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 Ketoconazole in Binary and Ternary Solvents of Polyethylene Glycols 200, 400 or 600 with Ethanol and Water at 298.2 K. Data Report and Analysis

The solubilities of ketoconazole in binary and ternary mixtures of water, ethanol and polyethylene glycols 200, 400 or 600 (185 data points) were determined at 298.2 K. Williams–Amidon and Jouyban–Acree cosolvency models were used to model the data, with overall mean relative deviations (OMRDs) for the solubility data in binary and ternary solvents of 17.5 and 23.5%, respectively. For predicting the solubility data of ketoconazole the trained versions of the models were used and the OMRD values were 47.7 and 33.0%, respectively.     

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.     

Solubility prediction of polycyclic aromatic hydrocarbons in non-aqueous solvent mixtures

This study is aimed at evaluating the applicability of the Jouyban–Acree model for predicting the solubility of polycyclic aromatic hydrocarbons (PAHs) in binary and ternary solvent mixtures at different temperatures by employing a large solubility data set. The solubility is predicted in solvent mixtures at different temperatures within an acceptable error range based on the experimental solubility data of PAHs in mono-solvents. The results reveal that the Jouyban–Acree model could be recommended for practical applications in chemical industries.     

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.     

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.     

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.     

Solubility prediction of paracetamol in binary and ternary solvent mixtures using Jouyban-Acree model

The Jouyban-Acree model has been used to predict the solubility of paracetamol in water-ethanol-propylene glycol binary and ternary mixtures based on model constants computed using a minimum number of solubility data of the solute in water-ethanol, water-propylene glycol and ethanol-propylene glycol binary mixtures. Three data points from each binary solvent system and solubilities in neat solvents were used to calculate the binary interaction parameters of the model. Then the solubility at other binary solvent compositions as well as in a number of ternary solvents were predicted, and the mean percentage deviation (+/-S.D.) of predicted values from experimental solubilities was 7.4(+/-6.1)%.     

Models to predict solubility in ternary solvents based on sub-binary experimental data

The capability of the extended forms, of two well established cosolvency models, i.e. the combined nearly ideal binary solvent/Redlich-Kister equation and the modified Wilson model, used to predict the solute solubility in non-aqueous ternary solvent mixtures is presented. These predictions are based on the measured solubilities of anthracene in binary solvent mixtures. As a result the values of average percent deviations were less than 2% for the anthracene solubility in ternary mixtures. This work was also extended to other cosolvency models, ie. the extended Hildebrand solubility approach and the mixture response surface method, which are also commonly used for correlating solubility data in ternary solvents. The accuracy of the models is compared with each other and also with a published solubility model for ternary mixtures. The results illustrate that all models produced comparable accuracy.     

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.     

Solubilization of naproxen using N-methyl-2-pyrrolidone or ethanol and β-cyclodextrin

Solubility trend of naproxen in the presence of 5 and 10 mM of β-CD was measured at 298.2 K and compared with solubility profiles in the absence of β-CD for water + cosolvent mixtures. The saturated solutions of the given volume fractions were reached using shake-flask method, and then the solubility values were measured by UV spectrophotometric method at 256 nm. Afterwards, the experimental solubility data points of naproxen in water + ethanol (EtOH) and water + N-methyl-2-pyrrolidone with and without β-cyclodextrin (β-CD) were correlated with Jouyban–Acree model. Calculation results revealed that the back-calculated solubilities were in good agreement with the corresponding experimental values. By applying the correlated equations, one can rapidly predict the solubility of naproxen in all solvent compositions.     

Solubility prediction of paracetamol in water-ethanol-propylene glycol mixtures at 25 and 30 degrees C using practical approaches

The solubility of paracetamol in water-ethanol-propylene glycol binary and ternary mixtures at 25 and 30 degrees C was determined using flask shake method. The generated data extended the solubility database for further computational investigations and also was used to assess the prediction capability of the Jouyban-Acree model. A new version of the model was proposed for modeling the solubility data in water-cosolvent mixtures with the cosolvent concentration of <50% which is required in pharmaceutical formulations. The accuracy of the predicted solubilities was evaluated by the mean percentage deviation (MPD) between the predicted and experimental solubilities. The overall MPD of the Jouyban-Acree model and the log-linear model of Yalkowsky for the entire composition range of the cosolvents were 11.0+/-8.7 and 55.4+/-17.8%, respectively; the corresponding values for the predicted solubilities in mixtures having a cosolvent concentration of <50% were 12.0+/-9.1 and 22.0+/-11.0%.     

Solubility and preferential solvation of phenacetin in methanol + water mixtures at 298.15 K

The mole fraction solubility of phenacetin (PNC) in methanol + water binary solvent mixtures at 298.15 K was determined along with density of the saturated solutions. All these solubility values were correlated with the Jouyban–Acree model. Preferential solvation parameters of PNC by methanol (δx_1,3) were derived from their thermodynamic solution properties using the inverse Kirkwood–Buff integrals (IKBI) method. δx_1,3 values are negative in water-rich mixtures but positive in methanol mole fraction of >0.32. It is conjecturable that in the former case the hydrophobic hydration around non-polar groups of PNC plays a relevant role in the solvation. The higher solvation by methanol in mixtures of similar cosolvent compositions and methanol-rich mixtures could be explained in terms of the higher basic behaviour of methanol.     

