1 s2.0 S0048969719357936 Main
1 s2.0 S0048969719357936 Main
1 s2.0 S0048969719357936 Main
H I G H L I G H T S G R A P H I C A L A B S T R A C T
a r t i c l e i n f o a b s t r a c t
Article history: With steady growth on CO2 emission over the years, removal of CO2 from the environment is a critical issue in
Received 5 September 2019 preventing global warming and climate change. Due to negligible volatility and remarkable thermal stability,
Received in revised form 1 November 2019 ionic liquids have become potential media for CO2 capture. However, their drawbacks such as high price, toxicity
Accepted 25 November 2019
and inefficient energy consumption have severely limited their applications in CO2 capture. Here, a promising
Available online 28 November 2019
deep eutectic solvent was synthesized by a one-pot method, simply mixing NH4Cl with monoethanolamine
Editor: Huu Hao Ngo (MEA) at 30 °C for 30 min to form [MEAHCl][MEA] confirmed by 1H NMR. [MEAHCl][MEA] with EG exhibits a
rapid initial kinetics of CO2 absorption, around 22.5 wt% within 10 min. It also has good thermal-stability, high
Keywords: tolerance to water contents, economically feasibility of regeneration and robust performance in recycle. This
Greenhouse gas novel capture system which can be prepared on-site is feasible for industrialization and offers an efficient, inex-
CO2 emission pensive and safe system for CO2 capture.
CO2 capture © 2019 Elsevier B.V. All rights reserved.
Deep eutectic solvent
Solvent regeneration
⁎ Corresponding author at: Biochemical Engineering Research Center, Anhui University of Technology, No. 59 Hudong Road, Ma'anshan, Anhui 243002, PR China.
E-mail address: [email protected] (X. Xu).
https://doi.org/10.1016/j.scitotenv.2019.135798
0048-9697/© 2019 Elsevier B.V. All rights reserved.
2 Y. Bi et al. / Science of the Total Environment 705 (2020) 135798
1. Introduction presence of water but with various drawbacks like timing consuming
procedure for DES synthesis, and great energy consumption during syn-
CO2 emission mainly from the combustion of fossil fuels (Valencia- thesis and regeneration. Moreover, EDA readily reacts s with moisture
Marquez et al., 2017) most contributes to global warming and climate to produce toxic and irritating mist, further causing serious damage to
change (Cai et al., 2017; Leron and Li, 2013). Since it has steadily health even with very short exposure. Hence, an efficient, inexpensive
grown over the years, removal of CO2 from the environment has become and safe system is greatly pivotal for CO2 capture in industrial scale.
a major issue in reducing CO2 emission rates and further slowing climate Here, we report that a DES of [MEAHCl][MEA] was prepared using a
change. The conventional method using monoethanolamide (MEA) one-pot method by simply mixing MEA and NH4Cl at 30 °C for 30 min.
scrubbing technology is efficient for CO2 capture through chemical ab- The characterization of DES with and without the presence of Glycerol
sorption but with the problems including degradation at high tempera- (G) and ethylene glycol (EG) before and after CO2 absorption was inves-
ture and in oxidizing environment (Yu et al., 2012), corrosive effect tigated using IR, TGA and NMR, and TGA-FTIR. The capacity of CO2 up-
(Mirza et al., 2017; Sreedhar et al., 2017; Yang et al., 2008) and intensive take was determined at different temperatures and water contents.
energy consumption for solvent regeneration (Kvamsdal and Rochelle, Feasibility of solvent regeneration was further explored.
2008; Zeng et al., 2017). Combination of MEA and diethanolamine
(DEA) reduces degradation rate and corrosion effects and lowers energy
2. Materials and methods
consumption during regeneration (Barzagli et al., 2010) but with slow
absorption rates. Hence, it is highly desirable to develop new systems
2.1. Materials
for CO2 capture.
