Combined Nearly Ideal Binary solvent/Redlich-Kister Research Articles

Thermodynamic Properties of 1,5-Pentanediamine Adipate Dihydrate in Three Binary Solvent Systems from 278.15 K to 313.15 K

In this work, solubility data of 1,5-pentanediamine adipate dihydrate in binary solvent systems of water + methanol, water + ethanol and water + N,N-dimethylformamide were experimentally measured via a static gravimetric method in the temperature range from 278.15 K to 313.15 K under atmospheric pressure. The results indicated that the solubility of 1,5-pentanediamine adipate dihydrate increased with the rising of temperature in all the selected binary solvent systems. For water + N,N-dimethylformamide, solubility increased as the mole fraction of water increased. However, the rising tendency changed when the temperature was higher than 303.15 K for water + methanol, and it would show a cosolvency phenomenon for water + ethanol. Furthermore, the solubility data were fitted with modified an Apelblat equation, NRTL model, combined nearly ideal binary solvent/Redlich Kister (CNIBS/R-K) model and Jouban–Acree model. The calculation results agreed well with the experimental data. Finally, the mixing thermodynamic properties of 1,5-pentanediamine adipate dihydrate in all tested solvents were calculated based on the experimental data and NRTL model.

Determination and correlation of naproxen solubility in polyethylene glycol dimethyl ether 250 and water mixtures

ABSTRACT The equilibrium solubility of naproxen (NAP) in the mixtures of polyethylene glycol dimethyl ether 250 (PEGDME 250) and water is determined at different temperatures (293.15–313.15 K). Some cosolvency models including the van’t Hoff, the mixture response surface (MRS), the Jouyban-Acree, the Jouyban-Acree–van’t Hoff, the combined nearly ideal binary solvent/Redlich–Kister (CNIBS/R-K), the Buchowski–Ksiazczak, the modified Wilson (MW) and the MW–van’t Hoff models can describe the equilibrium of solid–liquid systems successfully. Therefore, the performance of these models in correlation of current data was examined by calculation of average relative deviation (ARD%). The results present a good applicability of selected models in correlation of NAP solubilities; however, the van’t Hoff, CNIBS/R-K, MRS and Jouyban-Acree models (ARDs% ≤15.3) were more applicable than the others. At the end, the respective apparent thermodynamic quantities of dissolution and mixing processes, namely Gibb’s energy, enthalpy and entropy, are computed based on the van’t Hoff and Gibbs equations.

Solubility measurement and thermodynamic modelling of curcumin in twelve pure solvents and three binary solvents at different temperature (T = 278.15–323.15 K)

In the research, the solubility of curcumin was studied by static equilibrium method combined with HPLC. The solubility data of curcumin was measured in twelve pure solvents (dimethyl sulfoxide, tetrahydrofuran, acetone, ethyl acetate, isopropanol, acetonitrile, 1-butanol, ethanol, methanol, xylenes, n-hexane and n-heptane) and three binary solvent mixtures (acetone + tetrahydrofuran, acetonitrile + tetrahydrofuran and n-hexane + tetrahydrofuran) at different temperature (T = 278.15–323.15 K) under atmospheric pressure. The solubility values demonstrate that the solubility increased with the increase of temperature in all solvents. The modified Apelblat model and the Buchowski-Ksiazczak λh model were used to fitted the solubility data in pure solvents, the combined nearly ideal binary solvent/ Redlich-Kister (CNIBS/R-K) model and the Jouyban-Acree model were employed to adopt the solubility data in binary solvent mixtures. The RADmax of the modified Apelblat model and the λh model are 2.621% and 5.831%, the RMSDmax are 6.9 × 10-4 and 1.62 × 10-3, respectively. The RADmax of the CNIBS/R-K model and the Jouyban-Acree model are 2.249% and 4.901%, the RMSDmax are 9.33 × 10-3 and 3.67 × 10-3. Meanwhile, the KAT-LSER model was used to explore the effect of the solvation of curcumin. The fitting results of all equations prove the accuracy of the experimental data, these solubility data are very important for optimizing the extraction process and recrystallization of curcumin.

