Arab J Sci Eng

DOI 10.1007/s13369-014-1223-3

RESEARCH ARTICLE - SPECIAL ISSUE - CHEMISTRY

A New QSPR Model for Predicting the Densities of Ionic Liquids

Mohanad El-Harbawi · Brahim Belhaouari Samir ·
Moulay-Rachid Babaa · M. I. Abdul Mutalib

Received: 3 September 2013 / Accepted: 31 January 2014

© King Fahd University of Petroleum and Minerals 2014

Abstract A new mathematical model for the prediction Keywords Density · Ionic liquids · QSPR · Mathematical
of ionic liquids (ILs) densities using quantitative structure– modeling
property relationship approach is presented. The model was
developed based on a data set containing 918 experimen-
tally measured density data for 747 pure ILs which were
quoted from Shen et al. (Chem Eng Sci 66:2690–2698, 2011).
MATLABTM software was used in the development of the
algorithm, and the code was written based on a combination
of multiple linear regression (MLR) method and polynomial
equation. The results showed that the model is capable of
predicting IL densities with very high accuracy at a corre-
lation of determination value R 2 = 99.5 %. The proposed
model can be considered comparable to (if not more accu-
rate than) other established models which have been devel-
oped using the traditional MLR, polynomial, and artificial
neural network methods. In addition, this model is practical,
cost-effective and can be used as alternative to experimental
measurement of density of ILs.

Electronic supplementary material The online version of this

article (doi:10.1007/s13369-014-1223-3) contains supplementary
1 Introduction
material, which is available to authorized users.

M. El-Harbawi (B)
Department of Chemical Engineering, King Saud University,
Riyadh 11421, Saudi Arabia
e-mail: melharbawi@ksu.edu.sa; mohanad_75@yahoo.com
B. B. Samir
Department of Mathematics, College of Science and General
Studies, Alfaisal University, Riyadh 11533, Saudi Arabia
M.-R. Babaa
School of Engineering, Nazarbayev University, 53 Kabanbay Batyr
Ave., Astana 010000, Republic of Kazakhstan
M. I. A. Mutalib
Chemical Engineering Department, Universiti Teknologi PETRONAS,
31750, Bandar Seri Iskandar, Tronoh, Perak, Malaysia
Ionic liquids (ILs) have been the subject of increasing atten-
tion due to their unique physicochemical properties such as
high thermal stability, large liquid range, high ionic conduc-
tivity, high solvating capacity, negligible vapor pressure, and
non-flammability that make them ideal solvents for green
chemistry [1–4]. They are often referred to as designer sol-
vents because of their structure and ability to be modified
and produce a set of desired properties [5] for a specific pur-
pose, such as catalysts [6–11], extraction processes [12–16],
solvent for CO2 capture [17–23], sulfur removal [24–29],
and electrochemistry [30–32]. Among the physicochemical
properties of ionic liquids, density is crucial in the industrial
process design involving ionic liquids [33–35].

