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Solubility, Density, and Metastable Zone Width of Pyridoxine


Hydrochloride in Water and Ethanol Solvent Mixtures
Kun Zhou,*,, Yueyong Yan, Lianying An,, Dongni Xiang, and Hongbin Wang

College of Materials and Chemistry & Chemical Engineering, and Mineral Resources Chemistry Key Laboratory of Sichuan Higher
Education Institutions, Chengdu University of Technology, Chengdu 610059, China

ABSTRACT: The solubility of pyridoxine hydrochloride in water


and ethanol solvent mixtures was measured using a laser
monitoring observation technique at the temperature range from
(278.15 to 323.15) K. The mole fraction of ethanol in the solvent
mixtures (x3) ranges from 0.0 to 0.6012. For the seven group data
studied, the experimental solubility data were well-correlated with
the results calculated by means of a semiempirical equation.
Densities of pyridoxine hydrochloride in solvent mixtures were
investigated at temperatures from (293.15 to 323.15) K. The
eects of ethanol mole fraction, cooling rate, and saturation
temperature on the metastable zone width (MZW) were also
studied. The results show that the MZW of pyridoxine hydro-
chloride becomes narrower by increasing the saturation temper-
ature, increasing ethanol mole fraction, and reducing the cooling
rate. For the density and the MZW, all results were correlated by empirical equations.

INTRODUCTION
Pyridoxine hydrochloride with the chemical name 5-hydroxyl-6-
namic data of pyridoxine hydrochloride in solvent mixtures
have never been reported. In this work, the solubility of
methyl-3,4-pyridine dimethanol hydrochloride, also known as pyridoxine hydrochloride in binary water and ethanol solvent
vitamin B6 is a colorless or white crystal, and is widely used in mixtures was measured at the temperature range of (278.15 to
over-the-counter preparations as well as for medical therapy. 323.15) K, while the density and MZW data were measured in
The vitamins of the B group are water-soluble compounds and the temperature range from (293.15 to 323.15) K under
contain the pyridine ring in their molecules.1 Pyridoxine atmospheric pressure. And the concentration of pyridoxine
hydrochloride was the rst of the B6 group of vitamins to be hydrochloride was determined by ultravioletvisible spectros-
copy (UVvis).5


isolated and it is essential in living organisms for its
participation in more than 100 enzymatic reactions, including
the transfer of amino groups, water or acids in metabolism of EXPERIMENTAL SECTION
proteins, the metabolism of amino acids and the maintenance Materials. A white powered crystal of pyridoxine hydro-
of body cells. In industrial manufacturing, pyridoxine hydro- chloride (C8H11NO3HCl, molecular mass 205.64, Figure 1)
chloride is crystallized from pure water in the purication step, purchased from Guangzhou Shu-nuo Chemical Engineering
and the nal crystal is granular. However, it is well recognized Co., Ltd., China, was used to measure the thermodynamic data.
that the particle size plays a signicant role in the dissolution It was prepared by recrystallization from pure water three times
rate in solvents, especially for drugs. The reduction of particle in the laboratory. And it was washed with chloroform, dried in a
size to micro- and nanometer range has improved the solubility vacuum drying oven at 333.15 K for 24 h, and stored in
of drugs in the production practice. The application of binary
solvent mixtures is a very prevalent and highly powerful
technique of transforming (decreasing or increasing) the
solubility of a solute. The solubility of solutes can be greatly
changed by using binary solvent mixtures. Under some
circumstances, the solubility even can be altered by several
orders of magnitude in solvent mixtures,2,3 whereas, only
solubility in some pure solvents for example acetone, methanol,
Figure 1. Chemical structure of pyridoxine hydrochloride.
chloroform, dichloromethane, and ethanol was reported in
much of the literature.4 To design an optimized crystallization
process and crystallizer, the solubility, density, and metastable Received: July 6, 2015
zone width (MZW) values of pyridoxine hydrochloride in Accepted: November 5, 2015
solvent mixtures are needed. Unfortunately, the thermody- Published: November 13, 2015

