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

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Measurement and Correlation of the Solubility of Pyrimethanil in Seven Monosolvents and Two Different Binary Mixed Solvents Ling Liu,†,‡ Dejiang Zhang,†,‡ Yingdan Cui,†,‡ Shijie Xu,†,‡ Haiyan Yang,†,‡ Mingchen Li,†,‡ Zhe Ding,†,‡ and Songgu Wu*,†,‡,§ †

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National Engineering Research Center of Industry Crystallization Technology, School of Chemical Engineering and Technology, and §Key Laboratory of Modern Drug Delivery and High Efficiency, Tianjin University, Tianjin 300072, People’s Republic of China ‡ Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, People’s Republic of China S Supporting Information *

ABSTRACT: The solubility of pyrimethanil in two binary solvents (water + methanol and water + ethanol) and seven monosolvents (methanol, ethanol, n-propanol, isopropanol, nbutanol, isobutanol, and cyclohexane) was measured by a gravimetric method within the temperature range of 283.15 to 323.15 K at atmospheric pressure. In the investigated temperature range, the solubility of pyrimethanil in all monosolvents or mixed solvents increases with increasing temperature. The solubility in the monosolvents was wellcorrelated using the NRTL model, the Apelblat model, and the Wilson model. Furthermore, the NRTL model and the modified version of the Jouyban−Acree model (the Apel-JA equation) were employed to correlate the solubility in binary solvents. The results showed that these models have a satisfactory correlation. When we measured the solubility, we found that the solvent has a great influence on the crystal habit. Therefore, these results can give guidance for practical industrial processes such as the design of the crystallization process and control of the crystal morphology. controlling release formulations,6 the synthesis of salts, and the efficiency and degradation on fungi or residues in crops,7 with a few literature reports citing the solubility data systematically. The solid-state forms of PYL have been widely studied. In addition to a large number of inorganic or organic salts and cocrystalline species with other fungicides, two solvent-free forms have been reported.8,9 Form I is the thermodynamically stable form at room temperature.10 Our objectives are (1) to investigate the solubility of pyrimethanil (form I) in seven commonly used organic solvents and two binary solvents from 283.15 to 323.15 K at atmospheric pressure by a gravimetric method, (2) to correlate the experimental solubility data in the monosolvents with the NRTL model, the Apelblat model, and the Wilson model and in the mixed solvents with the NRTL model and the modified Jouyban−Acree model (the Apel-JA equation), and (3) to study the relationship between the multiple morphologies of the obtained PYL crystals with respect to the composition of the solvents during evaporation crystallization at room temperature at 0.1 MPa. This research will provide guidance for the industrial antisolvent crystallization process of PYL.

1. INTRODUCTION Pyrimethanil (PYL, (4,6-dimethyl-pyrimidin-2-yl)-phenylamine, Figure 1, C12H13N3, CAS registry no. 53112-28-0) is

Figure 1. Molecular structure of PYL.

a highly effective anilinopyrimidine fungicide that possesses a unique action mechanism compared to that of other citrus postharvest fungicides. Previous studies showed that PYL, through inhibiting enzyme biosynthesis, induces subsequent cell division, which contributes to lower mutagenicity or genotoxicity but excellent performance, particularly against gray mold and pear scab on fruits, vegetables, and ornamental plants.1 Crystallization as the key step in practical production has a critical effect on the quality of the final product with respect to the particle size distribution, crystal form, morphology, and purity.2,3 The solubility of solutes in solvents is an important indicator in guiding the design, operation, and optimization of industrial crystallization processes.4,5 However, previous investigations of pyrimethanil were mainly concerned with © XXXX American Chemical Society

Received: February 27, 2018 Accepted: July 11, 2018

A

DOI: 10.1021/acs.jced.8b00124 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

Table 1. Mass Fraction Purity and Density at 20 °C for the Materials Used in This Work chemical name pyrimethanil methanol ethanol n-propanol isopropanol n-butanol isobutanol cyclohexane

CAS 53112-28-0 67-56-1 64-17-5 71-23-8 67-63-0 71-36-3 78-83-1 110-82-7

molar mass/(g·mol−1)

mass fraction purity

density/(g·cm−3)

a

199.25 32.04 46.07 60.07 60.07 74.12 74.12 84.16

>0.980 >0.995b >0.995b >0.995b >0.995b >0.995b >0.995b >0.995b

analysis method HPLCa GCb GCb GCb GCb GCb GCb GCb

c

0.792 0.789c 0.804c 0.786c 0.810c 0.798c 0.778c

a

High-performance liquid chromatography. bGas chromatography. Both the analysis method and the mass fraction purity were provided by the suppliers. cReference 11.

