pubs.acs.

org/journal/ascecg Research Article

Superbase Ionic Liquid-Based Deep Eutectic Solvents for Improving

CO2 Absorption
Hong Yan, Lei Zhao, Yinge Bai, Fangfang Li, Haifeng Dong, Hui Wang, Xiangping Zhang,
and Shaojuan Zeng*
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ABSTRACT: Carbon dioxide (CO2) is a detrimental greenhouse gas to the environment as the main contributor to global
warming. However, the development of efficient methods for CO2 absorption and separation is still a great challenge. Ionic liquids
(ILs) have emerged as promising solvents for CO2 separation due to negligible vapor pressure and adjustable structures. In this work,
a new strategy that three superbase ILs are designed as hydrogen bond acceptor (HBA) and further combined with ethylene glycol
(EG) as hydrogen bond donor (HBD) to form novel IL-based deep eutectic solvents (DESs) was proposed for efficient and
reversible absorption of CO2. The results indicated that both excellent recyclability and high CO2 mass capacity up to 0.141 g CO2/g
DES under 40 °C and 100 kPa are achieved by [HDBU][Im]/EG with the mass ratio of 7:3, and the value is much higher than those
of most of the reported IL-based DESs. The superior CO2 absorption and desorption performances were attributed to the synergistic
interaction between both IL and EG with CO2 to form carbamate and carbonate, respectively. This work provides a feasible method
for designing IL-based solvents in CO2 separation applications.
KEYWORDS: deep eutectic solvents, superbase ionic liquids, CO2 absorption, interaction mechanism

■ INTRODUCTION
As one of the main culprits of global warming, carbon dioxide
(CO2) emission from the combustion of fossil fuels has been
causing a serious environmental problem.1−3 Meanwhile, the
recycled CO2 as an important chemical has been widely used
in various fields, such as regulators in electronic industries,
refrigerants in food processing industries, raw materials for
producing major chemicals (e.g., methanol and poly(propylene
carbonate)), and so on. Hence, CO2 capture and recovery are
very important for the environment and effective utilization of
carbon resources. To date, the most widely used absorbents for
CO2 capture in industries are amine-based solvents, such as
monoethanolamine (MEA), diethanolamine (DEA), diglycol-
amine (DGA), and N-methyldiethanolamine (MDEA).4
However, those absorbents were confronted with the loss of
organic amines due to high volatility and high energy
consumption during regeneration.5 Therefore, it is imperative
to develop novel methods for efficient and energy-saving
capture of CO2, which will satisfy the requirements of green
and sustainable development.
Ionic liquids (ILs) have been widely studied for CO2
absorption because of their prominent properties, such as
negligible vapor pressure, tunable structures, and good affinity
toward CO2.6−11 Davis et al.12 reported for the first time that
the amino-functionalized IL with single amino group 1-(3-
propylamino)-3-butylimidazolium tetrafluoroborate ([Apbim]-
[BF4]) can absorb 0.5 mol CO2/mol IL (0.074 g CO2/g IL) at
25 °C and 100 kPa due to the formation of reversible
carbamate. Subsequently, 1,3-bis(2-aminoethyl)-2-methyl-imi-
dazolium bromide (DAIL-Br) with two amino groups on
Received: November 29, 2019
Revised: January 17, 2020
Published: January 22, 2020

© 2020 American Chemical Society https://dx.doi.org/10.1021/acssuschemeng.9b07128

