Solubility Determination and Thermodynamic Modeling of 2

Jul 24, 2019 - The solubility data of 2-mercaptobenzimidazole in different organic solvents including methanol, ethanol, isopropanol, n-propanol, 1-bu...
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Solubility Determination and Thermodynamic Modeling of 2‑Mercaptobenzimidazole in 12 Solvents from T = 278.15 K to T = 318.15 K Yong Xie,*,†,‡,§ Dianmei Li,‡ Yangyang Wang,‡ Ziyi Yang,‡ DeJin Zhang,†,§ and Hongyan Wang†,‡,§ †

Key Lab of Spin Electron and Nano Materials of Anhui Higher Education Institutes, Suzhou 234000, China School of Chemistry & Chemical Engineering, and §Fine Chemical Product Development Research Institute, Suzhou University, Suzhou 234000, China

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‡

ABSTRACT: The solubility data of 2-mercaptobenzimidazole in different organic solvents including methanol, ethanol, isopropanol, n-propanol, 1-butanol, toluene, cyclohexane, 2-butanone, acetonitrile, acetone, ethyl acetate, and 1,4-dioxane were determined experimentally by the isothermal saturation method at temperatures from T = 278.15 to 318.15 K at P = 101.1 kPa. In the study temperature range, the data increased with increasing temperature, and the sequence of solubility from high to low is as follows: 1,4-dioxane > acetone > 2-butanone > methanol > ethanol > n-propanol > 1-butanol > isopropanol > ethyl acetate > acetonitrile > toluene > cyclohexane. The modified Apelblat equation and Buchowski−Ksiazaczak λh equation were used to describe the relationship between the solubility data of 2-mercaptobenzimidazole in different solvents and temperature. The maximum values of root-mean-square deviation and relative average deviation were 2.05 × 10−4 (in isopropanol) and 3.08% (in toluene), respectively, and were all obtained by λh equation. Relatively, the modified Apelblat equation is the best model to correlate the solubility values of 2-mercaptobenzimidazole in these solvents. Furthermore, the solubility behavior was analyzed from the properties of solvent including the polarity, dipole moment, dielectric constants, and Hildebrand solubility parameters. reactant. When the final reaction was finished, in order to purify the final solution, the organic solvent and carbon disulfide were removed by vacuum evaporation. Then, the solid state of MBI is obtained. Finally, the crude product of MBI was purified by using recrystallization with methanol, ethanol, or hot water.5,12−14 A white crystal form of MBI was obtained by cooling the solution. Customarily, solvent crystallization is usually used as a more effective purification method and widely used in the separation and purification of products in the industrial production process. The final crystallization process has great influence on the yield of the solute. However, a basic step in purification and improving productivity of the chemical substance is to determine its solubility behavior. The dissolution process of MBI in different solvents is an important physical and chemical property of MBI, and it can help to understand phase equilibrium in the

1. INTRODUCTION Benzimidazole heterocyclic compounds are essential pharmacophores in molecular design of modern drugs because of the

Figure 1. Chemical structure of MBI.

broad spectrum of important biological and pharmacological properties.1,2 2-Mercaptobenzimidazole (MBI, CAS no. 58339-1) is a useful chemical product in industry; it acts as an antioxidant, inhibitor, antiseptic, and adsorbent.3−5 Figure 1 provides the chemical structure of MBI. It is used in natural rubber and latex and has a moderate effect on oxygen and weather aging and can prevent the adverse effect caused by excess sulfur during vulcanization of products.6−11 To date, the product MBI for appraisal was synthesized in an organic solvent by using o-phenylene diamine which was in finite amounts as the raw material and carbon disulfide as the © XXXX American Chemical Society

Received: February 26, 2019 Accepted: July 8, 2019

A

DOI: 10.1021/acs.jced.9b00190 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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

molar mass g·mol−1

melting points

MBI

583-39-1

150.2

575.15a

methanol ethanol n-propanol isopropanol ethyl acetate acetone acetonitrile toluene 1,4-dioxane cyclohexane 2-butanone 1-butanol

67-56-1 64-17-5 71-23-8 67-63-0 141-76-8 67-64-1 75-05-8 108-88-3 123-91-1 110-82-7 78-93-3 71-36-3

chemicals

32.04 46.07 60.10 60.10 88.11 58.08 41.05 92.14 88.11 84.16 72.11 74.12

source Shanghai Peng Suo Biochemical Technology Co., Ltd Sinopharm Chemical Reagent Co., Ltd., China

mass fraction purity

analytical method

0.996

HPLCb

0.996 0.994 0.995 0.994 0.995 0.995 0.995 0.995 0.994 0.996 0.995 0.996

GCc GC GC GC GC GC GC GC GC GC GC GC

a

Taken from ref 13. bHigh-performance liquid phase chromatograph. cGas chromatography.

