One-step assembly of a hierarchically porous phenolic resin-type polymer with high stability for CO2 capture and conversion

Article abstract of DOI:10.1039/c6cc07149j

A hierarchically porous phenolic resin-type polymer has been successfully prepared by a solvothermal reaction. Given the relatively high surface area, hierarchical pores, good stability and abundant -OH reactive groups, this polymer exhibits high CO₂ adsorption and efficient catalytic conversion for CO₂ cycloaddition.

Full text of DOI:10.1039/c6cc07149j

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Graphical Abstract
A hierarchically porous phenolic resin-type polymer with high stability has been
rationally synthesized and behaves as an excellent adsorbent and catalyst for CO2
capture and conversion.

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One-step Assembly of A Hierarchically Porous Phenolic Resin-Type
Polymer with High Stability for CO2 Capture and Conversion
Received 00th January 20xx,
Accepted 00th January 20xx
Meili Ding and Hai-Long Jiang*
DOI: 10.1039/x0xx00000x
www.rsc.org/
A hierarchically porous phenolic resin-type polymer has been while the practical applications of MOFs still suffer from their
successfully prepared by solvothermal reaction. Given the long-term stability as well as other issues.6 Unlike zeolites and
relatively high surface area, hierarchical pores, good stability and MOFs, mesoporous silicas have larger pore sizes, leading to the
abundant –OH reactive groups, this polymer exhibits high CO2 weak interaction with CO2 molecules. Generally, some basic
adsorption and efficient catalytic conversion for CO2 cycloaddition. substances (i.e., transition metal oxide particles, amines) are
required to be implanted into mesoporous silicas to enhance
CO2 capture capacity.7 For carbon-based materials, the high
With the improvement of human living standard and the
increase of industrial activities, the concentration of
atmospheric CO2 is rising constantly, which not only results in
the global warming but also threatens to the living
environment of human. On the other hand, carbon dioxide is a
clean, free, renewable and abundant C1 source for producing
valuable molecules, such as formic acid, carbon monoxide and
cyclic carbonates.1 Therefore, the development of reliable
technologies for CO2 capture and conversion (C3) is obviously
important and imperative. So far, a diversity of functional
materials, including aqueous amine solutions, ionic liquids,
metal carbonates and porous materials, etc., have been
applied to realize CO2 capture and/or conversion.2 Amongst
them, porous materials, such as zeolites, mesoporous silicas,
carbon-based materials, metal-organic frameworks (MOFs)
and porous polymers, featuring large surface area are able to
capture/enrich CO2 molecules, thus facilitating the CO2
conversion.2c,2d,3 The excellent CO2 capture performance of
zeolites can be created by ion exchange with alkali metal
cations.4 However, the application of zeolites in CO2 capture
from power plant flue gas is practically difficult because of the
deactivation by moisture, which leads to a dramatically
reduction of the CO2 adsorption capacity.5 Comparing with
zeolites, the common strategies to improve the CO2 capture
properties of MOFs are based on the exposed metal sites, N-
donor ligands as well as polar groups involved in the structure,
stability and low density make them suitable for capturing CO2,
even in humidity.8 The major reason for preventing their
applications is the “physical” CO2 adsorption on carbon
materials, which makes them sensitive to temperature and
relatively poor in selectivity.2c Unlike the aforementioned
adsorbents, porous polymers are constructed by various
monomers via polymerization. The diversity of monomer
endows them with abundant structures as well as particular
binding and catalytic sites. Moreover, the strong covalent
bonds guarantee the chemical stability of polymers.
Consequently, porous polymers with considerable surface area
are ideal candidates for carbon capture and conversion.
Although there have been significant progress on the carbon
capture and conversion over porous polymers based on the
above mentioned advantages in recent years,9 almost all these
reports for CO2 conversion require harsh and energy-intensive
reaction conditions (high temperature/pressure). Hence, to
realize the practical CO2 capture and conversion, the following
prerequisites for the porous polymers are expected: 1) the
synthesis conditions are simple with high yield; 2) possessing
hierarchical pores: enough micropores and relatively high
surface area to improve the CO2 capture capacity and some
mesopores/macropores facilitating efficient transport of
catalytic substrates and products; 3) particular binding and
active sites to activate substrates and/or CO2 molecules; 4)
mild reaction conditions for catalyzing CO2 conversion; 5)
excellent catalytic recyclability and reusability.
Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key
Laboratory of Soft Matter Chemistry, Collaborative Innovation Center of Suzhou
Nano Science and Technology, Department of Chemistry, University of Science and
Technology of China, Hefei, Anhui 230026, P. R. China
Email: jianglab@ustc.edu.cn
†Electronic Supplementary Information (ESI) available: Experimental procedures,
characterization data/figures referred in the text. See DOI: 10.1039/x0xx00000x
With these in mind, a hierarchically porous phenolic resin-
type polymer (PRP-1) with high stability was facilely prepared
by one-step polymerization reaction from phloroglucinol
(1,3,5-trihydroxybenzene) and 4,4'- biphenyldicarboxaldehyde
(Scheme 1). The deliberately introduced polar hydroxyl group
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Fig. 1 (a) Nitrogen sorption isotherms of PRP-1 at 77 K. (b) Pore size
distribution curve based on the DFT calculation model. Inset: Pore size
distribution falling in the range of mesporous and macroporous sizes.
Scheme 1. Schematic illustration of the preparation of PRP-1.
(Fig. 2a). Its adsorption capacity reaches 92 mg/g (273 K) and
71 mg/g (298 K), respectively, at the pressure up to 1 bar.
These values are moderately high and comparable to some
reported porous materials.10 The isosteric heat of CO2
adsorption (Qst) for PRP-1 calculated by the virial method gives
25 kJ/mol at zero coverage and decreases slightly along with
the increase of CO2 loading (Fig. 2b). Such a low value implies
that the adsorbent could be well regenerated at a low energy
penalty. In sharp contrast, for the monoethanolamine (MEA)
solution, the most widely used CO2 adsorbent, its CO2 uptake
capacity is 70-106 mg/g at 1 bar but it requires a very high
energy to be regenerated due to the strong chemical bond
between CO2 and amine.11 Therefore, PRP-1 not only
possesses the good CO2 adsorption performance that is similar
to the monoethanolamine solution but also prevents high
energy consumption for regeneration.
in the PRP-1 would not only improve its CO2 uptake but also
effectively promote the CO2 cycloaddition reaction, thanks to
the ring opening of epoxides triggered by the hydrogen bonds
between hydroxyl groups and epoxides.9b As a result, the PRP-
1 exhibits high CO2 adsorption (Qst = 25 kJ/mol, 92 mg/g at 273
K, 1 bar), efficient catalytic behavior for CO2 cycloaddition with
epoxides under mild conditions (60 °C and 1 bar CO2) and
outstanding recyclability.
PRP-1 was synthesized at 220 °C by solvothermal reaction
with phloroglucinol and 4,4'-biphenyldicarboxaldehyde in
dioxane in the absence of catalyst, avoiding the troublesome
separation process. The successful preparation of PRP-1 was
approved by solid state CP/MAS 13C NMR and Fourier
transform infrared (FT-IR) spectroscopy (Fig. S1 and S2, ESI†).
FT-IR spectrum reveals that there is a broad peak at ~3400 cm-
1, attributed to the stretching vibration of the O-H bond. The
peak around 1690 cm-1 is corresponding to the unreacted
aldehyde group of the 4,4'-biphenyldicarboxaldehyde. The
morphology observation for PRP-1 by field-emission scanning
electron microscopy (FE-SEM) shows that it is composed of
spherical microparticles with diameter 1–3 μm, which are
constructed by the stacking of much smaller nanoparticles
with porous structures, as observed from the high
There always remain concerns about the recyclable use of
solid adsorbents for industrial use. To examine the recyclability
of PRP-1, we simulated temperature and vacuum swings by
using an ASAP2020 analyzer and saturating with CO2 up to
around 1 bar at 298 K and then a high vacuum for 120 min
at80 °C.6c,12 As displayed in Figure 2c, there is no apparent
drop in CO2 uptake capacity during 10 cycles, which indicates
that CO2 molecules can be completely desorbed during the
moderate thermal treatment process and the PRP-1 can be
magnification SEM image (Fig. S4, ESI†).