123

Even though there are many experimental standard test
methods have been developed in the past to measure the den-
sity, most of these methods are time-consuming and expen-
sive to be conducted. In addition, ILs density data are either
scarce and sometimes absent due to the large number of ILs
synthesized every year. Therefore, it is desirable to have pre-
dictive models for calculating the ILs properties as alternative
to the experimental measurements.
QSAR method was developed in nineteenth century by
Mills [36], who proposed a QSPR models for predicting the
melting and boiling points of homologous series. In the last
decade, QSPRs are being applied in many disciplines [37–
56]. There are many QSAR models developed in the past
to predict the density of ILs. For instance, Palomar et al.
[57] used COSMO-RS software to determine the density of
40 imidazolium salts. Later, they proposed a computational
approach based on a new priori molecular descriptor of 45
imidazolium-based ILs derived from COSMO-RS and arti-
ficial neural network (ANN) [58]. The model was validated
against experimental data, and the correlation coefficient, R 2
obtained was 99.5 %. Trohalaki et al. [59] employed electro-
static, quantum mechanical and thermodynamic descriptors
to derive QSPR model to predict the density of triazolium
bromides using CODESSA software. The model’s accuracy
exceeded 90 %. Valderrama et al. [60] proposed a method
using ANN and group contribution method (ANN + GCM) to
predict the density of ILs. The average absolute relative devi-
ation (AARD) for this method was 0.15 %. Lazzus [61] used
data of 131 imidazolium-based ILs to train a NN model devel-
oped with particle swarm optimization and also obtained
a high-accuracy model (AARD = 0.44 and R 2 = 0.9934).
Lazzus [62] also employed the polynomial expansion (PE)
and derived a QSPR model from 238 experimental data sets
for 163 ILs. The model shows a lower accuracy when com-
pared against the experimental values (R 2 = 0.9307 and
AARD = 2 %). The same author [63] went on and devel-
oped another model using a combined method of AAN and
GCM. A higher accuracy was obtained with a correlation
coefficient, R 2 = 0.9972 based on a 250 ILs experimen-
tal data. Valderrama and Zarricueta [64] proposed a gen-
eralized correlation based on a set of 602 density data for
146 ILs. The AARD of 2.6 % was obtained. Qiao et al. [65]
used a combined least square method and GCM to develop
a model and estimate the density of ILs based on a data set
containing 123 ILs with 6,750 data points, whereas Shen
et al. [66] utilized Valderrama and Robles [67] GCM com-
bined with Patel–Teja equation of state (GC–PT) to esti-
mate the density of ILs based on a data set of 747 pure
ILs. The results showed an AARD of 4.4 % for 918 data
points of density at ambient temperature and atmospheric
pressure.
In all the literature mentioned above, multiple linear
regression (MLR) and ANN methods were the main
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Arab J Sci Eng
approaches used by the researchers in their work to develop
correlation models for predicting density of ILs. In this work,
a new and more accurate model is proposed based on a com-
bination of MLR method and polynomial equation to pre-
dict the density of 747 ILs using QSPR for a data set of
918 ILs.
2 Model Development
The data set used for developing the proposed model was
taken from Shen et al. [66] (provided by Table S1 in the
supplementary Materials). In their work, the authors used
47 functional groups as molecular descriptors, which were
defined according to the Valderrama and Robles [67] group
contribution method. In this work, group contribution method
was used to correlate structural molecular properties called
“descriptors” with mathematical functions representing the
property of a molecule by means of statistical methods. The
descriptors here are the functional groups. Their contribu-
tions are obtained by fitting the adopted mathematical func-
tion to the set of experimental data. In our case, the group con-
tribution method expresses the density as a function of a sum
of contributions of all the functional groups constituting the
molecule. Shen et al. [66] collected a total of 918 experimen-
tal density data for 747 pure ILs and developed a model to pre-
dict the density at atmospheric pressure and ambient temper-
ature based on Patel–Teja (PT) equation of state (EOS). The
list of 747 ILs studied covers a wide range of alkyl-substituted
cations based on imidazolium, pyridinium, triazolium, tetra-
zolium, hexafluorophosphate, tetraalkylammonium, and so
on with anions including hexafluorophosphate, tetrafluo-
roborate halide bis(trifluoromethylsulfonyl)imide, bis(per-
fluoroethylsulfonyl)imide, carboxylic acid, alkyl sulfate, and
dialkylphosphate.
In this work, the new model is developed based on a com-
bination of MLR method and polynomial equation using the
same molecular descriptors reported by Shen et al. [66]. Gen-
erally, the data set consists of a response variable, which
is denoted as Y , and many predictor variables, which are
denoted as X 1 , X 2 , . . . , X p , with subscript p representing
the total number of predictor variables. The true relationship
between Y and X 1 , X 2 , . . . , X p can be approximated by a
regression model expressed as [68]:
Y = f (X 1 , X 2 , . . . X p ) + ε (1)
where ε is defined as a normal random error expressing the
discrepancy in the approximation. The linear form of Eq. (1)
can be expressed as:
Arab J Sci Eng

YMLR = α0 + α1 X 1 + α2 X 2 + · · · + αn X n + ε (2) (Eq. 9) between the predicted density values and the experi-
mental published data.
where ao , a1 , . . ., an , are defined as regression coefficients
N

for MRL model, i.e., constants to be derived from the data. 100  ΦCal − ΦExp
Equation (2) was then integrated with a polynomial model ARD = (7)
N ΦExp i
(Eq. 3) [69]. The interaction between MLR and polynomial i=1
models is expressed as ωX i . The final hybrid model can be
N  
described by Eq. (4): 100   ΦCal − ΦExp 
AARD =   (8)
N ΦExp i
YPolynomial = γ0 + γ1 ω1 + γ2 ω2 + · · · + γm ωm + ε (3) i=1

