Fluid Phase Equilibria 367 (2014) 57–62

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Fluid Phase Equilibria

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Thermodynamic models for determination of the solubility of

2,5-bis(2-furylmethylidene)cyclopentan-1-one in different solvents at
temperatures ranging from 308.15 to 403.15 K
Tatchanok Prapasawat a,b,c , Milan Hronec b , Magdaléna Štolcová b ,
Anchaleeporn Waritswat Lothongkum a , Ura Pancharoen c,∗ , Suphot Phatanasri c,∗∗
a
Department of Chemical Engineering, Faculty of Engineering, King Mongkut’s Institute of Technology Ladkrabang, Bangkok 10520, Thailand
b
Department of Organic Technology, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, 81237
Bratislava, Slovak Republic
c
Department of Chemical Engineering, Faculty of Engineering, Chulalongkorn University, Patumwan, Bangkok 10330, Thailand

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

Article history: The solubility data of 2,5-bis(2-furylmethylidene)cyclopentan-1-one (F2 C) in solid–liquid equilibrium in

Received 19 October 2013 alternative solvents are vital for a preliminary study of industrial applications aimed at producing sus-
Received in revised form 25 January 2014 tainable and renewable materials and fuels. The solubility behavior of F2 C in different solvents, such as
Accepted 27 January 2014
tetrahydrofuran, mixed water-tetrahydrofuran (1:1, v/v), methanol, and water at temperatures ranging
Available online 3 February 2014
from 308.15 to 403.15 K was investigated. An isothermal method was employed to measure the solu-
bility data of F2 C. The experimental data showed that the solubility of F2 C increased as the temperature
Keywords:
increased and was strongly affected by the surface tension and polarity index. The solubility of F2 C in the
Solubility
2,5-Bis(2-furylmethylidene)cyclopentan-1-
studied solvents increased in the following order: H2 O < methanol < H2 O-THF mixture < THF. The thermo-
one dynamic models, such as the polynomial empirical equation, the Van’t Hoff, and the modified Apelblat
Enthalpy models were investigated to describe the experimental data. It was found that the modified Apelblat
Entropy model was the most suitable for predicting the solubility behavior of F2 C with a temperature increment.
Thermodynamic model The calculated thermodynamic parameters indicated that in each studied solvent the dissolution process
of F2 C is endothermic and spontaneous.
© 2014 Elsevier B.V. All rights reserved.

1. Introduction polynomial empirical equation, Van’t Hoff, modified Apelblat,

At the present time, the amount of fossil fuels has dramatically
decreased. Thus, it is insufficient to cover the demand for energy
consumption. According to this fact, alternative renewable and sus-
tainable sources of energy and fuels are being developed [1].
The transformation of biomass to chemical products and fuels
generate the necessity to have data about the physicochemical
properties of these materials. For instance, the solubility of these
compounds plays a great role for understanding the solid–liquid
equilibria (SLE) or phase equilibria in the development of a
crystallization process, or liquid-liquid equilibria in extraction
and extractive or azeotropic distillation processes. [2–6]. Con-
sequently, a number of thermodynamic models, such as the
∗ Corresponding author. Tel.: +66 2 2186891; fax: +66 2 2186877.
∗∗ Corresponding author. Tel.: +66 2 2186890; fax: +66 2 2186877.
E-mail addresses: ura.p@chula.ac.th (U. Pancharoen), s phatanasri@yahoo.com
(S. Phatanasri).
Buchowski–Ksiazczak, Wilson, NRTL, and UNIQAC equations were
used for estimating the solubility [5,7–17].
The present work is focused on the study of the solu-
bility of 2,5-bis(2-furylmethylidene)cyclopentan-1-one (F2 C) in
various solvents, such as tetrahydrofuran (THF), mixed water-
tetrahydrofuran, methanol, and water in the temperature range
from 308.15 to 403.15 K. The compound F2 C is easily prepared by
aldol condensation of furfural with cyclopentanone in an aqueous
medium [18]. By subsequent hydrogenation/hydrodeoxygenation
reaction it can be transformed into diesel and jet fuels. Thermo-
dynamic models of F2 C solubility corresponding to mathematic
expressions were developed and employed to correlate and pre-
dict the solubility data. Among these thermodynamic models, the
polynomial empirical equation, the Van’t Hoff, and the modified
Apelblat models are outstanding in applicability, and their fitting
is acceptable [5,7–13]. Thermodynamic parameters of dissolu-
o ), standard molar
tion, including standard molar enthalpy (HDiss
o ) and Gibbs free energy (Go ) were determined
entropy (SDiss Diss
from the solubility data.