2.2.3. Crystal Morphologies. To prepare the crystals, pyrimethanil was dissolved in different solvents at 313.15 K, and then the saturated solutions were evaporated in a glass dish at room temperature at 0.1 MPa. The morphology of the obtained crystals was observed and captured with a polarizing microscope (Eclipse E200, Nikon Instruments). 2.3. Solubility Measurements. In this work, the PYL’s solubility in both monosolvents and binary solvents was investigated by a gravimetric method.12−14 (See Table S1 and the Supporting Information text for the measurement verification.) Approximately 25−30 mL of a known-composition solvent was transferred to a glass flask (50 mL) and then was precooled or preheated at the target temperature in an air bath shaker (type HNY-200R, Tianjin Honuor Instrument Co., China). The standard uncertainty in temperature is 0.1 K. Then, excess solid solute was added to the system, and undissolved solid and solution were constantly shaken at a speed of 200 rpm for 12 h to ensure the mixture reached complete equilibrium. After keeping the system at a constant temperature for 3 h to accomplish complete separation, all of the samples were filtered through the membrane filter (0.45 μm, Φ13 mm, Tianjin Jinteng Experimental Equipment Co., Ltd.) and injected into a preweighed Petri dish before the total mass together with the preweighed Petri dish was analyzed with an electronic balance (type ML204/02, Mettler Toledo, Switzerland) with a standard uncertainty of u(B) = 0.0001 g. The solution was dried in the drying cabinet at 308.15 K for 36 h, and then the residual solute together with the Petri dish was weighed again. We performed each experiment three times, and the final solubility data was calculated by averaging the testing values of the repeated measurements. The solubility (x1) of pyrimethanil expressed as a mole fraction in monosolvents and mixed solvent can be calculated as

2. EXPERIMENTAL SECTION 2.1. Materials. Pyrimethanil (≥0.980 mass fraction) was purchased from Changshu Hengrong Commercial and Trading Co., Ltd., China. HPLC was used to identify the purity of PYL (Agilent 1200, Agilent Technologies, USA). All other reagents were analytical grade and purchased from Tianjin Jiangtian Chemical Technology Co., Ltd., China. The distilled− deionized water used in the binary solvents was prepared with an Ultrapure water system (Nanopure, Thermo) in our laboratory, and its conductivity was npropanol > isobutanol > ethanol > methanol > isopropanol > cyclohexane. Meanwhile, altering the system temperature positively within the investigated temperature range enhances the solubility of pyrimethanil significantly.

the raw material is stable and no phase transformation occurs, so these results were not listed here. 4.2. Melting Properties of PYL. The analysis of the thermograms of pyrimethanil obtained by differential scanning calorimetry (DSC) is shown in Figure 3. The onset temperature of the endothermic peak in this curve was defined as the melting temperature of PYL. Tm = 369.29 K (with an standard uncertainty of u(Tm) = 0.5 K), and ΔfusH = 25.44 kJ· mol−1 (with an expanded uncertainty of U(ΔfusH) = 0.97 kJ· mol−1, 0.95 level of confidence). It shows great consistency with the literature.29 4.3. Solubility Values in Solvents. In comparison with the experimental solution properties in the various systems, the solubility data is shown in Tables 3−5 and the plotted curves for the studied systems are shown in Figures 4−6. 4.3.1. Solubility in Seven Monosolvents. Alcohols are commonly used as organic solvents in industrial operation processes, including chemical reactions, preparation, and E



