Solubility of Sulfachloropyridazine in Pure and Binary Solvent Mixtures

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Cite This: J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Solubility of Sulfachloropyridazine in Pure and Binary Solvent Mixtures and Investigation of Intermolecular Interactions Rongrong Li,*,† Sangfei Ye,† Yongfei Chen,† Ming Jiang,‡ Yanxian Jin,† Wenping Jia,† Xiaoying Chen,† Shiyun Zhan,† and Deman Han*,† †

School of Pharmaceutical and Chemical Engineering, TaiZhou University, Taizhou, Zhejiang 318000, PR China School of Life Science, TaiZhou University, Taizhou, Zhejiang 318000, PR China

‡

ABSTRACT: The solubility of sulfachloropyridazine in pure methanol, ethanol, isopropanol, 1-butanol, water, acetonitrile, ethyl acetate, acetone, 1,4-dioxane and (methanol + water), (ethanol + water), and (isopropanol + water) binary solvent mixtures was determined by using a isothermal saturation method with temperatures ranging from (283.15 to 323.15) K. The descending order of the solubility in pure solvents was as follows: 1,4-dioxane > acetone > acetonitrile > ethyl acetate > methanol > ethanol >1-butanol > isopropanol > water. In three mixed solvents, the solubility of sulfachloropyridazine increased with increasing temperature and mass fraction of alcohol. At the same mass fraction of methanol, ethanol, or isopropanol and temperature, the solubility of sulfachloropyridazine in (methanol + water) was greater than that in the other mixed solvents. The obtained solubility data were correlated with modified Apelblat equation and Jouyban−Acree model. The results of correlation showed good agreement with experimental data; the largest values of relative average deviations and the root-mean-square deviations between the experimental and calculated solubilities were 3.61 × 10−2 and 6.37 × 10−4, respectively. Furthermore, molecular dynamics simulation was carried out to explain the dissolving ability of the model compound.

1. INTRODUCTION Sulfachloropyridazine (4-amino-N-(6-chloro-3-pyridazinyl)benzenesulfonamide, CAS reg. no. 80-32-0) is a synthetic antibacterial drug of the sulfanilamide class, the structure of which is shown in Figure 1. It is usually used as an inhibitor of both Gram-positive and Gram-negative aerobic bacteria and id also being effective against chlamydia.1,2

ethyl acetate, acetone, 1,4-dioxane, and their binary solvent mixtures, including (methanol + water), (ethanol + water), and (isopropanol + water), was measured. To explain the dissolving ability of sulfachloropyridazine, MD simulation was employed to calculate the interactions of solute−solvent, solute−solute, and solvent−solvent, respectively. To extend the applicability of the solubility, values of the experimental solubility were correlated with modified Apelblat equation and Jouyban− Acree model.

2. EXPERIMENTAL SECTION 2.1. Materials. Sulfachloropyridazine having a mass fraction of 0.997 was purchased by Sinopharm Chemical Reagent Co., Ltd., China, which was confirmed by a high-performance liquid phase chromatograph (HPLC). The solvents with analytical grade were also purchased from Sinopharm Chemical Reagent Co., Ltd., China. The mass fraction purities of these solvents were all > 0.994, which were determined by gas chromatography (GC). All materials above were used without additional purification. The detailed information on the chemicals used in this work was collected and is tabulated in Table 1. 2.2. Solubility Determination. The solubility of sulfachloropyridazine in pure and binary solvents was determined by the isothermal saturation method8,9 within the temperatures

Figure 1. Structure of sulfachloropyridazine.

According to a survey performed in China, large amounts of sulfachloropyridazine and its derivatives are used in veterinary medicine and added to feed or otherwise administered in animal husbandry, especially pigs and cattle.3,4 As a result of the extensive use of sulfachloropyridazine in the animal industry, it has been detected in environmental media such as soils, surface water, and groundwater in various places throughout the world.5−7 The solubility is necessary to determine the transport of sulfachloropyridazine in the environment and assess its risk to terrestrial and aquatic ecosystems. However, as far as we are aware, up to now, no solubility data of sulfachloropyridazine have been published. In the present study, the solubility of sulfachloropyridazine in methanol, ethanol, isopropanol, 1-butanol, water, acetonitrile, © XXXX American Chemical Society