2.2. Buchowski−Ksiazaczak λh Model. The λh model is also a semiempirical model which was proposed by Buchowski and co-workers initially.17 This model is another model to correlate the solid−liquid solubility values of MBI in different solvents at distinct temperature. There are two parameters in this model. The equation was described as follows ÄÅ É ij 1 ÅÅ λ(1 − x) ÑÑÑÑ 1 yzz − lnÅÅÅ1 + ÑÑ = λhjjj z j T /K x Tm/K zz{ ÅÅÇ ÑÑÖ (2) k λ and h are also adjustable parameters in this equation; Tm in the above equation refers to the melting temperature of MBI in Kelvin.

development of a crystallization process. More importantly, the knowledge of accurate solubility is required for the design of the crystallization process. To the best of the authors’ present knowledge, no solubility data of MBI have been reported by previous studies. In the previous publications, MBI obtained from the known process is purified by crystallization in aqueous alcohol and recrystallization in methanol and ethanol.5,12−14 Ethanol is a safe and commonly used cosolvent to be used in the pharmaceutical industry as a result of its sensitive dissolution. Isopropanol is a colorless and flammable chemical compound with a strong odor. It is relatively nontoxic, compared to alternative solvents. Acetone, 2-butanol, and ethyl acetate are very important organic chemical raw materials and industrial solvents because of their excellent solubility, fast drying, and wide application. Furthermore, in chemical and pharmaceutical industries, acetonitrile, cyclohexane, and toluene as solvents were used widely. From the abovementioned considerations, for the sake of obtaining high purity MBI, the information of MBI solubility in distinct solvents at different temperatures is a necessary procedure. We select 12 commonly used safe solvents including methanol, acetone, ethanol, 1,4-dioxane, isopropanol, toluene, n-propanol, 1-butanol, ethyl acetate, acetonitrile, 2-butanone, and cyclohexane in the process of industrial separation and purification. In this work, the objectives are to determine the MBI solubility in 12 solvents using the isothermal static method and use different correlation models to describe the solubility behavior of MBI.

3. EXPERIMENTAL SECTION 3.1. Materials and Apparatus. The purity of MBI in mass fraction is 0.996, and it is provided by Shanghai Peng Suo Table 2. Solubility (x) of Benzoic Acid in Toluene with the Relative Deviation at the Temperature (283.15, 293.15, 303.15 and 313.15 K) under 101.2 kPaa xexp

xref

100RD

283.15 293.15 303.15 313.15

0.129 0.138 0.164 0.197

0.128 0.139 0.166 0.196

0.78 −0.72 −1.22 0.51

a Standard uncertainties u are u(T) = 0.02 K, u(p) = 400 Pa; relative standard uncertainty ur is ur(x) = 0.021. xexpexperiment data, xref taken from ref 19, RD is the relative deviation of the experiment value with the reference data.

2. SOLUBILITY MODELS In this work, the solubility data are correlated with modified Apelblat model15,16 and Buchowski−Ksiazaczak λh model.17 2.1. Modified Apelblat Equation. The modified Apelblat model is a semiempirical model, and it can be used to describe the relationship between the solubility values in mole fraction and temperature. The formula is shown as follows15,16 ln x = A + B /(T /K) + C ln(T /K)

T/K

Biochemical Technology Co., Ltd. The purity was determined by a high-performance liquid phase chromatograph. The solvents in this experiment (methanol, acetonitrile, ethanol, toluene, isopropanol, ethyl acetate, n-propanol, 1,4-dioxane, 1butanol, acetone, 2-butanone, and cyclohexane) were purchased from Sinopharm Chemical Reagent Co., Ltd., China. The purities of all these solvents in this experiment were all more than 0.994 in mass fraction. The purity of solvents was determined by gas chromatography and used without any pretreatment. The specific information including CAS no., mole mass, and melting points of these samples was tabulated in Table 1.