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cal Table 5. Experimental (xexp 1 ) and Calculated (x1 ) Mole Fraction Solubility Data of PYL in the ethanol + Water Binary Mixed a,b Solvent (p = 0.1 MPa)

x02

103xexp 1

0.3 0.4 0.5 0.6 0.7 0.8 0.9

1.187 2.777 5.283 8.079 10.06 12.39 14.35

0.3 0.4 0.5 0.6 0.7 0.8 0.9

1.444 3.272 6.076 9.262 12.48 15.16 16.27

0.3 0.4 0.5 0.6 0.7 0.8 0.9

1.704 4.053 7.549 10.85 15.20 18.05 19.51

0.3 0.4 0.5 0.6 0.7 0.8 0.9

2.142 4.948 9.018 12.93 18.46 22.27 24.67

0.3 0.4 0.5 0.6 0.7 0.8 0.9

2.658 5.901 11.42 16.47 21.84 28.08 31.04

103xcal,NRTL 1

103xcal,ABC‑JA 1

x02

103xexp 1

1.171 2.790 5.267 8.134 10.68 12.49 13.77

0.3 0.4 0.5 0.6 0.7 0.8 0.9

3.316 7.754 14.43 23.12 29.14 36.45 40.16

1.395 3.287 6.169 9.500 12.47 14.62 16.17

0.3 0.4 0.5 0.6 0.7 0.8 0.9

4.242 10.06 19.18 31.13 38.97 48.33 54.14

1.693 3.959 7.397 11.38 14.97 17.61 19.56

0.3 0.4 0.5 0.6 0.7 0.8 0.9

5.506 12.52 27.23 41.63 52.80 64.37 72.82

2.093 4.863 9.064 13.96 18.42 21.78 24.35

0.3 0.4 0.5 0.6 0.7 0.8 0.9

7.665 15.76 35.27 52.94 71.93 87.61 99.98

T = 283.15 K 1.127 2.652 4.826 7.269 9.490 11.37 12.71 T = 288.15 K 1.410 3.289 5.988 9.057 12.00 14.41 15.98 T = 293.15 K 1.755 4.089 7.485 11.27 15.10 18.11 20.13 T = 298.15 K 2.192 5.068 9.287 14.02 18.97 22.87 25.54 T = 303.15 K 2.736 6.254 11.65 17.69 23.65 29.02 32.39

103xcal,NRTL 1 T = 308.15 K 3.419 7.864 14.67 23.08 30.49 37.27 41.49 T = 313.15 K 4.30 9.94 18.91 30.26 39.84 48.63 54.25 T = 318.15 K 5.46 12.51 25.48 40.30 53.21 64.45 71.88 T = 323.15 K 7.117 15.94 33.76 53.27 72.81 87.81 97.80

103xcal,ABC‑JA 1 3.357 7.746 14.44 22.37 29.86 35.86 40.76 4.346 10.02 18.72 29.17 39.24 47.55 54.61 5.702 13.15 24.67 38.69 52.52 64.35 74.76 7.573 17.50 33.01 52.18 71.56 88.72 104.4

a exp x1

is the experimental solubility of pyrimethanil in methanol + and xcal,Apel‑JA are the calculated solubilities by water solvent. xcal,NRTL 1 1 eqs 4, 5, 12, and 14, respectively. x02 is the initial mole fraction of ethanol in the mixtures free of solute. bThe relative uncertainty in the solubility measurement is ur(x1) = 0.05. The relative uncertainty in the initial mole fraction of ethanol in the mixtures free of solute x02 is ur(x02) = 0.01. The standard uncertainty in temperature is u(T) = 0.05 K. The relative uncertainty in pressure is ur(p) = 0.01.

2.631 6.085 11.33 17.49 23.12 27.63 31.12

solvents. According to the general principle of “like dissolves like”,31 n-butanol obviously shows that the highest solubility in the above solvents may be governed by a fat-soluble group such as the benzene ring and the pyrimidine ring. From the perspective of the pyrimethanil chemical structure, we note that the molecular structure of pyrimethanil (A) consists of a secondary amine group, a benzene ring, and a pyrimidine ring, which indicates that the solubility may depend on hydrogen bonding forces between the N−H and O−H in the alcohols.21 The lower solubility in the cyclohexane compared to that in alcohols demonstrated that the existence of the hydrogen bonding acceptor in alcohols exerts a notable superiority of the solubility property. Furthermore, the steric effects should be taken into consideration. The branched-chain alcohols show lower solubility than the straight-chain alcohols, which can be attributed to the branch chain inducing a lower hydrogen propensities and weakening the interaction between