2015 American Chemical Society 307 DOI: 10.1021/acs.jced.5b00552


J. Chem. Eng. Data 2016, 61, 307312
Journal of Chemical & Engineering Data Article

Table 1. Detailed Information of Materials Used in the Study


initial mass fraction purication nal mass fraction analysis
chemical name source purity method purity method
pyridoxine Guangzhou Shu-nuo Chemical Engineering Co., Ltd., 0.980 recrystallization 0.990 HPLCa
hydrochloride China
ethanol Chengdu Ke-long Chemical Reagent Co., Ltd., China 0.995 none GCb
a b
High-performance liquid chromatography. Gasliquid chromatography.

desiccators. The mass fraction of pyridoxine hydrochloride, chloride is 325 nm. Using the standard solution in the
measured by HPLC, is greater than 99.0 %. Ethanol was appropriate concentration range, the working curve is prepared
analytical grade reagents purchased from Chengdu Ke-long for the concentration estimation of pyridoxine hydrochloride
Chemical Reagent Company. Its mass fraction was better than Measurement of Density. The density of pyridoxine
99.5 %. The water used in the experiment was distilled by an hydrochloride in water + ethanol was determined using a U
ultrapure water unit in the laboratory. More detailed type vibrating-tube digital densimeter (Density/Specic Gravity
information on the chemicals used in the study is shown in Meter DA 505, KEM Co, Ltd., Japan). Before experiment, the
Table 1. digital densimeter was calibrated with deionized and double-
Measurement of Solubility. The measurement apparatus distilled water at the experimental temperature. The saturation
of the solubility is similar to that described in the literature.6 A solution was maintained in a thermostat bath for 2 h. At the test
150 mL jacketed vessel was used to determine the solubility. temperature, the solution density can be read directly from
The temperature uctuation was controlled within 0.05 K densimeter after the sample is pumped into the densimeter
through a thermostat bath (type 501, China). A mercury-in- through the sucker. The standard uncertainty in the cell
glass thermometer (standard uncertainty of 0.05 K) was used temperature was 0.01 K. The standard uncertainty in density
for the measurement of the temperature in the vessel. The measurements is 3 kg/m3.
mixtures of pyridoxine hydrochloride and solvent in the vessel Measurement of Metastable Zone Width (MZW).
were stirred with a magnetic stirrer. To prevent the evaporation MZW data of pyridoxine hydrochloride in water and ethanol
of the solvent, a condenser vessel was introduced. The solvent mixtures were measured by the laser method at the
concentration of pyridoxine hydrochloride was determined by temperatures range of (293.15 to 323.15) K. The main factors
UVvis analysis. The masses of the samples and solvents were aecting the MZW are the cooling rate, the saturation
determined using an analytical balance (Sartorius CP124S, temperature, the stirring rate, the presence of impurities, and
Germany) with the standard uncertainty of 0.1 mg. the addition rate of antisolvent.8 First, the saturation solution
In this study, the solubility determination of pyridoxine preparation method is the same as measurement of solubility
hydrochloride is conducted by adding excessive amounts of and density. Then, a certain volume of sample was added into
pyridoxine hydrochloride to the solution that is stirred and kept jacketed crystallizer, and in order to eliminate microcrystals, the
at a settled temperature. At the outset, predetermined amounts mixture was heated for 10 min at 3 C higher than saturation
of mixed solvent (water + ethanol) were loaded into a jacketed temperature before cooling. Finally, under a constant stirring
vessel, and after that, masses of pyridoxine hydrochloride were rate, the sample was cooled at ve cooling rates of (5, 10, 15,
transferred into the solvent. According to the concentration of 20, and 25) Kh1. When the crystals appeared, the intensity of
solute determined at dierent dissolution times, the solution laser beam penetrating the crystallizer signicantly reduced.
attained equilibrium when the concentration did not change The saturation temperature and nucleation temperature were
any more. Then the magnetic stirrer was turned o. After the denoted as To and Tnuc, respectively. The MZW (Tmax) can be
solution settle for 2 h, the upper portion of the solution was calculated by eq 3.9
taken, ltered, and diluted into a 50 mL volumetric ask. To
prepare the solutions for UVvis analysis, they were diluted to Tmax = To Tnuc (3)
50 mL with the same system.7 To reduce the error of
experiment, the results were taken from an average of three
measurements for each temperature. The standard uncertainty
in the mole fraction solubility values was estimated to 0.05.
RESULTS AND DISCUSSION
Solubility. The solubilities of pyridoxine hydrochloride in
The mole fraction solubility x1 and the composition of water and ethanol solvent mixtures under dierent temper-
ethanol in solvent mixtures x3 were calculated by eq 1 and eq 2: atures are presented in Table 2 and plotted in Figure 2.
m1/M1 The temperature dependence of pyridoxine hydrochloride
x1 = solubility in solvents mixtures can be expressed by the following
m1/M1 + m2 /M 2 + m3 /M3 (1) modied empirical equation.10,11
m3 /M3 B
x3 = ln(x1) = A + + C ln(T /K)
m2 /M 2 + m3 /M3 (2) T /K (4)