(1)

In eq 1, x refers to the solubility of MBI in mole fraction. Values of A, B, and C are the empirical parameters in the modified Apelblat model and may be obtained by correlating the experimental solubility data. B

DOI: 10.1021/acs.jced.9b00190 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 3. Experimental and Calculated Mole Fraction Solubility (x) of MBI in Different Solvents at the Temperature Range from T = (278.15 to 318.15) K under P = 101.1 kPaa 100 xcal T/K 278.15 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15

278.15 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15

278.15 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15

278.15 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15

278.15 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15

278.15 283.15

100 x 0.625 0.730 0.848 0.964 1.091 1.228 1.376 1.515 1.685 100 RAD 0.532 0.634 0.746 0.868 0.998 1.141 1.265 1.417 1.583 100 RAD 0.102 0.115 0.129 0.146 0.163 0.183 0.205 0.228 0.257 100 RAD 0.484 0.559 0.650 0.759 0.872 0.999 1.139 1.309 1.508 100 RAD 0.340 0.435 0.528 0.635 0.755 0.880 1.017 1.160 1.320 100 RAD 0.410 0.490

modified Apelblat equation Methanol 0.628 0.731 0.843 0.963 1.092 1.229 1.373 1.524 1.68 0.29 Ethanol 0.534 0.635 0.746 0.866 0.995 1.132 1.275 1.424 1.577 0.40 Acetonitrile 0.102 0.115 0.129 0.145 0.163 0.183 0.205 0.229 0.256 0.21 n-Propanol 0.485 0.563 0.651 0.752 0.867 0.998 1.146 1.314 1.503 0.43 Isopropanol 0.347 0.431 0.526 0.634 0.752 0.881 1.019 1.165 1.316 0.54 1-Butanol 0.410 0.491

100 xcal λh equation

T/K

0.640 0.734 0.838 0.952 1.078 1.216 1.366 1.53 1.709 1.19 0.550 0.639 0.739 0.851 0.976 1.114 1.266 1.434 1.618 1.66 0.101 0.115 0.130 0.146 0.164 0.184 0.205 0.229 0.254 0.60 0.478 0.560 0.653 0.758 0.875 1.005 1.150 1.311 1.488 0.62 0.360 0.434 0.520 0.619 0.732 0.862 1.010 1.176 1.364 2.30 0.412 0.491

C

100 x

288.15 293.15 298.15 303.15 308.15 313.15 318.15

0.580 0.690 0.809 0.941 1.085 1.250 1.441 100 RAD

278.15 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15

1.210 1.276 1.352 1.435 1.521 1.603 1.689 1.787 1.886 100 RAD

278.15 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15

0.198 0.236 0.275 0.318 0.366 0.413 0.463 0.518 0.577 100 RAD

278.15 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15

1.406 1.526 1.656 1.806 1.946 2.100 2.273 2.461 2.650 100 RAD

278.15 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15

4.36 × 10−4 5.51 × 10−4 7.05 × 10−4 8.99 × 10−4 1.16 × 10−3 1.49 × 10−3 1.88 × 10−3 2.27 × 10−3 2.81 × 10−3 100 RAD

278.15 283.15 288.15 293.15

2.01 2.73 3.51 4.35

× × × ×

10−3 10−3 10−3 10−3

modified Apelblat equation 1-Butanol 0.583 0.687 0.806 0.939 1.088 1.254 1.438 0.27 Acetone 1.207 1.279 1.355 1.434 1.516 1.603 1.693 1.787 1.885 0.15 Ethyl Acetate 0.199 0.235 0.275 0.318 0.364 0.413 0.465 0.519 0.576 0.29 1,4-Dioxane 1.406 1.528 1.658 1.797 1.946 2.106 2.276 2.457 2.65 0.14 Cyclohexane 4.16 × 5.48 × 7.14 × 9.20 × 1.17 × 1.48 × 1.85 × 2.29 × 2.81 × 1.46 Toluene 2.11 × 2.72 × 3.45 × 4.30 ×

λh equation 0.582 0.686 0.804 0.937 1.087 1.255 1.443 0.39 1.206 1.279 1.355 1.435 1.517 1.603 1.693 1.786 1.884 0.17 0.204 0.237 0.273 0.313 0.358 0.408 0.462 0.522 0.588 1.35 1.399 1.526 1.660 1.802 1.952 2.111 2.278 2.455 2.641 0.29

