Solubility of 1-(3-bromopropoxy)-4-chlorobenzene in aqueous ethanol mixtures from (273.15 to 303.15) K

Article abstract of DOI:10.1007/s10953-013-9962-4

1-(3-Bromopropoxy)-4-chlorobenzene is an important intermediate for the manufacture of omoconazole nitrate. The solubilities of 1-(3-bromopropoxy)-4- chlorobenzene in aqueous ethanol solutions were measured within the temperature range of (273.15-303.15) K using a laser monitoring system. For the temperature range investigated, the solubilities of 1-(3-bromopropoxy)-4-chlorobenzene in the aqueous ethanol mixtures increase with increasing temperature. The solubility data were regressed by the Buchowski-Ksiazaczak λh and the modified Apelblat models. The modified Apelblat equation and the Buchowski-Ksiazaczak λh equation provided accurate mathematical representations of the experimental results. The calculated solubilities showed good agreement with the experimental data. The root-mean-square deviations of the modified Apelblat model were lower than those of the Buchowski-Ksiazaczak λh model. This study provided valuable data for the purification of 1-(3-bromopropoxy)-4-chlorobenzene by crystallization.

Full text of DOI:10.1007/s10953-013-9962-4

J Solution Chem (2013) 42:272–281
DOI 10.1007/s10953-013-9962-4
Solubility of 1-(3-Bromopropoxy)-4-Chlorobenzene
in Aqueous Ethanol Mixtures From (273.15 to 303.15) K
•
Xin-Min Jiang Yong-Hong Hu Wen-Ge Yang Zi-Yu Lei
•
•
•
•
Rong-Rong Tang Fei Shen
Received: 20 December 2011 / Accepted: 8 April 2012 / Published online: 6 February 2013
Ó Springer Science+Business Media New York 2013
Abstract 1-(3-Bromopropoxy)-4-chlorobenzene is an important intermediate for the
manufacture of omoconazole nitrate. The solubilities of 1-(3-bromopropoxy)-4-chloro-
benzene in aqueous ethanol solutions were measured within the temperature range of
(273.15–303.15) K using a laser monitoring system. For the temperature range investi-
gated, the solubilities of 1-(3-bromopropoxy)-4-chlorobenzene in the aqueous ethanol
mixtures increase with increasing temperature. The solubility data were regressed by the
Buchowski–Ksiazaczak kh and the modified Apelblat models. The modified Apelblat
equation and the Buchowski–Ksiazaczak kh equation provided accurate mathematical
representations of the experimental results. The calculated solubilities showed good
agreement with the experimental data. The root-mean-square deviations of the modified
Apelblat model were lower than those of the Buchowski–Ksiazaczak kh model. This study
provided valuable data for the purification of 1-(3-bromopropoxy)-4-chlorobenzene by
crystallization.
Keywords 1-(3-Bromopropoxy)-4-chlorobenzene ꢀ Solubility ꢀ Correlation ꢀ
Modified Apelblat equation
Nomenclature and Units
x
Mole fraction solubility
xci alc
xei xp
T
Calculated value of the solubility
Experimental value of the solubility
Absolute temperature
X.-M. Jiang ꢀ Y.-H. Hu ꢀ W.-G. Yang (&) ꢀ Z.-Y. Lei ꢀ R.-R. Tang
College of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology,
No. 200, North Zhongshan Road, Nanjing 210009, China
e-mail: yonghonghu11@126.com
X.-M. Jiang
e-mail: jiangxinmin6396@126.com
Y.-H. Hu ꢀ R.-R. Tang ꢀ F. Shen
Jiangsu Engineering Technology Research Center of Polypeptide Pharmaceutical,
Nanjing 210038, China
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J Solution Chem (2013) 42:272–281
273
x
Tm
Volume fraction of ethanol in the solvent mixture
Melting point
A, B, C
k, h
cx
Empirical constants in Eq. 4
Empirical constants in Eq. 8
Activity coefficient on a mole fraction basis
Enthalpy of fusion
Heat capacity difference between the solid and the liquid
DfusH
DCp
Tt
rmsd
R
Triple point temperature
Root-mean-square deviation
Gas constant
C1, C2, C3 Molar concentration of ethanol, 1-(3-bromopropoxy)-4-chlorobenzene and
water, respectively, in saturated solutions
1 Introduction
1-(3-Bromopropoxy)-4-chlorobenzene (CAS: 2033-76-3) is an important intermediate for
the manufacture of omoconazole nitrate [1], a broad-spectrum antifungal agent with strong
antifungal activity [2, 3] that is used to treat diseases caused by infections with Tricho-
phyton mentagrophytes or Candida albicans, such as tinea pedis [4–7]. It can be also used
as an intermediate in the synthesis of potassium channel blockers [8], non-imidazole
histamine H(3) receptor ligands [9], antitumor agents [10], and hepatitis C virus entry
inhibitors [11]. 1-(3-Bromopropoxy)-4-chlorobenzene commonly occurs as a white pow-
der. The chemical structure of 1-(3-bromopropoxy)-4-chlorobenzene is shown in Fig. 1.