In recent years various methods were developed to capture CO2 such
MEA, MEAHCl, NH4Cl, EG and G were purchased from Tansuo
as liquid hydrocarbon surfactants (Zhang et al., 2010), liquid polymers
(China) with AR purity N98%. Pure CO2 and N2 were supplied from Nan-
Chen et al., 2009; Ngoy et al., 2014) and ionic liquids (ILs). Due to negli-
jing special gas (China).
gible volatility and remarkable thermal stability, ILs have been inven-
tively investigated as potential candidates for CO2 capture (Sistla and
Khanna, 2015; Zhang et al., 2013). The CO2 capture capacity of ILs 2.2. CO2 capture and solvent regeneration
through physical absorption was tuned by tuning the properties of cat-
ions or anions (Goodrich et al., 2010; Gurkan et al., 2010; Niedermaier The experimental procedures for DES preparation, CO2 uptake and
et al., 2013) and aprotic heterocyclic anions (AHAs) (Wang et al., DES recycle were shown in Fig. 1.
2011).Anions were demonstrated to have more influence on CO2 solubil- DES Preparation: DES of [MEAHCl][MEA] was prepared by stirring a
ity than cations (Alfarano et al., 2005; Anthony et al., 2005; Kanakubo mixture of NH4Cl and MEA at molar ratios from 1:4 to 1:6 at 30 °C. After
et al., 2015). Task-specific ionic liquids (TSILs) with amino-function 30 min, the mixture became a clear solution without any precipitant. EG
groups group was employed for better absorption performance (Bates or G was introduced into DES of [MEAHCl][MEA] at room temperature
et al., 2002). However, due to high molecular weight of ILs, once converg- at a certain molar ratio.
ing CO2 uptake capacity from CO2 mole/IL mole into gravimetric values, CO2 uptake: CO2 uptake was measured using a weight method. CO2
the CO2 uptake capacity of ILs is less attractive, 18.5 wt% in dual amino- gas was introduced into an absorption vial (5 mL) containing around
functionalized IL of aqueous 1,3-bis(3-aminopropyl) imidazolium bro- 2.5 g of DES at a flow rate of 10 mL min−1 of CO2 at different tempera-
mide (Zhang et al., 2013), and 16.4 wt% in pure superbases derived protic tures. The weight at different time points was determined using an elec-
ILs (Wang et al., 2010). Other disadvantages of ILs like high price, toxicity tronic balance with an accuracy of ±0.1 mg. The weight percentage of
(Ghazali et al., 2019; Murshid et al., 2019), inefficient energy consump- CO2 uptake was calculated by the ratio of the weight increase at a
tion of ILs lead to the applications of ILs for CO2 capture only suitable
for laboratory scale but not for industrial scale (Sreedhar et al., 2017).
Deep eutectic solvents (DESs) with merits of low cost, good renew-
ability and low toxicity (Vigier et al., 2015) are considered to be green
solvents and have emerged as alternatives to ILs for CO2 capture
(Mota-Morales et al., 2018). DESs are prepared by mixing a hydrogen
bond acceptor (HBA) and a hydrogen bond donor (HBD) at a certain
molar ratio to form a low melting point mixture through hydrogen
bonding interaction (Abbott et al., 2004; Smith et al., 2014). Natural
DES based on L-arginine and glycerol at the ratio of 1:6 had the absorp-
tion capacity of 0.511 mol/mol at 60 °C after 2 h at 100 mL min−1of CO2
and then CO2 was able to be released at 100 °C (Ren et al., 2018). Imid-
azole tailored DES containing MEA and 1-butyl-3-methylimidazolium
(BMIMCI) with the molar ratio of 4:1 was able to absorb CO2 with
21.4 wt% after 50 h CO2 bubbling at room temperature but only around
10 wt% at the initial 1 h (Cao et al., 2015). Task-specific ternary DES sys-
tems comprising choline chloride (ChCl), glycerol and superbases were
developed to capture CO2 at a capacity of ~10 wt% (Sze et al., 2014), less
than conventional ILs. The CO2 absorption of MEA−[C3OHmim]BF4 and
MEA−[C3OHmim]Cl reached to 26.9 wt% and 28.6 wt%, respectively
(Huang et al., 2011). The presence of ethylene glycol or diethylene gly-
col in [TETA·Cl] increased CO2 absorption by enhancing the basicity of
DES through activation \\NH− or \\NH2 (Zhang et al., 2018a). The in-
troduction of metal chloride to TMAC/MEA at the ratio of 1:5:0.1 im-
proved CO2 absorption to 36.81 wt% at 50 °C after 1 h uptake but with
difficulty in solvent recycle (Li et al., 2019). DES based on hydrochloride
salt and ethylenediamine (EDA) exhibited ed. a high CO2 uptake rate at Fig. 1. The flow chart of the procedures of DES preparation, CO2 uptake and solvent
25.2 wt% after 2.5 min uptake at 30 °C and had good performance in the regeneration.