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

4.25 5.54 7.16 9.18 1.17 1.47 1.84 2.29 2.82 1.33

× × × × × × × × ×

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

10−3 10−3 10−3 10−3

2.18 2.73 3.39 4.18

× × × ×

10−3 10−3 10−3 10−3

DOI: 10.1021/acs.jced.9b00190 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 3. continued 100 xcal T/K

100 x

298.15 303.15 308.15 313.15 318.15

5.30 × 10−3 6.38 × 10−3 7.53 × 10−3 8.87 × 10−3 1.04 × 10−2 100 RAD

278.15 283.15 288.15

1.029 1.097 1.169

modified Apelblat equation Toluene 5.28 × 6.37 × 7.59 × 8.92 × 1.03 × 1.15 2-Butanone 1.030 1.096 1.167

10−3 10−3 10−3 10−3 10−2

100 xcal λh equation

T/K

× × × × ×

293.15 298.15 303.15 308.15 313.15 318.15

5.12 6.22 7.52 9.04 1.08 3.08

10−3 10−3 10−3 10−3 10−2

1.021 1.094 1.170

100 x

modified Apelblat equation

1.243 1.328 1.413 1.506 1.616 1.721 100 RAD

2-Butanone 1.244 1.326 1.415 1.510 1.612 1.722 0.14

λh equation 1.250 1.334 1.421 1.513 1.609 1.709 0.48

a

Standard uncertainties u are u(T) = 0.02 K, u(p) = 400 Pa; relative standard uncertainty ur is ur(x) = 0.041.

Figure 2. Mole fraction solubility (x) of MBI in selected solvents at different temperatures: (a) □, 1,4-dioxane; ▽, acetone; ○, 2-butanone; ■, methanol; ●, ethanol; ▲, n-propanol; △, 1-butanol; ▼, isopropanol. ★, ethyl acetate; ☆, acetonitrile. (b) ■, toluene; and ●, cyclohexane.

1 μL of the solution to analyze using HPLC. The determination process was performed repeatedly. The mole fraction solubility (xe) of MBI in pure solvent was calculated with eq 3.

3.2. Solubility Determination. The dissolution process of MBI + solvent system was obtained by the isothermal saturation method; the experiment temperatures cover the range of T = 278.15−318.15 K under atmosphere pressure.18 Comparing the experiment solubility of benzoic acid in toluene with the reference, the reliability of verification of the experimental apparatus was verified. The compared results are tabulated in Table 2.19 Excessive amount of MBI was added into the 100 mL glass vessel filled with about 60 mL corresponding solvent. The system temperature to be determined was kept via circulating water from the smart thermostatic water-circulator bath through the outer jacket. The magnetic stirrer was used to make solution well-distributed. For the sake of obtaining the solid−liquid equilibration time, the supernatant was taken out using a 3 mL syringe attached with a 0.2 μm pore syringe filter at every 2 h and then analyzed by the high-performance liquid phase chromatograph (HPLC). If the composition of the liquid phase does not change, the system is assumed to be in solid−liquid equilibrium. From the experimental results, it takes 12 h for the solution to reach equilibrium for the studied system. When the solid−liquid system arrived at equilibrium, stirring was stopped, and the mixture was allowed to precipitate to settle for 1 h before sampling. Next, about 3 mL upper equilibrium liquor was obtained with a 5 mL syringe attached with a 0.2 μm pore filter. Before sampling, the syringe was preheated or precooled using the thermostatic water bath. Then, the upper equilibrium liquid was taken out rapidly to a preweight 25 mL volumetric flask which was covered with a rubber bung, weighed again using the analytical balance, and diluted to 25 mL with corresponding solvent finally, taking out

xe =

m1/M1 m1/M1 + m2 /M 2

(3)