0378-3812/$ – see front matter © 2014 Elsevier B.V. All rights reserved.
http://dx.doi.org/10.1016/j.fluid.2014.01.039
58 T. Prapasawat et al. / Fluid Phase Equilibria 367 (2014) 57–62
O 320.0
O O
Fig. 1. Chemical structure of 2,5-bis(2-furylmethylidene) cyclopentan-1-one.
2. Experimental
2,5-Bis(2-furylmethylidene)cyclopentan-1-one (structure
shown in Fig. 1) was prepared by aldol condensation of fur-
fural with cyclopentanone in aqueous solution according to the
literature [19]. Analytical grade methanol (99.8% wt) and tetrahy-
drofuran (THF, 99.5% wt) were supplied by Centralchem® (Slovak
Republic). Re-distilled water was used for the experiments. The
properties of these solvents are presented in Table 1.
2.1. Apparatus and procedures
The solubility of F2 C was investigated, in various solvents, by an
isothermal method [16]. In the experiment, as shown schematically
in Fig. 2, 30 ml of the studied solvent, together with an amount of
F2 C, which was weighed to the 5th decimal place using a 5-figure
analytical balance, were put into a 50 ml-stainless steel closed ves-
sel equipped with a magnetic stirrer. The vessel was heated and
stirred in a thermostatically controlled silicone-oil bath with an
accuracy of ±0.1 K. The system for measuring the solubility of F2 C
was stirred for 240 min and then left about 120 min for achieving
a static state. Subsequently, at the desired temperature, a sample
solution of about 0.5 mL was collected by pushing the Teflon con-
tainer into the stainless steel vessel which contained the solution.
Then Teflon container valve was switched to the sampling position
until the saturated solution flowed into the hole of the container.
Afterwards, the Teflon container was switched back to a closed
position for collecting the saturated solution at the desired tem-
perature. To prevent volatilization of solvents, the stainless steel
vessel was cooled down to an ambient temperature with cooling
water [16]. The stainless steel vessel was immediately closed after
the Teflon container was pulled out, while the saturated solution
was still inside the container. Then the Teflon container was cleaned
Fig. 2. Scheme of the system of thermostatically controlled silicone-oil bath: (1)
stainless steel vessel (2) Teflon sample container (3) magnetic bar (4) silicone-oil
bath (5) thermostatic magnetic stirrer and (6) temperature controller.
280.0
240.0
Solubility (g/L)
200.0
160.0
120.0
80.0
40.0
0.0
293.15 313.15 333.15 353.15 373.15 393.15 413.15
T/K
Fig. 3. Solubility of F2 C in different solvents at temperatures from 308.15 to
403.15 K; ( ) tetrahydrofuran, () water-tetrahydrofuran (1:1 vol.), () methanol
and (䊉) water.
with methanol and blown with dry air. Next, the Teflon container
was weighed to get the weight of such solution. Each experimental
operation was replicated three times. Then the amount of F2 C in
each sample taken from the experiment was analyzed in triplicate
using the high performance liquid chromatography (HPLC) in order
to ensure that the data from the analytical procedure was precise.
The analyses were performed using a modular HPLC system
with a Shimadzu LC10AD high-pressure binary solvent delivery
system (Kyoto, Japan), a Rheodyne injector valve with 20 ␮L sample
loop (Cotati, USA) and a Shimadzu SPD-M10Vp photodiode-array
detector. The data was processed using Shimadzu Class10 software.
The column LiChrospher® 100 RP-18e, 5 ␮m, (4.0 mm × 250 mm)
(Merck, Germany) was performed at the ambient temperature.
The mobile phase consisted of a mixture of tetrahydrofuran
(purity > 99.95%) and deionized water of 60:40 (v/v). Analyses were
separated under isocratic conditions at 0.4 mL/min and detected
at 390 nm [20]. The retention time of F2 C was about 10.5 min. All
data was determined using three independent samples and each
one was analyzed in triplicate. The inter-day assay precision RSD
values for samples were ≤3.8.
The solubility of F2 C represented in terms of mole fraction (xi )
in the corresponding solvent was obtained from Eq. (1).
m1 /M1
xi = (1)
m1 /M1 + m2 /M2 + m3 /M3
where m1 , m2 and m3 denote the mass of F2 C (m1 ) and solvents
(m2 and m3 ), and M1 , M2 and M3 are the molecular weights of these
components.
3. Results and discussion
3.1. Solubility data
The experimental data of solubility of F2 C in tetrahydrofuran,
mixed water-tetrahydrofuran (1:1, v/v), methanol and water at
temperatures from 308.15 to 403.15 K are shown in Fig. 3 and listed
in Table 2. In each solvent, the solubility of F2 C is a function of
temperature but the increment of solubility with temperature is
different [7]. The solubility of F2 C depends not only on the temper-
ature but also on the structure of the solvent. As is seen from the
figure, the solubility of F2 C increases with decreasing polarity index
of the solvent [17] and follows the order: water (78.5) < methanol
(32.7) < tetrahydrofuran (7.5). In addition, surface tension has also
an impact on the solubility behavior of F2 C. In water, the surface
tension is much higher than in other tested liquids [17].
 T. Prapasawat et al. / Fluid Phase Equilibria 367 (2014) 57–62 59