Y. Bi et al. / Science of the Total Environment 705 (2020) 135798 3
2.3. Characterization
1
H NMR and 13C NMR spectra were recorded using BRUKER
AVANCE-400400 MHz (Switzerland). Fourier transform infrared (FT-
IR) spectra (Nicolet IS10, Thermo-Fisher Scientific spectrometer, USA)
were obtained using KBr as window material. Thermal stability of
DESs was determined by thermogravimetric analysis (TGA, SDT650,
TA, USA) by heating samples to 350 °C at 5 °C min−1. Viscosity (η) of
the mixtures was determined at different temperatures using a rheom-
eter (Youli Ltd. Shanghai, China). Conductivity of the mixtures was mea-
sured at different temperatures using a conductivity meter (FE38,
Mettler Toledo, Shanghai, China). The viscosity and conductivity of
each sample were measured at least three times and the average
value was reported.
Fig. 3. Characterization of the reaction between DES and CO2. a. 13C NMR before and after CO2 absorption by [MEAHCl][MEA]. b. 1H NMR after CO2 absorption by [MEAHCl][MEA]. c. FTIR
spectra for MEA, DES before and after CO2 absorption.
assigned to νCOO asymmetric stretching mode and the peak for showed the peak at around 2350 cm−1 attributed to CO2 from around
νCOO bend mode at 821 cm−1 were also attributed to the formation 8 min to 24 min for [MEAHCl][MEA] after CO2 absorption, and the
of carbamate groups (Gurkan et al., 2010). The peaks at 1017 cm−1 peaks of 2900 and 1050 cm−1 from around 19 min assigned to νC\\H
for the C\\N stretching mode and at 1068 cm−1 for the C\\O sym- stretching mode and νN\\H stretching mode of amine for [MEAHCl]
metric stretch mode all appeared on FTIR spectra of DES before and [MEA] before and after CO2 uptake (Fig. 4c). The time overlap between
after CO2 absorption, but enhanced after CO2 absorption, indicating CO2 release and DES evaporation from 19 min to 24 min further con-
the reaction between DES and CO2. firmed that the DES of [MEAHCl][MEA] cannot be regenerated.
3.3. CO2 uptake by DES 3.4. CO2 uptake by [MEAHCl][MEA] in the presence of glycerol/ethylene
glycol
To evaluate the potential of [MEAHCl][MEA] for CO2 capture, the CO2
uptake was determined at different molar ratios at 20 °C after 50 min of To improve thermal-stability of [MEAHCl][MEA], glycerol or ethyl-
absorption at a flow rate of 10 mL/min of CO2. As demonstrated in ene glycol was introduced to [MEAHCl][MEA] ([MEAHCl]:[MEA] =
Fig. 4a, the CO2 uptake capacity increased with MEA contents 1:4). TGA was performed to investigate the thermal-stability of
(Adeyemi et al., 2017), reaching to around 0.25 g/g at the ratio of 1:4. [MEAHCl][MEA] in the presence of G and EG before and after CO2 ab-
The capacity of CO2 uptake by [MEAHCl][MEA] was much higher than sorption. The TGA results (Fig. 5a and FigS4, ESI) displayed that the pres-
30 wt% MEA (Rochelle, 2009), implicating the role of Cl− in enhancing ence of 30 wt% G and 10 wt% EG in [MEAHCl][MEA] clearly improved
the absorption of CO2 in MEA. The better performance of [MEAHCl] the thermal-stability by around 40 °C, compared with [MEAHCl][MEA]
[MEA] than [ChCl][MEA] (Fig. 4a and Fig. S2, ESI) suggests that using (Fig. 4b). Most importantly, [MEAHCl][MEA] with 30 wt% G and 10 wt
[MEAHCl] instead of [ChCl] as HBA has better CO2 uptake capacity. In ad- % EG became less stable after CO2 absorption than [MEAHCl][MEA], im-
dition, the presence of amine functional groups in HBA may affect the plicating that [MEAHCl][MEA] can be regenerated in the presence of G/
basicity of DES which may be a reason for the better CO2 absorption ca- EG without solvent loss (Fig. 5a). Hence, [MEAHCl][MEA] at the ratio of
pacity. In comparison with [MEAHCl][EDA] (Trivedi et al., 2016), the less 1:4 with the presence of 10 wt% EG /30 wt% G was used for the further
CO2 uptake capacity by [MEAHCl][MEA] is probably caused by the dif- experiments.