Non-electrostatic energies as a metric for prediction of deferasirox solubility in binary solvent mixtures: Polarized Continuum Model tactic

The aim of this work is to enhance deferasirox (DFX) solubility by employing the co-solvency approach. Drug solubility was studied in six different binary solvent mixtures including acetone (1) + water, acetone (1) + methanol, acetone (1) + acetonitrile, glycerol (1) + methanol, glycerol (1) + ethanol, glycerol (1) + water at 298.15 ± 0.05 K. Molecular modeling is employed to study the solvent-solvent interactions involved in the co-solvency data using the density functional theory and polarizable Continuum Model (DFT/PCM). The accuracy of the DFT/PCM theory is evaluated by comparison of its prediction values with the experimental solubility data. These results lead to the conclusion that, for acetone + water, acetone + methanol, acetonitrile + acetone and water + glycerol systems non-electrostatic effects are more important in solvent-solvent interactions. While for other solvent systems electrostatic energies are dominant. This work constitutes a major advance in the application of non-electrostatic energiesin DFT/PCM calculation and prediction of drug solubility pattern in some binary solvent mixtures. Semi-empirical models are used to determine the predictability power of the experimental co-solvency data. The combined nearly ideal binary solvent/Redlich-Kister (CNIBS/R-K) and the modified Wilson models were able to predict the experimental solubility data with MRD value of less than 35%.

Solubility of meloxicam in aqueous binary mixtures of formamide, N-methylformamide and N,N-dimethylformamide: Determination, correlation, thermodynamics and preferential solvation

In this research the experimental solubility of meloxicam (MLX) in {formamide (FM) + water}, {N-methylformamide (NMF) + water} and {N,N-dimethylformamide (DMF) + water} mixtures were determined at five temperatures, 293.15 K, 298.15 K, 303.15 K, 308.15 K and 313.15 K. MLX solubility increases with the cosolvent proportion in the mixtures and with temperature arising. Experimental solubility of MLX was modelled by using three well-known cosolvency models, namely the combined nearly ideal binary solvent/Redlich-Kister (CNIBS/R-K), Modified-Wilson model and Jouyban-Acree model. The mean relative deviation (MPD%), in the accuracy of each mathematical model in relation to experimental solubility, shown CNIBS/R-K model is better in contrast to the other models. The model results were below of 3.21% for (FM + water) mixtures, to each temperature in the study. Furthermore, these were below of 1.72% for (NMF + water) mixtures and below of 1.70% for (DMF + water) mixtures, respectively. Apparent thermodynamic quantities of dissolution and mixing, as well as the preferential solvation parameters of MLX were calculated. Gibbs energies and enthalpies of dissolution were positive whereas the respective entropies were negative. MLX is preferentially solvated by water molecules in water-rich mixtures but preferentially solvated by cosolvent molecules in mixtures of cosolvent-rich mixtures.

Measurement and modeling of sodium chloride solubility in binary mixtures of water + polyethylene glycol 400 at various temperatures

The solubilities of sodium chloride in the binary solvent system water + PEG 400 were measured by a synthetic method using of a laser-assembled instrument at five temperatures between 298.2 K and 318.2 K. The mole fraction solubility decreased nonlinearly with increasing mass fraction of PEG 400, less pronounced in the water-rich range, steeper with increasing mass fractions of PEG 400 of about 0.6. The highest mole fraction solubility of the salt was 0.1004 measured in neat water at 313.2 K, the lowest solubility was 0.0352 at 293.2 K in pure PEG 400.For the purpose of obtaining solubilities at temperatures and solvent compositions others than the measured ones the following correlation models were applied: The Yalkowsky, the van't Hoff, the combined nearly ideal binary solvent/Redlich-Kister (CNIBS/R-K), the Jouyban-Acree, and the van't Hoff-Jouyban-Acree model. The Overall Mean Percentage Deviation (OMPD) and Mean Percentage Deviation (MPD) were used to evaluate the constructed models for the entire set of the fifty-five data and for the sub-sets of the solubilities, respectively. The lowest OMPD values of 0.6% and 1.2%, respectively, and thus the best prediction abilities, exhibited the van't Hoff and the CNIBS/R-K models. The van't Hoff-Jouyban-Acree model with OMPD of 4.9% allows the calculation of the solubility at any temperature and at any solvent composition by a single model equation.