Received: December 30, 2017 Accepted: May 29, 2018

A

DOI: 10.1021/acs.jced.7b01134 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 1. Detailed Information on the Materials Used in the Work

a

chemicals

molar mass g·mol−1

source

mass fraction purity

analytical method

sulfachloropyridazine methanol ethanol isopropanol acetone acetonitrile ethyl acetate 1,4-dioxane 1-butanol

284.72 32.04 46.07 60.10 58.08 41.05 88.11 88.11 74.12

Sinopharm Chemical Reagent Co., Ltd.,China

0.997 0.996 0.998 0.999 0.998 0.996 0.998 0.995 0.996

HPLCa GCb GC GC GC GC GC GC GC

High-performance liquid phase chromatograph. bGas chromatograph.

stable system of NVT simulation was simulated in the NVE ensemble for 300 ps.12 The time step used is 1.0 fs. According to the results of the simulation, the radial distribution function (RDF) was analyzed from the trajectory files that could evaluate the chance of finding a particle from the solute at a certain distance.11,12 In this work, it was used to explain the dissolving ability of the model compound in different pure solvents.

ranging from T = 283.15 to 323.15 K under atmosphere pressure. This work was similar to our previous research,10 and HPLC was employed to determine the solubility of sulfachloropyridazine in different solvents. To begin with, an excessive amount of sulfachloropyridazine and 25 mL of pure or mixed solvents was introduced to the jacketed glass vessel. The circulating (water + isopropanol) came from the thermostatic circulator bath kept at a certain temperature with an accuracy of ±0.05 K through the outer jacket. The mixture underwent continuous stirring for at least 24 h; after that, the stirring was stopped and the mixture was permitted to settle for 1 h before sampling. Then, the supernatant was withdrawn by a 5 mL preheated syringe connected to a filter (PTFE 0.2 μm) and transferred to a preweighed volumetric flask of 25 mL with a rubber stopper as quickly as possible to avoid evaporation of solution. The total amount of the sample and flask was weighed again with the analytic balance. Then, the sample was diluted to 25 mL with corresponding solvent and analyzed with the HPLC. Furthermore, each experiment was carried out three times, and the average value was employed to calculate the mole fraction solubility. The mole fraction solubility of sulfachloropyridazine (xw,T) in pure solvents and binary solvent mixtures was obtained by eqs 1 and 2, respectively. xw , T =

m1/M1 m1/M1 + m2 /M 2

(1)

xw , T =

m1/M1 m1/M1 + m2 /M 2 + m3 /M3

(2)

3. RESULTS AND DISCUSSION 3.1. Result of X-ray Diffraction Investigations. The PXRD patterns of sulfachloropyridazine in different solvents and raw material are presented in Figure 2. The identical diagrams obtained before and after the experiments confirmed that there is no phase transformation in this work.

where m1 stands for the mass of sulfachloropyridazine, m2 stands for the mass of methanol, ethanol, and others, and m3 stands for the mass of water. M1, M2, and M3 are the corresponding molar mass. 2.3. X-ray Diffraction Investigations. The PXRD used in this work is a Rigaku D/max-2500 (Rigaku, Japan) using Cu Kα radiation (1.5405 Å). In this work, a step size of 0.02° and a scanning rate of 0.067°/s over a diffraction angle (2θ) range of 10−80° were used before and after the experiments to confirm the form of sulfachloropyridazine. 2.4. Molecular Dynamics (MD) Simulation. The COMPASS force field in Materials Studio was applied to perform the geometry optimizations and energy minimizations of solute and solvent molecules, first.11 Then, a cubic box of 1 sulfachloropyridazine molecule and 300 organic solvent molecules was created using Amorphous Cell after energy minimization of the simulation box, with a period of 200 ps run in NVT ensemble using Nosé for thermostat. At last, the most

Figure 2. PXRD patterns of sulfachloropyridazine in different solvents and raw material.

