Solubility of Acetaminophen and Ibuprofen in Polyethylene Glycol 600, N-Methyl Pyrrolidone and Water Mixtures

The solubility of acetaminophen and ibuprofen in binary and ternary mixtures of N-methyl pyrrolidone, polyethylene glycol 600 and water at 25 °C were determined and the solubilities are mathematically represented by the Jouyban–Acree model. The density of the solute-free solvent mixtures was measured and employed to train the Jouyban–Acree model and then the densities of the saturated solutions were predicted. The overall mean relative deviations (OMRDs) for fitting the solubility data of acetaminophen and ibuprofen in binary mixtures are 3.2% and 6.0%, respectively. The OMRDs for fitting the solubilities in ternary solvent mixtures for acetaminophen and ibuprofen are 15.0% and 28.6%, respectively, and the OMRD values for predicting all solubilities of acetaminophen and ibuprofen by a trained version of the Jouyban–Acree model are 9.4% and 17.8%, respectively. The prediction OMRD for the density of saturated solutions is 1.9%.     

Solubilization of Trans-Resveratrol in Some Mono-Solvents and Various Propylene Glycol + Water Mixtures

This research deals with the determination of solubility, Hansen solubility parameters, dissolution properties, enthalpy–entropy compensation, and computational modeling of a naturally-derived bioactive compound trans-resveratrol (TRV) in water, methanol, ethanol, n-propanol, n-butanol, propylene glycol (PG), and various PG + water mixtures. The solubility of TRV in six different mono-solvents and various PG + water mixtures was determined at 298.2–318.2 K and 0.1 MPa. The measured experimental solubility values of TRV were regressed using six different computational/theoretical models, including van’t Hoff, Apelblat, Buchowski–Ksiazczak λh, Yalkowsly–Roseman, Jouyban–Acree, and van’t Hoff–Jouyban–Acree models, with average uncertainties of less than 3.0%. The maxima of TRV solubility in mole fraction was obtained in neat PG (2.62 × 10⁻²) at 318.2 K. However, the minima of TRV solubility in the mole fraction was recorded in neat water (3.12 × 10⁻⁶) at 298.2 K. Thermodynamic calculation of TRV dissolution properties suggested an endothermic and entropy-driven dissolution of TRV in all studied mono-solvents and various PG + water mixtures. Solvation behavior evaluation indicated an enthalpy-driven mechanism as the main mechanism for TRV solvation. Based on these data and observations, PG has been chosen as the best mono-solvent for TRV solubilization.     

Solubility Data of Diazepam in Binary and Ternary Mixtures of PEGs 200 and 400 with N-Methyl Pyrrolidone and Water at 298.2 K: Experimental Data and Modeling

Experimental solubilities of diazepam in binary and ternary solvents of polyethylene glycols 200 and 400 with N-methyl pyrrolidone and water at T = 298.2 K are reported. The Jouyban–Acree model was used to fit solubility data of diazepam in the binary and ternary solvent mixtures (106 data points) in which the overall mean relative deviations (OMRD %) is 13.1 % and the prediction OMRD % is 31.7 %. The combined version of the Jouyban–Acree model with Hansen solubility parameters was used for fitting and predicting the solubility data and the OMRDs % are 10.0 and 20.8 %, respectively. Also, the previously proposed trained versions of the Jouyban–Acree model were used for predicting the reported data in this work and all results are listed in the tables. The density of the solute-free solvent mixtures were measured and employed to calculate the constants of the Jouyban–Acree model and then the densities of the saturated solutions were predicted.     

Further calculations on solubility of dipyrone in some binary solvent mixtures at various temperatures

The recently reported solubility data of dipyrone in binary solvent mixtures of {ethanol + water}, {methanol + ethanol} and {methanol + 1-propanol} at various temperatures have been used to report further numerical results based on the Jouyban–Acree model.     

