Chemical Engineering Science 223 (2020) 115752

Contents lists available at ScienceDirect

Chemical Engineering Science

journal homepage: www.elsevier.com/locate/ces

Prediction of CO2 solubility in ionic liquids using machine learning

methods
Zhen Song a, Huaiwei Shi a,b, Xiang Zhang c, Teng Zhou a,b,⇑
a
Process Systems Engineering, Otto-von-Guericke University Magdeburg, Universitätsplatz 2, D-39106 Magdeburg, Germany
b
Process Systems Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Sandtorstr. 1, D-39106 Magdeburg, Germany
c
Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong, China

h i g h l i g h t s

A dataset containing 10,116 CO2 solubilities in ionic liquids is collected.

Two machine learning models, ANN-GC and SVM-GC, are developed.

Both of the models can give reliable predictions on the CO2 solubility.

The ANN-GC model performs slightly better than the SVM-GC model.

a r t i c l e i n f o a b s t r a c t

Article history: A comprehensive database containing 10,116 CO2 solubility data measured in various ionic liquids (ILs) at
Received 31 January 2020 different temperatures and pressures is established. Based on this database, the relationship between CO2
Received in revised form 23 April 2020 solubility and IL structure, temperature and pressure is correlated using group contribution (GC) meth-
Accepted 25 April 2020
ods. Two different machine learning algorithms, namely artificial neural network (ANN) and support vec-
Available online 30 April 2020
tor machine (SVM), are employed to develop the GC models. For the 2023 test-set data, the estimated
MAE and R2 are 0.0202 and 0.9836, respectively for the ANN-GC model and for the SVM-GC model they
Keywords:
are 0.0240 and 0.9783, respectively. The distributions of prediction errors are plotted for both models to
CO2 solubility
Ionic liquids
provide more comprehensive knowledge on the model performance. The results indicate that both of the
Machine learning models can give reliable predictions on the CO2 solubilities in ILs and the ANN-GC model performs
Group contribution slightly better than the SVM-based model.
Artificial neural network Ó 2020 Elsevier Ltd. All rights reserved.
Support vector machine

1. Introduction
In the past few years, ionic liquids (ILs) have attracted intensive
attention as alternatives for conventional organic solvents in car-
bon capture due to their unique properties, such as thermal stabil-
ity, negligible volatility and high gas solution capacity (Theo et al.,
2016; Zeng et al., 2017). However, the large number of cations and
anions makes it challenging to rationally select and design the
most suitable ILs. In the past decade, the computer-aided molecu-
lar design (CAMD) method (Austin et al., 2016; Gani et al., 2016)
has been extensively used for the optimal design of ILs for various
separation processes (Chávez-Islas et al., 2011; Chen et al., 2019a,
b; Liu et al., 2020; Roughton et al., 2012) including CO2 capture
(Chong et al., 2015, 2016; Valencia-Marquez et al., 2017).
⇑ Corresponding author at: Process Systems Engineering, Otto-von-Guericke
University Magdeburg, Universitätsplatz 2, D-39106 Magdeburg, Germany.
E-mail address: zhout@mpi-magdeburg.mpg.de (T. Zhou).
When using CAMD to design ILs for carbon capture, the devel-
opment of reliable models for predicting the CO2 solubility in ILs
is of central importance. Traditional thermodynamic models, such
as PSRK (Holderbaum and Gmehling, 1991), group contribution-
based SAFT (Mourah et al., 2010), cubic equation of state combined
with UNIFAC (Fredenslund et al., 1975) or COSMO-RS (Eckert and
Klamt, 2002), can estimate gas solubilities. Importantly, they can
well represent the temperature and pressure effects due to their
very sound thermodynamic basis. However, these models some-
times cannot give quantitatively satisfying solubility predictions.
Besides the rigorous thermodynamic modeling, another powerful
method for solubility (or widely speaking property) prediction is
the quantitative structure-property relationship (QSPR) approach
where the property of interest is quantitatively correlated with
certain structural descriptors of the molecules. Due to the develop-
ment of advanced software packages, such as CODESSA (Katritzky
et al., 2002), for the calculation of molecular descriptors, the QSPR
method has been widely used to predict the physical and chemical