Table 6. Parameters of the Apelblat Model for PYL in Seven Monosolvents solvent

A

10−2B

C

ARD %

methanol ethanol n-propanol isopropanol n-butanol isobutanol cyclohexane

−765.0387 −865.1223 −931.7570 −872.0883 −450.3709 −893.8067 −763.6961

302.6324 349.2161 379.7040 350.9650 162.8895 359.0744 296.4948

115.8086 130.6418 140.5710 131.7085 68.8869 135.1058 115.8092

0.9651 1.2687 3.0903 2.1444 1.6275 2.6333 1.7168

From the perspective of physicochemical properties of the investigated solvents11 (shown in Table 2), the sequence of the experimental solubility data in four homologous normal alcohols can be ranked as methanol < ethanol < n-butanol < n-propanol, which is in accord with the order of the length of the alcohol’s alkyl chain and the negative polarity of the F



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Table 7. Parameters of the NRTL Model for PYL in Seven Monosolvents solvent

10−2Δg12

10−2Δg21

α12

ARD %

104 RMSD


−52.0724 −47.7337 −47.1943 −54.3609 −43.9857 −55.1360 −72.2295

117.5916 108.0702 103.2524 127.1315 93.1268 120.8910 175.3123

0.1400 0.1400 0.1400 0.1400 0.1400 0.1400 0.1400

2.6068 2.5346 4.5433 1.7271 1.0117 2.5605 1.7000

7.6746 10.1868 21.8414 5.6206 8.1895 12.3968 9.6634

Table 8. Parameters of the Wilson Model for PYL in Seven Monosolvents solvent

10−2Δλ12

10−2Δλ21

ARD %


10.6724 18.0997 24.0447 31.0925 21.1450 35.0297 53.0364

37.3060 28.5667 19.4418 23.2277 15.5063 12.3368 13.3713

2.9349 3.6175 6.1639 3.4734 1.6533 4.5504 2.2351

Table 9. Parameters of the NRTL Model for PYL in Two Binary Mixed Solvents parameter −5

10 Δg12 10−4Δg13 10−5Δg21 10−5Δg23 10−5Δg31 10−5Δg32 ARD % α12 α13 α23 104 RMSD

methanol + water

ethanol + water

−0.061 0.9317 0.1328 1.5447 0.2736 0.0556 3.7948 0.1300 0.2000 0.2000 0.8189

−0.2136 −6.3527 0.6942 −6.4814 3.6974 0.464 3.1591 0.1800 0.2000 0.5000 0.7727

Figure 3. DSC curve of PYL.

Table 10. Parameters of the Apel-JA Model for PYL in Two Binary Mixed Solvents parameter

methanol + water

ethanol + water

10−2A1 10−2A2 10−2A3 10−2A4 10−2A5 10−2A6 10−2A7 10−2A8 10−2A9 ARD %

3.8826 −213.973 −0.5787 −1.79164 84.7536 −97.8259 70.8615 −20.7847 2.6904 3.5258

−4.446 153.8714 0.6719 −3.9800 215.3717 −38.6424 −3.0354 9.7337 0.6021 2.4622

Figure 4. Mole solubility of PYL in monosolvents at temperatures ranging 283.15 to 323.15 K. ■, methanol; red ●, ethanol; blue ▲, npropanol; green ▼, isopropanol; pink ▲, n-butanol; yellow ▲, isobutanol; and blue ⧫, cyclohexane.

The solubility data of PYL is shown in Tables 4 and 5, and graphical plots are depicted in Figures 5 and 6. The solubility is positively correlated with temperature at a fixed composition of the two alcohol + water systems. The experimental data shows that the presence of water in solvent mixtures (methanol + water and ethanol + water) leads to a significant decrease in solubility compared to that in monosolvents. At a fixed temperature, the solubility shows a dramatic decline with the increasing addition of water. According to solution molecular thermodynamics, there are two intermolecular relationship including the solvent−solvent and solute−solvent cross-association in the alcohol + water mixtures. When pyrimethanil dissolves in the alcohol solvent,

the PYL and the alcohols.32 In this instance, hydrogen bonding is the critical factor in determining the solubility. 4.3.2. Solubility in Binary Solvents. Antisolvent crystallization is extensively applied in the manufacturing process of active pharmaceutical ingredients. In this study, methanol and ethanol, commonly used organic solvents, exhibited excellent solubility of PYL, and poor solvent water was selected as the antisolvent for the investigation of the solubility in binary systems. G



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Figure 7. Pyrimethanil crystals obtained from (a) methanol, (b) ethanol + water (x02 = 0.9), (c) ethanol + water (x02 = 0.7), and (d) ethanol + water (x02 = 0.3) solvents.