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cations was designed and synthesized in our group, and the
CO2 capacity of 10 wt % DAIL aqueous solution was 1.05 mol
CO2/mol IL (0.185 g CO2/g IL) at 30 °C and 100 kPa.13
Then, Wang et al.14 synthesized a series of phosphonium-based
ILs by the reaction of trihexyl tetradecane phosphine
hydroxide ([P66614][OH]) with weak proton donors imidazole
(Im), pyrazole (Pyr), tetrazole (Tetz), indole (Ind), and
benzotriazole (Benz) in one step, and they suggested that the
absorption capacity of ILs depends on the pKa of nitrogen
heterocyclic reactant. The CO2 capacity of [P66614][Pyr] and
[P66614][Im] were 1.02 mol CO2/mol IL (0.08 g CO2/g IL)
and 1.00 mol CO2/mol IL (0.08 g CO2/g IL) at 25 °C and
100 kPa, respectively. However, the high viscosity of
functionalized ILs is not favorable for the mass transfer of
CO2; therefore, the combination of ILs with other organic
solvents will be an effective way to overcome the problem.
Among them, IL-based deep eutectic solvents (DESs),
consisting of a hydrogen-bond donor (HBD) and hydrogen-
bond acceptor (HBA), show the advantages of wide liquid
range, brilliant CO2 affinity, and low volatility similar to ILs,
which are applied as new absorbents in CO2 separation.15−18
Up to now, the choline-based DESs were the most reported
absorbents, and the maximum CO2 capacity was below 0.070 g
CO2/g DES due to physical interaction.19,20 IL-based DESs,
such as quaternary ammonium IL and quaternary phospho-
nium IL-based DESs, have also been reported for CO2 capture.
Trivedi et al.20 reported that the mass capacity of [MEA]Cl-
ethylenediamine (EDA) DES with the molar ratio of 1:3 is up
to 0.337 g CO2/g DES at 30 °C and 100 kPa, but the
desorption temperature is a bit high (100 °C) and the viscosity
increases obviously after absorption. Cui et al.21 prepared a
series of DESs by mixing azole anion-functionalized ILs with
ethylene glycol (EG), and the capacity of tetraethylphospho-
nium 1,2,4-triazole/ethylene glycol ([P2222][Triz]/EG) with
the molar ratio of 1:2 is 0.91 mol CO2/mol IL at 25 °C and
100 kPa was proposed, but its corresponding mass capacity of
0.106 g CO2/g DES was not as high as expected due to the
larger molecular weight of the cation. Therefore, it is important
to develop novel IL-based DESs with high mass CO2 capacity
and great recyclability at relatively mild conditions.
In this work, three superbase ILs, including 1,8-diazabicyclo-
[5,4,0]undec-7-ene imidazole ([HDBU][Im]), 1,8-
diazabicyclo[5,4,0]undec-7-ene indole ([HDBU][Ind]), and
1,8-diazabicyclo[5,4,0]undec-7-ene 1,2,4-triazole ([HDBU]-
[Triz]) with low molecular weight of the cation, were
synthesized and further combined with the less viscous EG
to prepare IL-based DESs for an efficient and reversible
capture of CO2. The physiochemical properties and CO2
absorption performance including the effect of IL type and
IL/EG mass ratios, temperature, pressure on CO2 capacity,
and recyclability of IL-based DESs were evaluated. The
absorption mechanism of CO2 was also studied by the
combination of Fourier transform infrared (FTIR) and 13C
NMR spectra as well as quantum chemical calculations.
■
EXPERIMENTAL SECTION
Materials. CO2 (99.999%) and N2 (99.999%) were supplied by
Langfang Tianhong Gas Factory. Chemicals were analytical grade and
used for the synthesis of superbase ILs and IL-based DESs. 1,8-
Diazabicyclo[5.4.0]undec-7-ene (DBU, 99.0%), Im (99.0%), Ind
(98.0%), and phosphorus pentoxide (≥98%) were purchased from
Aladdin Industrial Corporation. Triz (99%) was purchased from
Shanghai Macklin Biochemical Co., Ltd. Ethanol (99.7%) was
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purchased from Tianjin Damao Chemical Reagent Factory. EG
(96%) was purchased from Beijing Chemical Works Co., Ltd. All the
chemical reagents mentioned above were used without further
purification.
Synthesis and Characterization of ILs and DESs. Three