https://doi.org/10.1016/j.ces.2020.115752
0009-2509/Ó 2020 Elsevier Ltd. All rights reserved.
2 Z. Song et al. / Chemical Engineering Science 223 (2020) 115752
properties of ILs, including heat capacity (Sattari et al., 2013), elec-
trical conductivity (Gharagheizi et al., 2013), thermal decomposi-
tion temperature (Gharagheizi et al., 2012), toxicity (Zhao et al.,
2014), and viscosity (Zhao et al., 2015).
The most commonly used QSPR methods in CAMD are group
contribution (GC) methods where the molecular descriptors are
the occurrences of functional groups in the molecule. A large num-
ber of GC models have been developed for pure-component prop-
erty predictions, for instance (Gharagheizi et al., 2014; Hukkerikar
et al., 2012; Marrero and Gani, 2001; Sattari et al., 2016). Tradition-
ally, GC methods correlate properties with the group numbers
using a linear expression (Ceriani et al., 2009; Lazzus and Pulgar-
Villarroel, 2015; Huang et al., 2013). However, certain properties
cannot be appropriately described by linear models where in these
cases nonlinear GC models are required to generate more accurate
predictions. Recently, the machine learning (ML) algorithms have
been significantly developed and are now very popular for building
complex nonlinear QSPR or GC models for estimating various types
of properties including CO2 solubility (Tatar et al., 2016;
Sedghamiz et al., 2015), H2S solubility (Faúndez et al., 2016;
Zhao et al., 2016), surface tension (Mulero et al., 2017), octanol-
water partition coefficient (Wang et al., 2019), critical properties
(Su et al., 2019), odor of fragrance molecules (Zhang et al., 2018),
and toxicity of ILs (Cao et al., 2018).
Artificial neural networks (ANN) belong to a set of very popular
ML algorithms inspired by biological neural systems. Numerous
works have shown the high accuracy of the ANN-based GC models
for property predictions (Mondejar et al., 2017; Gharagheizi and
Salehi, 2011; Fatehi et al., 2017). Recently, another ML method,
the support vector machine (SVM), has also attracted substantial
attention for data classification and regression. Due to its remark-
able generalization performance, the SVM approach has obtained
extensive applications in QSPR or GC modeling (Zhao et al., 2014;
Zhao et al., 2015). A rigorous comparison of the predictive abilities
of ANN and SVM based GC models is thus very favorable.
The main objective of this work is to develop ML-based GC mod-
els that could be used for predicting the solubility of CO2 in ILs. To
do this, a comprehensive database consisting of 10,116 CO2 solubil-
ity data measured in various types of ILs at wide temperature and
pressure ranges is first established. Based on the collected solubility
data, an ANN-GC model and an SVM-GC model are developed for
predicting the CO2-in-IL solubilities. The performances of the
obtained models are evaluated and compared. An application
example is provided in the end to guide the readers in predicting
CO2 solubility using our models. Moreover, the original MATLAB
codes are also included in the Supporting Information. Interested
readers can directly make use of the code for their own predictions.
2. Experimental data
In total, 10,116 data points on the CO2 solubility (mole fraction
0.0000648–0.9516) measured in various types of ILs (in total 124
different ILs) from 243.2 K to 453.15 K and from 0.00798 bar up
to 499.9 bar are collected. These data are updated from an earlier
work performed by Lei et al. (2014). The detailed CO2 solubility
data are tabulated in the Supporting Information together with
the corresponding IL abbreviation, temperature and pressure. The
abbreviations, full names, and structures of all the involved cations
and anions are also provided in the Supporting Information. The
cations include imidazolium, pyrrolidinium, pyridinium, piperi-
dinium, ammonium, phosphonium, and sulfonium, and anions
contain tetrafluoroborate [BF4], chloride [Cl], dicyanamide [DCA],
nitrate [NO3], hexafluorophosphate [PF6], thiocyanate [SCN], tri-
cyanomethanide [C(CN)3], hydrogen sulfate [HSO4], bis(trifluoro
methylsulfonyl)amide [Tf2N], methylsulfate [MeSO4], etc.
To build a GC model for predicting CO2 solubility in ILs, IL mole-
cules must be decomposed into building groups in advance. In
order to broaden the applicability of the obtained model, we
decompose ILs into cation cores, cation substituents, and anions.
After performing the decomposition for all the involved ILs, 51 dif-
ferent building groups including 13 cation cores, 28 anions and 10
substituent groups are resulted. A full list of the groups is provided
in the Supporting Information along with their numbers of occur-
rence in each IL.
The experimental data are divided into a training set (8093
points, 80% of the data) to build the model and a test set of the
remaining 2023 data points to evaluate the predictive capability
of the obtained model. Considering the sparsity of the feature
(group number) matrix, instead of performing random selection,
we employ a hybrid artificial-random strategy to decompose the
dataset. Specifically, the data points consisting of the least fre-
quently used groups are equally divided into five folders. Subse-
quently, all the other data points are randomly distributed into
the five folders. Finally, one fold of data is used for testing and
the other four folds of data are used for model training. The result-
ing training and test data are also tabulated in the Supporting
Information.
3. ANN-GC modeling
An artificial neural network (ANN) consists of many layers and
each layer contains a certain number of neurons that receive data
and generate data using transformation functions. In the past few
decades, the number of applications of ANN for quantitative prop-
erty predictions has increased significantly. The ANN-based GC
models have been proven to perform better than the conventional
linear and polynomial ones (Zhou et al., 2018; Mondejar et al.,
2017). The applications of ANN-GC methods include the prediction
of surface tension (Gharagheizi et al., 2011c), density (Valderrama
et al., 2009), critical property (Gharagheizi et al., 2011a), solubility
in water (Gharagheizi et al., 2011b), viscosity (Paduszyński and
Domańska, 2014), etc.
As shown in Fig. 1, a popular ANN architecture comprising of a
three-layer feed forward network is employed in this work. The
input layer receives IL structure information (represented as 51
group numbers) and the temperature and pressure, which in total
gives an input vector p with a size of 53  1. The hidden layer
transfers and delivers this input information to the output layer
where the solubility is predicted and the summation of errors is
quantified. For a known input vector p, the output from the hidden
layer f1(a1) is determined by Eq. (1) and the output of the output
layer f2(a2) (i.e., CO2-in-IL solubility) is calculated by Eq. (2).
f 1 ða1 Þ ¼ f 1 ðW 1  p þ b1 Þ ð1Þ
f 2 ða2 Þ ¼ f 2 ðW 2  f 1 ða1 Þ þ b2 Þ ð2Þ
The MATLAB tansig and purelin transfer functions are employed
in the hidden and output layers, respectively. This combination of
transfer functions is very effective for building a three-layer neural
network. In fact, we tried also other functions and found that the
tansig and purelin functions are indeed the best for our regression.
The expressions of the functions are given below.
2
f 1 ð xÞ ¼ 1 ð3Þ
1 þ e2x
f 2 ð xÞ ¼ x ð4Þ
There are five parameters in this ANN, i.e., the number of neu-
rons in the hidden layer, weight matrices W1 and W2, and bias vec-
tors b1 and b2. The number of neurons in the hidden layer is
normally specified before the weight and bias parameters are
 Z. Song et al. / Chemical Engineering Science 223 (2020) 115752 3