Crystallization processes are critical in determining the quality of the final product.
Crystallization from solvent mixtures are employed in the manufacture of pharmaceuticals,
organic fine chemicals, and specialty chemicals [12]. Both the solvent power and the
temperature coefficient of solubility must be considered when choosing a solvent for a
cooling crystallization process to produce 1-(3-bromopropoxy)-4-chlorobenzene; the for-
mer quantity influences the volume of the crystallizer, and the latter determines the crystal
yield [13]. Therefore, the solubility of 1-(3-bromopropoxy)-4-chlorobenzene in pure sol-
vents and solvent mixtures plays a crucial role in the development and operation of
crystallization processes, and determines supersaturation generation methods and the yield
from the crystallization process.
In this paper, the experimentally measured solubilities of 1-(3-bromopropoxy)-4-chloro-
benzene in ethanol and ethanol–water mixtures are reported, and the solubility data were
correlated with the modified Apelblat equation and the Buchowski–Ksiazaczak kh equation.
Fig. 1 Structure of 1-(3-
bromopropoxy)-4-chlorobenzene
O
Br
Cl
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J Solution Chem (2013) 42:272–281
2 Materials and Methods
2.1 Materials
The 1-(3-bromopropoxy)-4-chlorobenzene was synthesized in our laboratory [14]. In brief,
p-chlorophenol was dissolved, with stirring, in water containing sodium hydroxide and
then added dropwise to excess refluxing ethylene dibromide. The reaction mixture was
heated under reflux for 6 h, cooled, and then extracted into ether. Fractionation under
reduced pressure yielded p-chlorophenoxyethyl bromide as a colorless oil, which was then
cooled to give the target compound as a colorless solid. It was purified by recrystallization
using 95 % ethanol. The purity was checked by high performance liquid chromatography
and was found to be higher than 99 %. The ethanol for dissolving the 1-(3-bromopropoxy)-
4-chlorobenzene was analytical purity grade with mass fraction purity higher than 99.5 %,
which was obtained from the Shanghai Chemical Reagent Co., Ltd. The analytical balance
(model: BSA224S) was provided by Sartorius Scientific Instruments (Beijing) Co., Ltd.,
and had an uncertainty of 0.0001 g. The differential scanning calorimeter (model:
NETZSCH DSC 204) was provided by Tanjin Keqi Technology Co., Ltd. Distilled
deionized HPLC water was used in the experiments. All chemicals were used without
further purification.
2.2 Differential Scanning Calorimetry (DSC) Measurements
The characterization of the samples by DSC was carried out on a DSC instrument
(NETZSCH DSC 204). Approximately 15–20 mg of 1-(3-bromopropoxy)-4-chloroben-
zene powder was put into a hermetic DSC sample pan and heated under a nitrogen
atmosphere. For each DCS experiment, an empty DSC sample pan was used as a blank
reference. The experiments were performed at a heating rate of 10 Kꢀmin-1 over the
temperature range (273–423) K. The calibration run was made with Al2O3 (sapphire) as a
standard. Aluminum crucibles containing the samples were purged with nitrogen at a flow
rate of 30 mLꢀmin-1. Several runs, with a heating rate of 1 Kꢀmin-1 around the melting
temperature, were averaged. The overall measured accuracy was approximately 1 K. All
thermal analyses were carried out at least three times. The deviation in the melting tem-
perature was 0.2 %, and the enthalpy of fusion (melting), DfusH, was 2.9 %.
