Solubility Data In Monosolvents Research Articles

Equilibrium solubility of dinitolmide in several neat solvents and binary aqueous co-solvent mixtures: Experimental determination and thermodynamic analysis

The dinitolmide solubility in twelve pure solvents such as methanol, ethanol, n-propanol, isopropanol, n-butanol, ethylene glycol (EG), ethyl acetate, dimethyl sulfoxide (DMSO), acetonitrile, cyclohexane, 1,4-dioxane and water and co-solvent mixtures of ethanol (1) + water (2), isopropanol (1) + water (2) and EG (1) + water (2) was studied by using a saturation shake-flask method over the temperatures from 283.15 K to 328.15 K under local atmospheric pressure p = 101.2 kPa. It was highest in solvent DMSO and lowest in solvent water. The achieved solubility data in monosolvents was mathematically described through the modified Apelblat equation; and in the binary mixtures, the Jouyban-Acree model. For the monosolvents, the maximum values of root-mean-square deviation and relative average deviation were 2.71 × 10−4 and 1.27%, respectively; and for the binary solvent mixtures, 0.276 × 10−4 and 1.46%. The solubility was correlated to KAT parameters and cavity term based on linear solvation energy relationships concept to investigate on the solvent effect. Results showed that the solubility in monosolvents depended significantly upon the Hildebrand parameter and nonspecific dipolarity/polarizability interactions. Quantitative values for the local mole fraction of ethanol (isopropanol or EG) and water around the dinitolmide were computed by using the Inverse Kirkwood–Buff integrals method. Dinitolmide was preferentially solvated by water in water-rich compositions; while in the intermediate and co-solvent-rich compositions for the aqueous mixtures of ethanol (isopropanol or EG), dinitolmide is preferentially solvated by the co-solvent. The preferential solvation magnitude of dinitolmide was higher in isopropanol mixtures than that in the other two solvent mixtures. Furthermore, transfer Gibbs free energy (ΔtrGo), enthalpy (ΔtrHo), and entropy (ΔtrSo) were deduced, demonstrating that the solubilization capacity was more favorable in the intermediate concentration of ethanol (isopropanol or EG).

Solubility Determination and Correlation of Glibenclamide in 11 Monosolvents and (Acetone + Acetonitrile) Binary Solvents from 283.15 K to 323.15 K

Glibenclamide (GCM) is an oral antihyperglycemic drug and widely used to treat type-II diabetes. The quality of the GCM product impacts the efficacy of the medicine. However, the quality of the product is determined by the crystallization process, in which the solubility property plays a significant role. In this study, GCM solubility in 11 monosolvents (methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, acetone, acetonitrile, methyl isobutyl ketone, methyl acetate and ethyl acetate) and (acetone + acetonitrile) binary solvents, has been determined through a gravimetric method from 283.15 K to 323.15 K. It elucidates that GCM has the highest solubility in acetone among the 11 monsolvents. Meanwhile, the solubility of GCM in (acetone + acetonitrile) binary solvents increases when the mole fraction of acetone rises. Then, we correlated the solubility data in monosolvents using the modified Apelblat model and nonrandom two-liquid (NRTL) model. Besides, the modified Apelblat model, the CNIBS/R-K...

Solubility Measurement and Thermodynamic Properties of Levetiracetam in Pure and Mixed Solvents

In this work, the solid–liquid equilibrium for levetiracetam in 10 neat solvents (methanol, ethanol, n-propanol, isopropanol, acetone, acetonitrile, ethyl acetate, 1,4-dioxane, toluene, and cyclohexane) and binary liquid mixtures (ethanol + ethyl acetate) was measured by using a static gravimetric method at temperatures T = 283.15–323.15 K under pressure of 101.2 kPa. In general, the equilibrium solubility was highest in methanol and lowest in cyclohexane. The modified Apelblat equation, λh equation, Wilson model, and NRTL model were used to correlate the solubility data in monosolvents; and the Jouyban–Acree model, van’t Hoff–Jouyban–Acree model, and Apelblat–Jouyban–Acree model were used to correlate the experiment data in the binary solvent mixtures. Compared with the results of the above models, the calculated solubility provided good results with the experimental data. Consequently, for the monosolvents, the values of root-mean-square deviation and relative average deviation were not exceeding 9.91 ×...

