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%.     

Mathematical representation of solubility of electrolytes in binary solvent mixtures using Jouyban-Acree model

Applicability of a solution model for calculating salt's solubility in binary solvent mixtures was shown. The accuracy of the proposed model was evaluated by computing mean percentage deviation (MPD) employing available solubility data of electrolytes in binary solvents at various temperatures from the literature. The overall MPD (+/-S.D.) for correlation of solubility data was 4.7+/-5.1% and for prediction using model trained by a minimum number of experimental data points was 10.5+/-12.5%.     

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 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 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)%.     

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 prediction of drugs in water-polyethylene glycol 400 mixtures using Jouyban-acree model

A numerical method is proposed for predicting solubility of drugs in water-PEG 400 mixtures based on the Jouyban-Acree cosolvency model. The accuracy of the proposed method is evaluated by computing mean percentage deviation (MPD) and compared with that of log-linear model of Yalkowsky. The overall MPDs of the Jouyban-Acree model and the most accurate version of Yalkowsky's model are 39.8 (+/-46.7) % and 175.8 (+/-266.4) %, respectively, and the mean difference is statistically significant (p < 0.0005). The proposed method produces acceptable residual distribution and the probability of solubility prediction with residual log of solubility <0.5 unit is 0.86. The applicability of the proposed method could be extended for predicting the solubility of drugs in water-PEG 400 mixtures at various temperatures. The impact of various log P values computed using different software is also studied and the results of ANOVA revealed that there are no significant differences between the accuracy of the predicted solubilities employing various log P values.     

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.     

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.     

Experimental and predicted solubilities of 3,4-dichlorobenzoic acid in select organic solvents and in binary aqueous–ethanol mixtures

Experimental solubilities are reported for 3,4-dichlorobenzoic acid dissolved in methyl butyrate, and in 16 alcohol, 5 alkyl acetate, 5 alkoxyalcohol and 6 ether solvents. Solubilities were also measured in nine binary aqueous–ethanol solvent mixtures at 298.15?K. The measured solubility data were correlated with the Abraham solvation parameter model. Mathematical expressions based on the Abraham model predicted the observed molar solubilities to within 0.12 log units.     

Comparison of different algorithms to calculate electrophoretic mobility of analytes as a function of binary solvent composition

Ten different mathematical models representing the electrophoretic mobility of analytes in capillary electrophoresis in mixed solvents of different composition have been compared using 32 experimental data sets. The solvents are binary mixtures of water-methanol, water-ethanol and methanol-ethanol, respectively. Mean percentage deviation (MPD), overall MPD (OMPD) and individual percentage deviation (IPD) have been considered as comparison criteria. The results showed that a reorganized solution model, namely the combined nearly ideal binary solvent/Redlich-Kister equation, is the most accurate model among other similar models concerning both correlation ability and prediction capability.     

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.     

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.     

Determination and Correlation of the Solubility of Acetylpyrazine in Pure Solvents and Binary Solvent Mixtures

The solubilities of acetylpyrazine in seven pure solvents and one binary solvent mixture were determined by a dynamic analytic method at temperatures ranging from 268.15 to 308.15 K under atmospheric pressure. For pure solvents, the solubility of acetylpyrazine increases with increasing temperature and solvent polarity. For the binary solvent mixture of ethyl acetate and isopropanol, the solubility increases with increasing temperature and mole fraction of ethyl acetate. The solubility data were correlated with some thermodynamic models, including the modified Apelblat model, λh model, CNIBS/R-K model, and NRTL model. In addition, the relationship between solubility and solvent polarity was investigated by using the Arrhenius equation. All the models or equations gave satisfactory correlation results. The results showed that the solubility of acetylpyrazine generally rises with the increase of solvent polarity at the same temperature. Moreover, the dissolution thermodynamic properties of acetylpyrazine in different solvents were calculated and are discussed based on the NRTL model.     

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.     

Solubilities of families of heterocyclic polynuclear aromatics in organic solvents and their mixtures

The solubilities of anthracene, acridine, xanthene, thioxanthene, carbazole, dibenzofuran, and dibenzothiophene have been experimentally determined in benzene, cyclohexane, thiophene, and pyridine from ambient temperature to approximately 440 K. The results have been correlated using the classical equation for solid-liquid solubility to obtain the experimental activity coefficient of the solute in the solvent. These experimental activity coefficients have been regressed, using three common solution models, to find the binary interaction parameters needed in those models. The solubilities of biphenyl, dibenzofuran, and dibenzothiophene have been experimentally determined in five binary mixtures of the solvents. The experimental activity coefficients have been found and compared to the values predicted by the four solution models, using the binary interaction parameters obtained from the solubilities in the pure solvents and solventsolvent binary interaction parameters obtained from literature vaporliquid equilibria data. The effect of substituting various heteroatoms into the ring structure has been discussed.