2.3 Solubility Measurements
Solubilities of 1-(3-bromopropoxy)-4-chlorobenzene in pure ethanol and ethanol–water
mixtures were determined, as a function of temperature and the volume fraction of ethanol,
using a laser monitoring system [15–19]. A 50 mL jacketed solubility cell was used to
determine the solubilities. The temperature of the jacketed solubility cell was controlled
with a super thermostatic water-circulator bath (type HWC-52, Shanghai Candy Precision
Instrument Co., Ltd.), with a temperature stability of 0.05 K and a temperature uncer-
tainty of 0.1 K. A glass bushing with a mercury glass thermometer was inserted into the
inner chamber of the vessel to measure the temperature; the uncertainty in temperature was
0.05 K (calibrated by using a standard thermometer). The solubility cell permits the laser
beam to pass through it, and the power of the laser is converted into an electrical signal and
detected by a galvanometer. As the solute gradually dissolved, the light intensity contin-
uously increased until coming to the solubility equilibrium point. As the concentration
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J Solution Chem (2013) 42:272–281
275
dependence of the light intensity was linear with the concentration of suspended particles,
the concentration of the suspended particles can be calculated. Then, the final mass dis-
solved can be determined. The temperature range for the solubility measurement in
aqueous ethanol is 273.15–303.15 K.
3 Calculations
The saturated mole fraction solubility (xi) of 1-(3-bromopropoxy)-4-chlorobenzene in
aqueous ethanol can be obtained as follows:
C2
xi ¼
ð1Þ
C1 þ C2 þ C3
where C1, C2 and C3 denote the molar concentrations of ethanol, 1-(3-bromopropoxy)-4-
chlorobenzene and water in the saturated solutions, respectively. The measured xi values of
1-(3-bromopropoxy)-4-chlorobenzene in aqueous ethanol solution between the tempera-
tures of 273.15–303.15 K are presented in Table 1. The uncertainties of the saturated
solution mole fraction solubilities are about 2.0 %. The uncertainties in the solubility
values are due to uncertainties in the weighing procedure, temperature measurements,
excess addition of solute, and instabilities of the water bath.
In order to more quantitatively describe the solid–liquid equilibrium, the relationship
between solubility and temperature can be represented as follow [20]:
ꢀ
ꢁ
ꢀ
ꢁ
ꢀ
ꢁ
ꢀ ꢁ
1
D
fusH Tt
DCp
Tt
T
DCp
Tt
ln
¼
ꢁ 1
ꢁ
ln
ꢁ 1
þ
ln
ð2Þ
cxx
RTt
T
R
R
T
where cx is the activity coefficient of 1-(3-bromopropoxy)-4-chlorobenzene on a mole
fraction basis, x is the mole fraction solubility of 1-(3-bromopropoxy)-4-chlorobenzene,
DfusH is the enthalpy of fusion of 1-(3-bromopropoxy)-4-chlorobenzene, DCp is the dif-
ference of the heat capacity between the solid and the liquid, T is the absolute temperature
(K), Tt is the triple-point temperature, and R is the gas constant. The value of DCp is so
small relative to DfusH=T that the second and third terms can be neglected. For solid–liquid
equilibria, pressure changes usually do not have important effects on equilibrium unless the
pressure changes are very large (10–100 MPa) [21]. The normal melting temperature, Tm,
can be substituted for the triple point temperature Tt. With these substitutions, Eq. 2 can be
rewritten as [22]:
ꢀ
ꢁ
D
fusH
Tm
T
ln ðcxxÞ ¼
1 ꢁ
ð3Þ
RTm
Since solid–liquid equilibria data are often not available, particularly for mixed sol-
vents, correlation and prediction schemes are frequently employed. Therefore, to find
a proper equation for the solubility data for 1-(3-bromopropoxy)-4-chlorobenzene, the
modified Apelblat equation and the Buchowski–Ksiazaczak kh equation were used in this
paper.