Table 1
Properties of solvents.

Solvents Properties

M.W. (g/mol) D (g/mL) Source Purity (%) Analysis method

Water 18.02 0.9982 – 100.0 HPLC

Methanol 32.04 0.7915 Centralchem® 99.8 HPLC
THF 72.11 0.8892 Centralchem® 99.5 HPLC
F2 C 240.25 1.361 – 95.0 HPLC

3.2. Thermodynamic models
The correlation between temperature and solubility of F2 C in
different solvents can be explained by thermodynamic models,
e.g. by the polynomial empirical equation, the Van’t Hoff, and the
modified Apelblat models. These equations are widely used to
describe the solubility behavior of solute for not only ideal but
also non-ideal solutions. In addition, the selected thermodynamic
models can describe the influence of temperature on the solubility
of various organic compounds [8,21]. The polynomial empirical
equation can be easily applied for correlating the solubility data
[12,21]. The correlation of solubility with the polynomial empirical
equation is based on the assumptions described by Zhang et al.
[12] as shown in Eq. (2).
The polynomial equation was used to identify the solubility of
F2 C in different solvents. The correlation is displayed in Fig. 4 and
the parameters are listed in Table 3.
xi = A + BT + CT 2 + DT 3 + . . . + ˛T n ; n≥1 (2)

The correlations of experimental data and data calculated using

Table 2
the thermodynamic models obtained from the absolute relative
Mole fraction solubilities of F2 C in different solvents at temperatures from 308.15
to 403.15 K calculated from the experiment, the polynomial empirical equation (Eq. deviation (AD) expressed by Eq. (3) are listed in Table 2. The param-
(2)), the Van’t Hoff model (Eq. (6)) and the modified Apelblat (Eq. (7)) model.a eters of models obtained from linear and non-linear regressions and
their values are listed in Tables 3–5. The relative average deviation
T (K) 103 xi 103 AD
(RAD) and the corresponding root-mean square deviation (RMSD)
Eq. (2) Eq. (6) Eq. (7) along with the R-square as expressed by Eqs. (4)–(5) are shown in
(a) THF Tables 3–5.
308.15 30.588 0.109 0.087 0.042  
313.15 35.318 0.071 0.050 0.026 x e − x c 
318.15 43.063 0.026 0.042 0.049 AD = (3)
xe
323.15 46.438 0.003 0.016 0.010
 