where m1 and m2 are MBI and corresponding solvent mass, respectively, and M1 and M2 are the molar mass of MBI and the solvent. 3.3. Analysis Method. High-performance liquid-phase chromatography (HPLC) was used to analyze the concentration of MBI. The chromatography column was a type of LPC18 (250 mm × 4.6 mm) which is a reverse phase column. The column box was set to 303.15 K during the whole analysis process. The wavelength of the ultraviolet detector was set to 280 nm. The mobile phase of the analysis was pure methanol, and the flow rate was 1.0 mL·min−1. In order to ensure the repeatability of the experiment, each measurement was repeated three times, and each equilibrium mixture was taken out with at least three samples at a specified temperature. The final results were the average solubility value of three analysis results. In this experiment, the Beijing Fuli gas chromatograph was used to the GC analysis which equipped a flame photometric detector. Cross-linked HP-5 was used as a fused silica capillary column. The operation conditions were as follows: injection and detector temperature was 250 °C; column temperature was set to 100 °C; atmosphere flow rate was 450 mL·mL−1; and nitrogen and hydrogen flow rate were set to 40 mL·mL−1, respectively. D

DOI: 10.1021/acs.jced.9b00190 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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4. RESULTS AND DISCUSSION 4.1. Solubility Data and Result Analysis. The experimental solubility results in mole fraction of MBI in

and Hildebrand solubility parameters except for the solvent of isopropanol. In the other seven solvents, except for 1,4-dioxane and acetonitrile, the order of solubility (acetone > 2-butanone > ethyl acetate > toluene > cyclohexane) is the same as that of solvent polarity, dipole moment, dielectric constants, and Hildebrand solubility parameters. In most cases, for a single reason, it is too complicated to explain the solubility behavior listed in Table 3. Many factors affect these results, such as solvent−solvent interactions, solute−solvent interactions, and molecular shapes and sizes. 4.2. Correlation of Solubility Data. The solubility of MBI in the studied solvents is correlated with eqs 1 and 2 by using the nonlinear regression method.21 For the modified Apelblat model and λh model, eq 4 is the objective function

Table 4. Physical Properties of the Used Solvents Including Hildebrand Solubility Parameters (δH), Dipole Moment (μ), and Polarity, Dielectric Constants (ε)a solvent

polarity (water 100)

μ (298 K) (D)

ε (293 K)

103 δH (298 K) (J·m−3)1/2

1,4-dioxane isopropanol cyclohexane ethanol 2-butanone methanol toluene ethyl acetate 1-butanol acetone acetonitrile n-propanol

16.4 54.6 0.6 65.4 32.7 76.2 9.9 23 60.2 35.5 46 61.7

0.4 1.66 0.3 1.7 2.8 1.7 0.4 1.7 1.66 2.9 3.2 1.7

2.21 18.3 2.01 22.4 18.5 32.6 2.38 6.02 18.2 20.6 37.5 20.1

21.1 24.3 8.2 28.3 19.62 30.6 8.9 19.2 11.4 21.1 25.1 25.1

F=

∑ (xie − xic)2

(4)

i=1

In addition, relative average deviation (RAD) and rootmean-square deviation (rmsd) values are used to analyze and appraise the thermodynamic models. The rmsd and RAD are described as eqs 5 and 6, respectively.

a

Taken from ref 20.

N

RAD =

xe − xc 1 ∑ i e i N i=1 xi

ÄÅ N É ÅÅ ∑ (x c − x e)2 ÑÑÑ1/2 ÅÅ i = 1 i ÑÑ i ÑÑ rmsd = ÅÅÅ ÑÑ ÅÅ N ÑÑÖ ÅÇ

methanol, ethanol, isopropanol, 1,4-dioxane, n-propanol, toluene, cyclohexane, ethyl acetate, 1-butanol, acetone, acetonitrile, and 2-butanone are tabulated in Table 3 and graphed in Figure 2; the experiment temperatures cover the range of T = 278.15−318.15 K. With the increase of temperature, the solubility curve also shows an upward trend. The largest solubility data are obtained in 1,4-dioxane, and the lowest are obtained in cyclohexane. The sequence of solubility of MBI from high to low as follows: 1,4-dioxane > acetone > 2-butanone > methanol > ethanol > n-propanol > 1butanol > isopropanol > ethyl acetate > acetonitrile > toluene > cyclohexane. In five alcohols, the solubility decreases with the increase of carbon chain length except for isopropanol. The properties of solvent including the polarity, dipole moment, dielectric constants, and Hildebrand solubility parameters were cited and listed in Table 4.20 From Tables 3 and 4 and Figure 2, we can find that the order of solubility is related to the properties of solvents. In five alcohols, the order of solubility is entirely consistent with the polarity of solvent, and this orderliness is also applicable to dielectric constants