Figure 5. Experimental solubility data of PYL in the methanol + water binary mixed solvent at different mole fractions of methanol (x02) from 0.3 to 0.7 (p = 0.1 MPa): ■, 285.15 K; red ●, 288.15 K; blue ▲, 293.15 K; green ▲, 298.15 K; yellow ▲, 303.15 K; pink ▲, 308.15 K; blue ⧫, 313.15 K; red pentagon, 318.25 K; and red ●, 323.15 K.

In conclusion, the proportion of water in the binary mixtures has a vital effect on controlling the multiple morphologies of single crystals formed during evaporative crystallization at room temperature at 0.1 MPa.

5. CONCLUSIONS The PYL’s solubility in seven monosolvents and two mixed solvent was determined by a gravimetric method within the temperature range of 283.15 to 323.15 K at 0.1 MPa. The solubility is positively correlated with temperature in both monosolvents and mixtures of solvent at fixed solvent composition. Meanwhile, the solubility in the two binary solvents is negative with respect to the mole fraction of water. Moreover, the solubility in monosolvents is ranked as nbutanol > n-propanol > isobutanol > ethanol > methanol > isopropanol > cyclohexane and partially depends on the order of the polarity within the investigated solvents. Furthermore, a variety of morphologies of pyrimethanil crystals were obtained in the binary solvents during the evaporative crystallization at room temperature at 0.1 MPa. The experimental solubility value in monosolvents generally showed good agreement with the Apelblat model, the Wilson model, and the NRTL model. The solubility in binary solvents was well correlated using the modified Jouyban−Acree model (Apel-JA model) and NRTL model. The minor deviation of the above models verified that all of the selected thermodynamic models are in satisfactory agreement with the experimental data. Compared to other models, the Apelblat equation with the lowest deviation (maximum 3.09 ARD %) is more suitable to correlating and predicting the relationship between temperature and solubility accurately. On the basis of the above results, it can be used to predict the solubility in a wider temperature range and optimize the practical crystallization conditions of pyrimethanil.36

Figure 6. Experimental solubility data of PYL in the ethanol + water binary mixed solvent at different mole fractions of ethanol (x02) from 0.3 to 0.7 (p = 0.1 MPa): ■, 285.15 K; red ●, 288.15 K; blue ▲, 293.15 K; green ▲, 298.15 K; yellow ▲, 303.15 K; pink ▲, 308.15 K; blue ⧫, 313.15 K; red pentagon, 318.25 K; and red ●, 323.15 K.

the addition of water contributes to strong solvent−solvent interaction with alcohol and then weakens the original strong intermolecular forces between alcohol and PYL, leading to a significant decrease in solubility.33 4.4. Crystal Morphologies. Pyrimethanil crystals with a stable form are usually platelike products.8 In this work, in the monosolvents, the morphologies of pyrimethanil crystals are still platelike (Figure 7a), in spite of the slightly different aspect ratio in different monosolvents (Figure 7b,c).34 Nevertheless, in the binary solvents, the addition of water results in a significantly increased length of crystals, which varies with the amount of water in the binary solvents. For example, crystals from the methanol/ethanol + water system (x02 = 0.3) are inclined to be rodlike; however, the crystals tend to be platelike in the methanol + water solvent (x02 = 0.9). The difference in the crystal length can range up to a few micrometers, and the magnitude depends on the composition of water in the binary solvents. Other studies have shown that the polarity and the volatile rate are the major factors in determining the crystal growth.35

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ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.8b00124. Comparison of mole fraction solubility data of hippuric acid with the literature (DOCX) H



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AUTHOR INFORMATION

Corresponding Author

*Tel: 86-22-27405754. Fax: +86-22-27374971. E-mail: [email protected]. ORCID

Songgu Wu: 0000-0003-4329-4654 Funding

The authors are grateful for the financial support of National Natural Science Foundation of China (NNSFC 21676179 and NNSFC 91634117) and Major National Science and Technology (projects 2017ZX07402003 and 2017ZX09101001). Notes

The authors declare no competing financial interest.

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REFERENCES

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