1   xi − xi 
333.15 59.031 0.057 0.058 0.034 e N
c
343.15 71.262 0.073 0.062 0.028 RAD =  x  e (4)
353.15 81.567 0.050 0.024 0.012 N i
363.15 94.930 0.053 0.011 0.020 i=1
373.15 106.777 0.031 0.027 0.046 
N
383.15 124.832 0.053 0.019 0.019 (xc
i=1 i
− xie )2
393.15 142.022 0.056 0.030 0.006 RMSD = (5)
N
403.15 165.593 0.087 0.009 0.041
The Van’t Hoff model presented in Eq. (6) was normally used to
(b) Water-THF (1:1, v/v) predict the relation of solubility vs. reciprocal temperature (1/T) in
313.15 1.469 0.075 0.078 0.079
solid–liquid equilibrium [5,7,20]
323.15 2.324 0.059 0.053 0.054
333.15 3.379 0.004 0.112 0.115 B
343.15 3.715 0.057 0.081 0.077 ln xi = A + (6)
T
353.15 5.445 0.022 0.029 0.033
363.15 6.855 0.053 0.001 0.004 where xi is the mole fraction of F2 C in different solvents, T is the
373.15 8.298 0.069 0.058 0.053 absolute temperature (K), and A and B are the parameters of the
383.15 10.547 0.056 0.051 0.047
393.15 13.916 0.091 0.006 0.008
398.15 15.423 0.083 0.003 0.004 180.0
403.15 17.939 0.071 0.049 0.049
160.0
(c) Methanol 140.0
323.15 0.946 0.105 0.005 0.023
333.15 1.178 0.066 0.020 0.016 120.0
343.15 1.401 0.014 0.010 0.015
353.15 1.632 0.046 0.010 0.001 100.0
10 xi
3

363.15 1.957 0.046 0.009 0.018 80.0

373.15 2.153 0.015 0.052 0.044
383.15 2.591 0.019 0.011 0.010 60.0
393.15 3.043 0.048 0.010 0.004
403.15 3.533 0.033 0.027 0.010 40.0

20.0
(d) Water
353.15 0.007 0.763 0.107 0.279 0.0
363.15 0.012 0.094 0.130 0.168 293.15 313.15 333.15 353.15 373.15 393.15 413.15
373.15 0.020 0.173 0.164 0.166
T/K
383.15 0.038 0.102 0.003 0.048
393.15 0.062 0.072 0.077 0.253
Fig. 4. Correlation of the mole fraction of solubility of F2 C in different solvents at
398.15 0.081 0.062 0.015 0.236
temperatures from 308.15 to 403.15 K using the polynomial empirical equation;
403.15 0.111 0.095 0.002 0.127
( ) tetrahydrofuran, () water–tetrahydrofuran (1:1, v/v), () methanol and (䊉)
a
Standard uncertainties u are u(t) = ±0.1 K, ur (xi ) = ±0.007. water. Dashed lines calculated from the model.
60 T. Prapasawat et al. / Fluid Phase Equilibria 367 (2014) 57–62

Table 3
Parameters of the polynomial empirical equation for F2 C solubility in different solvents at temperatures from 308.15 to 403.15 K.a

Solvent 104 A B 107 C 106 D 105 RAD 106 RMSD R2

THF 100,977.0 0.0625 −21,089.2 7.00 5.578 573.371 0.9934

Water–THF 1.0 0.3991 −25,000.0 3.84 5.820 75.773 0.9941
Methanol 21,000.0 0.0317 −2000.0 0.40 4.369 9.010 0.9982
Water −989.2 −0.0010 39.9 – 17.017 0.602 0.9935
a
Standard uncertainties u are u(A) = u(C) = ±0.1, u(B) = ±0.001, u(D) = ±0.01.

180.0 180.0

160.0 160.0

140.0 140.0

120.0
120.0
100.0

10 x i
100.0
10 x i

3
80.0
3

80.0
60.0
60.0
40.0
40.0
20.0
20.0
0.0
0.0 293.15 313.15 333.15 353.15 373.15 393.15 413.15
293.15 313.15 333.15 353.15 373.15 393.15 413.15 T /K
T/ K
Fig. 6. Correlation of mole fractions of solubility of F2 C in different solvents at
Fig. 5. Correlation of mole fractions of solubility of F2 C in different solvents at tem-
temperatures from 308.15 to 403.15 K using the modified Apelblat model; ( )
peratures from 308.15 to 403.15 K using the Van’t Hoff model; ( ) tetrahydrofuran, tetrahydrofuran, () water–tetrahydrofuran (1:1, v/v), () methanol and (䊉) water.
() water–tetrahydrofuran (1:1, v/v), () methanol and (䊉) water. Dashed lines Dashed lines calculated from the model.
calculated from the model.