(5)

(6)

xci

where N is the number of experimental data points; and xei are the calculated and experimental solubility of MBI, respectively. The Mathcad software was used to correlate the solubility data with thermodynamic models and calculate the models’ parameters. During the process of solubility regression, the melting temperature (Tm) of MBI is cited from ref 13. The regressed calculation values of parameters A, B, and C in the modified Apelblat equation, λ and h in λh equation, and the values of rmsd are presented in Table 5. In terms of the regressed calculation parameters values, the solubility of MBI in the different solvents at different temperatures can be calculated. Table 3 tabulates the calculation RAD values between experimental and correlation values. For the sake of demonstrating the discrepancy between the solubility of calculated and experimental, the computed ones with the

Table 5. Parameters of the Modified Apelblat Equation and λh Equation for MBI in Different Solvents λh equation

modified Apelblat equation solvent

A

B

C

104 rmsd

λ

h

104 rmsd

methanol ethanol n-propanol isopropanol ethyl acetate acetone acetonitrile 1,4-dioxane cyclohexane 2-butanone 1-butanol toluene

85.634 136.480 −62.410 191.425 109.253 −30.359 −68.879 −38.454 54.810 −64.849 22.064 206.911

−5855.044 −8302.419 430.275 −11 228.48 −7096.284 322.955 1041.571 339.176 −6535.236 1720.732 −3555.081 −12 621.528

−12.376 −19.876 9.867 −27.846 −15.984 4.403 10.349 5.858 −7.765 9.610 −2.626 −30.614

0.41 0.57 0.45 0.36 0.13 0.27 0.06 0.39 0.002 0.22 0.27 0.01

0.326 0.435 0.484 0.849 0.142 0.029 0.037 0.128 0.010 0.042 0.696 0.015

6517.138 5424.90 5142.929 3467.806 16 177.568 22 603.526 52 430.880 9714.081 416 684.485 20 803.444 3970.127 231 766.276

1.37 1.94 0.83 2.05 0.58 0.28 0.13 0.65 0.002 0.72 0.35 0.02

E

DOI: 10.1021/acs.jced.9b00190 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Figure 3. Comparison of experimental and calculated solubility data: (a,c) □, 1,4-dioxane; ▽, acetone; ○, 2-butanone; ■, methanol; ●, ethanol; ▲, n-propanol; △, 1-butanol; ▼, isopropanol. ★, ethyl acetate; ☆, acetonitrile; (b,d) ■, toluene; ●, cyclohexane.

modified Apelblat equation and λh equation are shown graphically in Figure 3. The values of rmsd and RAD were no more than 2.05 × 10−4 (in isopropanol) and 3.08% (in toluene), respectively, and were all obtained by λh equation. From the results of calculation, relatively, modified Apelblat equation is the best model to correlate the solubility data of MBI in these solvents.

China (nos. KJ2017A435 and 2015hx016) and Project of Famous Teacher Studio of Anhui Province, China (no. 2016msgzs071). Notes

The authors declare no competing financial interest.

■

5. CONCLUSIONS The equilibrium solubility was obtained experimentally for MBI in these 12 pure organic solvents within the temperature range from T = 278.15 K to T = 318.15 K under 101.1 kPa. The mole fraction solubility of MBI in the selected pure solvents increased with the increase in temperature. At a fixed temperature, they ranked as 1,4-dioxane > acetone > 2butanone > methanol > ethanol > n-propanol > 1-butanol > isopropanol > ethyl acetate > acetonitrile > toluene > cyclohexane. The modified Apelblat equation and Buchowski−Ksiazaczak λh equation were used to correlate the determined solubility data of MBI in these solvents. The values of rmsd and RAD were not exceeding 2.05 × 10−4 and 3.08%, respectively. Relatively, modified Apelblat equation is more suitable to describe the relationship between the solubility data of MBI in these solvents and temperature.

■

REFERENCES

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. ORCID

Yong Xie: 0000-0002-0718-8603 Funding

The research is supported by the Major Project of Natural Scientific Research Foundation of Higher University Anhui, F

DOI: 10.1021/acs.jced.9b00190 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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DOI: 10.1021/acs.jced.9b00190 J. Chem. Eng. Data XXXX, XXX, XXX−XXX