3.2. Solubility Data. The measured and calculated mole fraction solubilities of sulfachloropyridazine in pure and mixed solvents are presented in Tables 2 and 3 and directly plotted in Figures 3 and 4. It can be seen from Tables 2 and 3 and Figures 3 and 4 that at a given temperature the solubility sulfachloropyridazine in pure solvents can be ranked as 1,4dioxane > acetone > acetonitrile > ethyl acetate > methanol > ethanol > isopropanol > 1-butanol > water. Regarding the binary mixed solvents, the solubility of sulfachloropyridazine increased with increasing temperature and mass fraction of alcohols. In addition, the solubility data furnished in Tables 2 and 3 indicated that the solubility data of sulfachloropyridazine B

DOI: 10.1021/acs.jced.7b01134 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

a

C

10−2 10−2 10−2 10−2 10−1 10−1 10−1 10−1 10−1

calc

× × × × × × × × ×

calc 6.390 7.186 8.087 9.107 1.026 1.156 1.304 1.470 1.658

2.426 × 10−5 3.288 × 10−5 4.385 × 10−5 5.758 × 10−5 7.453 × 10−5 9.514 × 10−5 1.200 × 10−4 1.490 × 10−4 1.840 × 10−4 acetone 10−2 10−2 10−2 10−2 10−1 10−1 10−1 10−1 10−1

× × × × × × × × ×

exp 4.725 5.133 5.692 6.271 6.965 7.793 8.668 9.659 1.085

10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−2

× × × × × × × × ×

exp 1.868 1.932 2.023 2.125 2.243 2.394 2.584 2.833 3.124

10−2 10−2 10−2 10−2 10−2 10−2 10−2 10−2 10−2

× × × × × × × × ×

calc 4.701 5.161 5.687 6.288 6.976 7.760 8.656 9.679 1.085

methanol 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−2 acetonitrile 1.880 1.932 2.009 2.112 2.242 2.404 2.600 2.835 3.115

× × × × × × × × ×

calc

× × × × × × × × ×

exp 3.806 4.322 4.837 5.432 6.158 6.890 7.766 8.789 1.009

10−2 10−2 10−2 10−2 10−2 10−2 10−2 10−2 10−2

10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−2

solvent ethanol

× × × × × × × × ×

exp

10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−2

1.352 1.406 1.515 1.646 1.788 1.981 2.188 2.436 2.685

× × × × × × × × ×

calc 3.849 4.302 4.823 5.421 6.108 6.897 7.804 8.845 1.004

10−2 10−2 10−2 10−2 10−2 10−2 10−2 10−2 10−2

exp

× × × × × × × × ×

calc 1.333 1.420 1.525 1.650 1.798 1.973 2.179 2.419 2.701

10−2 10−2 10−2 10−2 10−2 10−2 10−2 10−2 10−2

× × × × × × × × ×

calc 3.109 3.437 3.821 4.271 4.796 5.411 6.129 6.969 7.952

isopropanol 3.102 × 10−3 3.451 × 10−3 3.825 × 10−3 4.288 × 10−3 4.763 × 10−3 5.384 × 10−3 6.139 × 10−3 7.019 × 10−3 7.924 × 10−3 ethyl acetate

Standard uncertainties u are u(T) = 0.02 K and u (p) = 400 Pa. Relative standard uncertainty in mole fraction ur is ur(x) = 0.017.

× × × × × × × × ×

exp

10−5 10−5 10−5 10−5 10−5 10−5 10−4 10−4 10−4

6.467 7.154 8.042 9.079 1.022 1.156 1.312 1.475 1.652

× × × × × × × × ×

283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15

exp

2.254 3.309 4.395 5.901 7.528 9.517 1.187 1.485 1.843

T/K

283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15

water 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3

× × × × × × × × ×

exp 9.94 1.065 1.163 1.287 1.433 1.589 1.788 2.037 2.347

10−2 10−1 10−1 10−1 10−1 10−1 10−1 10−1 10−1

× 10−3 × 10−3 × 10−3 × 10−3 × 10−3 × 10−3 × 10−3 × 10−3 × 10−3 1,4-dioxane

exp 3.353 3.719 4.211 4.736 5.309 5.957 6.760 7.679 8.668

× × × × × × × × ×

calc 9.940 1.070 1.165 1.281 1.421 1.592 1.797 2.043 2.340

10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3

10−2 10−1 10−1 10−1 10−1 10−1 10−1 10−1 10−1

× × × × × × × × ×

calc 3.348 3.743 4.196 4.714 5.307 5.987 6.765 7.656 8.676

1-butanol

Table 2. Experimental and Calculated Mole Fraction Solubility (xew,T and xcw,T) of Sulfachloropyridazine in Different Pure Solvents at the Temperature Range from T = (283.15 to 323.15) K under 101.1 kPaa