together with the calculated data (Tables 2–5), it was indicated

Table 4
Parameters of the Van’t Hoff model for F2 C solubility in different solvents at tem-
that the solubility of F2 C calculated from the studied models
peratures from 308.15 to 403.15 K.a showed good agreement, while the values of the absolute rela-
tive deviation did not exceed 0.76. In addition, considering the
Solvent A B 105 RAD 106 RMSD R2
corresponding root-mean square deviation and the R-square, the
THF 10.36 −2111.79 3.629 265.200 0.9943 modified Apelblat model achieved maximum at 2.85 × 10−4 and
Water–THF 11.11 −3334.49 4.721 37.858 0.9941
0.9982. Accordingly, it was shown that the modified Apelblat
Methanol 6.43 −2093.35 1.710 5.252 0.9972
Water 14.56 −6833.23 10.225 0.822 0.9824 model proved to be more accurate and suitable for the descrip-
tion of dissolution of F2 C in the studied solvents at various
a
Standard uncertainties u are u(A) = u(B) = ±0.01.
temperatures.

model. As is seen from Fig. 5, the calculated data are in accordance 3.3. Thermodynamic parameters
with the experimental data with R2 > 0.9824. The parameters from
the regression are shown in Table 4. Thermodynamic parameters of F2 C solute relating to the mole
The modified Apelblat model (Eq. (7)) which is a semi-empirical fraction of solubility at the corresponding temperatures were esti-
model obtained from the Clausius–Clapeyron equation was mostly mated. In previous studies, the Van’t Hoff equation expressing the
adopted to describe the thermodynamic solubility of polar and non logarithm of the mole fraction of a solute vs. reciprocal temperature
polar solutions [5,7,10,21]. (1/T) was employed to evaluate the values defined in Eq. (8). The
o ) can be obtained
B standard molar enthalpy of dissolution (HDiss
ln xi = A + + C ln T (7)
T from the slope of this equation in the so-called Van’t Hoff plot
where xi and T are the mole fraction of F2 C and absolute tempera- [5,7,20,22,23].
 
ture (K), respectively, and A, B and C are model parameters which ∂ ln xi
o
are obtained from the regression curve as shown in Table 5. The HDiss = −R · (8)
∂(1/T )
correlative data between experimental data and modified Apelblat
model are illustrated in Fig. 6. where R represents the gas constant (8.314 J mol−1 K−1 ), xi is the
According to the above mentioned correlations of experimen- mole fraction of F2 C at system temperature and T is the correspond-
tal data obtained at different temperatures in various solvents ing absolute temperature of solution (K).

Table 5
Parameters of the modified Apelblat model for F2 C solubility in different solvents at temperatures from 308.15 to 403.15 K.a

Solvent A B C 105 RAD 106 RMSD R2

THF 74.18 −5367.91 −9.30 2.785 284.621 0.9973

Water–THF 6.88 −3115.43 0.62 4.750 37.246 0.9941
Methanol −23.93 −506.10 4.41 1.556 3.903 0.9982
Water −688.74 30,997.38 101.64 14.928 0.765 0.9962
a
Standard uncertainties u are u(A) = u(B) = u(C) = ±0.01.
 T. Prapasawat et al. / Fluid Phase Equilibria 367 (2014) 57–62 61

Table 6
Thermodynamic parameters of dissolution of F2 C in different solvents at mean temperatures.a

Solvent Thermodynamic parameter

H/kJ mol−1 S/J mol−1 K−1 G/kJ mol−1 % H % S

Water 6833.2 14.56 1355.76 55.51 44.49

Methanol 2093.4 6.43 −240.64 47.28 52.72
Water–tetrahydrofuran 3334.5 11.11 −684.22 45.35 54.65
Tetrahydrofuran 2111.8 10.36 −1519.88 36.77 63.23
a
Standard uncertainties u are u(T) = ±0.1 K, u(H) = u(G) = ±0.1 kJ mol−1 , u(S) = ±0.1 J mol−1 K−1 .

6.00 that the solubility strongly depends on the temperature [7,17]. The
positive standard molar entropy of dissolution means that in each
4.00 solvent the entropy is the driving force of the dissolution process
[7]. In addition, the standard molar Gibbs energy for all solvents is
2.00 negative except water. The negative value of the standard molar
Gibbs energy indicates that the dissolution process is spontaneous.
10 ln xi