100   
N
AAE = ΦCal − ΦExp i (9)

n 
m 
k N
i=1
Ymodel = α0 + αi X i + γi ω +
i
δi ωX i (4)
i=1 i=1 i=1 where, ΦCal is the calculated values, and ΦExp is the experi-
where α0 , α1 , . . . , αn are the parameters for MRL model, ment values.
γ1 , . . . , γm are the parameters for polynomial model, δ1 , . . . , The determination of the coefficients for the model based
δk are the parameters for the interaction between the descrip- on the descriptors, which give the relationship between the
tors, n is number of parameters for MLR model, m is num- density of each IL and its molecular structures, is an impor-
ber of parameters for polynomial model, k is number of tant step in QSPR modeling. For this purpose, the combined
interactions between MLR model and polynomial models, MLR model and the polynomial equation were used to deter-
k mine the coefficients based on functional group contributions
i=n+1 δi ωX i is the interaction between MLR and polyno-
mial models, and as given by the Eq. 4 and the calculations were performed
using MATLAB programming language. The model was

n
built by randomly partitioning the data set into training and
ω= X i ; αi = βi for i ≤ 1; γi = βi+n for i ≤ m;
i=1
test sets (50–50 % training–testing split). In Table S1, data
δi = βi+n+m for i ≤ k; n + m + k + 1 = p, from raw 1 to 459 were used for training process, while the
rest of the data (from raw 460 to 918) were used for prediction
The least square method was used to estimate the parame- purpose. In the training process, the code trained the data to
ters ( p) of the proposed model. The algebra matrix for the obtain the optimal coefficients based on the least square error
proposed model is illustrated by Eqs. (5) and (6): between the predicted density values and the experimental
values. In order to compress the number of coefficients with-
Ymodel = Ψβ  (5) out decreasing the accuracy of the model, R 2 , the hypothesis
testing method was used to identify and eliminate insignifi-
where, cant coefficients. The most significant coefficients obtained
from the hypothesis testing method were only selected and
β = (α 0 , α 1 , . . . , α n , γ 1 , . . . , γ m , δ1 , δ2 , . . . , δk )
used in Eq. (4) to predict the ILs density values. The optimal
= (Ψ  Ψ )−1 Ψ  Y
model is obtained by searching for the optimal modeling para
where Ψ  is the transpose matrix given by Eq. (6). meters. The finalized model built from the optimal parame-

⎡ ⎤
1, X 1,1 , . . . , X n,1 ω1 , ω12 , . . . , ω1m ωX 1,1 , . . . , ωX n,1
⎢ .. .. .. .. .. .. .. .. ⎥
Ψ = ⎣. . . . . . . . ⎦ (6)
1, X 1,N , . . . , X n,N ω N , ω2N , . . . , ωm
N ωX 1,N , . . . , ωX n,N

where N is the number of the density experimental val-
ues for the ILs, X i = (X i,1 , X i,2 , . . . , X i,N ), and ω =
(ω1 , ω2 , . . . , ω N )
MATLAB software version 7.8.0.347 was used to develop
the code and calculate the ILs densities following the algo-
rithm shown in Fig. 1. The accuracy of the developed model
is confirmed using three indicators, i.e., the average relative
deviation (ARD) (Eq. 7), the average absolute relative devi-
ation (AARD) (Eq. 8), and the average absolute error (AAE)
ters has undergone validation with a testing/prediction set to
ensure that the model is appropriate and useful.
3 Results and Discussions
The developed model was initially trained with the train-
ing data set using least square error method. MATLAB code
utilized experimental data (50 % of the whole data set) for

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 Arab J Sci Eng

Fig. 1 Algorithm for

estimation of IL densities using
MATLAB 7.8.0.347 Start

Data collections

Structural formula

Descriptor computation

50% 50%

Data collections Data collections

(training set) (testing set)

Data preprocessing to remove

outliers

Development of the hybrid model

General model compression using

hypothesis testing

R2 significantly
No decreases?