ference in the basicity between two solvents. We then examined whether carbamate was formed during CO2 ab-
Thermal-stability of solvents is an important factor for CO2 absorp- sorption in the presence of G or EG. The FTIR results revealed that the
tion. Fig. 4b shows that there was a weight loss for [MEAHCl][MEA] sol- peak at ~2900 cm−1 disappeared, suggesting the formation of carba-
vent with the temperature increasing from 60 °C, indicating that mate groups between [MEAHCl][MEA] and CO2, which was further con-
[MEAHCl][MEA] easily experiences thermal degradation like MEA. firmed by the peak at 821 cm−1 for νCOO bend mode (Fig. 5b). The CO2
Both TGA and isothermal TGA results (Fig. 4b and Fig. S3, ESI) exhibited uptake kinetics with time at different temperatures of 20, 40, 60 and
that [MEAHCl][MEA] became more stable after CO2 absorption than be- 80 °C at a flow rate of 10 mL/min of CO2 was monitored for 250 min
fore absorption, implicating that [MEAHCl][MEA] is not able to be re- (Fig. 5c). The CO2 uptake increased rapidly in the first 10 min for all
generated after CO2 uptake. Furthermore, TGA-FTIR results (Fig. 4c) the tested systems, reaching to around 0.225 g/g and 0.16 g/g for
Y. Bi et al. / Science of the Total Environment 705 (2020) 135798 5
Fig. 4. CO2 absorption and DES characterization before and after CO2 absorption. a. CO2 absorption by [MEAHCl][MEA] at 20 °C. b. TGA. c. TGA-FTIR.
[MEAHCl][MEA] with EG and G, respectively, remarkably higher than for all the tested systems. A dramatic increase in the viscosity for
most DES (Ali et al., 2014; Bates et al., 2002; Luo et al., 2014a; [MEAHCl] [MEA] and [MEAHCl] [MEA] with G was observed after CO2
Saravanamurugan et al., 2014; Wang et al., 2011) and ILs (Zhang et al., absorption at the temperature b40 °C (Fig. 6a). In contrast, the viscosity
2013), then slightly increased afterwards except for the temperature of [MEAHCl] [MEA] with EG after the same amount of CO2 absorption
at 80 °C (Fig. 5c). The gradual decline with time in the CO2 uptake at was much less (Fig. 6a), implicating that the presence of EG leads to
80 °C and the decrease in CO2 uptake with temperature increasing low viscosity, then resulting in a more rapid CO2 uptake at the initial
imply that less CO2 solubility at high temperature plays a pivotal role stage (Fig. 5c), and eventually causing the better performance for CO2
in CO2 uptake. In addition, the reduction in the basicity and polarity in uptake due to the less reduction in the mass transfer rate. We further
the presence of G, quantified by Kamlet-Taft empirical scale (Ab Rani determined the conductivity of [MEAHCl][MEA] and [MEAHCl][MEA]
et al., 2011; Jessop et al., 2012) could be one reason for the poorer per- with and without EG/G. As seen in Fig. 6b, the conductivity increased
formance of [MEAHCl][MEA] with G than that with EG. However, ac- with temperature. A dramatic reduction in the conductivity was ob-
cording to the CO2 uptake results (Fig. 5c), G/EG in [MEAHCl][MEA] served in the presence of G. Furthermore, CO2 absorption led to a signif-
only serves as solvent, not like PEG200 in TETA (Tao et al., 2018), icant drop in the conductivity for all the tested systems, especially for
which is also involved in the reaction between [MEAHCl][MEA] and CO2. [MEAHCl][MEA].