The contribution of enthalpy and entropy to the Gibbs energy in

0.00
the dissolution process was compared using Eqs. (13)–(14) [7,22,
3

0.0023 0.0025 0.0027 0.0029 0.0031 0.0033

25–26]:
-2.00  
H o 
%H =     × 100
Diss
(13)
-4.00 H o  + T · So 
Diss Diss
 
-6.00 T · So 
%S =    Diss  × 100 (14)
1/(T/K) H o  + T · So 
Diss Diss
Fig. 7. The Van’t Hoff plot of mole fraction solubility of F2 C in different solvents;
The values of %␰H and %␰S are shown in Table 6. The results reveal
( ) tetrahydrofuran, () water–tetrahydrofuran (1:1, v/v), () methanol and (䊉)
that the main contributor to the standard molar Gibbs energy of
water.
dissolution is the entropy because the value of %␰S is in average
53.89.
In the present work, only the mole fraction of solubility of F2 C in
the studied solvents at corresponding temperatures was measured.
o ) can be calculated 4. Conclusions
Thus, the standard molar Gibbs energy (GDiss
from Eq. (9) without activity coefficients as an apparent value
The solubility data of 2,5-bis(2-furylmethylidene)cyclopentan-
[22,24].
1-one (F2 C) in different solvents were measured at temperatures
o
GDiss = −RT ln xi (9) from 308.15 to 403.15 K. Besides temperature, the solubility of F2 C,
o ) can be in all studied solvents, was influenced by the surface tension and
The standard molar entropy of dissolution (SDiss
the polarity index of solvents. The maximal solubility of F2 C was
obtained according to the literature [7,20,22,24–26]:
observed in tetrahydrofuran. The solubility phenomena of F2 C were
o
HDiss o
− GDiss
o evaluated using the thermodynamic models. The data calculated
SDiss = (10)
T from the modified Apelblat model was in good agreement with the
By integrating Eq. (8) and substituting Eqs. (9)–(10), similarly as experiment. This model was the most suitable for the description
in the literatures [7,22–28], the following equation was obtained: of the dissolution of F2 C. The thermodynamic parameters of dis-
solution were estimated using Van’t Hoff equation. The positive
o
HDiss o
SDiss standard molar enthalpy and the positive standard molar Gibbs
ln xi = − + (11)
RT R energy indicated that the dissolution process of F2 C was endother-
This equation, the standard molar entropy of dissolution, can be mic and spontaneous.
calculated from the interception of the solubility in Fig. 7.
In addition, it can be seen that both HDiss o o
and SDiss are List of symbols
the mean values of dissolution at temperatures from 308.15 to
403.15 K. Thus, the mean value of GDisso can be calculated from
the equation described by Zhi et al. and Delgado et al. [22,25] A, B parameters of polynomial empirical equation, Van’t Hoff
o o o and modified Apelblat models
GDiss = HDiss − Tmean · SDiss (12)
C, D parameter of polynomial empirical equation and modi-
where Tmean is the mean temperature of the experiment. The fied Apelblat model
mean temperatures in solvents: tetrahydrofuran, mixed water- o
GDiss standard molar Gibbs energy
tetrahydrofuan, methanol and water are 350.65, 361.79, 363.15 and o
HDiss standard molar enthalpy of dissolution
381.00 K, respectively. m1 mass of F2 C
The standard thermodynamic parameters calculated by Eqs. m2 and m3 mass of solvents
(8)–(12) are listed in Table 6. The data show that the standard molar M1 molecular weight of solute
enthalpy of dissolution in the studied solvents is positive. Thus, the M2 and M3 molecular weight of solvents
dissolution process of F2 C in each solvent is endothermic. The high R gas constant (8.314 J mol−1 K−1 )