Journal of Chemical & Engineering Data Article

DOI: 10.1021/acs.jced.7b01134 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 3. Experimental and Calculated Mole Fraction Solubility (xew,T and xcw,T) of Sulfachloropyridazine in Methanol (w) + Water (1 − w), Ethanol (w) + Water (1 − w), and Isopropanol (w) + Water (1 − w) Mixtures with Various Composition at the Temperature Range from T = (283.15 to 323.15) K under 101.1 kPaa w 0.20 T/K

exp

0.40 calc

exp

0.60 calc

283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15

8.737 1.169 1.515 1.909 2.317 2.767 3.272 3.799 4.386

× × × × × × × × ×

10−5 10−4 10−4 10−4 10−4 10−4 10−4 10−4 10−4

8.260 1.137 1.451 1.866 2.307 2.836 3.446 4.199 5.092

× × × × × × × × ×

10−5 10−4 10−4 10−4 10−4 10−4 10−4 10−4 10−4

5.097 6.003 7.052 8.315 9.609 1.115 1.315 1.561 1.840

× × × × × × × × ×

10−4 10−4 10−4 10−4 10−4 10−3 10−3 10−3 10−3

283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15

4.758 6.511 9.301 1.266 1.641 2.023 2.451 2.896 3.378

× × × × × × × × ×

10−5 10−5 10−5 10−4 10−4 10−4 10−4 10−4 10−4

5.486 7.720 9.868 1.300 1.550 1.851 2.391 2.896 3.643

× × × × × × × × ×

10−5 10−5 10−5 10−4 10−4 10−4 10−4 10−4 10−4

3.915 4.725 5.858 7.069 8.339 9.735 1.117 1.273 1.427

× × × × × × × × ×

10−4 10−4 10−4 10−4 10−4 10−4 10−3 10−3 10−3

283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15

4.329 5.888 7.995 1.069 1.397 1.800 2.307 2.825 3.357

× × × × × × × × ×

10−5 10−5 10−5 10−4 10−4 10−4 10−4 10−4 10−4

4.814 6.733 8.633 1.120 1.354 1.686 2.104 2.618 3.209

× × × × × × × × ×

10−5 10−5 10−5 10−4 10−4 10−4 10−4 10−4 10−4

2.487 3.087 3.956 4.924 6.022 7.206 8.594 1.018 1.195

× × × × × × × × ×

10−4 10−4 10−4 10−4 10−4 10−4 10−4 10−3 10−3

exp

Methanol + Water 4.233 × 10−4 1.292 5.435 × 10−4 1.567 6.628 × 10−4 1.847 8.119 × 10−4 2.159 9.678 × 10−4 2.480 1.151 × 10−3 2.865 1.356 × 10−3 3.331 1.601 × 10−3 3.855 1.889 × 10−3 4.361 Ethanol + Water 3.250 × 10−4 1.127 4.282 × 10−4 1.358 5.231 × 10−4 1.602 6.539 × 10−4 1.882 7.619 × 10−4 2.199 8.857 × 10−4 2.584 1.094 × 10−3 3.013 1.290 × 10−3 3.467 1.570 × 10−3 4.133 Isopropanol+ Water 2.448 × 10−4 8.596 3.201 × 10−4 1.092 3.919 × 10−4 1.273 4.861 × 10−4 1.510 5.694 × 10−4 1.717 6.860 × 10−4 2.007 8.299 × 10−4 2.385 1.003 × 10−4 2.818 1.195 × 10−4 3.299