where m1, m2 and m3 are the mass of the solute, water and where x1 is the mole fraction solubility of pyridoxine
ethanol, respectively, and M1, M2 and M3 represent the hydrochloride, T is the absolute temperature, and A, B, and
molecular weight of the solute, water and ethanol, respectively. C are the parameters. The calculated solubility values of
To determine the concentration of pyridoxine hydrochloride pyridoxine hydrochloride (xcalcd) are also listed in Table 2. The
in the solution, the absorbance of experimental sample and the values of parameters A, B, and C and the root-mean-square
standard solution was measured at 325 nm, because the deviations (rmsd) are given in Table 3. The rmsd values shown
maximum absorption wavelength (max) of pyridoxine hydro- in Table 3 and Table 5 are dened as
308 DOI: 10.1021/acs.jced.5b00552
J. Chem. Eng. Data 2016, 61, 307312
Journal of Chemical & Engineering Data Article

Table 2. Experimental Mole Fraction Solubilities x1 of


Pyridoxine Hydrochloride in Binary System of Water (2) +
Ethanol (3) at Experimental Pressure P = 0.1 MPa and
Dierent Saturation Temperaturesa,b
T/K 102x1 102(x1 x1calc) T/K 102x1 102(x1 x1calc)
x3 = 0.0000
278.15 1.066 0.006 303.15 2.222 0.055
283.15 1.282 0.021 308.15 2.522 0.100
288.15 1.48 0.014 313.15 2.666 0.018
293.15 1.626 0.061 318.15 2.818 0.133
298.15 1.886 0.035 323.15 3.29 0.070
x3 = 0.1002
278.15 0.817 0.031 303.15 1.6359 0.038
283.15 0.9196 0.014 308.15 1.8145 0.046
288.15 1.0545 0.037 313.15 1.9988 0.065
293.15 1.2141 0.043 318.15 2.0824 0.010
298.15 1.425 0.002 323.15 2.1736 0.066
x3 = 0.2005 Figure 2. Solubility of pyridoxine hydrochloride in binary system of
278.15 0.5512 0.005 303.15 1.1505 0.006 water + ethanol mixture along temperature: , x3 = 0.0000; , x3 =
283.15 0.6435 0.006 308.15 1.287 0.007
0.1002; , x3 = 0.2005; , x3= 0.2998; , x3 = 0.4005; , x3 = 0.5011;
+, x3 = 0.6012.
288.15 0.7618 0.001 313.15 1.4144 0.004
293.15 0.8788 0.005 318.15 1.5678 0.012
298.15 1.0114 0.000 323.15 1.6783 0.013
Table 3. Parameters of eq 3 for Pyridoxine Hydrochloride in
x3= 0.2998
Binary System of Water (2) + Ethanol (3) Mixture
278.15 0.376 0.006 303.15 0.834 0.010 x3 A B C 104 rmsd
283.15 0.44 0.007 308.15 0.95 0.012 0 131.89 7938.71 19.17 6.45
288.15 0.528 0.006 313.15 1.083 0.003 0.1002 221.76 11878.23 32.68 4.06
293.15 0.614 0.015 318.15 1.219 0.005 0.2005 175.22 9955.78 25.70 0.71
298.15 0.778 0.045 323.15 1.344 0.002 0.2998 150.19 9123.89 21.85 1.64
x3 = 0.4005 0.4005 55.34 4690.41 7.83 1.08
278.15 0.363 0.003 303.15 0.745 0.005 0.5011 11.14 1446.17 1.87 1.88
283.15 0.434 0.005 308.15 0.847 0.001 0.6012 1.80 1634.23 0.24 0.22
288.15 0.498 0.001 313.15 0.931 0.022
293.15 0.576 0.001 318.15 1.089 0.023
298.15 0.666 0.007 323.15 1.182 0.003 increasing temperature; the solubility decreases with increasing
x3 = 0.5011 mole fraction of ethanol in the solvent mixtures. In the process