Input Hidden Layer Output Layer

W1 W2
f1(a1) Output
Input p (7×53) a1 (1×7) a2
(53×1) (7×1) (1×1) = f2(a2)
b1 b2
(7×1) a1 = W1×p + b1 (1×1) a = W ×f (a ) + b
2 2 1 1 2

Fig. 1. Schematic structure of the employed three-layer ANN (the dimensions of W1, W2, b1, and b2 are given in the brackets).

regressed. Generally, with too few neurons the network may not be are depicted in Fig. 3. Moreover, the histogram of the prediction
powerful enough for predicting the data. However, with a too large deviations is presented in Fig. 4. As depicted, most of the deviations
number of neurons, the network tends to perform over-fitting. In are close to zero and a very small proportion shows an absolute
this work, we start to train the ANN-GC model with two neurons error higher than 0.1. The largest absolute deviation is around
in the hidden layer and gradually increase the number until no sig- 0.20. It is clear that the ANN-GC model can provide an accurate
nificant improvement in the performance of the network is prediction on the CO2 solubilities in ILs at various temperatures
achieved for both training and test set data. Following this strategy, and pressures.
7 neurons in the hidden layer are finally identified and used. After-
wards, W1, W2, b1 and b2 are obtained by minimizing the summa-
tion of absolute errors between the experimental and model-
predicted CO2 solubility in the training dataset using the
Levenberg-Marquardt algorithm implemented in MATLAB. The
obtained W1, W2, b1, and b2 are provided in the Supporting
Information.
Fig. 2 compares the experimental and model-predicted CO2 sol-
ubility for the 8093 data points in the training set and 2023 points
in the test set. It is clear that both the training and test data dis-
tribute closely along the diagonal line, except for a small number
of outliers which may be attributed to experimental deviations
among different measurements. For providing intuition into the
predictive power of the model, the mean absolute error (MAE)
and the coefficient of determination (R2) are determined. The esti-
mated MAE and R2 for the training set are 0.0200 and 0.9842, and
for the test set, they are 0.0202 and 0.9836, respectively, which
demonstrates that the model is not overfitted on the training data.
Moreover, these statistical indicators show an overall high-quality
prediction of the model.
For a better illustration of the model performance, the errors
between the predicted and experimental solubilities (xpred exp
CO2  xCO2 )
Fig. 3. Error of the ANN-GC model for predicting the CO2 solubility.