Determination and mathematical modelling of budesonide solubility in N-methyl-2-pyrrolidone + water mixtures from T = 293.2 to 313.2 K

The solubilities of budesonide (BDS) in binary aqueous mixtures of N-methyl-2-pyrrolidone at temperatures ranging from 293.2 to 313.2 K were determined and mathematically correlated by three cosolvency models, i.e. Jouyban–Acree model, Jouyban–Acree–van’t Hoff model and modified Wilson model. The solubilities were measured using the shake-flask method and the models wereused to fit the solubility data of BDS in the solvent mixtures. The obtained mean relative deviations (MRDs %) for cosolvency models trained using whole data points varied between 5.0% and 31.0%. Solubilities were also predicted by the generally trained version of the Jouyban–Acree model with the MRD of 37.0%. Furthermore, the apparent thermodynamic properties of dissolution process of BDS in all the mixed solvents were calculated according to van’t Hoff and Gibbs equations. Dissolution of BDS in these mixed solvents is an endothermic process.     

Thermodynamic Characteristics of Phenacetin in Solid State and Saturated Solutions in Several Neat and Binary Solvents

The thermodynamic properties of phenacetin in solid state and in saturated conditions in neat and binary solvents were characterized based on differential scanning calorimetry and spectroscopic solubility measurements. The temperature-related heat capacity values measured for both the solid and melt states were provided and used for precise determination of the values for ideal solubility, fusion thermodynamic functions, and activity coefficients in the studied solutions. Factors affecting the accuracy of these values were discussed in terms of various models of specific heat capacity difference for phenacetin in crystal and super-cooled liquid states. It was concluded that different properties have varying sensitivity in relation to the accuracy of heat capacity values. The values of temperature-related excess solubility in aqueous binary mixtures were interpreted using the Jouyban–Acree solubility equation for aqueous binary mixtures of methanol, DMSO, DMF, 1,4-dioxane, and acetonitrile. All binary solvent systems studied exhibited strong positive non-ideal deviations from an algebraic rule of mixing. Additionally, an interesting co-solvency phenomenon was observed with phenacetin solubility in aqueous mixtures with acetonitrile or 1,4-dioxane. The remaining three solvents acted as strong co-solvents.     

Solubility of celecoxib in carbitol + water mixtures at various temperatures: experimental data and mathematical modelling

ABSTRACT

A brief review on various solubilisation techniques of coxibs is provided and the solubility of celecoxib (CXB) in binary solvent mixtures of {carbitol (1) + water (2)} is reported at temperatures ranging from 298.2 to 313.2 K. Three cosolvency models, i.e. Yalkowsky model, Jouyban–Acree model and the Jouyban–Acree–van’t Hoff model, have been used for correlating the reported data, and the mean relative deviations are employed to evaluate the accuracy of the fitness. Solubilities are also predicted by the generally trained version of the Jouyban–Acree model and its combined model with Abraham solute parameters previously proposed for {carbitol (1) + water (2)} binary mixtures. Furthermore, the apparent thermodynamic properties of dissolution process of CXB in all -investigated solvents were calculated according to van’t Hoff and Gibbs equations.     

Solubility of minoxidil in binary mixture of ethanol + water at various temperatures

ABSTRACT

The solubility of minoxidil in the aqueous binary mixtures of ethanol at different temperature are investigated and the obtained solubility data are fitted by using some cosolvency models including van’t Hoff equation, Yalkowsky model, Jouyban–Acree model and Jouyban–Acree–van’t Hoff model. The mean relative deviations (MRD%) are used to illustrate the models performance. Moreover, the apparent entropy, enthalpy, and Gibbs free energy of minoxidil dissolution process in the investigated solvent mixtures are computed using van’t Hoff and Gibbs equations. Finally, by means of the inverse Kirkwood–Buff integrals preferential solvation of minoxidil by water is observed in water-rich and ethanol-rich mixtures.     

