Fluid Phase Equilibria 427 (2016) 303e307

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Fluid Phase Equilibria

j o u r n a l h o m e p a g e : w w w . e l s e v i e r . c o m / l o c a t e / fl u i d

Solubility of disodium 4,40 -dinitrobibenzyl-2,20 -disulfonate in aqueous

organic solutions and its effects on the oxidation reaction of DSD acid
synthesis
Wen-Cai Wang, Yang-Yang Zhang-Bian, Guo-Liang Zhang, Qing Xia*, Feng-Bao Zhang**
School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, PR China

a r t i c l e i n f o

a b s t r a c t

Article history:
Received 3 June 2016
Received in revised form
13 July 2016
Accepted 27 July 2016
Available online 29 July 2016

The solubility of disodium 4,40 -dinitrobibenzyl-2,20 -disulfonate (DNDNa) in aqueous ethylene glycol
monoethyl ether solution and aqueous ethylene glycol monobutyl ether solution was measured over the
temperature range from 278 to 334 K at atmospheric pressure by a dynamic method. The solubility of
DNDNa in aqueous ethylene glycol monoethyl ether solution and aqueous ethylene glycol monobutyl
ether solution increased with temperature over all solvent mixture compositions investigated. A synergistic effect on DNDNa solubility was observed with the maximum solubility at solute-free mass
fraction of ethylene glycol monoethyl ether w03 0:6003 and solute-free mass fraction of ethylene glycol
monobutyl ether w04 0:4054 , respectively. The solubility data were correlated using the electrolyte
non-random two-liquid model and model parameters were determined simultaneously. It was found
that around 0.4 (solute-free mass ratio) ethylene glycol monobutyl ether solution is suitable as the reaction medium in oxidation 4-nitrotoluene-2-sulfonic acid to 4,40 -dinitrostilbene-2,20 -disulfonic acid.
The effect of different aqueous organic solutions on the oxidation reaction was discussed.
2016 Elsevier B.V. All rights reserved.

Keywords:
Disodium 4,40 -dinitrobibenzyl-2,20 disulfonate
Dynamic method
Synergistic effect
The E-NRTL model

1. Introduction
Crystalline
disodium
4,40 -dinitrobibenzyl-2,20 -disulfonate
(C14H10N2O10S2$2Na,DNDNa, CAS No. 6268-17-3) is an intermediate product of the oxidation reaction in 4,40 -diaminostilbene-2,20 disulfonic acid (DSD) synthesis [1]. As a signicant green chemical
intermediate, DSD acid is widely used for producing dyestuff,
brighteners and mothproong agents. We aim to search for suitable
oxidation medium that can better dissolve DNDNa.
DSD acid synthesis method is complex [2e4]. In a word, it
comprises sulfonation [5,6], oxidation [7,8], and reduction [9,10].
Oxidation is the most critical step among the three steps. In detail,
the oxidation reaction is a sequential reaction where DNDNa is the
intermediate product and disodium 4,40 -dinitrostilbene-2,20 disulfonate (DNSNa) is the target product as shown in Fig. 1. Air
(used as oxidizing agent) and alkaline medium (usually sodium
hydroxide aqueous solution) are used in the current industrial
application. The oxidation reaction is benecial to be carried out at

* Corresponding author.
** Corresponding author.
E-mail addresses: xiaqing@tju.edu.cn (Q. Xia), fbzhang@tju.edu.cn (F.-B. Zhang).
http://dx.doi.org/10.1016/j.uid.2016.07.028
0378-3812/ 2016 Elsevier B.V. All rights reserved.

low temperature and high concentration of alkaline medium. But

because of the low solubility of DNDNa, the sequential reaction is
stopped by the precipitation of intermediate product DNDNa. In
order to re-dissolve the intermediate product DNDNa, the second
step where DNDNa is oxidized to DNSNa has to be conducted at
high temperature and low concentration of alkaline medium.
Reacting at high temperature and dilute solution not only lead to
the increase of energy consumption and waste water production,
but also induce side reactions [11]. Research works [12,13] have
shown that some aqueous alcohol and aqueous ether solutions are
feasible to replace water as reaction medium due to the advantages
of mild reaction condition, high yield, easy product separation and
large production capacity. Suitable aqueous organic solutions
should have enough DNDNa dissolving capacity so that sequential
oxidation reaction can go through smoothly. Therefore, to continue
our systematic research on the solubility of reactant, intermediate
product and product of oxidation reaction, the solubility of DNDNa
in aqueous ethylene glycol monoethyl ether solution and aqueous
ethylene glycol monobutyl ether solution was measured by a dynamic method over the temperature range from 278 to 334 K at
atmospheric pressure. The experimental data were correlated with
electrolyte non-random two-liquid (E-NRTL) model [14] which