Yes
- Find the optimal parameters
- Find the optimal model
- Predict the density

Training set Testing set

2 2
- Calculate R , ARD, AARD and AAE - Calculate R , ARD, AARD and AAE
- Plot error histogram - Plot error histogram

Total set
- Calculate R2 , ARD, AARD and AAE
- Plot error histogram

End

training the code and then to calculate the coefficients of the
proposed model (αi , γi , δi ) in Eq. (4). Then, MATLAB code
used the remaining data (50 % of the whole data set) with the
obtained coefficients from the training data set to test how
good is the model has been trained and then how accurate
the model can predict the results. It should be noted that the
testing set is not used during the training process, and it is
only used to compare the predicted results.
The predicted results from the proposed model were
validated against the experimental data and found to be

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Arab J Sci Eng

Table 1 Overall deviations for the predicted ILs densities using the 900
proposed model 800
Deviation (%) Training set Predicted set Total set
700

Predicted Density
ARD 0.041 0.033 0.10 600
AARD 1.48 1.73 1.19
500
AAE 1.86 2.17 1.50
400

300

200
consistent with no significant deviation observed (Table S1).
Table 1 summarized the overall deviations between the exper- 100
imental data and predicted results using the proposed model.
0
Figure 2 shows a good fit obtained between the predicted 0 0.02 0.04 0.06 0.08 0.1 0.12 0.14 0.16 0.18 0.2
and experimental densities, with R 2 = 99.50 %. Further- Error
more, the average relative deviation, average absolute relative
Fig. 3 Results error histogram
deviation, and average absolute error for the prediction set
were respectively obtained equal to 0.033, 1.73, and 2.17 %,
respectively. It can be concluded from Fig. 3 that out of 918
components, there are about 836 components possess errors
<2 % between the predicted and experimental density val-
ues. In addition, there are only 5 ILs having errors exceeding
10 %. These errors could be due to the different methods
adopted in measuring the density as well as the conditions
of the experiment. Additionally, Figs. 4, 5, and 6 show the
average relative deviation, average absolute relative devia-
tion, and average absolute error histograms, respectively, for
the results obtained by the model.
The trend observed in the density values obtained by both
experiments and the proposed model exhibits a relationship
between the structure of the ILs and their corresponding den-
sities. Indeed, in the case of imidazolium-, phosphonium-,
and ammonium-based ILs, the increase of substituted alkyl
Fig. 4 ARD histogram of the model
2.8

2.6

2.4

2.2
Predicted density

R2 = 99.50%
2

1.8

1.6

1.4

1.2

0.8
0.5 1 1.5 2 2.5 3
Experimental density

Fig. 2 Comparison between predicted and experimental density values Fig. 5 AARD error histogram of the model

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chain length in both cations and anions leads to reduction in

the density of ILs. This can be clearly demonstrated by the
examples shown in Table 2. On the other hand, the presence
of heavy atoms such as fluoro-, bromo-, iodo-, and sulfur-
substituted groups leads to increase the density of ILs. Table 3
shows group of ILs that demonstrates this trend. As a conclu-
sion, these results support the fact that the molecular struc-
tures of both anion and cation are significantly influence the
density of ILs.
Table 4 shows a comparison between numbers of ear-
lier developed models versus the proposed developed model.
Based on the same data set, the proposed model predicts the
density of ILs with an AARD of 1.73 % which is clearly much
lower than the value obtained by Sheng et al. [66] (4.4 %).
Thus, our model shows higher accuracy. It is worth to know
that Lazuus [63] was able to develop models with high corre-
Fig. 6 AAE error histogram of the model lation coefficients, i.e., R 2 of 99.72 %. However, the number

Table 2 The influence of alkyl chain length on the density

IL formula IL designation ρexp (g/cm3 ) ρpre (g/cm3 )