278.15 0.299 0.006 303.15 0.549 0.021 of industrial crystallization, the initial temperature of crystal-
283.15 0.323 0.009 308.15 0.595 0.007 lization can be appropriately increased to improve the
288.15 0.364 0.010 313.15 0.605 0.048 production capacity of unit volume. According to Figure 2, it
293.15 0.425 0.004 318.15 0.724 0.001 is obvious to nd that the solubility of pyridoxine hydrochloride
298.15 0.484 0.012 323.15 0.818 0.019 in solvent mixtures is less than the solubility in pure water;
x3 = 0.6012 when the concentration of ethanol in the solution is relatively
278.15 0.179 0.000 303.15 0.297 0.000 small, the eect of temperature on the solubility is obvious; and
283.15 0.197 0.002 308.15 0.325 0.000 the higher is the concentration of ethanol, the smaller is the
288.15 0.225 0.004 313.15 0.354 0.001 eect of temperature. From Table 1, the calculated solubility of
293.15 0.246 0.001 318.15 0.384 0.003 pyridoxine hydrochloride shows good agreement with the
298.15 0.268 0.002 323.15 0.424 0.003 experimental values; and the value of rmsd in Table 3 is less
a
x1, x1calc, and x3 represent the experimental solubility data, the
than 7104, which can be used as the basic data to guide
calculated solubility data by eq 4 with parameters correlated from the industrial production.
experimental solubility data, and the mole fraction of ethanol in Density of Pyridoxine Hydrochloride in Water +
solvent mixtures, respectively. bThe standard uncertainty of T is u(T) Ethanol Mixtures. The density of pyridoxine hydrochloride
= 0.05 K, and the standard uncertainty of P is u(P) = 0.005 MPa; the in water + ethanol mixtures was measured within a temperature
standard uncertainty of x3 is u(x3) = 0.05; the relative standard range of (293.15 to 323.15) K and in mole fraction (x3) range
uncertainty u is ur(x1) = 0.05. from 0 to 0.6. An average value taken from three measurements
was considered as the nal result for each temperature. All
N (x x calc)2 1/2 experimental densities are listed in Table 4. With the increase of
rmsd = i = 1
1, i 1, i
saturation temperatures, there is a certain increase in density
N (5) when the mole fraction x3 is 0 or 0.2, while the density of
pyridoxine hydrochloride in solvent mixtures decrease slightly
where N is the number of experimental trials.12 As it can be when a signicant increase in the mole fraction of antisolvent
seen from Figure 2, and Table 3, the solubility of pyridoxine ethanol. The experimental data of density were tted to eq 6
hydrochloride in binary water + ethanol solvent mixtures is a below as a function of absolute temperature (T) and mole
function of temperature, and the solubility increases with fraction of pyridoxine hydrochloride (x1)13
309 DOI: 10.1021/acs.jced.5b00552
J. Chem. Eng. Data 2016, 61, 307312
Journal of Chemical & Engineering Data Article