Solubility and thermodynamics of lamotrigine in carbitol + water mixtures from T = (293.2 to 313.2) K

The solubility of lamotrigine (LTG) are measured in aqueous mixtures of carbitol at temperatures ranging from 293.2 to 313.2 K. LTG solubility increases with increasing mass fraction of carbitol, and maximum solubility is observed in neat carbitol. Four cosolvency mathematical models; i.e., Yalkowsky model, Jouyban–Acree model, Jouyban–Acree–van’t Hoff model and modified Wilson model are fitted to the experimental results, and back-calculation is performed by using the solubility data in monosolvents in which the mean relative deviation of the investigated models are 64.8%, 9.0%, 7.2%, and 46.7%, respectively. Furthermore, the apparent thermodynamic properties of the dissolution process are computed according to van’t Hoff and Gibbs equations. The preferential solvation is analyzed based on the inverse Kirkwood-Buff integrals by using the solubility values at 298.2 K. LTG is preferentially solvated by water in water-rich mixtures (0.00 < x1 < 0.12) and by carbitol in mixtures with solvent composition of 0.12 < x1 < 1.00.

Solid–liquid phase equilibrium and thermodynamic analysis of prothioconazole in mono-solvents and binary solvents from 283.15 K to 313.15 K

Solid-liquid phase equilibrium solubility of prothioconazole in seven mono-solvents and (2-propanol±cyclohexane, 1-butanol±cyclohexane) binary solvent mixtures was determined by gravimetric method from 283.15 K to 313.15 K at atmospheric pressure. The solubility of prothioconazole increased with increasing temperature in all tested solvents. In mono-solvents, the solubility values at a fixed temperature ranked as: 1-butanol>1-propanol>2-propanol>methanol>2-butanol>acetonitrile>toluene. In binary solvent systems, the maximum solubility values were achieved at a certain solvent composition. The Apelblat equation, λh equation and NRTL model were employed to correlate the solubility data in mono-solvents, and the Apelblat equation in two binary solvent mixtures. The selected thermodynamic models can all give acceptable results. Furthermore, the apparent standard Gibbs free energy, enthalpy and entropy for the dissolution of prothioconazole were calculated, which indicates that the dissolution process of prothioconazole is an endothermic and entropy favorable process.

Solubility modelling and dissolution properties of 5-phenyltetrazole in thirteen mono-solvents and liquid mixtures of (methanol + ethyl acetate) at elevated temperatures

The solid-liquid phase equilibrium of 5-phenyltetrazole in thirteen mono-solvents including methanol, ethanol, n-propanol, isopropanol, acetone, 2-butanone, acetonitrile, ethyl acetate, toluene, 1,4-dioxane, cyclohexane, dimethyl sulfoxide (DMSO), N,N-dimethyl formamide (DMF) and liquid mixtures (methanol+ethyl acetate) were obtained experimentally via the isothermal saturation method within the temperatures from (283.15 to 318.15)K under about 101.2kPa. It was intuitive to notice that the solubility values of 5-phenyltetrazole in studied solvents increased with increasing temperature. The descending order of the solubility data in different mono-solvents was as follows: DMSO>DMF>acetone>methanol>(ethanol, 2-butanone)>isopropanol>n-propanol>1,4-dioxane>ethyl acetate>acetonitrile>toluene>cyclohexane. For the binary solvent mixtures of (methanol+ethyl acetate) with given initial compositions, the maximum solubility was observed in neat methanol. The solubility data in mono-solvents were correlated and calculated by using the modified Apelblat equation and the Buchowski-Książczak λh equation; and in the binary solvent mixtures, by three cosolvency models. The largest values of RAD and RMSD were 1.25% and 4.83×10−4, respectively. The apparent dissolution enthalpy was positive, illustrating that the dissolution process of 5-phenyltetrazole was endothermic. Finally, the preferential solvation parameters (δx1,3) of 5-phenyltetrazole in (methanol+ethyl acetate) mixtures at (293.15–313.15)K were derived by using the inverse Kirkwood–Buff integrals method. The δx1,3 values were positive in methanol-rich compositions and negative in the other regions.

