Cosolvency and Mathematical Modeling Analysis of Chloroxine in

Aug 3, 2018 - Anhui Key Laboratory of Spin Electron and Nanomaterials of Anhui Higher Education Institues, Suzhou University, Suzhou , Anhui 234000 ...
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Cosolvency and Mathematical Modeling Analysis of Chloroxine in Some Binary Solvent System Hongwei Shi,* Yong Xie, Jigui Xu, Xiaojie Zhang, and Hongyan Wang

J. Chem. Eng. Data Downloaded from pubs.acs.org by UNIV OF READING on 08/04/18. For personal use only.

School of Chemistry and Chemical Engineering, Suzhou University, Suzhou, 234000, P. R. China Anhui Key Laboratory of Spin Electron and Nanomaterials of Anhui Higher Education Institues, Suzhou University, Suzhou, Anhui 234000, P. R. China ABSTRACT: Equilibrium solubilities of chloroxine in binary solvent mixtures of ethyl acetate plus methanol, ethanol, n-propanol, and isopropanol were measured by the static equilibrium method in the temperature range of 283.15−333.15 K at pressure of 1 atm. The solubility data is positively increased with increasing temperature at different solvent composition ranging from 0 to 1 and decreased with the increasing mass fraction of alcohol in each binary system, and the maximum solubility of 7.819 × 10−3 at 333.15 K was found in neat ethyl acetate. Under the same composition of ethyl acetate and temperature conditions, the solubility of chloroxine was greater in (methanol + ethyl acetate) than in the other three solution mixtures. Several mathematical models, that is, the Jouyban−Acree model, Van’t Hoff−Jouyban−Acree model and Apelblat−Jouyban−Acree model were adopted to correlate the measured solubility values. As a result, the calculated data are in alignment to measured values at evaluated temperatures and RAD (× 10−2) and RMSD (× 10−4) data were no more than 3.49 and 0.94, respectively. X-ray powder diffraction serves to analyze the equilibrium solid phase crystal of chloroxine and results turns out that no polymorphic transformation, solvate formation or crystal transition in the whole solvent crystallization process. extracting agent,14−17 which are successfully employed in solid−liquid extraction for rare earth elements such as Ce3+ and Tb3+. Meanwhile, research continues on the compatibility application of chloroxine in a shampoo that is rather efficient for curing dandruff and seborrheic dermatitis as an synthetic antibacterial substance.18 As an analytical reagent and extensive application in the field of medicine, it is required that the purity of the model compound is very high. In consideration of these factors, it is of meaningfulness to comprehensively determine the solubility of a drug in mixed solvents before obtaining high purity products. However, only in water was the solubility of chloroxine reported (at 25 °C, 1.5 × 10−4 mol· L−1).19 To study the dissolving properties and obtain the solubility data that helps crystallize purification for chloroxine, the solubility of chloroxine (3) in solvent mixtures of {ethyl acetate (EA) (1) + methanol (MeOH) (2)}, {ethyl acetate (EA) (1) + ethanol (EtOH) (2)}, {ethyl acetate (EA) (1) + npropanol (NPA) (2)}, and {ethyl acetate (EA) (1) + isopropanol (IPA) (2)} at temperatures ranging from 283.15 to 333.15 K at 1 atm was carried out. Moreover, the solubility data was correlated by the Jouyban−Acree model, Van’t Hoff−-Jouyban−Acree model, and Apelblat−Jouyban−Acree model. The experimental solubility and model parameters can

1. INTRODUCTION Progress on drug solubility is a widely increasing study subject to be useful and practical in pharmaceutical areas. Because of to a low concentration of drugs in aqueous medium, it might be preferable to place three methods, that is, i.e. cosolvents, multiple cosolvents containing hydrotropy and (cosolvents + buffer).1−5 Co-solvency is an optional and effective solubilization strategy considered as an alternative to the solubility, as anhydrous liquid mixtures are a crucial impact factor for medicinal industries in that they could be available for reaction medium or recrystallization solvents in the synthesis and purification process of numerous pharmaceuticals.6−10 Chloroxine (CAS Reg. No. 773-76-2, chemically named 5,7dichloro-8-hydroxyquinoline, chemical structure shown in Figure 1) is classified by one of some representative 8hydroxyquinoline derivatives which has efficient antifungal, antibacterial, antiamoebic, bacteriostatic, fungistatic, and antiprotozoal activities, especially used to treat intestinal amebiasis.11−13 It can extensively form a small number of metal chelates used as an analytical reagent and a chelating