0.80 calc

exp

calc

× × × × × × × × ×

10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3

1.322 1.597 1.876 2.207 2.556 2.965 3.409 3.931 4.542

× × × × × × × × ×

10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3

2.418 2.722 3.127 3.557 4.042 4.569 5.225 5.976 6.812

× × × × × × × × ×

10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3

2.399 2.747 3.136 3.570 4.051 4.616 5.222 5.922 6.749

× × × × × × × × ×

10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3

× × × × × × × × ×

10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3

1.164 1.448 1.705 2.042 2.341 2.669 3.177 3.670 4.355

× × × × × × × × ×

10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3

2.016 2.376 2.746 3.159 3.604 4.142 4.724 5.430 6.237

× × × × × × × × ×

10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3

2.000 2.377 2.730 3.167 3.613 4.084 4.731 5.414 6.321

× × × × × × × × ×

10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3

× × × × × × × × ×

10−4 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3

8.890 1.093 1.286 1.531 1.750 2.050 2.417 2.849 3.314

× × × × × × × × ×

10−4 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3

1.773 1.996 2.308 2.640 3.011 3.487 4.028 4.678 5.402

× × × × × × × × ×

10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3

1.743 2.035 2.320 2.677 3.014 3.465 4.013 4.656 5.330

× × × × × × × × ×

10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3 10−3

a Standard uncertainties u are u(T) = 0.02 K and u(p) = 400 Pa. Solvent mixtures were prepared by mixing different masses of the solvents with relative standard uncertainty ur(w) = 0.002. w represents the mass fraction of alcohol in mixed solvents. Relative standard uncertainty in mole fraction ur is ur(x) = 0.021.

30.6 (J·m−3)1/2 for methanol, 28.3 (J·m−3)1/2 for ethanol, 24.3 (J·m−3)1/2 for isopropanol, and 24.1(J·m−3)1/2 for 1-butanol).13 In isopropanol molecule, the hydroxyl group is located between two methyl functional groups; it hinders the interaction of the hydroxyl group of the isopropanol molecule with the solute molecule, so there is an abnormal phenomenon in the solubility of isopropanol solvent. Meanwhile, the solubility data have the same relationship with solvent polarity and dielectric constant.13 In addition, the same tendency of Hildebrand solubility parameters can also be found in the other solvents, except for acetone and 1,4-dioxane (103δH = 21.1 (J·m−3)1/2 for acetone, 25.1 (J·m−3)1/2 for acetonitrile, 19.2 (J·m−3)1/2 for ethyl acetate, 21.1(J·m−3)1/2 for 1,4-dioxane, and 14.8(J·m−3)1/2 for water).13 In pure acetone and 1,4-dioxane, the solubility parameters of the two solvents are the same; however the solubility data of sulfachloropyridazine in 1,4-dioxane are greater than that in acetone. In three mixed solvents, the sequence of solubility data is strictly consistent with the order of Hildebrand solubility parameters and polarity at the same composition. As shown in Figure 1, sulfachloropyridazine has two hydrogen donor groups and six hydrogen acceptor groups that contribute to form a hydrogen bond easily with those

Figure 3. Mole fraction solubility (x) of sulfachloropyridazine in selected solvents at different temperatures: (a) brown ■, acetone; ○, acetonitrile; orange ▲, ethyl acetate; blue ▼, 1,4-dioxane; (b) red ★, water; pink ●, methanol; blue △, ethanol; red ☆, isopropanol; teal ◆, 1-butanol. , predicted values via modified Apelblat equation.

in (methanol + water) mixture are larger than those in (ethanol + water) and (isopropanol + water) mixture at the same temperature and mass fraction of alcohols. In the systems of sulfachloropyridazine + alcohols, the order of solubility values from high to low is consistent with the order of Hildebrand solubility parameters at 298 K, except for isopropanol (103δH = D

DOI: 10.1021/acs.jced.7b01134 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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of the appearance of the interactions between solute molecules and solvent molecules, which was related to the solubility of the sulfachloropyridazine. In Figure 6a, the largest peak of the RDF appears at r = 2.8 Å in methanol. The value of g(r) before 3.5 Å in alcohols ranks as methanol > ethanol >1-butanol > isopropanol, and the solubility of sulfachloropyridazine decreased with decreasing the interaction between alcohol and sulfachloropyridazine molecules. In Figure 6b, before 3.5 Å, the same phenomenon occurred in 1,4-dioxane, acetone, acetonitrile, and ethyl acetate except for water. This anomaly can be explained by the structure of sulfachloropyridazine molecule. The hydrophilic amino groups increased the probability of water appearing around the solute; however, hydrophobic benzene rings and halogen elements impeded the combination of solute molecules with water molecules. This explains why the solubility value of sulfachloropyridazine in water is smaller than that in ethyl acetate. 3.4. Data Correlation. In this work, the modified Apelblat equation and the Jouyban−Acree model are employed to correlate the solubility of sulfachloropyridazine in pure and binary solvent mixtures at different temperatures, respectively. 3.4.1. Modified Apelblat Equation. The modified Apelblat equation14−16 expressed in eq 3 is a semiempirical model with three parameters. It has been widely used in describing the solubility of solute in pure solvents for binary solid−liquid phase equilibrium.