Viscosity Investigations on the Binary Systems of (1 ChCl:2 Ethylene Glycol) DES and Methanol or Ethanol

In this study, the viscosity behavior of two mixtures of Ethaline (1 ChCl:2 ethylene glycol) with either methanol or ethanol were investigated over the temperature range of 283.15–333.15 K at atmospheric pressure. The measured viscosities of neat Ethaline, methanol, and ethanol showed reliable agreement with the corresponding reported literature values. The mixture viscosities were modeled by an Arrhenius-like model to determine the behavior of viscosity with respect to temperature. The data were also modeled by the four well-known mixture viscosity models of Grunberg–Nissan, Jouyban–Acree, McAllister, and Preferential Solvation. All of the model results were reliable, with the Jouyban–Acree and Preferential Solvation models showing the most accurate agreement with the experimental measurements. The Jones–Dole viscosity model was also investigated for the measured viscosities, and by analyzing the results of this model, strong interactions among Ethaline and the alcohol molecules were proposed for both systems. As a final analysis, viscosity deviations of the investigated systems were calculated to study the deviations of the viscosity behaviors with respect to ideal behavior. Both systems showed negative viscosity deviations at all of the investigated temperatures, with the negative values tending towards zero, and hence more ideal behavior, with increasing temperatures. Moreover, in order to correlate the calculated viscosity deviations, the Redlich–Kister model was successfully used for both systems and at each investigated temperature.     

Theoretical and Experimental Study of the Thermodynamic Solubility of Pioglitazone HCl in Ethanol, <Emphasis Type="Italic">N</Emphasis>-Methyl Pyrrolidone or Propylene Glycol + Water Mixtures at Various Temperatures

The solubilities of pioglitazone HCl (99 data points) in binary solvent mixtures of ethanol, N-methyl pyrrolidone (NMP) or propylene glycol (PG) + water are reported at three temperatures ranging from 298.2 to 308.2 K. Three different cosolvency models, those of Yalkowsky, Jouyban–Acree and combined version of the Jouyban–Acree model with the van’t Hoff approach, have been used for correlating the reported data, and the corresponding overall mean relative deviations (OMRDs) are 88.9, 19.1 and 14.8%, respectively. Also, three previously trained versions of the Jouyban–Acree model have been used for predicting the solubilities of pioglitazone HCl in the aqueous binary solvent mixtures of ethanol, NMP and PG which the prediction OMRDs are 38.9, 93.0 and 50.0%, respectively.     

Solubility of Ketoconazole in Polyethylene Glycol 200 + Water Mixtures at 298.2–318.2 K

The solubility of ketoconazole in binary mixtures of polyethylene glycol 200 (PEG 200) + water is reported at temperatures ranging from 298.2 to 318.2 K. The Jouyban–Acree model and its combined version including the van’t Hoff equation were used for correlating the reported data; the obtained mean relative deviations are 9.5 and 9.9 %, respectively. Also, two previously trained versions of the Jouyban–Acree model were used for predicting the reported data points in which the prediction errors were 34.6 and 31.0 %.     

Solubility prediction of deferiprone in N-methyl-2-pyrrolidone + ethanol mixtures at various temperatures using a minimum number of experimental data

Experimental solubility of deferiprone (DFP) in N-methyl-2-pyrrolidone (NMP) + ethanol (EtOH) mixtures at 293.2, 298.2, 303.2 and 308.2 K was determined and mathematically represented using various models. The trained versions of the van’t Hoff equation, its combined version with log-linear model, Jouyban–Acree model and a combination of van’t Hoff + Jouyban–Acree model were reported to simulate DFP solubility in the binary mixture compositions at various temperatures. The mean percentage deviation (MPD) was used as an accuracy criterion. The obtained overall MPDs for back-calculated and predicted solubility of DFP in NMP + EtOH mixtures varied from 1.1% to 3.2% and 2.6% to 6.6%, respectively. Some of apparent thermodynamic quantities for the dissolution processes of DFP are also reported.     