Received: March 28, 2018 Accepted: July 9, 2018

Figure 1. Chemical structure of chloroxine. © XXXX American Chemical Society

A

DOI: 10.1021/acs.jced.8b00257 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 1. Sources, Purity, and Properties of Materials and Reagents Used in This Work chemicals

molar mass (g·mol−1)

source

mass fraction purity

purification method

analytical method

chloroxine methanol ethanol n-propanol isopropanol ethyl acetate

214.05 32.04 46.07 60.10 60.06 88.11

Maya Reagent Co., Ltd. Sinopharm Chemical Reagent Co., Ltd., China

0.995 0.998 0.996 0.996 0.997 0.998

recrystallization

HPLCa GCb GC GC GC GC

a

High-performance liquid chromatography. bGas chromatography.

where m1 represents the mass of chloroxine, m2 represents the mass of ethyl acetate, and m3 represents the mass of MeOH, EtOH, NPA, and IPA, respectively. M1, M2, and M3 are the molecular mass of chloroxine, ethyl acetate, and the others. 2.3. Analysis Method. The system composition of chloroxine was tested by using HPLC (Agilent-1260) equipped with a reverse phase column of LP-C18 (250 mm × 4.6 mm). The temperature of chromatographic column was set to 303 K, and the absorption maxima wavelength of the standard sample was 248 nm confirmed via UV−vis scanning detector. The flow rate of mobile phase of HPLC was set as 0.8 mL·min−1 in neat methanol. The final results are the average value in triplicate determination. The relative standard uncertainty of the determination was estimated to be 0.0247 in mole fraction. 2.4. X-ray Powder Diffraction. Given the detection conditions of 40 kV tube voltage and 30 mA current, the chloroxine and crystal samples were characterized by X-ray powder diffraction (XPRD) carried out on a Bruker AXS D8 Advance (Bruker, Germany) instrument which checked out by means of Cu Kα radiation (λ = 1.54184 nm). What’s more, the acquired data were gathered ranging from 5° to 80° (2θ) at a scanning speed of 5°·min−1 at 1 atm.

guide the crystallization, purification in laboratorie,s and related industries.

2. EXPERIMENTAL SECTION 2.1. Materials. Chloroxine with a purity of 0.980 (mass fraction) was purchased from Maya Reagent. The crude material was purified three times in methanol. Its final composition was 0.995 (mass fraction), which was confirmed by a high-performance liquid chromatography (HPLC). Pure MeOH, EtOH, NPA, and IPA with purities greater than 0.994 provided by Sinopharm Chemical Reagent Co., Ltd., China were determined by using gas chromatography (GC, FULI 9790, China). The comprehensive information on these materials was tabulated in Table 1. 2.2. Solubility Determination. The solubility of chloroxine in solvent mixtures of {EA (1) + MeOH (2)}, {EA (1) + EtOH (2)}, {EA (1) + NPA (2)}, and {EA (1) + IPA (2)} were determined by static technique.20−24 A large amount of chloroxine and about 60 mL of mixed solvents were added into the vessel. The solution was continuously mixed and stirred by a magnetic stirrer at a desired temperature. About 1 mL lof iquid phase was extracted out every 2 h and analyzed by HPLC. The sampling system is default in solid−liquid equilibrium when the analysis results coincide. The results showed that 24 h was enough to reach equilibrium. Then, the magnetic stirrer was turned off in order for undissolved solute to precipitate. After a period of time, the upper saturated liquid of about 1 mL was quickly bextracted with a pretreated syringe attached with a filter (PTFE 0.2 μm) into a 25 mL preweighed volumetric flask. Using an analytical balance, the flask filled with the samplewas weighed once again. Finally, it was diluted to 25 mL with methanol and analyzed by HPLC. Once the system was in equilibrium, stirring was stopped. One hour later, the clear liquor was withdrawn with a 2 mL syringe that was precooled or preheated in advance, and then the liquor was transferred rapidly to a to a volumetric flask that was preweighed. The sample was diluted with methanol and tested with HPLC. The solubility of chloroxine (xw,T) in mole fraction in the four cosolvent mixtures was acquired with eq 1, and the initial composition of solvent mixtures (w) is computed with eqs 2 and 3. x w,T =

m1 M1

+

m1 M1 m2 M2

+

m3 M3

3. RESULTS AND DISCUSSION 3.1. XPRD Analysis. The solid equilibrating with liquor is verified by X-ray powder diffraction if there is any the existence of the polymorph transformation or solvate formation for crystal samples. The XRD patterns of all crystal phases in both monosolvents and the binary mixtures are plotted in Figure 2.