Solubility of ketoconazole in 1,4-dioxane + water mixtures at T = (293.2 to 313.2) K

Abstract The solubility of ketoconazole was measured in aqueous mixtures of 1,4-dioxane at T = (293.2 to 313.2) K using the shake flask method. To mathematically represent the generated solubility data, combined nearly ideal binary solvent/Redlich-Kister (CNIBS/R-K), van't Hoff, Jouyban-Acree, Jouyban-Acree-van't Hoff, UNIQUAC, and NRTL models were applied. Differences of experimental and predicted values were expressed as the percentage of averaged relative deviation (% ARD). Apparent thermodynamic quantities of ketoconazole dissolution and mixing were reported at harmonic temperature. Moreover, the dissolution mechanism of ketoconazole was studied in 1,4-dioxane + water mixtures. Based on the inverse Kirkwood-Buff integrals, the preferential solvation parameters were calculated and it is observed that ketoconazole is preferentially solvated by water in water-rich and 1,4-dioxane-rich mixtures.

Solubility of mesalazine in {1-propanol/water} mixtures at different temperatures

Mesalazine solubility is important to study in solvent mixtures for chemical and pharmaceutical engineering. Therefore, solubility of the drug was determined in water/1-propanol mixtures at T = (293.2 to 313.2) K. To represent the solid-liquid equilibrium for these systems, the van't Hoff, Apelblat, combined nearly ideal binary solvent/Redlich-Kister (CNIBS/R-K), modified Wilson, Jouyban-Acree, Jouyban-Acree-van't Hoff, Wilson, NRTL and UNIQUAC models were employed. The thermodynamic quantities of dissolution and mixing were calculated for mesalazine in aqueous 1-propanol solutions at harmonic temperature. Further, calculations of inverse Kirkwood-Buff integrals show that this drug is preferentially solvated by water in all the mixtures, with exception of x1 = 0.20, at 298.2 K.

The solubility of ketoconazole in binary carbitol + water mixtures at T = (293.2–313.2) K

The solid-liquid equilibrium of ternary {ketoconazole + carbitol + water} systems was studied by a shake-flask technique at T = (293.2–313.2) K and atmospheric pressure. The temperature and solvent composition dependency models of Jouyban-Acree, Jouyban-Acree-van't Hoff, NRTL, UNIQUAC and Wilson as well as solvent composition dependency models of combined nearly ideal binary solvent/Redlich-Kister (CNIBS/R-K) and modified Wilson were utilized for modeling the experimental solubility data. To predict the solubility data, Yalkowsky and extended Yalkowsky models were utilized. It was observed that the solubility of ketoconazole was increased with the enhancement in temperature and concentration of carbitol. According to the % ARD values, order of performance of the models with temperature and solvent composition dependencies are Jouyban-Acree-van't Hoff > NRTL > Jouyban-Acree > UNIQUAC > Wilson. The % ARD values indicate that in comparison between the models with solvent composition dependency, CNIBS/R–K model has a better consistency with the experimental data. Further, the computed thermodynamic properties of dissolution for ketoconazole in aqueous carbitol solutions suggest that except in neat water, enthalpy has the main contribution to standard Gibbs free energies of dissolution. Finally, preferential solvation analysis based on the inverse Kirkwood-Buff integrals demonstrates that ketoconazole is preferentially solvated by water in water-rich mixtures but preferentially solvated by carbitol in mixtures of 0.12 < x1 < 1.00.