Solid-liquid equilibrium of erythromycin thiocyanate dihydrate in four mono-solvents and three binary solvent mixtures

Solid-liquid equilibrium data of erythromycin thiocyanate dihydrate in four mono-solvents (methanol, ethanol, propan-1-ol and propan-2-ol) and three organic+water solvent mixtures (acetonitrile+water, acetone+water and ethanol+water) were determined by a gravimetric method under atmospheric pressure. The effects of content of organic solvents and temperature on the solubility were investigated and discussed. It was found that the content of organic solvents can significantly affect the solubility of erythromycin thiocyanate dihydrate. The modified Apelblat equation and NRTL model were applied to correlate the solubility data in mono-solvents. The GSM, two modified Jouyban-Acree models (the Van't-JA equation and the Apel-JA equation) and NRTL model were used to correlate the experimental data in three binary solvents systems. Computational results indicated that the AIC (Akaike's Information Criterion) values of two Jouyban-Acree models and NRTL model were lower than that of GSM in binary solvents mixtures, which means that the former three models are better for correlating the experimental solubility data. In addition, the mixing thermodynamic properties of erythromycin thiocyanate dihydrate in different solvents were also calculated based on the experimental solubility data and the NRTL model.

Measurement and prediction of dabigatran etexilate mesylate Form II solubility in mono-solvents and mixed solvents

UV spectrometer method was used to measure the solubility data of dabigatran etexilate mesylate (DEM) Form II in five mono-solvents (methanol, ethanol, ethane-1,2-diol, DMF, DMAC) and binary solvent mixtures of methanol and ethanol in the temperature range from 287.37K to 323.39K. The experimental solubility data in mono-solvents were correlated with modified Apelblat equation, van’t Hoff equation and λh equation. GSM model and Modified Jouyban-Acree model were employed to correlate the solubility data in mixed solvent systems. And Regressed UNIFAC model was used to predict the solubility of DEM Form II in the binary solvent mixtures. Results showed that the predicted data were consistent with the experimental data.

Solubility of Naproxen in Polyethylene Glycol 200 + Water Mixtures at Various Temperatures.

The solubility of naproxen in binary mixtures of polyethylene glycol 200 (PEG 200) + water at the temperature range from 298.0 K to 318.0 K were reported. The combinations of Jouyban-Acree model + van't Hoff and Jouyban-Acree model + partial solubility parameters were used to predict the solubility of naproxen in PEG 200 + water mixtures at different temperatures. Combination of Jouyban-Acree model with van't Hoff equation can be used to predict solubility in PEG 200 + water with only four solubility data in mono-solvents. The obtained solubility calculation errors vary from ~ 17 % up to 35 % depend on the number of required input data. Non-linear enthalpy-entropy compensation was found for naproxen in the investigated solvent system and the Jouyban-Acree model provides reasonably accurate mathematical descriptions of the thermodynamic data of naproxen in the investigated binary solvent systems.

Solubility of Glibenclamide in the Aqueous Mixtures of Polyethylene Glycol 400, Propylene Glycol and N-Methyl-Pyrrolidone at 298.2 K

Experimental solubilities of glibenclamide in polyethylene glycol 400 (PEG 400)-water, propylene glycol (PG)-water and N-methyl-pyrrolidone (NMP)-water mixtures at 298.2 K, and the experimental solubility in the mono-solvents at 298.2, 303.2, 308.2 and 313.2 K are reported. The Jouyban-Acree model was used to fit the solubility data of each drug in the binary solvent mixtures in which the mean relative deviations (MRD) for aqueous mixtures of PEG 400, PG and NMP were 7.5, 17.1 and 29.2 %, respectively, and the overall value was 17.9 %. The van't Hoff equation was used to fit the solubility data in mono-solvents at four different temperatures in which the overall MRD value was 7.2 %. A predictive method for density of saturated solutions of glibenclamide in binary solvents using the trained versions of the Jouyban-Acree model and the experimental densities of the saturated solutions in the mono-solvents was also presented.