Figure 4. Experimental and predicted solubility data of sulfachloropyridazine in (a) methanol (w) + water (1 − w) mixed solutions; (b) ethanol (w) + water (1 − w) mixed solutions; and (c) isopropanol (w) + water (1 − w) mixed solutions with various mass fractions at different temperatures. Red dots, predicted values; surface, experimental values.

solvents. However, the solubility results cannot be fully explained; various factors (the rule of “like dissolves like”, hydrogen bond, van der Waals force, polarity, dielectric constant and dipole moment, and so on) should be considered as a whole. 3.3. MD Simulation. The interaction between solute and solvent molecules was measured by RDF at 298.15 K in this work. The results at other temperatures should be similar to this one. The centroid of solute and solvent molecules was selected to represent the whole molecular. To ensure the accuracy of this method, the g(r) plot of 100 pure water molecules was investigated and is shown in Figure 5. The g(r)

ln x = A + B /(T /K ) + C ln(T /K )

(3)

In eq 3, x is the mole fraction solubility of sulfachloropyridazine in six organic solvents; A, B, and C are adjustable parameters in the modified Apelblat equation. The parameters A and B indicate the influence of solution nonideality upon the solute solubility and the variation of solute activity coefficient, respectively. The value of parameter C reflects the influence of temperature upon the fusion enthalpy of a solute. 3.4.2. Jouyban−Acree model. The Jouyban−Acree model provides accurate mathematical descriptions for the solubility dependence on both temperature and solvent composition for binary and ternary mixed solvents17−19 and is described as eq 4. ln xw , T = w1 ln x1, T + w2 ln x 2, T +

w1w2 T

2

∑ Ji (w1 − w2)i i=0

(4)

where xw,T is the solubility of solute in mole fraction in the binary solvent mixtures at temperature T in Kelvin; w1 and w2 denote the mass fractions of solvents 1 (water) and 2 (methanol, ethanol, or isopropanol) in the absence of the solute (sulfachloropyridazine), respectively; x1,T and x2,T are the mole fraction solubilities of solute in pure solvent, and Ji stands for the Jouyban−Acree model parameters. The relative average deviation (RAD) and root-mean-square deviation (RMSD) were computed to evaluate the correlation accuracy of the computation using eqs 5 and 6.

Figure 5. g(r) plots of pure water molecular interaction between O−O and O−H.

plots of intermolecular interactions between solute and different solvents are shown in Figure 6. As shown in Figure 6, when R is ethyl acetate > methanol > ethanol >1-butanol > isopropanol > water. Moreover, in the three mixture with given initial composition, the solubility of sulfachloropyridazine increased with increasing temperature and mass fraction of alcohol. The dependence of sulfachloropyridazine solubility upon temperature and solvent composition was correlated by the modified

Corresponding Authors

■

AUTHOR INFORMATION

*E-mail: [email protected] (R.L.). *E-mail: [email protected] (D.H.). ORCID

Rongrong Li: 0000-0001-6112-6203 Funding

The project was supported by the National Natural Science Foundation, China (21506138, 21375092, and 21575097), Science and Technology Plan Project, Zhejiang Province (2015C33224, 2016C37040), and Taizhou Science and Technology Project (No. 131 KY08). Notes

The authors declare no competing financial interest. F

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(18) Eghrary, S. H.; Zarghami, R.; Martinez, F.; Jouyban, A. Solubility of 2-butyl-3-benzofuranyl 4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl ketone hydrochloride (amiodarone HCl) in ethanol + water and nmethyl-2-pyrrolidone + water mixtures at various temperatures. J. Chem. Eng. Data 2012, 57, 1544−1550. (19) Jouyban, A.; Martinez, F.; Acree, W. E. Further calculations on solubility of 3-amino-1-adamantanol in ethanol + water binary solvent mixtures at various temperatures. J. Mol. Liq. 2016, 219, 211−215.

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DOI: 10.1021/acs.jced.7b01134 J. Chem. Eng. Data XXXX, XXX, XXX−XXX