To evaluate the pore character of PRP-1, N2 sorption
isotherms were investigated at 77 K (Fig. 1a). The Brunauer–
Emmett–Teller (BET) surface area of PRP-1 reaches 835 cm2/g.
The sorption curves rise up at high relative pressure range and
the adsorption and desorption branches do not overlap
between relative pressure of 0.9-1.0, suggesting the presence
of mesopores and macropores in PRP-1. Pore size distribution
analysis based on the density-functional theory (DFT) method
clearly demonstrates the formation of hierarchical pores (Fig.
1b). Although a relatively large proportion of pores are less
than 2 nm, there are quite a few pore widths fall in the
mesporous and macroporous ranges, manifesting the
hierarchically porous structure of PRP-1, in which the
micropores would effectively improve the CO2 capture while
mesopores and macropores facilitate the transport of catalytic
reactants and products, namely, favorable for the CO2 capture
and conversion.
Fig. 2 (a) CO2 sorption isotherms at 273 K and 298 K. (b) Isosteric heat
of adsorption (Qst) for the adsorption of CO2. (c) Ten cycles of CO2
uptake at 298 K. After each cycle, the sample was regenerated at 80 °C
under vacuum for 120 min.
To examine the above expectations, the CO2 uptake
performance of PRP-1 was investigated at 273 K and 298 K
2 | J. Name., 2012, 00, 1-3
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Table 1 The catalytic CO2 cycloaddition reaction of epichlorohydrin with
well recycled. It should to be stressed that the good cycle
stability of PRP-1 is closely related to its structural stability,
particularly thermally stable up to 300 °C based on TG data (Fig.
different conditions.a
S5, ESI†), and the low activation temperature.
Currently, the catalytic CO2 cycloaddition with epoxides has
become one of the most intensively studied routes for CO2
fixation. The resultant cyclic carbonates are highly valued as
intermediates for the production of engineering plastics, as
electrolyte solvents for lithium ion batteries, as polar aprotic
solvents and degreaser, and as additives in fuel, etc.13
Therefore, CO2 cycloaddition reaction is a green route to the
preparation of valuable products by utilizing CO2 as a raw
material. The CO2 cycloaddition with epichlorohydrin was first
chosen to evaluate the optimized conditions and the
corresponding catalytic properties of PRP-1 (Table 1). The best
catalytic activity over PRP-1 was obtained with the co-catalyst
tetrabutyl ammonium bromide (TBAB) and 1 bar CO2 at 60 °C
for 24 h (entry 1). In the absence of TBAB, PRP-1 or CO2, the
conversion of substrate was greatly reduced or even did not
proceed (entries 2-4). Apparently, all these components are
indispensable for the CO2 cycloaddition reaction under such
conditions. In addition, temperature and the type of co-
catalyst are also very crucial for this reaction. When the
reaction temperature was decreased down to room
temperature and the co-catalyst was substituted by tetrabutyl
ammonium chloride (TBAC), only 5% and 70% of
epichlorohydrin were converted to the target products,
respectively (entries 5,6). At a higher temperature, the higher
reaction energy is able to greatly boost the reaction efficiency,
although the CO2 solubility in the reaction system would be
slightly decreased, in reference to that at room temperature.
For the co-catalyst, the ionic radius of bromide ion is larger
than chloride ion, which makes the quaternary ammonium ion
force bromide ion away from it easier than chloride ion and
finally improves the catalytic activity.14 To demonstrate the
reaction stability and reusability of PRP-1, recycling
experiments for the CO2 cycloaddition of epichlorohydrin were
conducted. Fortunately, the conversion and selectivity of
catalyst did not change remarkably and the powder XRD
pattern was maintained even after six rounds of circulation
Entry
1
Catalyst
PRP-1+TBAB
PRP-1
Conversionh (%)
Selectivityh (%)
89
<1
48
0
>99
>99
>99
-
2
3
TBAB
4b
5c
6d
7e
8f
PRP-1+TBAB
PRP-1+TBAB
PRP-1+TBAC
PRP-1+TBAB
S-PRP-1+TBAB
phloroglucinol+TBAB
5
>99
>99
>99
>99
>99
70
87
56
92
9g
a
Reaction conditions: 1 mmol epichlorohydrin, 50 mg PRP-1, 0.17
mmol tetrabutyl ammonium bromide (TBAB), 2 mL acetonitrile, 1 bar
d
b
CO2, 60 °C, 1 d. CO2 was substituted by N2. Room temperature.
c
0.17 mmol tetrabutyl ammonium chloride (TBAC). e The sixth round of
f
catalytic reaction. The -OH groups were protected by a substitution
reaction. g 22.2 mg phloroglucinol (calculated by the weight ratio of the
h
two raw materials for PRP-1) was used. Determined by GC and using n-
dodecane as standard.