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W.-C. Wang et al. / Fluid Phase Equilibria 427 (2016) 303e307

Table 2
The mole fraction solubility data of DNDNa (x1) at different compositions of aqueous
ethylene glycol monoethyl ether mixtures at temperature Texp and pressure 0.1 MPa.
The w03 represents the solute-free mass fraction of ethylene glycol monoethyl ether
in binary solution.a
x1  103

Texp/K

x1  103

Texp/K

x1  103

Texp/K

0:0000
0.481
0.597
0.713
0.821

279.7
284.3
290.4
296.2

0.912
1.007
1.103
1.231

300.2
304.3
308.3
312.7

1.347
1.495
1.637
1.808

317.0
321.5
326.1
330.4

w03 0:1907
0.387
0.529
0.672
0.808

278.8
282.8
289.0
294.8

0.926
1.054
1.193
1.422

299.0
302.9
306.6
313.0

1.646
1.855
2.047
2.237

317.8
322.9
327.1
330.7

w03 0:4062
0.136
0.295
0.455
0.615
0.776

278.6
282.6
286.8
290.7
294.5

0.949
1.140
1.334
1.532
2.062

298.4
302.3
306.0
309.8
320.0

2.289
2.564
2.792

323.8
328.7
332.9

w03 0:6003
0.393
0.648
0.867
1.087

280.1
286.0
290.6
295.0

1.431
1.851
2.270
2.684

300.9
307.6
314.4
320.9

3.097
3.503

327.3
333.7

w03 0:7923
0.039
0.107
0.178
0.252
0.330

278.5
282.2
285.8
289.5
293.5

0.411
0.495
0.581
0.674
0.780

297.4
301.3
305.1
308.9
312.7

0.892
1.015
1.154
1.287
1.411

316.5
320.2
324.0
328.1
332.6

w03

Fig. 1. The oxidation reaction route in DSD acid synthesis.

provided a thermodynamic framework for representation of phase

behavior of mixed-solvent electrolyte systems.
2. Experimental section
2.1. Experimental materials
DNDNa was recrystallized three times from deionised water
(electrical conductivity 18 MU cm). Then the obtained DNDNa was
dried to constant weight at 353.15 K. The puried crystalline
DNDNa had a purity of 0.997 (mass fraction), which was tested by
HPLC analysis (Hitachi L-7100, Japan). Other chemical reagents
were analytical grade and used without further purication. The
detailed information of the materials used in the experiment is
listed in Table 1.

a
Standard uncertainties u are u(T) 0.3 K, u(x) 2  105, uc(w) 2  104,
u(P)v 0.001 MPa.

ensure the accuracy of the experimental data in this work.

2.2. Apparatus and procedure

The solubility experiment was conducted by the dynamic
method using the apparatus which were described in detail previously [15,16]. Amounts of solute and mixture solvent (A certain
quality of ethylene glycol monoethyl ether or ethylene glycol
monobutyl ether and water were weighed accurately by the
analytical balance (Gibertini, Crystal 200, Italy, accuracy of
0.0001 g) respectively. The exact concentrations of the mixture
solvent were calculated by the weighing data) were weighed
accurately by analytical balance and then transferred into a jacketed glass vessel. The mixture was continuously stirred and
heated at a heating rate less than 0.2 K h1.The temperature of the
system was controlled by a refrigerated/heating circulator (Julabo
FP45-HE, Germany, temperature stability 0.01 K) and detected by
a platinum resistance thermometer Pt-100 (calibrated with a precision of 0.01 K), which was immersed in the inner chamber. A coldwater condenser was connected with the vessel to prevent volatilization of the solvent. The laser monitoring system (JS2-1009016,
Beijing, China) was used to observe the course of dissolution and
determine the solid-liquid-equilibrium (SLE) temperature. Duplicate experiments were carried out for each mixture composition to

3. Thermodynamic modeling basis

3.1. Solubility equations description
The SLE exists in saturated solution between a salt compound
and its respective dissociated ions. The formula is shown as follows:

Xn Yn s!n Xl n Yl

(1)

where n, ndenote the electrolyte stoichiometric coefcient.