values of the standard molar enthalpy indicate that more energy is o
SDiss standard molar entropy of dissolution
required for overcoming the cohesive forces of the solute and the T absolute temperature (K)
solvent in the dissolution process [7]. In addition, it also implies Tm melting point (K) of F2 C
62 T. Prapasawat et al. / Fluid Phase Equilibria 367 (2014) 57–62
Tmean mean temperature of the experiment
xi mole fraction of F2 C
Acknowledgments
The authors are sincerely grateful to the Royal Golden Jubilee
Ph.D. Programme (Grant no. PHD50K0329) under the Thailand
Research Fund. Many thanks also go to the Laboratory of Catalyzed
Processes, Department of Organic Technology, Faculty of Chemical
and Food Technology, Slovak University of Technology in Bratislava,
Slovak Republic for supplying chemicals and instruments for exper-
iments and analyses.
References
[1] www.environment.nationalgeographic.com/environment/global-warming/
biofuel-profile (last accessed 09.09.13).
[2] E. Wilhelm, Chapter 1: Thermodynamics of nonelectrolyte solubility, in: T.M.
Letcher (Ed.), Developments and Applications in Solubility, Thomas Graham
House, Science Park, Cambrige, UK, 2007, p. 3.
[3] S.P. Pinho, E.A. Macedo, Fluid Phase Equilibr. 116 (1996) 209–216.
[4] U. Domańska, Chapter 8: Solubility of Organic Solids for Industry, in: T.M.
Letcher (Ed.), Developments and Applications in Solubility, Thomas Graham
House, Science Park, Cambrige, UK, 2007, p. 94.
[5] X.M. Jiang, Y.H. Hu, Z. Meng, W.G. Yang, F. Shen, Fluid Phase Equilibr. 341 (2013)
7–11.
[6] X.M. Jiang, Y.H. Hu, W.G. Yang, Z.Y. Lei, R.R. Tand, F. Shen, J. Solut. Chem. 42
(2013) 272–281.
[7] K. Wang, Y.H. Hu, W.G. Yang, S. Guo, Ying Shi, J. Chem. Thermodyn. 55 (2012)
50–55.
[8] Y.X. Mo, L.P. Dang, H.Y. Wei, Fluid Phase Equilibr. 300 (2011) 105–109.
[9] E. Manzurola, A. Apelblat, J. Chem. Thermodyn. 34 (2002) 1127–1136.
[10] R. Heryanto, M. Hasan, E.C. Abdullaha, A.C. Kumoro, ScienceAsia 33 (2007)
469–472.
[11] F.X. Chen, M.R. Zhao, C.C. Liu, F.F. Peng, B.Z. Ren, J. Chem. Thermodyn. 50 (2012)
1–6.
[12] Y. Zhang, L.S. Wang, R.H. Zhou, X.M. Liu, J. Chem. Eng. Data 56 (2011) 2090–2094.
[13] H. Yan, Z. Wang, J.K. Wang, Ind. Eng. Chem. Res. 51 (2012) 2808–2813.
[14] W. Yang, Y.H. Hu, Z.G. Chen, X.M. Jiang, J.K. Wang, R.R. Wang, Fluid Phase
Equilibr. 314 (2012) 180–184.
[15] H. Salimnezhad, F. Feyzi, Iran J. Chem. Eng. 5 (2008) 39–48.
[16] N. Sunsandee, M. Hronec, M. Štolcová, N. Leepipatpiboon, U. Pancharoen, J. Mol.
Liq. 180 (2013) 252–259.
[17] N. Wang, Q. Fu, G. Yang, Fluid Phase Equilibr. 324 (2012) 41–43.
[18] S.S. -Jørgensen, P. Rasmussen, A.A. Fredenslund, Chem. Eng. Sci. 35 (1980)
2389–2403.
[19] M. Shi-Ying, Z. Ze-Bao, Acta Crystallogr. Sect. E. Struct. Rep. 65 (2009) 3084.
[20] V.P. -Azar, A. Shayanfar, F. Martínez, W.E. Acree Jr., A. Jouyban, Fluid Phase
Equilibr. 308 (2011) 72–77.
[21] L. Wang, T.T. Lv, J. Mol. Liq. 181 (2013) 29–33.
[22] W.B. Zhi, Y.H. Hu, W.G. Yang, Y.M. Kai, Z. Cao, J. Mol. Liq. (2013) 201–205.
[23] B. Schröder, L.M.N.B.F. Santos, I.M. Marrucho, J.A.P. Coutinho, Fluid Phase Equi-
libr. 289 (2010) 140–147.
[24] D. Wei, X.R. Zhang, Fluid Phase Equilibr. 339 (2013) 67–71.
[25] D.R. Delgado, A.R. Holguín, O.A. Almanza, F. Martínez, Y. Marcus, Fluid Phase
Equilibr. 305 (2011) 88–95.
[26] A.R. Holguín, D.R. Delgado, F. Martínez, Y. Marcus, J. Solut. Chem. 40 (2011)
1987–1999.
[27] W.S. Choi, K.J. Kim, J. Chem. Eng. Data 56 (2010) 43–47.
[28] P. Wang, J.K. Wang, J.B. Gong, M.J. Zhang, Fluid Phase Equilibr. 306 (2011)
171–174.