The modified Apelblat equation has been previously used by Apelblat and Manzurola to
correlate solute concentrations in solid–liquid equilibrium systems [23–25]:
ln x ¼ A þ B=ðT=KÞ þ C lnðT=KÞ
where x is the mole fraction of the solute, T is the absolute temperature, and A, B and C are
ð4Þ
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J Solution Chem (2013) 42:272–281
Table 1 The mole fraction solubilities of 1-(3-bromopropoxy)-4-chlorobenzene (xi) in different compo-
sitions of ethanol–water mixtures over the temperature range 273.15–303.15 K
xei xp ꢂ 102
T (K)
Apelblat equation
kh equation
xci al ꢂ 102
xci al ꢂ 102
RD
RD
x = 100 %
273.15
278.15
283.15
288.15
293.15
298.15
303.15
x = 95 %
273.15
278.15
283.15
288.15
293.15
298.15
303.15
x = 90 %
273.15
278.15
283.15
288.15
293.15
298.15
303.15
x = 85 %
273.15
278.15
283.15
288.15
293.15
298.15
303.15
x = 80 %
273.15
278.15
283.15
288.15
293.15
298.15
303.15
2.1857 0.0005
2.8054 0.0003
3.6621 0.0002
4.8813 0.0006
6.5783 0.0008
9.3282 0.0009
14.194 0.0013
2.2933
2.7959
3.5696
4.7567
6.5955
9.4889
14.128
-0.048
0.003
2.0775
2.7430
3.6438
4.8951
6.7004
9.4583
14.0707
0.049
0.022
0.005
0.025
0.026
-0.002
-0.018
-0.014
0.009
-0.003
-0.017
0.005
1.5277 0.0005
1.7630 0.0003
2.1523 0.0006
2.7010 0.0014
3.4315 0.0002
4.3956 0.0009
6.3084 0.0007
1.5587
1.7787
2.1206
2.6329
3.3949
4.5337
6.2554
-0.020
-0.008
0.015
1.5233
1.8045
2.1700
2.6639
3.3668
4.4452
6.3070
0.003
-0.024
-0.008
0.014
0.025
0.011
0.019
-0.031
0.008
-0.011
0.001
0.6879 0.0003
0.8929 0.0002
1.1626 0.0005
1.5405 0.0009
2.2612 0.0010
3.1779 0.0012
4.6184 0.0001
0.6808
0.8793
1.1680
1.5922
2.2231
3.1735
4.6242
0.010
0.015
0.7041
0.9142
1.1982
1.5946
2.1744
3.0846
4.6869
-0.024
-0.024
-0.031
-0.035
0.038
-0.005
-0.034
0.017
0.001
0.029
-0.001
-0.015
0.5041 0.0007
0.6263 0.0005
0.7894 0.0006
1.0596 0.0007
1.3882 0.0003
1.8973 0.0011
2.7233 0.0009
0.5116
0.6261
0.7924
1.0345
1.3901
1.9186
2.7146
-0.015
0.001
0.5237
0.6473
0.8106
1.0347
1.3585
1.8639
2.7553
-0.039
-0.033
-0.027
0.024
-0.004
0.023
-0.001
-0.011
0.003
0.021
0.018
-0.011
0.2163 0.0012
0.2838 0.0008
0.3837 0.0009
0.5695 0.0003
0.7931 0.0002
1.1216 0.0016
1.7534 0.0001
0.2216
0.2891
0.3903
0.5441
0.7811
1.1523
1.7434
-0.024
-0.018
-0.017
0.045
0.2223
0.2977
0.4019
0.5501
0.7709
1.1241
1.7604
-0.028
-0.049
-0.047
0.034
0.015
0.028
-0.027
0.006
-0.002
-0.004
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277
Table 1 continued
xei xp ꢂ 102
T (K)
Apelblat equation
xci al ꢂ 102
kh equation
xci al ꢂ 102
RD
RD
x = 75 %
273.15
278.15
283.15
288.15
293.15
298.15
303.15
x = 70 %
273.15
278.15
283.15
288.15
293.15
298.15
303.15
0.2374 0.0003
0.2743 0.0007
0.3421 0.0009
0.4493 0.0002
0.5846 0.0005
0.7784 0.0010
1.1102 0.0020
0.2360
0.2796
0.3444
0.4397
0.5803
0.7898
1.1063
0.006
0.2381
0.2875
0.3523
0.4409
0.5687
0.7681
1.1219
-0.003
-0.048
-0.030
0.019
0.005
-0.016
-0.005
0.016
0.027
0.006
0.013
-0.010
-0.010
0.0798 0.0008
0.0996 0.0004
0.1357 0.0010
0.1817 0.0002
0.2585 0.0006
0.3644 0.0008
0.5501 0.0021
0.0802
0.1016
0.1335
0.1816
0.2551
0.3690
0.5487
-0.005
-0.019
0.016
0.0804
0.1045
0.1373
0.1834
0.2514
0.3596
0.5544
-0.007
-0.049
-0.012
-0.009
0.027
0.001
0.013
-0.013
0.002
0.013
-0.008
parameters obtained by fitting the experimental solubility data and are shown in Table 2