Table 4. Experimental Density of Pyridoxine Hydrochloride in the Binary System of Water (2) + Ethanol (3) at Experimental
Pressure P = 0.1 MPa and Dierent Saturation Temperaturesa,b
T0/K /(kgm3) 102( calc) T0/K /(kgm3) 102( calc)
x3 = 0.0000
293.15 1093.5 0.087 313.15 1133.3 0.141
298.15 1104.7 0.179 318.15 1141.5 0.108
303.15 1111.0 0.080 323.15 1154.6 0.032
308.15 1120.8 0.077
x3 = 0.2005
293.15 845.7 0.105 313.15 872.5 0.235
298.15 848.6 0.037 318.15 881.0 0.019
303.15 852.2 0.257 323.15 890.0 0.097
308.15 862.2 0.031
x3 = 0.4005
293.15 782.1 0.035 313.15 766.3 0.023
298.15 774.5 0.150 318.15 764.1 0.069
303.15 774.4 0.224 323.15 764.0 0.029
308.15 767.0 0.126
x3 = 0.6012
293.15 741.7 0.057 313.15 729.9 0.052
298.15 737.5 0.114 318.15 729.2 0.099
303.15 736.2 0.076 323.15 724.8 0.043
308.15 732.6 0.023
a
x3 represents the mole fraction of ethanol in solvent mixtures. bThe standard uncertainty of T is u(T) = 0.05 K, and the standard uncertainty of P is
u(P) = 0.005 MPa; the standard uncertainty of x3 is u(x3) = 0.05; the relative standard uncertainty u is u() = 3 kg/m3.

Table 5. Parameters, k1, k2, k3, and k4 of eq 6 Table 6. MZW Data for Pyridoxine Hydrochloride in Water
+ Ethanol Solvents with the Temperature Range from
104 rmsd
(293.15 to 323.15) K and Pressure P = 0.1 MPaa
x3 k1 k2 k3 k4
0 655.0 13573.0 1.5 43.3 10.98
0.2005 1005.6 37092.2 0.6 133.5 14.36 Tmax/K
0.4005 1059.9 47985.3 0.8 139.7 11.72 c (Kh1) T0 = 293.15 K T0 = 303.15 K T0 = 313.15 K T0 = 323.15 K
0.6012 818.1 56964.6 0.1 137.5 7.27 x3 = 0.0000
5 5.1 4.4 2.4 1.4
3
/(gcm ) = k1 + k 2x1 + k 3(T /K) + k4x1(T /K) (6) 10 6.5 5.8 4.2 2.7
15 7.5 6.8 5.5 4.2
where is the density and T is temperature. And the values of 20 8.6 7.6 6.5 5.9
coecients k1, k2, k3, and k4 of eq 6 are listed in Table 5. The 25 9.7 8.5 7.6 6.8
deviation between the experimental and calculated values is less x3 = 0.2005
than 0.003 g/cm3. 5 3.5 2.8 2 1.2
Metastale Zone Width. According to Nyvlts studies,1416 10 5.4 4.2 3.6 2.4
the relationship between the supersaturation Cmax and the 15 6.6 5.4 5 3.8
supercooling Tmax can be expressed by 20 7.6 6.5 6.2 5.4
25 8.2 7.4 6.8 6.2
dC
Cmax = T x3 = 0.4005
dT max (7) 5 2.3 2 1.5 1
10 3.8 3.3 2.8 2.1
where dC/dT is the slope of the solubility of pyridoxine
15 5.7 5.2 4.3 3.8
hydrochloride dependence on the temperature change. In
20 7.3 6.4 5.2 4.6
industrial crystallization, the primary nucleation rate B0 is
25 8 7.6 6.2 5.1
generally expressed by empirical formula:17
x3 = 0.6012
m
B0 = k 0Cmax (8) 5 1.9 1.4 1 0.9
10 3.2 3 2.2 2
where k0 denotes the nucleation rate constant, and m is the 15 5.1 4.3 3.8 3
nucleation order. When the supersaturation is produced by 20 7.4 5.7 5 4.4
cooling, the nucleation rate can be expressed by the production 25 8.5 7.3 5.9 5.3
rate of supersaturation. a
The standard uncertainties are u(T) = 0.05 K, u(P) = 0.005 MPa,
u(Tmax) = 0.06 K.
dC
B0 =
dT (9) dC m 1
= k 0 (Tmax )m
where is the cooling rate, So eq 8 may be rewritten in the dT (10)
form:
310 DOI: 10.1021/acs.jced.5b00552
J. Chem. Eng. Data 2016, 61, 307312
Journal of Chemical & Engineering Data Article