Fig. 2. Comparison between the experimental and ANN-GC predicted CO2 Fig. 4. Distribution of the prediction error of the ANN-GC model.
solubility.
4 Z. Song et al. / Chemical Engineering Science 223 (2020) 115752
4. SVM-GC modeling
Support vector machine (SVM) is another popular ML algorithm
and has attracted wide attention in many science and engineering
areas due to its remarkable generalization performance. In the
early years, SVM was mainly employed for pattern recognition
and now this algorithm is extensively used for data regression
and classification (Wang, 2005). Concisely, the SVM method first
maps the input into a high-dimensional feature space by a nonlin-
ear kernel function and then conducts linear regression in this fea-
ture space. The performance of the fitted SVM model depends on
the selected kernel function and the corresponding kernel param-
eters as well as a few internal parameters of the algorithm.
The same type of input descriptors and the same sets of training
and test data are employed for developing the SVM-GC model. The
prediction or approximation function of the SVM model is given by
Eq. (5)
X
l
f ðxÞ ¼ ai K ðx; xi Þ þ b ð5Þ
i¼1
where x denotes the input vector and f(x) is the output. xi is the i-th
feature vector and ai is the weight for this feature vector. Training
points with nonzero weights are called support vectors. Vector a
and the constant b (bias) are adjustable model parameters that
are optimized during the training process. K(x, xi) is a selected ker-
nel function. The Gaussian radial basis function (RBF) kernel is
applied in this work because it has been widely demonstrated to
be very effective.
K ðx; xi Þ ¼ expðr  kx  xi k2 Þ ð6Þ
r is an adjustable parameter of the kernel controlling the ampli-
tude of the RBF function. By default, the kernel parameter r equals
1=sc2 where the kernel scale sc is fitted by the MATLAB SVM solver.
All of the determined parameters for the SVM-GC model are pre-
sented in the Supporting Information.
The comparison between experimental and SVM-GC predicted
CO2 solubility for both training and test data is shown in Fig. 5. It
can be seen that except for a few outliers, most of the solubility
data can be well reproduced by the obtained model. The estimated
MAE and R2 are 0.0231 and 0.9807 for the training set and 0.0240
and 0.9783 for the test set, respectively. These two measures also
Fig. 5. Comparison between the experimental and SVM-GC predicted CO2
solubility.
indicate a high performance of the SVM-GC model for CO2-in-IL
solubility predictions.
Similarly, in order to provide a more comprehensive knowledge
on the model prediction errors, the deviations between the pre-
dicted and experimental solubilities (xpred exp
CO2  xCO2 ) are plotted
against the experimental observations in Fig. 6. In addition, the dis-
tribution of the prediction error is presented in Fig. 7. As seen, most
of the errors fall into the range of [0.05, 0.05] and a very small
amount of them are outside of [0.1, 0.1]. The largest absolute
deviation is around 0.25. These plots demonstrate that the
obtained SVM-GC model can well represent the CO2 solubility in
ILs at various temperature and pressure conditions.
5. Model comparison
From the above sections, we know that both the ANN-GC and
SVM-GC models can well represent the CO2-in-IL solubility. Table 1
summarizes the estimated MAE and R2 for both models. These sta-
tistical indicators generally show a slightly better performance of
the ANN model.
In order to better compare the models, Fig. 8 plots the cumula-
tive probability of the absolute error between experimental and
 
 exp 
model-predicted CO2 solubility (xpred
CO2  xCO2 ) in the test set for
both models. As seen, the error probability curve of the ANN-GC
model is slightly above that of the SVM-GC model in the entire
absolute error range. 91.2% of the ANN-GC predictions and 89.2%
of the SVM-GC predictions show an absolute error less than 0.05.
Besides, 98.9% of the ANN-GC data show a less than 0.10 absolute
error and for the SVM-GC model this value is 97.8%. It is observed
that both of the models can provide reliable predictions on the CO2
solubility and the ANN-GC model performs slightly better than the
SVM-GC model. Besides, ANN-GC has a smaller number of model
parameters and is thus preferentially recommended.
6. Application examples
In this section, an application example is provided where the
ANN-GC and SVM-GC models are employed to predict the CO2 sol-
ubility in [Bmim][BF4] at 298.2 K and 49.3 bar (Entry 1525 in the
collected database). As indicated in the Supporting Information,
the first two elements of the input vector are the temperature
and pressure and subsequently the number of the 51 different
groups present in the IL molecule. Following this, it is known that
Fig. 6. Error of the SVM-GC model for predicting the CO2 solubility.
 Z. Song et al. / Chemical Engineering Science 223 (2020) 115752 5

X
4153  
xSVM ¼ ½ai exp r  kx  xi k2  þ b ¼ 0:443
i¼1

The experimental CO2 solubility is 0.477. Therefore, the relative

deviations of the ANN-GC and SVM-GC models are 2.72% and
7.13%, respectively.