together with the corresponding root-mean-square deviations (rmsd) of the modified A-
pelblat equation. This equation is readily applied in engineering. As such, we employed the
modified Apelblat equation to correlate the solubility data of 1-(3-bromopropoxy)-4-
chlorobenzene in aqueous ethanol. The rmsd can be defined as follows:
1
2
"
#
N
X
1
rmsd ¼
ðxci alc ꢁ xei xp
Þ
ð5Þ
2
N
i¼1
where N is the number of experimental points and xci alc and xiexp represent the calculated
and the experimental solubility values, respectively. The relative deviations (RD) between
Table 2 Apelblat equation fitting parameters of 1-(3-bromopropoxy)-4-chlorobenzene in different com-
positions of ethanol–water mixtures
x (%)
Apelblat equation
A
B
C
104 rmsd
102 RAD
100
95
90
85
80
75
70
-1,099.6
-1,005.6
-762.58
-842.25
-902.73
-925.60
-941.17
43,066
39,991
28,244
32,244
33,903
36,095
35,843
167.22
152.42
116.61
128.15
137.70
140.36
143.11
9.7267
6.5542
2.5191
1.3247
1.6611
0.6449
0.2498
1.814
1.686
1.186
0.8286
2.171
0.9143
0.9857
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J Solution Chem (2013) 42:272–281
the experimental values and corresponding calculated value are also listed in Table 1. RD
are calculated according to:
xei xp ꢁ xci alc
RD ¼
ð6Þ
xei xp
The relative average deviations (RAD) is defined as
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
exp
xi ꢁ xci alc
N
X
ꢂ
ꢂ
ꢂ
RAD ¼ ð1=NÞ
ð7Þ
xei xp
i¼1
The values of the RAD are listed in Table 2. As is evident, the solubility of 1-(3-
bromopropoxy)-4-chlorobenzene in aqueous ethanol can be effectively regressed with the
modified Apelblat equation.
The Buchowski–Ksiazaczak kh equation, Eq. 8, is an alternate way to describe solution
behavior, and was first proposed by Buchowski et al. [26]. The kh equation has been shown
to fit the experimental data well for many systems with only two parameters, k and h. In the
present study, the solubility data were also correlated with the kh equation:
ꢃ
ꢄ
ꢀ
ꢁ
kð1 ꢁ xÞ
1
1
ln 1 þ
¼ kh
ꢁ
ð8Þ
x
T
Tm
where T is the absolute temperature and x is the mole fraction solubility of 1-(3-bromo-
propoxy)-4-chlorobenzene. As for the Buchowski–Ksiazaczak kh equation, recasting Eq. 8
into an exponential form yields:
h
i
1
1
1
T
1
ꢁ
¼
ekh
ꢁ 1 þ 1
ð9Þ
ð
Þ
T
m
x
k
which can be used to regress the experimental solubility data, by the nonlinear least-squares
method, to estimate the parameters k and h. The values of the two parameters k and h, together
with the rmsd of the Buchowski–Ksiazaczak kh equation and the RAD, are listed in Table 3.
4 Results and Discussion
4.1 Result of DSC
The DSC thermogram of 1-(3-bromopropoxy)-4-chlorobenzene was measured on a
DSC instrument (NETZSCH DSC 204). The determined melting point (Tm) of
Table 3 The kh equation fitting parameters of 1-(3-bromopropoxy)-4-chlorobenzene in different compo-
sitions of ethanol–water mixtures
x (%)
kh equation
k 9 103
h
104 rmsd
102 RAD
100
95
90
85
80
75
70
96.292
8.1865
24.378
8.1368
11.191
2.1526
2.7618
35,784.1
10,444.8
123,047
231,148
323,007
601,235
1085,401
9.4991
3.7946
6.0759
2.6501
1.4565
1.0988
0.4171
1.700
1.143
2.800
2.471
2.743
2.143
1.786
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J Solution Chem (2013) 42:272–281
279
1-(3-bromopropoxy)-4-chlorobenzene is 315.9 K, and the enthalpy of fusion (DfusH) of
1-(3-bromopropoxy)-4-chlorobenzene is -104.1 Jꢀg-1
.