Solubility of 2-Hydroxybenzoic Acid in Water, 1-Propanol, 2-Propanol, and 2-Propanone at (298.2 to 338.2) K and Their Aqueous Binary Mixtures at 298.2 K

Solubility of 2-hydroxybenzoic acid (salicylic acid, with measured melting point of 432 K) in water, 1-propanol, 2-propanol, and 2-propanone was determined at (298.2 to 338.2) K and atmospheric pressure. Also, the solubility of salicylic acid in binary mixtures of 1-propanol (1) + water (2), 2-propanol (1) + water (2), and 2-propanone (1) + water (2) at 298.2 K and atmospheric pressure was investigated. Phase separation occurred in x1= 0.114, 0.167 of 1-propanol (1) + water (2) and x1= 0.171, 0.237 of 2-propanone (1) + water (2) mixtures. The van’t Hoff and Grant equations were used to correlate the solubility of salicylic acid in monosolvents at different temperatures. The solubility values of salicylic acid in binary mixtures of solvents were calculated using the Jouyban–Acree model (J. Chem. Eng. Data2009, 54, 1168–1170). The mean deviation was used as an error criterion. The overall mean deviation of correlated solubility data in monosolvents at different temperatures, and in mixed solvents at 298.2 K...

Solubility of Phenothiazine in Water, Ethanol, and Propylene Glycol at (298.2 to 338.2) K and Their Binary and Ternary Mixtures at 298.2 K

The solubilities of phenothiazine in water, ethanol, and propylene glycol were measured at (298.2 to 338.2) K. Also, thesolubilityofphenothiazineinbinarymixturesofethanol þwater,propyleneglycol þwater,andethanol þpropyleneglycol,and the ternary mixture of ethanol þ propylene glycol þ water was investigated. The van't Hoff equation was used to correlate the solubility of phenothiazine in monosolvents at different temperatures. The solubility values of phenothiazine in binary and ternary mixtures of solvents were calculated using the JouybanAcree model (Jouyban, A.; Acree, W. E., Jr. J. Chem. Eng. Data 2009, 54, 1168� 1170). The mean deviation was used as an error criterion. The overall mean deviation of correlated solubility data in monosolvents at different temperatures and in mixed solvents at 298.2 K were 2.8 % and 14.2 %, respectively.

Solubility of Anthracene in C1−C3 Alcohols from (298.2 to 333.2) K and Their Mixtures with 2-Propanone at 298.2 K

The anthracene solubility in methanol, ethanol, 1-propanol, and 2-propanol from (298.2 to 333.2 K) and also in binary solvent mixtures of 2-propanone + C1-C3 alcohols at 298.2 K was reported. The van’t Hoff equation was used for correlation of the solubility data in monosolvents at different temperatures. The solubility of anthracene in mixed solvents was predicted using previously developed quantitative structure-property relationships (QSPR) that required knowledge of the solubility data in monosolvents. The overall mean percentage deviation of the correlated solubilities in monosolvents at different temperatures was 4.8 %. The corresponding value for solubility prediction methods in solvent mixtures varied from (8.5 to 11.9) %. Using ab initio prediction methods, the overall mean percentage deviations varied from (14.7 to 15.8) %.

Solubility of Phenanthrene in Binary Mixtures of C1−C4 Alcohols at 298.2 K

Experimental solubilities are reported for phenanthrene in binary solvent mixtures of methanol + 1-propanol, methanol + 1-butanol, ethanol + 1-propanol, ethanol + 1-butanol, and 1-propanol + 1-butanol at 298.2 K. Results of these measurements were used to evaluate the prediction capability of previously developed quantitative structure−property relationships employing the solubility data in monosolvents and the mean deviations (MDs) of the models' predicted values from the measured data varied between (1.7 and 42.5) %. The overall MDs (OMDs) for the prediction methods were 2.8 (± 2.7) % and 14.3 (± 23.3) %, respectively, for water-to-solvent and gas-to-solvent coefficients. Using ab initio prediction methods, the MDs varied between (6.2 and 155.8) %, and the OMDs were 11.4 (± 6.5) % and 92.1 (± 48.0) %.

Solubility of Clonazepam, Diazepam, Lamotrigine, and Phenobarbital inN-Methyl-2-pyrrolidone + Water Mixtures at 298.2 K

Experimental solubilities of clonazepam, diazepam, lamotrigine, and phenobarbital in binary solvent mixtures of N-methyl-2-pyrrolidone (NMP) + water at 298.2 K were reported. The solubility of clonazepam, diazepam, and lamotrigine was increased with the addition of NMP, and maximum values are in neat NMP. The solubility of phenobarbital was increased with addition of NMP, reached the maximum value, and then decreased with further increase in NMP concentration. The Jouyban−Acree model was fitted to the results of these measurements, and solubilities were back-calculated by employing the solubility data in monosolvents in which the overall mean deviation of the models was 10.7 %.