Xn Yn indicates the solid salt. n, n indicate the number of cations
X and anions Y respectively.
The temperature dependant solubility product constant (Ks) is a
value indicating the degree to which the salt dissociates in solution.
The solubility product constant associates with mole fraction of
ions and activity coefcients. The following formula can be used to
describe the SLE in electrolyte systems.

Ks an an g x n g x n

(2)

where Ks, a, g, x denote the solubility product constant, the ion

Table 1
Source and mass fraction purity of the materials used in the experiment.
Materials

Source

Mass fraction purity

DNDNaa
Ethylene glycol monoethyl ether
Ethylene glycol monobutyl ether

Hebei Huayu Chemical Co. Ltd., Hebei, China

Yuanli Chemical Reagents Co., Tianjin, China
Yuanli Chemical Reagents Co., Tianjin, China

0.997
0.9997
0.9995

DNDNa is the abbreviation of disodium 4,40 -dinitrobibenzyl-2,20 -disulfonate.

W.-C. Wang et al. / Fluid Phase Equilibria 427 (2016) 303e307

305

 

 .






T
In Ks m;n x0m Am 1  x0m An x0m Bm 1  x0m Bn
(3)
where T is absolute temperature in Kelvin; x0m is the solute-free
mole fraction of m component in the binary solvent mixture. A
and B are constants obtained via solubility data modeling, m and n
denote two components of a binary solvent mixture.

3.2. The E-NRTL thermodynamic model description

Fig. 2. Plot of mole fraction solubility of DNSNa (x1) vs. temperature (T) at different
solute-free ethylene glycol monoethyl ether mass fraction (w03 ) of aqueous solution:
points, experimental values, (,) w03 0:0000; (B) w03 0:1907; () w03 0:4062;
()w03 0:6003; (*) w03 0:7923; d, calculated from the E-NRTL model.

activity, the ion activity coefcient and the dissociated ion solubility in units of mole fraction, respectively. The subscripts () and
() refer to cation and anion, respectively. Equation (2) is universal
for SLE description of both single-component system and multicomponent system [17]. The solubility product of solid in binary
solvent mixture which is a function of temperature and solvent
mixture compositions can be written as follows [18].

The E-NRTL model which is suitable for multi-component

electrolyte systems is used for solubility data correlation [19] and
calculation of the activity coefcients in this work. The model
contains two fundamental assumptions about the liquid lattice
structure of electrolyte system: one for like-ion repulsion
assumption and the other for local electroneutrality assumption
[19]. The excess Gibbs free energy expression is the sum of two
contribution, one
resulting from the long-range ion-ion interaction

E;PDH
contribution (Gm
) is presented by the Pitzer-Debye-Hckel
model,
and the other from the short-range interaction contribution

E;lc
(Gm ) is presented by non-random two-liquid (NRTL) theory [19].
The E-NRTL model is described by the following expression.
*E;PDH
G*E
G*E:lc
m Gm
m

Taking the appropriate derivative form, Equation (4) leads to the

following equation:

ln g*i ln g*PDH
ln g*lc
i
i


Table 3
The mole fraction solubility data of DNDNa (x01 ) at different compositions of aqueous
ethylene glycol monobutyl ether mixtures at temperature Texp and pressure 0.1 MPa.
The w04 represents the solute-free mass fraction of ethylene glycol monobutyl ether
in binary solution.a
103

Texp/K

x01

Texp/K

x01

w04 0:1984
0.685
0.861
1.057
1.338

278.3
281.7
285.9
292.1

1.620
1.871
2.094
2.301

298.8
304.0
310.0
315.0

2.507
2.701
2.897

319.8
324.4
328.6

w04 0:4054
1.426
1.685
1.972
2.285

278.7
284.8
292.2
300.4

2.470
2.620
2.772
2.923

305.3
309.8
314.2
318.4

3.100
3.288
3.494

322.2
326.2
330.8

w04 0:5013
1.344
1.627
1.899

280.2
286.1
292.7

2.155
2.370
2.679

299.7
305.0
313.0

2.902
3.168
3.439

319.1
325.2
331.3

w04 0:6008
1.111
1.278
1.407
1.626

278.3
282.4
285.4
290.5

1.801
2.032
2.276
2.527

295.1
300.6
306.9
313.2

2.858
3.095
3.383

320.9
326.0
331.5

281.7
287.4
292.6
297.8

0.406
0.507
0.628
0.749

301.9
306.1
311.0
315.2

0.881
1.018
1.153

x01

103

103

Texp/K

PDH

(5)

lc

where ln gi
and ln gi are ion i asymmetric activity coefcients
introduced by the Pitzer-Debye-Hckel and the NRTL model,
respectively. To describe phase behavior over a large temperature
range, the interaction parameter tij has to be taken as temperature
dependant. The following format in general use is adopted [19].

tij aij bij T

(6)

where aij and bij are correlated parameters representing the temperature dependence of tij. The values of salt-water and organic
solvent-water non-randomness factor a are xed as 0.2 and 0.3.
Besides, the salt-organic solvent non-randomness factor a is
regressed in this work.