superbase ILs were synthesized by the one-step method according to
the literature.22 Taking [HDBU][Im] as a typical example, a certain
amount of Im (0.5 mol) was mixed with 50 mL ethanol, then
equimolar DBU was added by constant pressure funnel and stirred
under ambient conditions for 24 h. After the reaction, the mixed
solution was heated by rotary evaporator at 55 °C for 4 h to remove
the solvent. The sample was dried under vacuum at 55 °C for 40 h
and the final product [HDBU][Im] with light yellow was obtained.
The structures of superbase ILs studied in this work are shown in
Scheme 1.
Scheme 1. Structures of (a) [HDBU][Im], (b)
[HDBU][Ind], and (c) [HDBU][Triz]
The IL-based DESs were prepared by combining ILs and EG in
different mass ratios and stirred at 50 °C for 4 h to obtain
homogeneous and transparent liquids. FTIR spectra were obtained in
the range of 400−4000 cm−1 using a Thermo Nicolet 380
spectrometer. 1H and 13C NMR spectra were recorded using a
Bruker spectrometer (600 Hz) in drive pipe inside deuterated
chloroform (CDCl3) to confirm the structures of the studied ILs and
IL-based DESs. The NMR data of the superbase ILs are presented in
the Supporting Information. The densities and viscosities of the
superbase ILs were measured from 20 to 80 °C with a density meter
(Anton Paar DMA 5000) and an automated micro viscometer (Anton
Paar AMVn), respectively. The glass transition temperatures were
measured on a Mettler Toledo DSC1 from −120 to 50 °C at a
heating rate of 10 °C/min under an N2 atmosphere.
CO2 Absorption and Desorption Experiments. CO2 absorp-
tion and desorption experiments were performed by the weighing
method according to our previous work.23−25 Typically, 5 g of IL-
based DES was added into a self-made absorption tube with an inner
diameter of 2.0 cm. Then, the absorption tube was partially immersed
in a water bath at the desired temperature, and the standard
uncertainty of temperature was ±0.1 °C. After that, CO2 was passed
into the absorption tube at a flow rate of 200 mL/min. The weight of
the captured CO2 was obtained by the electronic balance with an
accuracy of ±0.0001 g until CO2 absorption in the DESs reached an
equilibrium. The effect of temperature was studied from 40 to 80 °C
on CO2 absorption in DESs at atmospheric pressure. For CO2
absorption under reduced pressure, the flow rates of CO2 and N2
were controlled separately to provide different pressures of CO2. The
desorption experiment was conducted using a flow rate of 100 mL/
min and the bubbled gas was changed to pure N2 at 70 °C until the
weight of the absorption tube remained unchanged.
Computational Methods. All of the calculations reported in this
paper were performed with the Gaussian 09 program, and the density
functional theory is considered as a powerful tool to clarify the
interaction mechanism.26 At the level of M062X/6-311+G (d,p), the
geometries of reactants, transition states, and products were
optimized. The solvent effects of DESs were simulated by the
SMD-GIL solvation model.27 The frequency calculations were carried
out at the same level to verify that the optimized structures are energy
minima without any imaginary frequency. However, transition states
only had one imaginary frequency. The energy difference between the
product (or transition state) and the reactant was the reaction energy
barrier.
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■
RESULTS AND DISCUSSION
Physiochemical Properties and CO2 Absorption of
Superbase ILs. The viscosity and density are important
parameters of ILs in gas separation. To investigate the changes
in density and viscosity of different DESs with temperature, the
related data of [HDBU][Im]/EG in the range from 20 to 80
°C were measured and shown in Figure 1a,b. The density and
viscosity of these ILs decreased with temperature and followed
the order of [HDBU][Triz] > [HDBU][Ind] > [HDBU][Im].