Solubility of Budesonide, Hydrocortisone, and Prednisolone in Ethanol + Water Mixtures at 298.2 K

Experimental solubilities of budesonide, hydrocortisone, and prednisolone in ethanol + water mixtures at 298.2 K are reported. The solubility of drugs was increased with the addition of ethanol and reached the maximum values of the volume fractions of 90 %, 80 %, and 80 % of ethanol. The Jouyban−Acree model was used to fit the experimental data, and the solubilities were reproduced using previously trained versions of the Jouyban−Acree model and the solubility data in monosolvents in which the overall mean relative deviations (OMRDs) of the models were 5.1 %, 6.4 %, 37.7 %, and 35.9 %, respectively, for the fitted model, the trained version for ethanol + water mixtures, and generally trained versions for various organic solvents + water mixtures. Solubilities were also predicted by a previously established log−linear model of Yalkowsky with the OMRD of 53.8 %.

Solubility of 7-Chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine-4-oxide, 7-Chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, and 7-Chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one in (Propane-1,2-diol + Water) at a Temperature of 303.2 K

Experimental solubilities of 7-chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine-4-oxide (chlordiazepoxide), 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one (diazepam), and 7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one (lorazepam) in (propane-1,2-diol + water) at T = 303.2 K were reported. The solubility of drugs increased with the addition of propane-1,2-diol and reached the maximum values in pure propane-1,2-diol. The Jouyban−Acree model was used to fit the experimental data, and the solubilities were reproduced using a previously trained version of the Jouyban−Acree model and the solubility data in monosolvents in which the overall mean relative deviations (OMRDs) of the back-calculated and predicted values with the corresponding experimental data were 4.2 % and 10.7 %. The solubilities of the three drugs were also predicted using a trained version of the log−linear model of Yalkowsky, and the OMRD was 21.1 %.

Solubility of Benzodiazepines in Polyethylene Glycol 200 + Water Mixtures at 303.2 K

Experimental solubilities of chlordiazepoxide, diazepam, and lorazepam in polyethylene glycol 200 (PEG 200) + water mixtures at 303.2 K were reported. The solubility of each drug increased exponentially with the addition of PEG 200 and reached the maximum value in neat PEG 200. The Jouyban−Acree model was used to mathematically describe the experimental data, and the solubilities were predicted using a previously trained version of the Jouyban−Acree model for PEG + water mixtures and the solubility data in monosolvents. The overall mean relative deviations of the models were 3.7 % and 18.3 %, respectively, for the fitted model and the trained version.

Solubility of Chlordiazepoxide, Diazepam, and Lorazepam in Ethanol + Water Mixtures at 303.2 K

Experimental solubilities of three benzodiazepines (chlordiazepoxide, diazepam, and lorazepam) in ethanol + water mixtures at 303.2 K are reported. The solubility of drugs was increased with the addition of ethanol and reached the maximum value of a volume fraction of 90 % of ethanol. The Jouyban-Acree model was used to fit the experimental data, and the solubilities were reproduced using previously trained version of the Jouyban-Acree model and the solubility data in monosolvents in which the overall mean relative deviations (OMRDs) of the models were 8.6 %, 21.9 % and 19.3 %, respectively, for the fitted model, the trained version for ethanol + water mixtures and generally trained version for various organic solvents + water mixtures.

Solubility of Lamotrigine, Diazepam, Clonazepam, and Phenobarbital in Propylene Glycol + Water Mixtures at 298.15 K

Experimental solubilities of four antiepileptic drugs, that is, lamotrigine, diazepam, clonazepam, and phenobarbital in propylene glycol + water mixtures at 298.15 K were reported. The solubility of drugs was increased with the addition of propylene glycol, and the maximum values are observed in neat propylene glycol. The Jouyban−Acree model was used to fit the experimental data, and the solubilities were reproduced using a previously trained version of the Jouyban−Acree model and the solubility data in monosolvents in which the overall mean deviations (OMDs) of the models were 6.0 % and 14.3 %, respectively. Solubilities were also predicted by a previously established log-linear model of Yalkowsky with an OMD of 37.7 %. More accurate predictions were provided using the Jouyban−Acree model in comparison with the log-linear model of Yalkowsky.