Figure 3. Plots of ln Tmax against ln for pyridoxine hydrochloride at various saturation temperatures. Initial composition: (a) x3 = 0.0000; (b) x3
= 0.2005; (c) x3 = 0.4005; (d) x3 = 0.6012.

Taking logarithms on both sides of eq 10, upon rearrangement However, the MZW tends to decrease with increasing
one obtains: saturation temperature at a settled cooling rate. Probably
because the viscosity of the solution is reduced, it can promote
1 m dC 1 1 the burst nucleation. At constant temperature and a xed
ln Tmax = ln ln k 0 + ln
m dT m m (11) cooling rate, the MZW becomes narrow with increasing the
ethanol mole fraction of solvent mixtures. Therefore, a
Obviously eq 11 indicates a linear dependence of ln Tmax on narrower MZW can be obtained by lower cooling rate, higher
ln . In industrial crystallization, Nyvlts equation is especially saturation temperature, and more ethanol in solvent mixtures,
helpful for the crystal product and process optimization design. because the narrower MZW is more advantageous to produce
Unfortunately, the two parameters have complicated units, and tiny crystals in the crystallization process. As shown in Table 7
their physical signicance still remains obscure.18 and Figure 3, it also shows that the presence of ethanol in
The experimental data of MZW are listed in Table 6 and solvents can aect the nucleation order. With the increasing of
plotted in loglog coordinates in Figure 3. The values of ethanol mole fraction, there are approximate parallel relation-
nucleation order, m, obtained from the linear regression ships for four tted lines obtained by linear regression.


analysis (shown in Figure 3), was presented in Table 7 in
detail. And the linear relationship between ln Tmax and ln of
CONCLUSION
pyridoxine hydrochloride at dierent saturation temperature is
summarized in Table 7. And all results show a good linear In this paper, the solubility of pyridoxine hydrochloride in a
relationship. As can be seen from Figure 3 and Table 6, in all binary system of water and ethanol solvent mixtures was
temperatures under consideration, the MZW of pyridoxine measured using a laser method at the temperatures from
hydrochloride increases with an increase of cooling rate. (278.15 to 323.15) K and at mole fraction of ethanol from 0.0
311 DOI: 10.1021/acs.jced.5b00552
J. Chem. Eng. Data 2016, 61, 307312
Journal of Chemical & Engineering Data Article

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AUTHOR INFORMATION
Corresponding Author
*Tel.: +86-28-84078939. Fax: +86-28-84079074. E-mail:
kunzhou925@163.com.
Funding
The authors are grateful for nancial support from the
Foundation for Young Scholar of Chengdu University of
Technology (KYGG201308).
Notes
The authors declare no competing nancial interest.

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312 DOI: 10.1021/acs.jced.5b00552


J. Chem. Eng. Data 2016, 61, 307312