Viscosity plays a critical role in CO2 uptake by DESs. The combination Due to inevitable water contents in flue gases, here the effect of
of [MEAHCl][MEA] and G exhibited more viscous than [MEAHCl][MEA] water contents in DES on the CO2 uptake was explored. The CO2 uptake
with EG (Fig. 6a). During the initial CO2 uptake, the formation of the in- kinetics by [MEAHCl][MEA] with G/EG containing 10 wt% and 20 wt% of
tramolecular hydrogen bond between the carbamate and the proton- water was determined. The effect of water contents on the CO2 uptake
ated OH may make great contribution in an increase in the viscosity was dependent on the solvent compositions, as shown in Fig. 7. The
6 Y. Bi et al. / Science of the Total Environment 705 (2020) 135798
Fig. 5. Characterization of [MEAHCl][MEA] (1:4) with G/EG before and after CO2 and the CO2 uptake kinetics. a. TGA. b. FTIR. c. CO2 uptake kinetics at different temperatures.
presence of water in [MEAHCl][MEA] with G significantly improved the was derived for the combination of [MEAHCl][MEA] with G and with
CO2 uptake rate during the initial absorption stage (Fig. 7a), probably EG, −64.02 and −60.47 kJ/mol, respectively. These values are in the
resulting from the free volume increase caused by the formation of range for chemical absorption, confirming that the CO2 uptake by
water-DES network, further leading to the reduction in the viscosity [MEAHCl][MEA] with G and EG is chemical absorption, consistent with
and causing in the enhancement in the mass transfer rate of CO2. In con- the FTIR and NMR results (Figs. 3 and 5), similar to [MEAHCl][EDA] in
trast, no obvious benefit for the CO2 uptake by [MEAHCl][MEA] with EG the previous report (Trivedi et al., 2016), but less than the conventional
was observed in initial absorption stage (Fig. 7b) because the viscosity MEA scrubbing process (Huang and Rüther, 2009). The less absorption
of [MEAHCl][MEA] with EG was in the similar range of DES with heat of [MEAHCl][MEA] with G/EG makes them more economically fea-
water. With the increase in the water contents the CO2 uptake capacity sible for regeneration.
decreased due to the decrease in the concentration of effective reac- Flue gases from different sources contain CO2 in the range from 10%
tants, consistent with the previous report (Su et al., 2009). to 25%. Hence, we detected the effect of CO2 concentration on CO2 cap-
ture by [MEAHCl][MEA] with G/EG. As shown in (Fig. S6, ESI), the con-
3.7. CO2 release and solvent regeneration centration of CO2 in the simulated flue gases affected the uptake
kinetics but not the CO2 uptake capacity. To explore the feasibility of sol-
Before evaluating the feasibility of CO2 release and solvent regener- vent regeneration, CO2 release and solvent reuse for CO2 absorption was
ation, the heat of absorption during CO2 uptake was first calculated exploited. After CO2 absorption reaching around 16 wt% at 20 °C, the de-
using the Van't Hoff plot. From Fig. S5 (ESI), the heat of absorption sorption was performed by heating the systems to 110 °C until no
Y. Bi et al. / Science of the Total Environment 705 (2020) 135798 7
Fig. 7. Effect of water contents on CO2 absorption. a. [MEAHCl][MEA] (1:4) with 30 wt%
Fig. 6. Viscosity and conductivity of different solvents before and after CO2 uptake. a. [G]. b. [MEAHCl][MEA] with 10 wt% [EG].
Viscosity. b. Conductivity.
Fig. 8. CO2 absorption-desorption by [MEAHCl][MEA] with EG. a. CO2 absorption-desorption cycles. b. 1H and 13C NMR of [MEAHCl][MEA] with EG before, after CO2 absorption and after
CO2 desorption. c. TGA-FTIR analysis of [MEAHCl][MEA] with EG. d. TGA-FTIR analysis during CO2 desorption.
Appendix A. Supplementary data Barzagli, F., Mani, F., Peruzzini, M., 2010. Continuous cycles of CO2 absorption and amine
regeneration with aqueous alkanolamines: a comparison of the efficiency between
pure and blended DEA, MDEA and AMP solutions by 13C NMR spectroscopy. Energy
Supplementary data to this article can be found online at https://doi. Environ. Sci. 3, 772–779. https://doi.org/10.1039/C9EE02.
org/10.1016/j.scitotenv.2019.135798. Bates, E.D., Mayton, R.D., Ntai, I., Davis, J.H., 2002. CO2 capture by a task-specific ionic liq-
uid. J. Am. Chem. Soc. 124, 926–927. https://doi.org/10.1021/ja017593d.
Cai, Y., Chen, Y., Li, Q., Li, L., Huang, H., Wang, S., Wang, W., 2017. CO2 hydrate formation
promoted by a natural amino acid l-methionine for possible application to CO2 cap-
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