Correct derivation of a combined version of the Jouyban–Acree and van’t Hoff model and some comments on ‘Determination and correlation of the solubility of myricetin in ethanol and water mixtures from 288.15 to 323.15 K’

The experimental data reported in the paper by Cai and co-workers [DOI: 10.1080/00319104.2016.1163560] pertaining to the solubility of myricetin dissolved in binary aqueous–ethanol solvent mixtures has been reanalysed. A correct mathematical derivation is provided for the correlation expression from a combination of the van’t Hoff and Jouyban–Acree models. Cai et al. who used the expression in their study, however, erroneously implied that the expression resulted from a simple transformation of the Jouyban–Acree model. No mention was made that one needed to assume a van’t Hoff-type mathematical representation for how the solute solubility varied with temperature in the two mixture co-solvents.     

Thermodynamic models for determination of the solubility of dibenzothiophene in (methanol + acetonitrile) binary solvent mixtures

In this paper, we focused on solubility and solution thermodynamics of dibenzothiophene. By the gravimetric method, the solubility of dibenzothiophene was measured in (methanol + acetonitrile) binary solvent mixtures at temperatures from (278.15 to 333.15) K under atmosphere pressure. The solubility data were fitted using a modified Apelblat equation, a variant of the combined nearly ideal binary solvent/Redich–Kister (CNIBS/R–K) model and Jouyban–Acree model. Computational results showed that the modified Apelblat equation was superior to the other two equations. In addition, the thermodynamic properties of the solution process, including the Gibbs free energy, enthalpy, and entropy, were calculated by the van’t Hoff analysis. The experimental results showed that methanol could be used as effective anti-solvents in the crystallization process.     

Naproxen solubility in binary and ternary solvents of polyethylene glycols 200, 400 or 600 with ethanol and water at 298.2 K – experimental data report and modelling

The solubilities of naproxen in the binary and ternary mixtures of polyethylene glycols 200, 400 or 600 with ethanol and water (185 data points) at 298.2 K are determined and mathematically represented by cosolvency models. The obtained overall mean relative deviations (OMRDs) for fitting the solubility data of naproxen in binary and ternary mixtures using Williams–Amidon and Jouyban–Acree model are 15.7% and 16.5%, respectively, and the OMRD values for predicting the solubility data of naproxen by the trained versions of Williams–Amison and Jouyban–Acree models are 71.1% and 64.4%, respectively.     

Solubility of Cinnarizine in (Transcutol + Water) Mixtures: Determination,Hansen Solubility Parameters,Correlation, and Thermodynamics

Between 293.2 and 313.2 K and at 0.1 MPa, the solubility of the weak base, cinnarizine (CNZ) (3), in various {Transcutol-P (TP) (1) + water (2)} combinations is reported. The Hansen solubility parameters (HSP) of CNZ and various {(TP) (1) + water (2)} mixtures free of CNZ were also predicted using HSPiP software. Five distinct cosolvency-based mathematical models were used to link the experimentally determined solubility data of CNZ. The solubility of CNZ in mole fraction was increased with elevated temperature and TP mass fraction in {(TP) (1) + water (2)} combinations. The maximum solubility of CNZ in mole fraction was achieved in neat TP (5.83 × 10⁻² at 313.2 K) followed by the minimum in neat water (3.91 × 10⁻⁸ at 293.2 K). The values of mean percent deviation (MPD) were estimated as 2.27%, 5.15%, 27.76%, 1.24% and 1.52% for the “Apelblat, van’t Hoff, Yalkowsky–Roseman, Jouyban–Acree, and Jouyban–Acree–van’t Hoff models”, respectively, indicating good correlations. The HSP value of CNZ was closed with that of neat TP, suggesting the maximum solubilization of CNZ in TP compared with neat water and other aqueous mixtures of TP and water. The outcomes of the apparent thermodynamic analysis revealed that CNZ dissolution was endothermic and entropy-driven in all of the {(TP) (1) + water (2)} systems investigated. For {(TP) (1) + water (2)} mixtures, the enthalpy-driven mechanism was determined to be the driven mechanism for CNZ solvation. TP has great potential for solubilizing the weak base, CNZ, in water, as demonstrated by these results.     

