Solubility, solution thermodynamics, and preferential solvation of piroxicam in ethyl acetate+ethanol mixtures

Cristancho, Diana M.; Jouyban, Abolghasem; Martínez, Fleming

doi:10.1016/j.molliq.2016.05.056

Cited by 28 publications

(5 citation statements)

References 26 publications

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“…The function D (eq ) is the derivative of the standard molar Gibbs energies of transfer of C 4 H 3 BrN 2 O (3) from neat water (2) to solvent mixtures with respect to the molar composition of organic solvents. The function Q (eq ) involves the second derivative of the excess molar Gibbs energy ( G 1 + 2 Exc ) of mixing with respect to the water proportion in the mixtures. − V cor is the correlation volume, and r 3 is the molecular radius of C 4 H 3 BrN 2 O calculated as shown in eq with N Av as the Avogadro’s number. κ T is shown in eq with the reported κ T values for methanol (1.248 GPa –1 ), ethanol (1.153 GPa –1 ), isopropanol (1.331 GPa –1 ), DMF (0.642 GPa –1 ), and water (0.457 GPa –1 ) at 298.15 K. − where x i is the mole fraction of component i and κ T , i o is the isothermal compressibility of the pure component i.…”

Section: Resultsmentioning

confidence: 99%

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Solubility and Data Correlation of 2-Bromo-5-hydroxypyrazine in Four Cosolvent Mixtures and Ten Mono-Solvents from 278.15 to 323.15 K

2023

J. Chem. Eng. Data

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The experimental solubility of 2-bromo-5-hydroxypyrazine dissolved in 10 mono-solvents (methanol, ethanol, isopropanol, N,N-dimethylformamide (DMF), npropanol, acetonitrile, acetone, ethylene glycol (EG), propylene glycol (PG), water) and cosolvent mixtures of methanol + water, ethanol + water, isopropanol + water, and DMF + water was determined by the isothermal saturation method between 278.15 and 323.15 K at 101.2 kPa. The largest solubility was observed in DMF + 2-bromo-5hydroxypyrazine for mono-solvent systems and in DMF + water for mixed solvent systems. The Jouyban−Acree model (J−A), van't Hoff−Jouyban−Acree model (V−J− A), and Apelblat−Jouyban−Acree model (A−J−A) were utilized to correlate the 2bromo-5-hydroxypyrazine solubility in mixtures, and the Apelblat model, van't Hoff model, λh model, and Jouyban model were used to correlate the 2-bromo-5hydroxypyrazine solubility in 10 mono-solvents. The preferential solvation of 2bromo-5-hydroxypyrazine in mixed solvents was researched by calculation of δx 1,3 . This study presents insights into modulating the 2-bromo-5-hydroxypyrazine crystallization process and in understanding equilibrium behaviors in different solvents.

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Section: Resultsmentioning

confidence: 99%

“…In this case, C 4 H 3 BrN 2 O is naturally preferentially dissolved by water. However, with the increasing content of organic solvents, this protective layer will be destroyed, which makes the contact between C 4 H 3 BrN 2 O and organic solvents easier. − …”

Section: Resultsmentioning

confidence: 99%

Solubility and Data Correlation of 2-Bromo-5-hydroxypyrazine in Four Cosolvent Mixtures and Ten Mono-Solvents from 278.15 to 323.15 K

2023

J. Chem. Eng. Data

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“…If δ x 1,3 > 0, felodipine is preferentially solvated by ethyl acetate, and conversely, preferentially solvated by isopropanol. Briefly speaking, the calculation process of preferential solvation parameters is provided in the Supporting Information. − …”

Section: Resultsmentioning

confidence: 99%

Solid–Liquid Phase Equilibrium and the Thermodynamic Correlation of Felodipine Form I in Pure and Mixed Solvents