(1)

w1 =

m2 m 2 + m3

(2)

w2 =

m3 m 2 + m3

(3)

Figure 2. XRD patterns of chloroxine: (a) raw material; (b) crystallized in MeOH; (c) crystallized in EtOH; (d) crystallized in NPA; (e) crystallized in IPA; (f) crystallized in EA; (g) crystallized in EA (1) + MeOH (2) mixture; (h) crystallized in EA (1) + EtOH (2) mixture; (i) crystallized in EA (1) + NPA (2) mixture; (j) crystallized in EA (1) + IPA (2) mixture. B

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Table 2. Experimental Mole Fraction Solubility (xeT,w 103) of Chloroxine in Solvent Mixturesa,b w T/K

0

EA (w) 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15 328.15 333.15 EA (w) 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15 328.15 333.15 EA (w) 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15 328.15 333.15 EA (w) 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15 328.15 333.15

+ MeOH (1 − w) 0.3976 0.4949 0.6107 0.7473 0.9033 1.095 1.306 1.538 1.810 2.121 2.484 + EtOH (1 − w) 0.3282 0.4001 0.5033 0.6223 0.7456 0.8876 1.048 1.242 1.452 1.682 1.954 + NPA (1 − w) 0.2582 0.3155 0.4033 0.5021 0.6164 0.7513 0.9100 1.099 1.301 1.551 1.828 + IPA (1 − w) 0.1981 0.2431 0.3199 0.4149 0.5235 0.6448 0.8010 0.9738 1.165 1.421 1.688

