyclic carbonates from
CO and epoxides catalysed by a
2
cobalt coordinated conjugated
microporous polymer
ethylene oxide achieved a record as
-1
high as 23300 h at mild conditions.
Layout 2:
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Author(s), Corresponding Author(s)*
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(Insert TOC Graphic here; max. width: 11.5 cm; max. height: 2.5 cm))
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Title
Text for Table of Contents
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