Encouraged by the excellent catalytic performance of PRP-1,
epoxides with different substituents have been further
examined. As displayed in Table 2, most of substituted
epoxides were smoothly converted with good to high yields,
Table 2 The CO2 cycloaddition with epoxides substituted with different
function groups catalyzed by PRP-1.a
Entry
1
Substrate
Time (d)
1
Con.c (%)
85
Sel.c (%)
100
(entry 7, Fig. S6 and S7, ESI†).
2
3
4
2
3
3
86
85
66
100
100
100
To prove that the catalytic property of PRP-1 was originated
from the -OH groups, which were protected via a substitution
reaction with epichlorohydrin to give substituted PRP-1
(denoted S-PRP-1). After the same catalytic process (entry 1),
only 56% of substrate was converted over S-PRP-1 (entry 8).
The S-PRP-1 also offers a certain activity because it is
impossible to realize the protection of all -OH groups.
Therefore, it can be concluded that the activity of PRP-1 arises
from the -OH groups. In addition, when phloroglucinol was
tried to catalyze this reaction, a high conversion (92%) can be
obtained (entry 9), which is not surprising as the catalyst is
homogeneous and fully accessible. By comparison, PRP-1 as a
heterogeneous catalyst achieves comparable conversion (89%).
The results imply that almost all -OH groups in PRP-1 are
accessible and effectively utilized, which should be ascribed to
its porous structure.
5b
2
92
100
a
Reaction conditions: 1 mmol substrate, 50 mg PRP-1, 0.17 mmol
TBAB, 2 mL acetonitrile, 1 bar CO2, 60 °C otherwise mentioned.
b
c
acetonitrile was substituted by DMF, 120 °C. Determined by GC and
using n-dodecane as standard.
including electron withdrawing substituents (-Br and -OPh),
electron donating substituent (-CH2CH3) and conjugated
benenzene group. The reaction activity of epibromohydrin is
higher than glycidyl phenyl ether with stronger electron
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According to the above results, the plausible reaction
mechanism was deduced based on the previous
literatures.9b,15 As shown in Scheme S1, firstly, the C-O bond of
epoxide is polarized by the hydrogen bond between expoxide
and the phenolic hydroxyl group of PRP-1. Meantime, the
nucleophilic attack of halide anion on the less sterically
hindered carbon atom of the epoxide leads to the ring
opening. Then, the electrostatic interaction between negative
charged oxygen and the carbon atom of CO2 could further
activate the CO2 molecule. Subsequently, the internally
nucleophilic attack of the intermediate results in the alkyl
carbonate. Finally, cyclic carbonate is obtained by
intramolecular ring-closure along with the release of the
bromide anion and the regeneration of PRP-1.
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In conclusion, a hierarchically porous phenolic resin-type
polymer, PRP-1, with high stability was successfully prepared
by an one-step polymerization process based on
phloroglucinol and 4,4'-biphenyldicarboxaldehyde. Thanks to
the high surface area, hierarchical pores, polar phenolic
hydroxyl group and excellent stability, the resultant PRP-1 not
only exhibits high and recyclable CO2 capture but also
possesses excellent activity and recyclability for catalyzing
conversion of CO2 cycloaddition with diverse epoxides under
mild conditions. Research endeavor toward the synthesis of
highly porous polymers for CO2 capture and conversion is
ongoing in our laboratory.
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This work was supported by the 973 program
(2014CB931803), the NSFC (21371162, 51301159 and
21521001), the Research Fund for the Doctoral Program of
Higher Education of China (20133402120020), the Scientific
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Scholars, State Education Ministry, the Recruitment Program
of Global Youth Experts and the Fundamental Research Funds
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