3.3. Correlation of experimental data

The E-NRTL model parameters were determined using Nelder
Mead Simplex Method [20] combined with Matlab (Mathwork,
MA). The optimization process was aimed at minimizing the
following objective function.

"

N
X

T exp  T

#0:5
N  1

(7)

i1

w04

0:7964
0.078
0.145
0.233
0.321

(4)

321.4
326.2
331.0

a
Standard uncertainties u areu(T) 0.3 K, u(x) 2  105, uc(w) 2  104,
u(P) 0.001 MPa.

where Texp and T represent the experimental and calculated equilibrium temperature, respectively. The s denotes the root mean
square deviation between Texp and T. The N is the number of total
experimental points. All the experimental data were used for
objective function minimization.

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W.-C. Wang et al. / Fluid Phase Equilibria 427 (2016) 303e307

the measured SLE temperature, x1 is the solubility of DNDNa in unit

of mole fraction, w03 is the solute-free mass fraction of ethylene
glycol monoethyl ether in solvent mixture. Fig. 2 presents the solubility curve of DNDNa at different values of w03 . As shown in Fig. 2,
the solubility of DNDNa in aqueous ethylene glycol monoethyl
ether solution increases with temperature over all investigated
solvent mixtures. But DNDNa is almost insoluble in pure ethylene
glycol monoethyl ether solvent because the solubility is so small
that we cannot measure it accurately. Overall, the solubility of
DNDNa increases with w03 rstly, the maximum value is reached at
w03 0:6003 above T 285 K, and then decreases with a further
increase of w03 . Furthermore, at temperature lower than 285 K, the
difference of the solubility at w03 0:0000, w03 0:1907 and
w03 0:6003 is relatively small.
The synergistic effect [21] was known as the dissolution capacity
of mixed solvent at a particular composition is much higher than
that of their individual components. Such effect was observed in
our investigated system as the solubility of DNDNa was largely
enhanced in the binary (ethylene glycol monoethyl ether water)
systems. Many experiments indicate that the synergistic effect
exists in the polar solvents containing hydroxyl groups [22e24]
(ethylene glycol monoethyl ether contains hydroxyl groups). The
hydrogen bonds competition between alike and unlike molecules is
believed to play an important role in determining the phase
behavior [25].

Fig. 3. Plot of mole fraction solubility of DNDNa (x1) vs. temperature (T) at different
solute-free ethylene glycol monobutyl ether mass fraction (w04 ) of aqueous solution:
points, experimental values, (,)w04 0:0000; (B) w04 0:1984; () w04 0:4054;
() w04 0:5013; ()w04 0:6008; (*) w04 0:7964; d, calculated from the E-NRTL
model.

Table 4
The parameters of solubility product equation for solute DNDNa in aqueous organic
solution.
Aa

Solvent system

374.66
222.89
4340.2

Water
Ethylene glycol monoethyl ether
Ethylene glycol monobutyl ether

4.2. Solubility of DNDNa in (ethylene glycol monobutyl

ether water) solvent mixture

Ba/K
6

1.6162  10
1.6629  106
3.1349  106

The solubility data of DNDNa determined in aqueous ethylene

glycol monobutyl ether solution are listed in Table 3, where Texp is
the measured SLE temperature, x01 is the solubility of DNDNa in unit
of mole fraction, w04 is the solute-free mass fraction of ethylene
glycol monobutyl ether in solvent mixture. Similarly, the solubility
in ethylene glycol monobutyl ether is too small to be determined
accurately. The solubility curves of DNDNa at different values of w04
are shown in Fig. 3. It can be discovered in Fig. 3 that the solubility
of DNDNa in aqueous ethylene glycol monobutyl ether solution
increases with w04 rstly, and reaches the maximum value at
w04 0:4054.Then the solubility of DNDNa instead decreases with a
further increase of w04 .

A and B are the parameters of solubility product Ks equation (dened by

Equation (3)).