Measurement and modeling correlation of capecitabine solubility in n-hexane + ethyl acetate and n-heptane + ethyl acetate at various temperatures

In this work, by using laser dynamic isothermal method, the solubilization behavior and thermodynamics of capecitabine solubility in the binary mixtures of n-hexane + ethyl acetate and n-heptane + ethyl acetate from (278.15 to 323.15) K were measured under atmospheric pressure. The measured results showed that the experimental solubility of capecitabine increased non-linearly with increasing temperature and ethyl acetate content (w1) in the studied mixture solvents. Six cosolvency mathematical models including the modified Apelblat equation, combined nearly ideal binary solvent/Redlich-Kister (CNIBS/R-K) equation, Wilson model, non-random two liquid (NRTL) model, UNIQUAC model, and the modified Jouyban-Acree-van't Hoff model were fitted to the experimental results. The maximum relative average deviation (ARD) was 0.27, the maximum root-mean-square deviation (RMSD) was 0.0007. The order of the relative average deviation (ARD) of the six cosolvency mathematical models is CNIBS/R-K > modified Jouyban-Acree-van't Hoff > NRTL > Wilson > modified Apelblat > UNIQUAC. Basically speaking, the measured solubility data in this study can be well correlated with the six thermodynamic models, while the modified Jouyban-Acree-van't Hoff model allowed the calculation of solubility of capecitabine at an arbitrary mixture composition and temperature in the studied binary solvent mixtures composition and temperature. Moreover, apparent thermodynamic properties of capecitabine dissolution process in the investigated mixed solvents including entropy, enthalpy and Gibbs free energy were computed using van't Hoff and Gibbs equations. Besides, the logarithm of activity coefficient of capecitabine (lnγ1) in the studied saturated solutions were also calculated with the NRTL model, UNIQUAC model, and Wilson model, respectively. The positive values of lnγ1 means that the repulsive interactions exist between capecitabine and the corresponding mixture solvents, and the solutions system positively deviate from Raoult's law. This work can give fundamental data for the crystallization and purification of capecitabine from ethyl acetate.

Measurement and Correlation of Solubilities of 5,5′-Dinitramino-3,3′-bi[1,2,4-triazolate] Carbohydrazide Salt (CBNT) in Various Pure Solvents and a Binary Mixture (Dimethyl Sulfoxide + Water) from 298.15 to 343.15 K

The solubilities of an energetic material, 5,5′-dinitramino-3,3′-bi[1,2,4-triazolate] carbohydrazide salt (CBNT), were measured in eleven pure solvents (deionized water, methanol, ethanol, ethylene glycol, isopropanol, ethyl acetate, 1,2-dichloroethane, acetone, N,N-dimethylformamide, N-methyl pyrrolidone, and dimethyl sulfoxide (DMSO)) and a binary solvent mixture of (DMSO + water) under atmospheric pressure using a gravimetric method. The solubility data in pure solvents were fitted using the modified Apelblat equation. The solubility data of CBNT in binary solvents were correlated by the modified Apelblat equation, the combined nearly ideal binary solvent Redlich–Kister (CNIBS/R-K) model and the Jouyban–Acree model. All the fitting processes gave satisfying values of the correlation coefficient (R2) and the root-mean-square-deviation. The measurements and the correlation of CBNT solubility provide fundamental data for its practical application.

Thermodynamic Models for Determination of Solid–Liquid Equilibrium of the Buprofezin in Pure and Binary Organic Solvents

Buprofezin is a kind of insecticide and an important chemical intermediate product. Data on solid–liquid equilibrium of buprofezin in different solvents is essential for the area of industrial applications. In this work, the solubility of buprofezin in methanol, ethanol, isopropanol, n-butanol, acetonitrile, n-hexane, ethyl acetate, N,N-dimethylformamide, and two binary solvent mixtures (methanol + ethyl acetate and acetonitrile + ethyl acetate) was measured at the temperature range of 278.15–328.15 K at atmospheric pressure by the gravimetric method. The experimental values showed that elevated temperatures increased the solubility of buprofezin in all selected solvents. The modified Apelblat model, the Buchowski–Ksiazaczak λh model, combined nearly ideal binary solvent/Redlich–Kister (CNIBS/R-K) model, Jouyban–Acree model, and an ideal model were used to describe and predict the diversification trend of solubility.