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1

0.4956 0.6198 0.7644 0.8860 1.161 1.361 1.619 1.880 2.198 2.550 2.971

0.6136 0.7680 0.9464 1.159 1.407 1.644 1.955 2.279 2.640 3.088 3.553

0.7800 0.9470 1.156 1.390 1.637 1.964 2.350 2.747 3.158 3.651 4.203

0.9476 1.141 1.421 1.689 1.999 2.364 2.808 3.207 3.714 4.244 4.847

1.129 1.325 1.615 1.964 2.299 2.742 3.218 3.731 4.209 4.789 5.473

1.274 1.533 1.900 2.299 2.715 3.175 3.647 4.160 4.701 5.326 5.999

1.415 1.721 2.069 2.506 2.951 3.410 3.953 4.486 5.080 5.760 6.476

1.544 1.890 2.352 2.791 3.241 3.764 4.334 4.886 5.532 6.217 6.965

1.691 2.040 2.502 2.999 3.519 4.050 4.658 5.265 5.882 6.606 7.323

1.823 2.234 2.747 3.252 3.819 4.407 5.029 5.716 6.353 7.102 7.819

0.4665 0.5692 0.6736 0.8387 1.017 1.199 1.420 1.662 1.907 2.191 2.464

0.6031 0.7418 0.9280 1.110 1.318 1.518 1.789 2.052 2.351 2.665 3.093

0.6837 0.8721 1.082 1.298 1.603 1.858 2.100 2.487 2.839 3.272 3.814

0.8984 1.090 1.329 1.601 1.924 2.201 2.585 2.992 3.394 3.824 4.342

1.056 1.286 1.590 1.904 2.246 2.546 2.940 3.406 3.872 4.328 4.857

1.193 1.496 1.846 2.219 2.620 2.981 3.412 3.865 4.379 4.868 5.412

1.358 1.688 2.033 2.418 2.837 3.317 3.790 4.299 4.853 5.421 6.050

1.464 1.792 2.263 2.701 3.168 3.665 4.203 4.741 5.332 5.979 6.645

1.680 2.009 2.472 2.993 3.457 3.958 4.576 5.197 5.822 6.455 7.144

1.823 2.234 2.747 3.252 3.819 4.407 5.029 5.716 6.353 7.102 7.819

0.2938 0.3841 0.4794 0.5966 0.7622 0.9096 1.102 1.322 1.547 1.879 2.225

0.3874 0.4880 0.6240 0.7911 0.9794 1.195 1.452 1.735 2.011 2.403 2.815

0.5333 0.6263 0.8280 1.027 1.294 1.523 1.864 2.163 2.519 2.936 3.346

0.7310 0.8790 1.066 1.298 1.543 1.863 2.222 2.605 3.058 3.514 4.017

0.8230 1.000 1.265 1.600 1.963 2.350 2.786 3.207 3.675 4.149 4.778

1.037 1.237 1.620 1.954 2.288 2.710 3.221 3.727 4.266 4.832 5.400

1.279 1.560 1.922 2.308 2.691 3.146 3.682 4.218 4.814 5.392 6.044

1.389 1.724 2.237 2.690 3.120 3.609 4.151 4.692 5.255 5.849 6.527

1.667 2.004 2.302 2.954 3.439 3.885 4.559 5.164 5.799 6.394 7.109

1.823 2.234 2.747 3.252 3.819 4.407 5.029 5.716 6.353 7.102 7.819

0.2709 0.3537 0.4639 0.5762 0.7257 0.8752 1.084 1.303 1.529 1.842 2.188

0.3603 0.4773 0.6109 0.7559 0.9276 1.108 1.340 1.587 1.834 2.112 2.493

0.4885 0.6148 0.8018 0.9840 1.158 1.404 1.670 1.933 2.253 2.634 3.068

0.6290 0.7830 0.9980 1.215 1.434 1.729 2.085 2.398 2.798 3.224 3.687

0.7500 0.9450 1.246 1.537 1.853 2.215 2.525 2.923 3.314 3.807 4.394

0.9780 1.205 1.482 1.788 2.160 2.551 3.016 3.454 3.957 4.507 5.101

1.134 1.405 1.829 2.148 2.529 3.006 3.465 3.995 4.511 5.130 5.760

1.293 1.636 2.082 2.451 2.962 3.391 3.949 4.488 5.115 5.728 6.427

1.498 1.862 2.300 2.815 3.313 3.834 4.408 5.050 5.692 6.366 7.050

1.823 2.234 2.747 3.252 3.819 4.407 5.029 5.716 6.353 7.102 7.819

Solvent mixtures of EA (w) + MeOH (1 − w), EA (w) + EtOH (1 − w), EA (w) + NPA (1 − w), EA (w) + IPA (1 − w) with various mass fractions within the temperature range from T = 283.15−333.15 K under p = 0.1 MPa. bStandard uncertainties u are u(T) = 0.02 K, u(p) = 0.25 KPa. Relative standard uncertainty ur is ur (x) = 0.0247. Solvent mixtures were prepared by mixing different masses of the solvents with relative standard uncertainty ur (w) = 0.01. w represents the mass fraction of ethyl acetate in mixed solvents. a

3.2. Experimental Solubility. The measured mole fraction solubility of chloroxine in solvent mixtures of {EA (1) + MeOH (2)}, {EA (1) + EtOH (2)}, {EA (1) + NPA (2)}, and {EA (1) + IPA (2)} are listed in Table 2. Moreover, the relationship between solubility and solvent composition and temperature is plotted in Figures 3 and 4. It can be

The XRD patterns of samples crystallized out of the mixtures show corresponding and identical characteristic peaks from 5° to 80° (2θ) compared with pure chloroxine. Therefore, it has been found that no solvate formation or polymorph transformation is observed during the whole crystallization processes. C

DOI: 10.1021/acs.jced.8b00257 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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fold. Table 2 also elucidated that the interactions between solvent and solvent molecules become weaken with increasing mass fraction of EA, the solubility of chloroxine decreased. Meanwhile, the solubility of chloroxine in (EA + MeOH) is greater than those in (EA + EtOH), (EA + NPA), or (EA + IPA) at the same temperature and solvent composition. This case may be due to polar properties of alcohols, that is, polarity (water 100) = 76.2 for methanol, 65.4 for ethanol, 61.7 for npropanol, and 54.6 for isopropanol.25 Obviously, the polarities values of the selected alcohols obey the following sequence from high to low: MeOH > EtOH > NPA > IPA, that would be corresponding to the measured solubilities in this work. Herein, the polarities of the three mixed solvents obey the following order as (EA + MeOH) > (EA + EtOH) > (EA + NPA) > (EA + IPA) given the same composition. The results obtained will be important for separation and purification of chloroxine. 3.3. Thermodynamic Modeling. The thermodynamic models in binary solvents have been summarized in refs 1 and 4. In general, three models are applied in correlating the chloroxine solubility in solvent mixtures of (EA + MeOH), (EA + EtOH), (EA + NPA), and (EA + IPA) at different temperature to Jouyban−Acree model,1,4,26 a combination of the Jouyban−Acree model with Van’t Hoff equation,1,4,27 and a combination of the Jouyban−Acree model with modified Apelblat equation.1,4,27 3.3.1. Jouyban−Acree Model. The Jouyban−Acree model, expressed as eq 4, gives a precise description for solute solubility in solvent mixtures1,4,26