4. Results and discussion

4.1. Solubility of DNDNa in (ethylene glycol monoethyl
ether water) solvent mixture
The solubility data of DNDNa investigated in aqueous ethylene
glycol monoethyl ether solution are given in Table 2, where Texp is

Table 5
The E-NRTL model parameters for the ternary systems: (DNDNa water ethylene glycol monoethyl ether) and (DNDNa water ethylene glycol monobutyl ether).
i

DNDNa
DNDNa
Water
DNDNa
Water

Water
ethylene
ethylene
ethylene
ethylene

a
b

glycol
glycol
glycol
glycol

monoethyl ether
monoethyl ether
monobutyl ether
monobutyl ether

aija

ajia

bija/K

bjia/K

aijb ajib

991.58
444.06
416.04
35.391
535.96

62.894
22.087
4.3768  105
813.62
7.2970  105

5.8083  109
11144
1.1726  105
9468.8
1.6526  105

2.6825  105
2849.2
4.8339  105
2.2053  105
1.1014  106

0.2
1.4890
0.3
1.1081
0.3

aij and bij are interaction parameters (dened by Equation (6)).

aij is the non-randomness factor which is dened in the E-NRTL model [19].

Table 6
The root-mean-square deviations s from the description by the E-NRTL model.
Solvent system
Water
Water0.1907
Water0.4062
Water0.6003
Water0.7923
a

ethylene
ethylene
ethylene
ethylene

glycol
glycol
glycol
glycol

monoethyl
monoethyl
monoethyl
monoethyl

ether
ether
ether
ether

s is the root-mean-square deviation (dened by Equation (7)).

sa/K

Solvent system

0.17
0.61
0.56
0.63
0.38

Water0.1984
Water0.4054
Water0.5013
Water0.6008
Water0.7964

sa/K
ethylene
ethylene
ethylene
ethylene
ethylene

glycol
glycol
glycol
glycol
glycol

monobutyl
monobutyl
monobutyl
monobutyl
monobutyl

ether
ether
ether
ether
ether

0.29
0.26
0.23
0.10
0.36

W.-C. Wang et al. / Fluid Phase Equilibria 427 (2016) 303e307

4.3. The parameters of the E-NRTL model

The parameters of the solubility product for DNDNa in different
solvents dened by Equation (3) are shown in Table 4. The correlated E-NRTL model parameters are represented in Table 5. Table 6
represents the root-mean-square deviations of SLE temperature
described by the E-NRTL model. The root-mean-square deviations
of SLE temperature vary from (0.17e0.63) K for ethylene glycol
monoethyl ether water system and the root-mean-square deviations of SLE temperature vary from (0.10e0.36) K for ethylene
glycol monobutyl ether water system, which indicates the
goodness of t of the solubility curves by means of the E-NRTL
model.
4.4. Effects of solubility data on oxidation reaction of DSD acid
synthesis
Comparing the solubility data of DNDNa in (ethylene glycol
monoethyl ether water) system with that in (ethylene glycol
monobutyl ether water) system, the largest solubility is achieved
in w04 0:4054 aqueous ethylene glycol monobutyl ether solution.
And the solubility of DNDNa in w04 0:4054 aqueous ethylene
glycol monobutyl ether solution is much higher than that in water.
That is to say, if the oxidation reaction is conducted in aqueous
ethylene glycol monobutyl ether solution, around 0.4 mass fraction
aqueous ethylene glycol monobutyl ether solution is a good choice.
In this case, the oxidation reaction might be carried out without
much precipitation so that the step of re-dissolving DNDNa at
extreme temperature can be omitted. The amount of energy consumption and sewage production would be reduced as well. Of
course, further study is required to determine the optimized reaction conditions and the recovery of organic solvent need to be
investigated as well.
5. Conclusions
The solubility of DNDNa in (ethylene glycol monoethyl
ether water) and (ethylene glycol monobutyl ether water)
systems at a temperature ranging from 278 to 334 K has been
measured by the dynamic method. The solubility in both systems
increases with temperature. The synergistic effect is observed in
(DNDNa ethylene glycol monoethyl ether water) and
(DNDNa ethylene glycol monobutyl ether water) systems with
maximum solubility at w03 0:6003 andw04 0:4054, respectively.

307

The E-NRTL model is used to correlate the solubility data. The

calculated results are satisfactory, and the root mean square deviations of the SLE temperature range from (0.10e0.63) K. From the
point of view of dissolving intermediate product DNDNa, about 0.4
mass fraction aqueous ethylene glycol monobutyl ether solution is
a suitable oxidation reaction medium in DSD acid synthesis
process.
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