Among them, the viscosity of [HDBU][Im] is 33 mPa·s at 30
°C, which is lower than the that of most of the conventional
Figure 1. Variation in densities (a), viscosities, (b) and CO2
absorption performance (c) of superbase ILs.
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ILs (e.g., 68.90 mPa·s of [Bmim][BF4]28,29), but [HDBU]-
[Triz] showed a relatively high viscosity of 900 mPa·s at the
same temperature. The results of Figure 1c showed that the
low viscosity of [HDBU][Im] probably promotes CO2
diffusion in ILs during absorption. In addition, the CO2
mass capacity of these ILs followed the order of [HDBU][Im]
> [HDBU][Ind] > [HDBU][Triz], and the highest value was
up to 0.194 g CO2/g IL for [HDBU][Im]. However, the
absorption time was long up to 1200 min due to the increased
viscosity of the [HDBU][Im]−CO2 system during the
absorption, finally forming a gelatinous state.
Characterization of IL-Based DESs. To overcome the
low CO2 mass transfer, three superbase ILs were used as HBA
and mixed with the less viscous EG as an HBD to prepare
novel IL-based DESs. Therefore, the melting points of the IL/
EG DESs with different IL/EG mass ratios were measured to
prove the formation of IL-based DESs, and the results are
shown in Figure 2. The melting points of three IL-based DESs
with different ILs (mass ratio of 7:3) were determined as −81,
−71, and −88 °C, respectively. For the [HDBU][Im]-based
DESs with different IL/EG mass ratios, the melting points
were −103, −99, −94, −89, and −88 °C lower than those of
pure IL and EG, which confirms the formation of the IL-based
DESs.14
CO2 Absorption Performance of IL-Based DESs. To
investigate the effect of IL types of IL-based DESs on CO2
absorption performance, CO2 absorption by three IL-based
DESs including [HDBU][Im]/EG, [HDBU][Ind]/EG, and
[HDBU][Triz]/EG with the mass ratio of 7:3 at 40 °C and
100 kPa was determined and shown in Figure 3 and Table 1,
respectively. Compared with the pure ILs, the absorption
process could reach an equilibrium in 40 min for IL-based
DESs, which indicated that the addition of EG significantly
improves the CO2 absorption rate in IL-based DESs due to the
lower viscosities of the DES-CO2 systems (the viscosities
before and after absorption shown in Table S1). The results
showed that compared with the IL/EG DESs, the viscosities of
all three DESs after absorbing CO2 increase slightly. For
example, the viscosity of the [HDBU][Im]/EG DES with
saturated CO2 increased from 31.48 to 166.41 mPa·s at 40 °C.
However, the three pure ILs after CO2 absorption become a
gelatinous state, although they had very low viscosities (19−
307 mPa·s at 40 °C), so the viscosities of CO2-IL systems
cannot be obtained because they are beyond the measurement
range of the instrument. Meanwhile, the amount of CO2
absorbed by IL-based DESs followed the order of [HDBU]-
[Im]/EG > [HDBU][Ind]/EG > [HDBU][Triz]/EG, which
is consistent with the order of ILs for CO2 absorption.
[HDBU][Im]/EG showed the highest capacity of up to 0.141
g CO2/g DES (Table 1), so the [HDBU][Im]/EG system was
selected for further investigation.
Effect of IL/EG Mass Ratio on CO2 Absorption. The
effect of IL/EG mass ratio on the CO2 capacity of the
[HDBU][Im]/EG system was investigated under 40 °C and
ambient pressure and is displayed in Figure 4. It demonstrated
that the CO2 capacity of pure EG is very low, with only 0.008 g
CO2/g EG at 25 °C and 100 kPa, and the CO2 capacity of IL-
based DESs increases with the increase of the IL/EG mass
ratio. For example, the mass capacity of [HDBU][Im]/EG
increased from 0.064 to 0.141 g CO2/g DES when the IL/EG
mass ratio changed from 3:7 to 7:3. Moreover, the absorption
rate almost had no obvious change. Therefore, the [HDBU]-
[Im]/EG mass ratio of 7:3 was selected as a suitable absorbent.
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Figure 3. CO2 absorption capacities of IL-based DESs at 40 °C and