Figure 3. Mole fraction solubility (x) of chloroxine in five pure solvents at different temperatures. ★, EA; ■, MeOH ; ○, EtOH;▲, NPA; ▽, IPA.

observed that the chloroxine solubility is a function of temperature and solvent composition. It is obvious that the solubility increases with a rise of temperature and mass fraction of EA, which is possible to purify chloroxine employing the cooling crystallization effectively. The solubility data in monosolvents obey the following order: EA > MeOH > EtOH > NPA > IPA. Apparently, the maximum solubility of chloroxine is observed in neat ethyl acetate (7.819 × 10−3 at 333.15 K). In four binary mixtures, the solubility of chloroxine in mole fraction expanded from 0.1981 × 10−3 to 7.819 × 10−3 at the evaluated temperature, resulting in an increase of 39.47

Figure 4. Mole fraction solubility (x) of chloroxine in EA (w) + alcohols (1 − w) mixed solutions with various mass fractions at different temperatures: w, mass fraction of EA; ☆, w = 1; Δ, w = 0.9; ○, w = 0.8; □, w = 0.7; ★, w = 0.6; ◊, w = 0.5; ◆, w = 0.4; ▼, w = 0.3; ▲, w = 0.2; ●, w = 0.1; ■, w = 0; , calculated curves by the Jouyban−Acree model. D

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Table 3. Data of Parameters Obtained Using Thermodynamic Models Jouyban−Acree EA + MeOH

RAD × 102 RMSD × 104 EA + EtOH

RAD × 102 RMSD × 104 EA + NPA

RAD × 102 RMSD × 104 EA + IPA

Van’t Hoff− Jouyban−Acree

Apelblat− Jouyban−Acree

parameter

value

parameter

value

parameter

value

J0 J1 J2

283.09 −20.94 −105.14

A1 B1 A2 B2 J0 J1 J2

2.88 −2567.43 4.23 −3407.46 274.06 −29.77 −127.71

A1 B1 C1 A2 B2 C2 J0 J1 J2

J0 J1 J2

0.71 0.25 328.65 −134.03 20.06

A1 B1 A2 B2 J0 J1 J2

2.15 0.72 2.88 −2567.43 3.65 −3292.18 317.79 −139.51 −7.09

J0 J1 J2

1.28 0.44 289.32 82.51 −203.25

A1 B1 A2 B2 J0 J1 J2

2.65 0.83 2.88 −2567.43 4.74 −3677.44 280.09 74.03 −226.3

J0 J1 J2

1.90 0.50 288.02 −59.66 −31.73

A1 B1 A2 B2 J0 J1 J2

3.49 0.94 2.88 −2567.43 5.62 −3996.67 275.71 −62.49 −62.5

187.22 −11105.05 −27.33 34.37 −4810.22 −4.46 269.65 6.99 −138.74 1.04 0.31 187.22 −11105.05 −27.33 63.43 −6072.67 −8.86 341.23 −153.65 51.54 1.57 0.45 187.22 −11105.05 −27.33 39.77 −5310.60 −5.19 296.99 71.87 −184.07 2.08 0.51 187.22 −11105.05 −27.33 75.00 −7237.12 −10.27 284.66 −50.15 −40.12 1.95 0.55

RAD × 102 RMSD × 104

ln x w,T = w1 ln x1,T + w2 ln x 2,T +

1.83 0.55

w1w2 T /K

A1 B1 C1 A2 B2 C2 J0 J1 J2

A1 B1 C1 A2 B2 C2 J0 J1 J2

A1 B1 C1 A2 B2 C2 J0 J1 J2

3.17 0.87

2

ln x T = A +

∑ Ji (w1 − w2)i

B T /K

(5)

i=0

(4)

