Solid–Liquid Equilibrium Solubility, Thermodynamic Properties, and Molecular Simulation of Phenylphosphonic Acid in 15 Pure Solvents at Different Temperatures

Wan, Yameng; Zhang, Pengshuai; He, Hui; Sha, Jiao; Yang, Kunpeng; Li, Tao; Ren, Baozeng

doi:10.1021/acs.jced.9b00362

Cited by 20 publications

(10 citation statements)

References 38 publications

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“…As reported in some literature, crude edaravone could be recrystallized by ethanol, − and the purity of the product completely meets the requirements of the medical field. In our previous work, the solubility data of edaravone in ethanol, methanol, isopropanol, n -propanol, ethyl acetate, toluene, acetonitrile, acetone, (ethyl acetate + methanol), and (ethyl acetate + ethanol) has been studied; − moreover, the co-solvency phenomenon was found in selected mixed solvents. The dissolution behavior of drugs in solvents is very important, especially in the preparation process.…”

Section: Introductionsupporting

confidence: 71%

“…The results of DSC curves for the raw material and excess solid solute in solvent are shown in Figure S1 (in the Supporting Information). As reported in our previous work, − the onset temperature and peak temperature of the raw material and excess solid solute in pure solvents were 400.15 and 403.15 K, respectively. More importantly, the DSC curves of excess solid solute in the mixed solvents were almost the same as those for raw materials, indicating that there is no solvate.…”

Section: Resultsmentioning

confidence: 99%

“…As mentioned in our previous work, − the order of solubility is contrary to the polarity of the three pure alcohols { n -propanol (61.7) < ethanol (65.4) < methanol (76.2)}. With the addition of acetonitrile or ethyl acetate, the co-solvency phenomenon appeared in the dissolution process of edaravone except for the mixtures of (acetonitrile + n -propanol).…”

Section: Resultsmentioning

confidence: 99%

“…As we all know, solutes and solvents with similar solubility parameters will be able to interact with each other, resulting in solvation, miscibility, or swelling. According to our previous work, the Hildebrand solubility parameters of the solute and selected solvents are edaravone 24.53 (J·cm –3 ) 1/2 , methanol 30.6 (J·cm –3 ) 1/2 , ethanol 28.30 (J·cm –3 ) 1/2 , n -propanol 25.54(J·cm –3 ) 1/2 , ethyl acetate 19.2 (J·cm –3 ) 1/2 , and acetonitrile 24.10 (J·cm –3 ) 1/2 . − When the solubility parameter of the solute is between the solubility parameters of the two solvents, it may cause the solubility of the solute to increase first and then decrease. However, in mixtures of (acetonitrile + n -propanol), the solubility parameters of n -propanol and solute are almost the same; so, when the concentration is w = 0.2, the difference of solubility parameters between mixed solvents and the solute becomes larger, and no co-solvency phenomenon is found.…”

Section: Resultsmentioning

confidence: 99%

“…The solubility of edaravone in (ethyl acetate + n -propanol), (acetonitrile + methanol), (acetonitrile + ethanol), and (acetonitrile + n -propanol) was determined by the isothermal saturation method. − Four mixtures were prepared by using an analytic balance with the standard uncertainty of 0.0001 g. The mass fractions of ethyl acetate or acetonitrile in the mixtures varied from 0.2 to 0.8. The experimental process is the same as our previous studies, − so it is only a simple description of the experimental steps. Excessive solute was added into the glass vessel fitting with about 50 mL prepared solvents.…”

Section: Methodsmentioning

confidence: 99%

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Solubility of Edaravone in Four Mixed Solvents at 273.15–313.15 K and Correlation of Jouyban–Acree and CNIBS/R–K Models

Yin

Tang

et al. 2020

J. Chem. Eng. Data

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The solubility of edaravone in four mixed solvents including (ethyl acetate + n-propanol), (acetonitrile + methanol), (acetonitrile + ethanol), and (acetonitrile + n-propanol) was determined by using the isothermal saturation method at temperatures ranging from (273.15 to 313.15) K under 101.3 kPa. At a certain composition in the four mixed solvents, the solubility data of edaravone increased with the rising temperature. At a certain temperature, the solubility data decreased monotonically with the increasing mass fraction of acetonitrile in the mixture of (acetonitrile + n-propanol). Whereas in (ethyl acetate + n-propanol), (acetonitrile + methanol), and (acetonitrile + ethanol), it increased first and then decreased with the increasing mass fraction of ethyl acetate or acetonitrile. The composition dependence of solubility has a maximum at around w ethyl acetate = 0.2 in (ethyl acetate + n-propanol) or w acetonitrile = 0.2 in (acetonitrile + ethanol) and w acetonitrile = 0.4 for mixtures of (acetonitrile + methanol). The results obtained in the selected four mixtures were correlated by the Jouyban–Acree model and CNIBS/R–K model. The largest relative average deviation and root-mean-square deviation values were found in (acetonitrile + methanol) calculated by the Jouyban–Acree model and were no more than 4.71 × 10–2 and 22.32 × 10–4, respectively. Statistical analysis of experimental and calculated values shows that the residual of CNIBS/R–K model is smaller, and the linear correlation coefficient is closer to 1. Therefore, the CNIBS/R–K model is more suitable to correlate the solubility values of edaravone in the four mixed solvents including (ethyl acetate + n-propanol), (acetonitrile + methanol), (acetonitrile + ethanol), and (acetonitrile + n-propanol). The experimental data and model parameters obtained will play an important role in the preparation and purification of edaravone.

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