Nie

Liu

et al. 2022

J. Chem. Eng. Data

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Because felodipine form I is used in marketed products, a co-solvent (ethyl acetate) is applied to enhance the solubility of poorly soluble form I in the present work. The solid−liquid equilibrium phase diagrams in pure and mixed solvents were established, and the effects of the solvent properties and intermolecular interaction on the solubility of felodipine were also studied. In pure solvent, the largest and smallest solubility data were obtained in ethyl acetate and toluene, respectively. The solubility increased to the maximum value at w = 0.8 with a mass fraction of ethyl acetate in (isopropanol + ethyl acetate) mixtures and then decreased with the increasing composition of the co-solvent. The modified Apelblat equation and the Jouyban−Acree model were applied to evaluate the solubility profile. All of the values of RAD were no more than 5%. More importantly, preferential solvation parameters (δ x1,3 ) of felodipine in (isopropanol + ethyl acetate) mixtures were calculated using the inverse Kirkwood−Buff integrals method. The results indicated that the values of δx 1,3 were all negative in ethyl acetate-rich and isopropanol-rich regions but positive in the composition of 0.45 < x 1 < 0.80. Felodipine is preferentially solvated by isopropanol in ethyl acetate-rich and isopropanol-rich regions. In the composition of 0.45 < x 1 < 0.80, felodipine is preferentially solvated by ethyl acetate.

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“…Such a solubility maximum is reported for many pharmaceuticals in binary mixtures of nonpolar or weakly polar solvent (cyclohexane, dichloromethane, dioxane, and AcOEt) with a protic one (alcohols and water). ,,,,,− The solubility maximum is found also in alcohol + water mixture for solutes with higher hydrophilicity, such as acetaminophen (paracetamol). ,, These solubility maxima have been often used for the validation of solubility models, ,,,,,, although most of the maxima can be explained even by the Hildebrand δ, as shown in Figure . In contrast, solubility enhancement in the mixture of a polar aprotic solvent with a protic one, such as the CH 3 CN + EtOH mixture in Figure c, has been rarely investigated so far, except for the recent research by Duereh et al − They proposed an application of the mixture of polar aprotic solvent (ketones, lactones, nitriles, and dimethyl sulfoxide) with protic one for pharmaceutical and polymer industries as alternative solvents replacing hazardous ones.…”

Section: Solubility Predictionmentioning

confidence: 99%

Solubilities of Organic Semiconductors and Nonsteroidal Anti-inflammatory Drugs in Pure and Mixed Organic Solvents: Measurement and Modeling with Hansen Solubility Parameter

et al. 2018

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The solubilities of five organic semiconductors and four nonsteroidal anti-inflammatory drugs (NSAIDs) were measured by a static analytical method in a set of seven representative organic solvents at 298.15 K and 0.10 MPa to determine the Hansen solubility parameter (HSP) of the solutes by a quantitative correlation with the extended Hansen model. Solubilities of the organic semiconductors (N,N′-di-1-naphthyl-N,N′diphenylbenzidine (NPB), 4,4′-bis(9H-carbazol-9-yl)biphenyl (CBP), anthracene, tetracene, and perylene) exhibited similar solvent dependence to each other, increasing in the order of ethanol < acetonitrile < hexane < acetone < carbon tetrachloride < chlorobenzene ≈ chloroform due to the large dispersion parameter δ D ≈ 21 and the small polarity and hydrogen bonding parameters (δ P, δ H ) ≈ (5, 5) of the solutes. In contrast, the solubilities of NSAIDs (naproxen, diclofenac, indomethacin, and niflumic acid) were hexane < carbon tetrachloride < acetonitrile ≈ chlorobenzene < ethanol ≈ chloroform < acetone, indicating the smaller δ D ≈ 19 and the larger (δ P , δ H ) ≈ (10, 11). The HSP analysis enabled us to estimate the solubilities in other solvents and solvent mixtures; for example, the solubility maximum of indomethacin in the mixtures of ethanol with ethyl acetate, acetone, and acetonitrile was well described by the minimum Hansen distance.

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Solubility, solution thermodynamics, and preferential solvation of piroxicam in ethyl acetate+ethanol mixtures

Cited by 28 publications

References 26 publications

Solubility and Data Correlation of 2-Bromo-5-hydroxypyrazine in Four Cosolvent Mixtures and Ten Mono-Solvents from 278.15 to 323.15 K

Solubility and Data Correlation of 2-Bromo-5-hydroxypyrazine in Four Cosolvent Mixtures and Ten Mono-Solvents from 278.15 to 323.15 K

Solid–Liquid Phase Equilibrium and the Thermodynamic Correlation of Felodipine Form I in Pure and Mixed Solvents

Solubilities of Organic Semiconductors and Nonsteroidal Anti-inflammatory Drugs in Pure and Mixed Organic Solvents: Measurement and Modeling with Hansen Solubility Parameter

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