Solubility, Three-Dimensional Hansen Solubility Parameters, and Solution Thermodynamics of 3,3′-Diaminodiphenyl Sulfone in 14 Neat Solvents from 283.15 to 328.15 K

Chen, Jiahong; Farajtabar, Ali; Jouyban, Abolghasem; Acree, William E.; Zhao, Hongkun

doi:10.1021/acs.jced.1c00062

Cited by 12 publications

(8 citation statements)

References 44 publications

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“…The FBX ∆ sol G 0 values were found to be lowest in PEG-400 and highest in water, which could be attributed to FBX solubility being highest in PEG-400 and lowest in water, respectively. The positive values of ∆ sol H 0 for FBX suggested that FBX dissolution was an endothermic in the mono solvents examined [40,41]. The FBX ∆ sol S 0 values in numerous mono solvents were also recorded as positive values in the range of 37.30-157.6 J mol −1 K −1 , suggesting an entropy-driven FBX dissolution in all mono solvents examined [40].…”

Section: Apparent Thermodynamic Studiesmentioning

confidence: 86%

“…The positive values of ∆ sol H 0 for FBX suggested that FBX dissolution was an endothermic in the mono solvents examined [40,41]. The FBX ∆ sol S 0 values in numerous mono solvents were also recorded as positive values in the range of 37.30-157.6 J mol −1 K −1 , suggesting an entropy-driven FBX dissolution in all mono solvents examined [40]. Based on the positive values of ∆ sol H and ∆ sol S 0 , the FBX dissolution was considered to be an endothermic and entropy-driven in all mono solvents examined [40,41].…”

Section: Apparent Thermodynamic Studiesmentioning

confidence: 98%

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Solubility and Thermodynamic Data of Febuxostat in Various Mono Solvents at Different Temperatures

et al. 2022

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This study examines the solubility and thermodynamics of febuxostat (FBX) in a variety of mono solvents, including “water, methanol (MeOH), ethanol (EtOH), isopropanol (IPA), 1-butanol (1-BuOH), 2-butanol (2-BuOH), ethylene glycol (EG), propylene glycol (PG), polyethylene glycol-400 (PEG-400), ethyl acetate (EA), Transcutol-HP (THP), and dimethyl sulfoxide (DMSO)” at 298.2–318.2 K and 101.1 kPa. The solubility of FBX was determined using a shake flask method and correlated with “van’t Hoff, Buchowski-Ksiazczak λh, and Apelblat models”. The overall error values for van’t Hoff, Buchowski-Ksiazczak λh, and Apelblat models was recorded to be 1.60, 2.86, and 1.14%, respectively. The maximum mole fraction solubility of FBX was 3.06 × 10−2 in PEG-400 at 318.2 K, however the least one was 1.97 × 10−7 in water at 298.2 K. The FBX solubility increased with temperature and the order followed in different mono solvents was PEG-400 (3.06 × 10−2) > THP (1.70 × 10−2) > 2-BuOH (1.38 × 10−2) > 1-BuOH (1.37 × 10−2) > IPA (1.10 × 10−2) > EtOH (8.37 × 10−3) > EA (8.31 × 10−3) > DMSO (7.35 × 10−3) > MeOH (3.26 × 10−3) > PG (1.88 × 10−3) > EG (1.31 × 10−3) > water (1.14 × 10−6) at 318.2 K. Compared to the other combinations of FBX and mono solvents, FBX-PEG-400 had the strongest solute-solvent interactions. The apparent thermodynamic analysis revealed that FBX dissolution was “endothermic and entropy-driven” in all mono solvents investigated. Based on these findings, PEG-400 appears to be the optimal co-solvent for FBX solubility.

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Section: Apparent Thermodynamic Studiesmentioning

confidence: 86%

Section: Apparent Thermodynamic Studiesmentioning

confidence: 98%

Solubility and Thermodynamic Data of Febuxostat in Various Mono Solvents at Different Temperatures

et al. 2022

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“…The λ h model including two parameters belongs to a semiempirical model, which is usually used for collection of the solubility data. , The expression of this model is shown in eq . herein, λ and h are the parameters obtained by the regression of the experimental solubility data. T m represents the melting point of sofosbuvir form A in Kelvin determined in this work.…”

Section: Results and Discussionmentioning

confidence: 99%

Research on Solubility Measurement, Solvent Effects, Preferential Solvation, and Model Correlation of Sofosbuvir Form A in Different Pure and Binary Solvents