Alkyl chain
length (cation)
C8 H11 N3 F6 S2 O4 C2 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide 1.525 1.5177
C9 H13 N3 F6 S2 O4 C3 1-propyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide 1.4805 1.476
C10 H15 N3 F6 S2 O4 C4 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide 1.4423 1.4388
C11 H17 N3 F6 S2 O4 C5 1-pentyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide 1.4081 1.4056
C12 H19 N3 F6 S2 O4 C6 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide 1.3781 1.3757
C13 H21 N3 F6 S2 O4 C7 1-heptyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide 1.3495 1.3487
C14 H23 N3 F6 S2 O4 C8 1-octyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide 1.3265 1.3242
C15 H25 N3 F6 S2 O4 C9 1-nontyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide 1.3031 1.3017
C16 H27 N3 F6 S2 O4 C10 1-decyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide 1.2849 1.2807
C18 H31 N3 F6 S2 O4 C11 1-dodecyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide 1.2496 1.2415
C20 H35 N3 F6 S2 O4 C12 1-tetradecyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide 1.1931 1.2032
Alkyl chain
length (anion)
C8 H16 N2 SO4 C2 1-ethyl-3-methylimidazolium ethylsulfate 1.23692 1.2553
C10 H20 N2 SO4 C4 1-ethyl-3-methylimidazolium n-butylsulfate 1.176335 1.1795
C12 H24 N2 SO4 C6 1-ethyl-3-methylimidazolium n-hexylsulfate 1.130375 1.1192
C14 H28 N2 SO4 C8 1-ethyl-3-methylimidazolium n-octylsulfate 1.09474 1.0729

Table 3 The influence of heavy metals on the density

IL formula Heavy metals ILs designation ρexp (g/cm3 ) ρpre (g/cm3 )

C11 H11 Br4 F6 I2 N3 S2 O4 4Br, 6F, 2S, 4I 1,3-Di(2,3-dibromopropyl)-4,5-diiodoimidazolium 2.8 2.8

bis(trifluoromethylsulfonyl)imide
C9 H9 Br2 F6 I2 N3 S2 O4 2Br, 6F, 2S, 2I 1-(2,3-Dibromopropyl)-3-methyl-4,5-diiodoimidazolium 2.55 2.55
bis(trifluoromethylsulfonyl)imide
C12 H12 Br4 F9 N3 S2 O4 4Br, 9F, 2S 1-(2,3-Dibromopropyl)-3-(3’,4’-dibromo-3’,4’,4’-trifluorobutyl)-3- 2.35 2.35
imidazolium
bis(trifluoromethylsulfonyl)imide
C9 H9 Br4 F6 N3 S2 O4 4Br, 6F, 2S 1-(2,3-Dibromopropyl)-3-methyl-4,5-dibromoimidazolium 2.26 2.26
bis(trifluoromethylsulfonyl)imide

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Arab J Sci Eng

Table 4 Comparison between several QSPR models for IL densities prediction

Method/model used No. of ILs Data point R 2 ( %) AARD ( %) References

Multilinear regression method and heuristic method 13 na >94.2 na [59]

Linear regression model 40 na >99 na [57]
Neural networks (NNs) 45 na 99.5 na [58]
Artificial neural networks (ANNs) 103 399 na 0.15 [60]
ANN with particle swarm optimization 131 1736 99.34 0.44 [61]
Polynomial expansion (PE) method 163 238 93.07 2 [62]
Artificial neural networks (ANNs) 250 773 99.72 0.48 [63]
Linear generalized model (LGM) 146 602 na 2.6 [64]
Least square method 123 7381 na 0.88 [65]
Group contribution Patel–Teja (GC–PT) model 747 918 na 4.4 [66]
MLR + polynomial methods 747 918 99.5 1.73 This study

of ILs involved in his study was 250, which is much less than
the number of ILs presented in this work.
It should be noted that the accuracy of any mathemati-
cal model developed using QSPR for property prediction is
strongly dependent on the number of experimental data used.
Therefore, the number of ILs in the data set has to be taken
into consideration when comparing the accuracies of differ-
ent models. It is also worthy to know that the errors between
the results predicted from the developed models and others
from experimental work could be due to the different meth-
ods adopted in measuring the density of ILs as well as the
conditions of the experiments.
4 Conclusion
In this paper, a new mathematical model for the prediction of
ILs’ density using QSPR approach has been proposed. The
model was developed using a combination of MLR method
and polynomial equation. A data set comprising of 918 exper-
imental measurements reported for 747 pure ILs densities
was used for developing and verifying the model. The results
show that the proposed model was able to predict the density
of ILs with very high accuracy at a R 2 value of 99.5 %. Thus,
the model can be considered reliable and can be used in the
absence of experimental measurements for determination of
ILs densities particularly for process design.
Acknowledgments The authors acknowledge the financial support
provided by the Deanship of Scientific Research at King Saud Univer-
sity for this work through Research Group No. RGP-VPP-303.
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