Solution Thermodynamics of Piroxicam in some Ethanol + Water Mixtures and Correlation with the Jouyban–Acree Model

The solubility of piroxicam (PIR) in several ethanol + water mixtures was determined at five temperatures from 293.15 to 313.15 K. The thermodynamic functions; Gibbs energy, enthalpy, and entropy of solution and of mixing were obtained from these solubility data and the drug properties of fusion by using the van’t Hoff and Gibbs equations. The greatest solubility value was obtained in pure ethanol. A non-linear enthalpy–entropy relationship was observed from a plot of enthalpy versus Gibbs energy of solution. Accordingly, the driving mechanism for PIR solubility in water-rich mixtures is the entropy, probably due to water-structure loss around the drug’s non-polar moieties by ethanol, whereas, in ethanol-rich mixtures the driving mechanism is the enthalpy, probably due to better PIR solvation by the co-solvent molecules. The solubilities and the derived thermodynamic properties in mixed solvents were correlated using the Jouyban–Acree model.     

Solubility of sildenafil citrate in propylene glycol + water mixtures at various temperatures

The solubility of sildenafil citrate (SC) in aqueous mixtures of propylene glycol (PG) was investigated. This study was carried out at different mass fractions of PG ranging from 0.1 to 0.9 at T = 293.2–313.2 K. The solubility of SC in the mixed solutions increased with increasing temperature and PG mass fraction.

The solubility values were correlated by two co-solvency models (Jouyban–Acree model and van’t Hoff–Jouyban–Acree model). The mean relative deviations (MRD) were 5.7% and 5.5%, respectively. Density of the SC-saturated solutions over the entire solvent composition and temperature range was also measured and the results correlated with the Jouyban–Acree model. Furthermore, the apparent thermodynamic properties, dissolution enthalpy, dissolution entropy and Gibbs free energy change of dissolution process of SC in all the mixed solvents were calculated according to van’t Hoff and Gibbs equations. Dissolution of SC in these mixed solvents is an endothermic process.     

Solid–liquid phase equilibrium and mixing thermodynamic analysis of coumarin in binary solvent mixtures

The solubility of coumarin in three aqueous solvent mixtures (methanol + water, ethanol + water and acetone + water) was experimentally determined by a gravimetric method at atmospheric pressure. The experimental solubility data were fitted using the modified Apelblat equation, non-random two-liquid (NRTL) equation, the combined nearly ideal binary solvent/Redlich–Kister equation and the Jouyban?Acree equation, respectively. All the equations were proven to be able to correlate the experimental data, and the modified Apelblat equation could obtain better correlation results than the other three models. The solubility of coumarin increases with increase in temperature. At the same temperature, the solubility increases with increase in mole fraction of organic solvents except for the ethanol–water system which shows a unimodal curve. In addition, the apparent thermodynamic properties of the mixing process were calculated based on the NRTL model and the experimental solubility data.     

Solubility of budesonide in {ethanol + water} mixtures from T = (293.2 to 313.2) K: Experimental measurement and mathematical modelling

The solubility of budesonide (BDS) in binary mixtures of ethanol and water at T = (293.2–313.2) K is determined and mathematically represented using two cosolvency models, i.e. Jouyban–Acree model and Jouyban–Acree–van’t Hoff model. The mean relative deviations for fitting the solubility data of BDS in binary mixtures of ethanol + water are 6.6% and 6.5%, respectively. Furthermore, the apparent thermodynamic properties, dissolution enthalpy, dissolution entropy, and Gibbs free energy change of dissolution process of BDS in all the mixed solvents were calculated according to van’t Hoff and Gibbs equations. Dissolution of BDS in these mixed solvents is an endothermic process.