100 kPa.

Table 1. CO2 Absorption by IL-Based DESs

pKa of nitrogen CO2
heterocyclic reactant capacity (
T (room temperature, g CO2/g
IL-based DESs (mass ratio) (°C) DMSO) DES)
[HDBU][Im]/EG (7:3) 40 18.630 0.141
[HDBU][Ind]/EG (7:3) 40 16.231 0.117
[HDBU][Triz]/EG (7:3) 40 13.932 0.108

Figure 4. CO2 capacities of IL/EG DESs with different mass ratios at

40 °C and 100 kPa.

Figure 2. Melting points of DESs with different ILs (a) and IL/EG
mass ratios (b) and (c).
Effects of Temperature and Pressure on CO 2
Absorption. Temperature and pressure play an important
role in CO2 absorption; therefore, the effects of temperature
and pressure on CO2 absorption capacity in [HDBU][Im]/EG
DES with the mass ratio of 7:3 are also presented in Figure 5.
The results showed that CO2 capacity decreases from 0.141 to
0.123 g CO2/g DES when the temperature increases from 40
to 80 °C at 100 kPa due to the exothermic process of CO2
absorption, thus the increase of temperature leads to the
decrease of CO2 capacity. On the other hand, the increasing
temperature was beneficial to the mass transfer, leading to an
obvious decrease in the CO2 absorption saturation time. When
2526
the pressure increased from 20 to 100 kPa at 40 °C, the CO2
capacity increased from 0.121 to 0.141 g CO2/g DES.
However, with varying pressure, the change of the CO2
capacity of [HDBU][Im]/EG was small, which meant that it
is suitable for low concentration of CO2 absorption due to
strong chemical interaction.
Regeneration and Recycle of [HDBU][Im]/EG DES.
Five consecutive absorption−desorption experiments by
[HDBU][Im]/EG DES were further performed to study the
regeneration and recycling performance of IL-based DES. As
demonstrated in Figure 6, CO2 absorbed in [HDBU][Im]/EG
with the mass ratio of 7:3 could be completely released under
70 °C with N2 purging, and CO2 absorption capacity remained
nearly unchanged. Furthermore, compared with the FTIR
spectra of fresh IL-based DES, the structure of [HDBU][Im]/
EG after desorption remained unchanged (Figure 8), which
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Figure 5. Effects of temperature at 100 kPa (a) and pressure at 40 °C
(b) on CO2 absorption by IL-based DES.
Figure 6. Five consecutive CO2 absorption and desorption cycles of
the IL-based DES CO2 absorption (CO2, 100 kPa, and 40 °C) and
desorption (N2, 100 kPa, and 70 °C).
indicated that the [HDBU][Im]/EG DES can reversibly
absorb CO2.
Mechanism for CO2 Absorption. With the aim to
understand the absorption mechanism of [HDBU][Im]/EG,
the interaction between [HDBU][Im]/EG and CO2 was
analyzed by combining the theoretical calculation and FTIR
and 13C NMR spectra.
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Quantum Chemistry Calculations. First, the binding
energies of the transition state and product between [HDBU]-
[Im]/EG and CO2 through quantum chemistry calculations
and two possible CO2 absorption mechanisms were speculated.
For the CO2 absorption of [HDBU][Im]/EG with the mass
ratio of 7:3, corresponding to the molar ratio of 1:2, we built
the model on the basis of IL/EG with the molar ratio of 1:2 to
make the calculation result more similar to the experiment. As
shown in Figure 7, the activation energy barriers of two
Figure 7. Optimized structures and potential energies of CO2
absorption in [HDBU][Im]/EG DES. P1: (carbonate), P2:
(carbamate), and TS1 and TS2: (transition state).
pathways about CO2 with [HDBU][Im]/EG were 3.66 and
8.54 kcal/mol, and the interaction energies of products IL +
carbonate (P1) and EG + carbamate (P2) were −11.57 and
−3.41 kcal/mol, respectively. The energy barriers of the
transition states of both paths were lower than those (29.32−
32.08 kcal/mol) in the literature,33 indicating that they are easy
to occur. Therefore, we speculated that both EG and [Im]−
may simultaneously react with CO2 to form a mixture of
carbonate and carbamate. To verify this speculation, [HDBU]-
[Im]/EG DES with the mass ratio of 7:3 before and after CO2
absorption was further characterized by FTIR and 13C NMR
spectra.
FTIR and NMR Analysis. The FTIR spectra of IL-based
DES before and after CO2 absorption are shown in Figure 8a.
Compared with those of fresh [HDBU][Im]/EG DES, three
new peaks at 1207, 1286, and 1644 cm−1 appeared in the
spectrum of the DES after CO2 absorption. The peak at 1207
cm−1 assigned to C6−N stretching vibrations, meaning that the
carbamate formed between the basic nitrogen of imidazole
anion and CO2. The peak at 1644 cm−1 might be assigned to
the C6O stretching vibration of carbamate formed by the
reaction with the imidazole anion,34 or C1O stretching
vibration of the carbonate formed by the reaction with EG,
which may be overlapped in the same region.35 Interestingly,
an additional peak at 1286 cm−1 was attributed to the C1−O
stretching vibration of carbonate from the interaction between
EG and CO2.21 In situ FTIR (Figure 8b) was also studied to
verify the results. On the basis of the above discussion, it was
speculated that both IL and EG of IL-based DES may
simultaneously react with CO2 to form the mixtures of
carbonate and carbamate.
Furthermore, 13C NMR spectra of [HDBU][Im]/EG,
[HDBU][Im], and EG before and after CO2 absorption are