Solubility of acetaminophen in 1-propanol + water mixtures at T = 293.2–313.2 K

ABSTRACT The mole fraction solubilities of acetaminophen (ACP) were measured in the binary solvent mixtures of {1-propanol + water} at T = 293.2–313.2 K. The Jouyban–Acree, Jouyban–Acree–van’t Hoff, combined nearly ideal binary solvent/Redlich–Kister (CNIBS/R-K) and modified Wilson models as well as a non-linear model presented by Machatha et al. were used to correlate the measured equilibrium solubilities. Furthermore, the experimental data were predicted with five predictive models, i.e. Yalkowsky, extended Yalkowsky as well as trained versions of Yalkowsky, Jouyban–Acree and Jouyban–Acree–Hansen models. Moreover, the apparent standard molar Gibbs energy, enthalpy, and entropy of dissolution and mixing (, , , , , ) of ACP in {1-propanol (1) + water (2)} mixtures were calculated at mean harmonic temperature T hm = 303 K based on van’t Hoff and Gibbs free energy equations. Additionally, preferential solvation parameters of ACP in the mixtures were also analysed based on the inverse Kirkwood–Buff integrals.

Lamotrigine solubility in 1-propanol + water mixtures at different temperatures: experimental data and mathematical modelling

ABSTRACT The solubility of lamotrigine (LTG) was determined in {1-propanol (1) + water (2)} mixtures over a temperature range of 293.15 to 313.15 K. The measured data were correlated to cosolvency models namely Jouyban-Acree, Jouyban-Acree-van’t Hoff, combined nearly ideal binary solvent/Redlich-Kister (CNIBS/R-K), modified Wilson and Machatha models. Among the models, Jouyban-Acree with temperature and solvent composition dependencies has more accuracy rather than Jouyban-Acree-van’t Hoff model and CNIBS/R-K model with solvent composition dependency is more compatible with the experimental solubility data. Furthermore, the apparent standard molar Gibbs energy, entropy, and enthalpy of dissolution and mixing , , , , and for LTG in the studied binary mixtures were calculated based on the van’t Hoff and Gibbs free energy equations which suggest that the dissolution process is more favourable in 1-propanol-rich mixtures and proceeds entropically. Finally, preferential solvation parameters of LTG by 1-propanol were also calculated by means of the inverse Kirkwood-Buff integrals.

Further computations on the solubility of 2-methyl-1,3-benzothiazol-5-amine in ethanol + water mixtures at several temperatures

ABSTRACT The recently reported solubility data of 2-methyl-1,3-benzothiazol-5-amine in the binary mixtures of {ethanol (1) + water (2)} at various temperatures have been used to present further numerical calculations and thermodynamic analysis. In this regard, the Jouyban-Acree, combined nearly ideal binary solvent/Redlich–Kister (CNIBS/R-K), Jouyban-Acree–van’t Hoff, Yalkowsky and modified Wilson models were used to correlate the solubility data. In addition, the prediction based on the minimum number of experimental data were examined by Jouyban-Acree–van’t Hoff and extended Yalkowsky models as well as trained version of Jouyban-Acree model presented in our previous research. Finally, the thermodynamic functions, apparent Gibbs free energy, enthalpy and entropy of the dissolution were calculated based on the van’t Hoff equation.

Solubility of p-Aminobenzoic Acid Potassium in Organic Solvents and Binary (Water + Isopropyl Alcohol) Mixture at Temperatures from (283.15 to 318.15) K

The solid–liquid equilibrium behavior of p-aminobenzoic acid potassium (KPAB) in pure organic solvents and binary (water + isopropyl alcohol) solvents were determined over the temperature range (283.15–318.15) K using a laser dynamic method. It was found that KPAB is easily dissolved in water, polyhydroxy alcohols and amides; slightly soluble in ethyl acetate, isopropyl alcohol, and n-propanol. The solubility of KPAB in both the mono- and binary mixed solvents increases with the increasing temperature, whereas it decreases with the rise of mole fraction of isopropyl alcohol in binary (water + isopropyl alcohol) mixed solvents. The solubility in pure solvents was correlated by the modified Apelblat equation, and the solubility in binary mixed solvents was correlated with the modified Apelblat equation and Combined Nearly Ideal Binary Solvent/Redlich–Kister (CNIBS/R-K) model. All the models give satisfactory correlation results with an average relative deviation (ARD) less than 2.5%, which provide basic dat...