Substituting eq 5 into eq 4, the van’t Hoff−Jouyban−Acree model can be acquired and described as eq 61,4,27

where xw,T stands for the solubility of solute in mole fraction in solvent mixtures at T/K; w1 and w2 denotes the content of solvents 1 (EA) and 2 (MeOH, EtOH, NPA, and IPA) free of the solute (chloroxine), respectively; x1,T and x2,T are the solute solubility in mole fraction in neat solvent; and Ji are the model parameters. In order to obtain the model parameters, the model requires the solute solubility in neat solvent at the highest and lowest temperatures. 3.3.2. Van’t Hoff-Jouyban−Acree model. The van’t Hoff equation is expressed as

i i B1 yz B2 yz ww zz + 1 2 zz + w2jjjA 2 + ln x w,T = w1jjjjA1 + z T /K j z T T /K /K { k { k

2

∑ Ji (w1 − w2)i i=0

(6)

A1, B1, A2, B2 and Ji are equation parameters. 3.3.3. Modified Apelblat−Jouyban−Acree Model. The Apelblat equation may be employed to describe a nonlinear relationship between solubility (ln xT) in neat solvent and E

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van’t Hoff-Jouyban−Acree, and Apelblat−Jouyban−Acree models, chloroxine solubility was well correlated obtaining RAD lower than 3.49% and RMSD lower than 0.94 × 10−4.

reciprocal of absolute temperature (1/T) and is expressed as1,4,27 ln x T = A +

B + C ln(T /K ) T /K

■

(7)

where A, B, and C are equation parameters. Combining eq 7 and eq 4, the Apelblat−Jouyban−Acree model may be acquired as eq 81,4,27 ln x w,T

ÉÑ ÄÅ ÑÑ ÅÅ B1 = w1ÅÅÅÅA1 + + C1 ln(T /K )ÑÑÑÑ ÑÑÖ ÅÅÇ T /K ÄÅ ÅÅi ÑÉÑ B2 ww Å Ñ + w2ÅÅÅÅjjjjA 2 + + C2 ln(T /K )ÑÑÑÑ + 1 2 ÅÅk Ñ T /K T /K Ñ Ö ÅÇ

*Tel: + 86 05572871072. E-mail: [email protected]. ORCID

Hongwei Shi: 0000-0002-9888-8663 Funding 2

The project was supported by Backup of Academic and Technical Leaders of Suzhou University (2018XJHB03); Research Team of Anhui Provincial Education Department (2016SCXPTTD), The Key project of Natural Science Research of Anhui Education Department (KJ2016A888, KJ2016A722, KJ2016SD62, KJ2017A435, KJ2017A436), and Key Domestic and International Visiting and Research Projects for key young and talented college teachers (gxfxZD2016260).

∑ Ji (w1 − w2)i i=0

(8)

The experimental solubility of chloroxine in the selected solvent mixtures is correlated and calculated with eqs 4, 6, and 8. The objective function is defined as F=

∑ (ln xie − ln xic)2 i=1

Notes

(9)

The authors declare no competing financial interest.

■

With the intention of demonstrating the deviations and evaluating the selected models, the relative average deviation (RAD) and root-mean-square deviation (RMSD) described as eqs 10 and 11, respectively, are employed RAD =

1 N

c e ij |x w,T − x w,T | yzz zz e z x w,T k {

∑ jjjj

(10)