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ACS Sustainable Chemistry & Engineering
Figure 8. Experimental IR spectra of IL-based DES before and after
CO2 absorption (a) and in situ FTIR of IL-based DES during CO2
absorption (b).
also recorded in Figure 9. The results showed that there is no
obvious change in the position of peak after mixing
Figure 9. 13
C NMR spectra of IL-based DES before and after CO2
uptake.
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[HDBU][Im] with EG, which proved no chemical interaction.
In contrast with the fresh IL-based DES, four new peaks were
observed in [HDBU][Im]/EG after CO2 absorption: 60.7,
66.9, 158.6, and 165.6 ppm. The shifts in 60.7 and 66.9 ppm
were corresponding to the C-2 and C-3 of EG, respectively.21
The peak of 158.6 ppm assigned to C-1 corresponded to the
carbonyl carbon of carbonate.36 The peak at 165.6 ppm might
come from the carbamate formed by the [Im]− anion and
CO2.14,37,38 Besides the four new peaks, the other peaks at
21.8, 35.2, and 42.6 ppm correspond to the anion [Im]‑ up-
shifted to 19.2, 31.9, and 38.2 ppm, respectively. The results
further proved the above conclusions.
Therefore, based on the above quantum chemistry
calculation, experimental results, and spectroscopic investiga-
tions, the possible mechanism of [HDBU][Im]/EG DES for
CO2 absorption was proposed as shown in Scheme 2. One
Scheme 2. Proposed Mechanism of CO2 Absorption by the
IL-Based DES
pathway was that the H atom on EG transfers to the
electronegative N of the IL to obtain the final product of IL +
P1, and the other was that IL reacts with CO2 directly to
generate EG + P2. Therefore, the process of IL-based DES for
CO2 absorption was proved to be the synergistic interaction
between EG, IL, and CO2, resulting in the mixed product of
carbamate and carbonate.
Comparison with Reported IL-Based Absorbents.
Compared with the reported IL-based absorbents in literature,
as shown in Table 2, the [HDBU][Im]/EG DES exhibited not
only high mass CO2 absorption performance but also good
regeneration performance along with low desorption temper-
ature, which shows great potentials in IL-based CO2 separation
applications.
■ CONCLUSIONS
In summary, three superbase ILs were synthesized and further
combined with EG to form a series of IL-based DESs for
improving CO 2 absorption. The melting points, CO 2
absorption performance under different conditions (IL types,
IL/EG mass ratios, temperature, and pressure), and recycla-
bility, as well as the interaction mechanism, were systematically
studied. Among these IL-based DESs, the [HDBU][Im]/EG
DES with the mass ratio of 7:3 showed the highest capacity of
CO2 of up to 0.141 g CO2/g DES at 40 °C and 100 kPa, which
is much higher than those of most of the reported IL-based
absorbents. Meanwhile, the CO2 absorption performance of
DES remained stable after five cycles of absorption and
desorption. The absorption mechanism proposed that both IL
and EG can simultaneously react with CO2 to form carbamate
and carbonate, respectively, which is confirmed by combining
spectral studies and quantum chemistry calculations. This
study provides a novel method to design IL-based DESs for
efficient CO2 separation.
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Table 2. Comparison of CO2 Capacity with Other Reported Key Laboratory of Ionic Liquids Clean Process, Institute of
Absorbents Process Engineering, Chinese Academy of Sciences, Beijing
100190, China
CO2 capacity g
absorbents T/°C P/kPa CO2/g absorbent refs Haifeng Dong − Key Laboratory of Green Process and
Engineering, State Key Laboratory of Multiphase Complex
[HDBU][Im] 40 100 0.194 this
worka System, Beijing Key Laboratory of Ionic Liquids Clean Process,
[HDBU][Ind] 40 100 0.133
Institute of Process Engineering, Chinese Academy of Sciences,
[HDBU][Triz] 40 100 0.076
Beijing 100190, China
[HDBU][Im]/EG (7:3) 40 100 0.141
Hui Wang − Key Laboratory of Green Process and Engineering,
[HDBU][Ind]/EG (7:3) 40 100 0.117
State Key Laboratory of Multiphase Complex System, Beijing
[HDBU][Triz]/EG (7:3) 40 100 0.108
Key Laboratory of Ionic Liquids Clean Process, Institute of
[HDBU][Im]/EG (6:4) 40 100 0.118
[HDBU][Im]/EG (5:5) 40 100 0.109
Process Engineering, Chinese Academy of Sciences, Beijing
[HDBU][Im]/EG (4:6) 40 100 0.082
100190, China; orcid.org/0000-0003-4322-6862
[HDBU][Im]/EG (3:7) 40 100 0.063
Xiangping Zhang − Key Laboratory of Green Process and
[P66614][Im] 23 100 0.08 14b
Engineering, State Key Laboratory of Multiphase Complex
[P66614][2-Op] 20 100 0.12 34b
System, Beijing Key Laboratory of Ionic Liquids Clean Process,
[Apbim][BF4] 25 100 0.074 12b
Institute of Process Engineering, Chinese Academy of Sciences,
10 wt % DAIL-Br solution 30 100 0.185 13b
Beijing 100190, China; College of Chemical and Engineering,
[aP4443][Gly] 30 100 0.13 39b
University of Chinese Academy of Sciences, Beijing 100049,
[TETA]Cl-EG (1:3) 40 100 0.175 40b
China; orcid.org/0000-0002-1431-0873
[MEA][Cl]-EDAc (1:3) 30 100 0.337 20b Complete contact information is available at:
[TEA][Cl]-EDAc (1:3) 30 100 0.242 20b https://pubs.acs.org/10.1021/acssuschemeng.9b07128
ChCl-Urea (1:2) 40 123 0.052 41b
[P2222][Triz]-EG (1:2) 25 100 0.106 21b Notes
a
Mass ratio. bMole ratio. The authors declare no competing financial interest.