7. Advantages and limitations

To date, various thermodynamic models have been used for

modeling the CO2 solubility in different solvents. Due to the very
sound thermodynamic basis, these models can well represent the
influences of temperature and pressure on the CO2 solubility. Most
of the time, they can also provide qualitatively correct predictions,
which is essential and sufficient for preliminary solvent selection
and process synthesis purposes. For the rigorous process design
or optimization, the quantitative accuracy of the thermodynamic
models can be improved by reducing the application range and
Fig. 7. Distribution of the prediction error of the SVM-GC model. regressing system-specific model parameters.
Despite the high quantitative accuracy of the obtained ML-GC
models, their limitations should not be ignored. Unlike the conven-
Table 1 tional models, the developed ML models are not derived from ther-
Statistical indicators for the regressed ANN-GC and SVM-GC models.
modynamic principles. Temperature and pressure are simply
Model MAE R2 considered as two inputs for the models, as illustrated in the above
ANN-GC 0.0202 0.9836 application example. Having been trained with a large number of
SVM-GC 0.0240 0.9783 solubilities measured at different conditions, the ML models can
indeed, most of the time, correctly predict the temperature and
pressure effects. However, there is no theoretical guarantee on this.
The other limitation of the ML models is that they are currently not
available in process simulators and to directly use them for opti-
mization is not easy. Nevertheless, many researchers (e.g.,
Schweidtmann et al., 2019; Eason and Biegler, 2018) are develop-
ing advanced algorithms to solve optimization problems involving
data-driven models. With such algorithms, we expect that the
developed ML models can be useful for computer-aided IL and pro-
cess design where the optimal solvent and operating conditions are
identified for a given carbon capture process.

8. Conclusion

Fig. 8. Cumulative probability of the absolute error between experimental and
model-predicted CO2 solubility in the test set.
for the ANN model, the input vector p is the transpose of [298.2,
49.3, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 1, 3,
0, 0, 0, 0, 0, 1, 0, 0, 0, 1, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0].
According to Eqs. (1)–(4), we have:
 
2
xANN ¼ W 2   1 þ b2 ¼ 0:464
1 þ e2ðW 1 pþb1 Þ
For the obtained SVM-GC model, there are in total 4153 support
vectors (xi), as presented in the Supporting Information. The fitted
kernel scale is 70.93 thus r equals 0.0002. The regressed weight
vector a and bias b are also provided in the Supporting Informa-
tion. Combining Eqs. (5) and (6), for a given input vector x (i.e., vec-
tor p in the ANN model), we have:
Two GC models have been developed using the ANN and SVM
algorithms for the prediction of the solubility of CO2 in different
types of ILs at various temperatures and pressures. The results
show that both of the models can give reliable predictions and
the ANN-GC model is slightly better than the SVM-GC model. In
the cases where experimental measurements are difficult, costly
or even infeasible, the obtained models can provide fast solubility
estimations. On the other hand, these models can be incorporated
into a CAMD framework to identify best ILs for carbon capture
processes.
An accurate model prediction is normally limited to the com-
pounds and conditions similar to those used in model training.
Since the training data already cover most of the known types of
ILs measured at extremely broad ranges of temperatures and pres-
sures (from 243.2 K to 453.15 K and from 0.00798 bar up to
499.9 bar), the obtained models are expected to possess a wide
application range. The regressed model parameters as well as the
original MATLAB codes are provided in the Supporting Information,
interested readers can thus make use of the models for their own
predictions.
It is worth mentioning that the experimental solubility data,
especially the cases of very low solubilities, may have large uncer-
tainties. Usually, these uncertainties should be taken into account
in model development. However, since most of the available liter-
6 Z. Song et al. / Chemical Engineering Science 223 (2020) 115752

ature has not reported the data uncertainties, they are not consid-
ered in the present work.
CRediT authorship contribution statement
Zhen Song: Conceptualization, Methodology, Writing - original
draft. Huaiwei Shi: Data curation, Investigation. Xiang Zhang:
Software, Validation. Teng Zhou: Supervision, Writing - review &
editing.
Declaration of Competing Interest
The authors declare that they have no known competing finan-
cial interests or personal relationships that could have appeared
to influence the work reported in this paper.
Appendix A. Supplementary material
Supplementary data to this article can be found online at
https://doi.org/10.1016/j.ces.2020.115752.
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