Solubility of anthracene in binary alcohol + 1-pentanol solvent mixtures at 25°C: Comparison of expressions derived from Mobile Order theory and the Kretschmer-Wiebe association model

A relatively simple expression is developed for predicting the solubility of an inert crystalline solute in binary alcohol + alcohol solvent mixtures based upon the Kretschmer-Wiebe association model. The predictive accuracy of the newlyderived expression is compared to equation(s) derived previously from Mobile Order theory using experimental anthracene solubilities in seven binary alcohol + 1-pentanol solvent mixtures at 25°C, which were measured as part of the present investigation. Computations show that both models accurately describe the solubility behavior of anthracene in the binary solvent systems studied. Average absolute deviations between observed and predicted values were 0.9% and 1.4% for the Kretschmer-Wiebe and Mobile Order predictive equations, respectively.     

Thermochemical investigations of nearly idial binary solvents. 6. Solubilities of iodine and benzil in systems of nonspecific interactions

Solubilities have been determined at 25°C for iodine in binary mixtures of carbon tetrachloride with cyclohexane, n-hexane, n-heptane, and octamethylcyclotetrasiloxane (OMCTS) and in mixtures of cyclohexane with n-hexane and OMCTS; and for benzil in binary mixtures of carbon tetrachloride with cyclohexane, n-hexane, and n-heptane, mixtures of n-hexane with cyclohexane and n-heptane, and mixtures of benzene with cyclohexane and toluene. With the exception of the benzene+cyclohexane system, the nearly ideal binary solvent model predicts these solubilities with a maximum deviation of 6% and an overall standard deviation of 2.4%. The model correctly predicts minima for solubility (mole fraction) of iodine in the OMCTS systems, and predicts solubilities within 4% for benzil in the carbon tetrachloride+n-hexane system, in which the solubility changes by a factor of 14. The failure of the model for predicting solubilities of benzil in mixtures of benzene and cyclohexane (maximum error of 25% for and 18-fold range of solubilities) is possibly due to specific interactions between benzil and benzene.     

Comments on “Solubility and Dissolution Thermodynamic Data of Cefpiramide in Pure Solvents and Binary Solvents”

Errors are found in the mathematical correlation based on the combined Jouyban–Acree and Modified Apelblat models for describing the variation in the mole fraction solubility of cefpiramide with temperature and solvent composition for the binary aqueous–ethanol solvent system. The equation coefficients given by Tang and coworkers, when substituted into the model equation, do not yield the authors’ calculated mole fraction solubilities of cefpiramide.     

Solubility prediction of anthracene in mixed solvents using a minimum number of experimental data

Numerical methods to predict the solubility of anthracene in mixed solvents have been proposed. A minimum number of 3 solubility data points in sub-binary solvents has been employed to calculate the solvent-solute interaction terms of a well established colsolvency model, i.e. the combined nearly ideal binary solvent/Redlich-Kister model. The calculated interaction terms were used to predict the solubility in binary and ternary solvent systems. The predicted solubilities have been compared with experimental solubility data and the absolute percentage mean deviation (APMD) has been computed as a criterion of prediction capability. The overall APMD for 25 anthracene data sets in binary solvents is 0.40%. In order to provide a predictive method, which is based fully on theoretical calculations, the quantitative relationships between sub-binary interaction terms and physicochemical properties of the solvents have been presented. The overall APMD value for 41 binary data sets is 9.19%. The estimated binary interaction terms using a minimum number of data points and the quantitative relationships have then been used to predict anthracene solubility data in 30 ternary solvent systems. The produced APMD values are 3.72 and 15.79%, respectively. To provide an accurate correlation for solubility in ternary solvent systems, an extension to the combined nearly ideal multicomponenet solvent/Redlich-Kister (CNIMS/R-K) model was proposed and the corresponding overall AMPD is 0.38%.     

4-(Methylsulfonyl)benzaldehyde Solubility in Binary Solvent Mixtures of Acetonitrile + (Methanol,Ethanol and Isopropanol): Determination and Modelling

The solubilities of 4-(methylsulfonyl)benzaldehyde in the binary mixed solvents acetonitrile + methanol, acetonitrile + ethanol and acetonitrile + isopropanol were determined experimentally using an isothermal dissolution equilibrium method within the temperature range from 283.15 to 318.15 K under atmospheric pressure. The solubility of 4-(methylsulfonyl)benzaldehyde increased with increasing temperature and mass fraction of acetonitrile in each binary system. At the same temperature and mass fraction of acetonitrile, the mole fraction solubility of 4-(methylsulfonyl)benzaldehyde is greater in (acetonitrile + methanol) than in the other two mixed solvents. The solubility data were correlated using the CNIBS/R-K model, Jouyban–Acree model, van’t Hoff–Jouyban–Acree model, Apelblat–Jouyban–Acree model, Ma model and Sun model. The maximum values of relative average deviation (RAD) and root-mean-square deviation (RMSD) are 1.53% and 1.17 × 10^?4, respectively. All of the selected models provided good representation of the experimental solubilities. Furthermore, the standard enthalpies of dissolution were calculated. The dissolution process for 4-(methylsulfonyl)benzaldehyde in these mixed solvents is endothermic. The experimental solubility and the models presented in this work are important for the production and purification of 4-(methylsulfonyl)benzaldehyde.     

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.     

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.