c e ∑i = 1 (x w,T )2 − x w,T

N

REFERENCES

(1) Yalkowsky, S. H. Solubility and Solubilization in Aqueous Media; American Chemical Society: New York, 1999. (2) Nozohouri, S.; Shayanfar, A.; Kenndler, E.; Jouyban, A. Solubility of celecoxib in N-methyl-2-pyrrolidone + 2-propanol mixtures at various temperatures. J. Mol. Liq. 2017, 241, 1032−1037. (3) Jouyban, A. Handbook of Solubility Data for Pharmaceuticals; CRC Press: BocaRaton, FL, 2010. (4) Martínez, F.; Jouyban, A.; Acree, W. E., Jr Pharmaceuticals Solubility is Still Nowadays Widely Studied Everywhere. Ulum-i Daroei 2017, 23, 1−2. (5) Pirhayati, F. H.; Shayanfar, A.; Fathi-Azarbayjani, A.; Martínez, F.; Sajedi-Amin, S.; Jouyban, A. Thermodynamic solubility and density of sildenafil citrate in ethanol and water mixtures: measurement and correlation at various temperatures. J. Mol. Liq. 2017, 225, 631−635. (6) Jouyban, A. Review of the cosolvency models for predicting solubility of drugs in water-cosolvent mixtures. J. Pharm. Pharm. Sci. 2008, 11, 32−58. (7) Kolár,̌ P.; Shen, J. W.; Tsuboi, A.; Ishikawa, T. Solvent selection for pharmaceuticals. Fluid Phase Equilib. 2002, 194−197, 771−782. (8) Rubino, J. T. Cosolvents and cosolvency. In Encyclopedia of Pharmaceutical Technology, 3rd ed.; Swarbrick, J., Boylan, J. C., Eds.; Marcel Dekker: New York, 1988. (9) Aulton, M. E. Pharmaceutics, The Science of Dosage Forms Design, 2nd ed.; Churchill Livingstone: London, 2002. (10) Muñoz, M. M.; Tinjacá, D. A.; Jouyban, A.; Martínez, F.; Acree, W. E. Study of some volumetric and refractive properties of {PEG 300 (1) + ethanol (2)} mixtures at several temperatures. Phys. Chem. Liq. 2018, 56, 391−402. (11) De, C. H.; Ferreira, L. F.; Coura, L. C.; Da, S. J. Treatment of intestinal amebiasis with a derivative of 8-hydroxyquinoline (5,7dichloro-8-hydroxyquinoline). Hospital 1963, 63, 49−56. (12) Ravagnan, G.; Oliva, B.; Bevilacqua, R. Antibacterial activity of the association of 5,7-dichloro-8-hydroxyquinoline and 5,7-dichloro8-hydroxyquinaldine with enzymes and bile. Il Farmaco; edizione pratica 1974, 29, 198−204. (13) Bambury, R. E. Bnger’s Medicinal Chemistry Part II; John Wiley: New York, 1979. (14) Martell, A. E.; Calvin, M. Chemistry of the Metal Chelate Compounds; Prentice Hall: Englewood Cliffs, NJ, 1953. (15) Chabereck, B. S.; Martell, A. E. Organic Sequestering Agents; Wiley: New York, 1959. (16) Pan, Z. W.; Chen, A. Z. Studies on Extraction Behavior of Cerium and Terbium with 5,7-Dichloro-8-Hydroxyquinoline Using

N

RMSD =

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(11)

where N denotes the number of data points. xew,T refers to the determined solubility in the present work, and xcw,T refers to the solubility computed by using models. On the basis of the determined solubility values, the equation parameters in eqs 4, 6, and 8 are attained with Mathcad software. The obtained data of equation parameters along with the RAD and the RMSD values are tabulated in Table 3. The solubility of chloroxine in binary mixtures of (EA + MeOH), (EA + EtOH), (EA + NPA), and (EA + IPA) is calculated. The calculated data employing the Jouyban−Acree model are plotted in Figure 4. It can be seen from Table 3 that the largest RAD is 3.49% acquired by the van’t Hoff− Jouyban−Acree model for the (EA + NPA) mixtures. In addition, the root-mean-square deviations (RMSD × 10−4) are all less than 0.94. On the whole, the three models may all be available to correlate the chloroxine solubility in (EA + MeOH), (EA + EtOH), (EA + NPA), and (EA + IPA) at all initial composition ranges, and the Jouyban−Acree model gives the best correlation results than the other two models.

4. CONCLUSION The solid−liquid equilibrium solubility of chloroxine in binary mixtures of (methanol, ethanol, n-propanol, and isopropanol) + ethyl acetate at different composition were measured with the static equilibrium method in the temperature T = 283.15 to 333.15 K under about 101.2 kPa. For all systems, the solubility in mole fraction of chloroxine is a function of the temperature as well as increasing with mass fraction of ethyl acetate for the cosolvent solutions system of (MeOH, EtOH, NPA, and IPA) + ethyl acetate, and the maximum solubility of chloroxine is observed in pure ethyl acetate. By using the Jouyban−Acree, F

DOI: 10.1021/acs.jced.8b00257 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

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DOI: 10.1021/acs.jced.8b00257 J. Chem. Eng. Data XXXX, XXX, XXX−XXX