Xing

Cong

et al. 2022

J. Chem. Eng. Data

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Solubility property is crucial to pharmaceutical development, form screening, and the production control of drugs. In this work, the equilibrium of sofosbuvir form A in different solvents was established, and the solubility was determined using isothermal saturation methods. The solvent effect, preferential solvation, and model correlation were investigated. The mole fraction solubility of sofosbuvir form A enhanced as the temperature increased. The mole fraction solubility was arranged in the following order acetone > ethanol > 1-butanol > acetonitrile > ethyl acetate > water > toluene > cyclohexane. The solvent effect results indicated that the hydrogen bond interactions were vital to dissolution of sofosbuvir form A. For mixture systems, the solubility enhanced with the increase of the acetone/ethanol composition. The preferential solvation was evaluated using a dimensionless parameter (δ) and the equilibrium constant of the solvent exchange process (K ps ). The results indicated that acetone or ethanol dissolved sofosbuvir preferentially. Besides, Apelblat, λh, Wilson, Jouyban−Acree, and Apelblat−Jouyban−Acree models were used to correlate the solubility data. The maximum values of relative average deviation and root mean square deviation were calculated to be 2.74% and 9.63 × 10 −4 in monosolvents and 1.38% and 3.47 × 10 −4 in mixed solvents, respectively. These models exhibited good correlation with the solubility results of sofosbuvir form A.

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“…The saturated MMMT solubility in the selected cosolvent solutions was measured at temperatures ranging from 278.15 to 323.15 K using the saturation shake-flask method , at p = 101.2 kPa. The use of the jacketed flask was continued throughout the entire dissolution process, which also provided a favorable place for the solute MMMT to reach saturation in the solvent.…”

Section: Methodsmentioning

confidence: 99%

Saturated Solubility Determination and Correlation of 2-Methyl-4-Methylamino-6-Methoxy-1,3,5-Triazine in Several Aqueous Cosolvent Systems from 278.15 to 323.15 K

Chen

Zhu

et al. 2021

J. Chem. Eng. Data

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2-Methyl-4-methylamino-6-methoxy-1,3,5-triazine is an important intermediate of tribenuron-methyl with poor aqueous solubility. In this study, we have considered five pure solvents as raw materials and formed four sets of mixed solvents according to their pairs by mixing methanol, ethanol, ethylene glycol (EG), and N,N-dimethyl formamide (DMF) in water. Taking 278.15 K as the starting temperature and referring to the principle of the isothermal static state, the temperature was gradually increased at 5 K intervals until it reached 323.15 K. Under normal pressure (101.1 kPa), when the mole fraction of the solute did not change, the value obtained by high-performance liquid chromatography (HPLC) was the equilibrium solubility of 2-methyl-4-methylamino-6-methoxy-1,3,5-triazine. The mole fraction of 2-methyl-4-methylamino-6-methoxy-1,3,5-triazine at 323.15 K obeyed the following descending sequence: DMF (0.4557) > methanol (0.1852) > ethanol (0.1364) > EG (0.05972). From the point of view of temperature, the influence on the solute cannot be ignored. The amount of 2-methyl-4-methylamino-6-methoxy-1,3,5-triazine dissolved increased from a low value to a high value when the temperature increased from low to high. In addition, a difference observed was that the water content of the mixed solvent was repulsive to the dissolution of the solute. When the water content increased from low to high, the mole fraction of 2-methyl-4-methylamino-6-methoxy-1,3,5-triazine decreased from high to low. In any temperature environment, the same proportion of water was added to the four organic solvents. Compared with other solvents, the mixture of DMF and water had an absolute dissolution advantage. We adopted three cosolvency models including the Jouyban–Acree, van’t Hoff–Jouyban–Acree, and modified Apelblat–Jouyban–Acree models to calculate and correlate the saturated solubility data of 2-methyl-4-methylamino-6-methoxy-1,3,5-triazine. The RAD and RMSD values were 8.90 × 10–3 and 6.36 × 10–4, respectively, as obtained from the van’t Hoff–Jouyban–Acree model, and the Jouyban–Acree model demonstrated a better fitting effect. The determination of solubility helps to obtain solubility parameters, which are a measure of intermolecular forces. Solubility is required in the fields of recrystallization and fractional crystallization in the chemical industry, as well as the synthesis and separation of compounds.

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Solubility, Three-Dimensional Hansen Solubility Parameters, and Solution Thermodynamics of 3,3′-Diaminodiphenyl Sulfone in 14 Neat Solvents from 283.15 to 328.15 K

Cited by 12 publications

References 44 publications

Solubility and Thermodynamic Data of Febuxostat in Various Mono Solvents at Different Temperatures

Solubility and Thermodynamic Data of Febuxostat in Various Mono Solvents at Different Temperatures

Research on Solubility Measurement, Solvent Effects, Preferential Solvation, and Model Correlation of Sofosbuvir Form A in Different Pure and Binary Solvents

Saturated Solubility Determination and Correlation of 2-Methyl-4-Methylamino-6-Methoxy-1,3,5-Triazine in Several Aqueous Cosolvent Systems from 278.15 to 323.15 K

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