Thermodynamic equilibrium and cosolvency of florfenicol in binary solvent system

The solubility of florfenicol in binary solvent mixtures of acetone+(methanol or ethanol or isopropanol) was experimentally measured at temperature ranging from 278.15K to 318.15K under atmospheric pressure (p=0.1MPa) by using the gravimetric method. In all the tested solvent systems, the solubility of florfenicol increases monotonically with increasing temperature at fixed solvent composition. While, as regards solvent composition, it shows a cosolvency phenomenon where the solubility has a maximum at a certain solvent compostion. The cosolvency was interpreted via mathematical model correlation using modified Apelblat equation, NRTL model, combined nearly ideal binary solvent/ Redlich–Kister (CNIBS/R-K) model, and Jouban-Acree model. Moreover, thermodynamic properties of the investigated systems including entropy, enthalpy and Gibbs free energy of the solubility data were calculated using NRTL model. The solubility results may be helpful to developing a proper crystallization process of yielding florfenicol nanoparticles.

Remarkes on “solubility and solution thermodynamics of meldrum's adduct in ethyl acetate plus (acetonitrile, ethanol, hexane) binary solvent mixtures”

Combined Nearly Ideal Binary Solvent/Redlich-Kister (CNIBS/R-K) equations and van't Hoff-Jouyban-Acree model reported by Liu and coworkers [J. Mol. Liq. 220 (2016) 354–363] for calculating the solubility of meldrum's adduct in ethyl acetate plus (acetonitrile, ethanol, hexane) binary solvent mixtures at various temperatures. The authors of cited reference erroneously curve-fit the solubility data with multiplying the solubility value by ten times in the case of published equation coefficients for the CNIBS/R-K model. In addition, the authors of cited reference applied original van't Hoff-Jouyban-Acree model to predict meldrum's adduct solubility in mixed solvents at different temperatures, but that overlooked the fact that they did not measure the solubility data for meldrum's adduct in neat solvents. Furthermore, in determining the numerical values of the equation coefficients, no pure solvent solubility data were included in the regression analyses.

Commentary on “experimental measurements and equilibrium study of functional d-sorbitol in good and anti-solvent binary mixtures”

Problems are identified regarding the published equation coefficients of Hu and coworkers [J. Mol. Liq. 238 (2017) 296–302] for mathematically describing the solubility behavior of d-sorbitol in binary acetonitrile+ethanol solvent mixtures using the modified Apelblat, Combined Nearly Ideal Binary Solvent/Redlich-Kister (CNIBS/R-K) and Jouyban-Acree models. The published equation coefficients for the modified Apelblat and CNIBS/R-K models calculate one thousand times the mole fraction solubility of d-sorbitol, rather than the mole fraction solubility as stated in the published paper. More serious errors were found regarding the authors' analyses using the Jouyban-Acree model.

Commentary on “Measurement and correlation of solubility of 1,3,5-trioxane in binary solvents from (288.15 to 328.15) K”

Combined Nearly Ideal Binary Solvent/Redlich-Kister (CNIBS/R-K) equations reported by Li and coworkers [J. Mol. Liq. 234 (2017) 469–480] for calculating the solubility of 1,3,5-trioxane in four binary aqueous-organic solvent mixtures do not describe the solute's observed solubility in the water mono-solvent. Failure of the published CNIBS/R-K expressions result because the authors did not measure the aqueous solubility of 1,3,5-trioxane. No aqueous solubility data were included in the regression analyses used in determining the numerical values of the equation coefficients. New CNIBS/R-K equations are derived by combining the measured solubility determined by Li and coworkers with previously published solubility data for 1,3,5-trioxane in water taken from the chemical literature.