■
*
ASSOCIATED CONTENT
sı Supporting Information
■ ACKNOWLEDGMENTS
This work was supported by the National Key R&D Program
The Supporting Information is available free of charge at of China (2017YFB0603301), the National Natural Science
https://pubs.acs.org/doi/10.1021/acssuschemeng.9b07128. Foundation of China (21890764, 21978306, and
1
H NMR and 13C NMR spectra of [HDBU][Im], 51661145012), Beijing Municipal Natural Science Foundation
[HDBU][Ind], and [HDBU][Triz], and the viscosities (2182071), Hebei Natural Science Foundation
of IL-based DESs before and after CO2 absorption (B2019103011), and the Key Research Program of Chinese
(Figures S3−S8, Table S1) (PDF) Academy of Science (ZDRW-ZS-2018-1-3).

■ AUTHOR INFORMATION
Corresponding Author
Shaojuan Zeng − Key Laboratory of Green Process and
Engineering, State Key Laboratory of Multiphase Complex
System, Beijing Key Laboratory of Ionic Liquids Clean Process,
Institute of Process Engineering, Chinese Academy of Sciences,
Beijing 100190, China; orcid.org/0000-0002-0070-6711;
Phone: +86-010-82544875; Email: sjzeng@ipe.ac.cn
Authors
Hong Yan − College of Chemical and Environmental
Engineering Harbin, University of Science and Technology,
Harbin 150040, China
Lei Zhao − College of Chemical and Environmental Engineering
Harbin, University of Science and Technology, Harbin 150040,
China; Key Laboratory of Green Process and Engineering, State
Key Laboratory of Multiphase Complex System, Beijing Key
Laboratory of Ionic Liquids Clean Process, Institute of Process
Engineering, Chinese Academy of Sciences, Beijing 100190,
China
Yinge Bai − Key Laboratory of Green Process and Engineering,
State Key Laboratory of Multiphase Complex System, Beijing
Key Laboratory of Ionic Liquids Clean Process, Institute of
Process Engineering, Chinese Academy of Sciences, Beijing
100190, China
Fangfang Li − Key Laboratory of Green Process and Engineering,
State Key Laboratory of Multiphase Complex System, Beijing
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