4.2 Solid–Liquid Equilibrium Data
The solubilities of 1-(3-bromopropoxy)-4-chlorobenzene in aqueous ethanol solutions were
determined between 273.15 and 303.15 K using the previously described laser detection
system. The volume fraction (x) of ethanol in the solvent mixtures was 0.70, 0.75, 0.80,
0.85, 0.90, 0.95 and 1.00. For each solvent composition studied the equilibrium solubility
mole fraction of 1-(3-bromopropoxy)-4-chlorobenzene increases with increasing temper-
ature. The solubility of 1-(3-bromopropoxy)-4-chlorobenzene in ethanol ? water mixed
solvents increases with increasing ethanol concentration at constant temperature, which
may be explained by the ‘‘like dissolves like’’ principle. As shown in Fig. 1, we can see
that the solute possesses lower polarity. In addition, the solvent’s polarity is in the fol-
lowing order: water [ ethanol. As we all know that a commonly used rule called ‘‘like
dissolves like’’ is usually used for predicting the solubility of a solute and to determine a
suitable solvent for purification of some compounds. This statement indicates that a solute
will dissolve best in a solvent that has a similar chemical structure or polarity to itself. For
example, a very polar solute such as urea is very soluble in highly polar water, less soluble
in fairly polar methanol, and practically insoluble in non-polar solvents. Therefore, the
solubility of 1-(3-bromopropoxy)-4-chlorobenzene in pure ethanol will be higher than in
ethanol ? water mixed solvents; meanwhile, the solubility of 1-(3-bromopropoxy)-4-
chlorobenzene in the mixed solvents decreases with increasing water composition at
constant temperature. The experimental results are shown in Fig. 2 and Table 1. It can be
seen that the solubility of 1-(3-bromopropoxy)-4-chlorobenzene gradually increases with
increasing temperature, whereas it decreases with increasing concentration of water in the
solution. Furthermore, we observe that these conclusions show good agreement with the
phenomena shown in the experimental figures and data.
4.3 Correlation of the Solubility by the Modified Apelblat and kh Equations
From Table 1, it can be found that the calculated solubilities show good agreement with
the experimental data. The RD calculated by the modified Apelblat equation among all of
Fig. 2 Mole fraction solubility
of 1-(3-bromopropoxy)-4-
chlorobenzene in different
compositions of ethanol–water
mixtures in the temperature range
273.15–303.15 K
14
100%
95%
12
10
8
90%
85%
80%
75%
70%
6
4
2
0
270
275
280
285
290
295
300
305
T/K
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J Solution Chem (2013) 42:272–281
the values do not exceed 4.8 %, and the RAD are 1.814, 1.686, 1.186, 0.8286, 2.171,
0.9143, and 0.9857 %. The RD calculated by the Buchowski–Ksiazaczak kh equation were
less than 4.9 %, and the RADs are 1.700, 1.143, 2.800, 2.471, 2.743, 2.143 and 1.786 %.
The precision of the solubilities calculated by the models can meet the demands of
engineering applications. From Tables 2 and 3, the rmsd of the modified Apelblat model
were lower than those of the Buchowski–Ksiazaczak kh model. In other words, the
regression result of the Buchowski–Ksiazaczak kh equation was slightly less accurate than
that of the modified Apelblat equation. As stated previously, we can draw the conclusion
that the modified Apelblat equation is more accurate than the Buchowski–Ksiazaczak kh
equation in the selected mixed solvents.
5 Conclusions
The melting point of 1-(3-bromopropoxy)-4-chlorobenzene determined by DSC is 315.9 K,
and the enthalpy of fusion is -104.1 Jꢀg-1. The solubilities of 1-(3-bromopropoxy)-4-
chlorobenzene in pure ethanol and ethanol–water mixtures were experimentally determined
using a laser monitoring system. The solubility of 1-(3-bromopropoxy)-4-chlorobenzene
increases sharply with increase of temperature, and it decreases rapidly with increas-
ing concentration of water. The experimental data were regressed by the Buchowski–
Ksiazaczak kh and modified Apelblat equations and the calculated solubilities show good
agreement with the experimental data and have acceptable precision for industrial
applications.
Acknowledgments This research work was financially supported by the Fundamental University Science
Project of Jiangsu Province in China (No. 12KJA180002). This Research work was also supported by the
Grant from the Natural Science Foundation of China (NSFC) (No. 31171644). We thank the editors and the
anonymous reviewers.
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