Thermodynamics of 4’-bromomethyl-2-cyanobiphenyl in different solvents

The melting properties and the heat capacity of the solid state and the melt state 4’-bromomethyl-2-cyanobiphenyl (OTBNBr) were determined. The enthalpy, entropy and Gibbs free energy of fusion were also calculated. The solubility of OTBNBr in eight organic solvents was experimentally measured at temperatures from (283.15 to 323.15) K by using a static method. The reasons for the differences of the solubility of OTBNBr in various solvents are discussed by using the intermolecular interaction. Furthermore, the experimental solubility values were well correlated by the modified Apelblat equation, the λh equation, the Wilson model and the van’t Hoff equation. Finally, the temperature dependence of the activity coefficient and the van’t Hoff enthalpy in the tested solutions was investigated and is discussed.     

Solubility of daidzin in different organic solvents and (ethyl alcohol + water) mixed solvents

The solubility of daidzin in different organic solvents and (ethyl alcohol + water) mixed solvents was measured by high performance liquid chromatography (HPLC) analysis method from T = (283.2 to 323.2) K at atmosphere pressure. The results show that at higher temperature more daidzin dissolves, and moreover, the solubility increases with the ethyl alcohol mole fraction increase in the (ethyl alcohol + water) mixed solvents. The experimental solubility values were correlated by a simplified thermodynamic equation, λh equation and modified Apelblat equation. Based on the solubility of daidzin, the enthalpy and entropy of solution were also evaluated by van’t Hoff equation. The results illustrated that the dissolution process of daidzin is endothermic and entropy driven.     

Experimental measurement and modelling of solubility of inosine-5′-monophosphate disodium in pure and mixed solvents

The solubility of biological chemicals in solvents provide important fundamental data and is generally considered as an essential factor in the design of crystallization processes. The equilibrium solubility data of inosine-5′-monophosphate disodium (5′-IMPNa₂) in water, methanol, ethanol, acetone, as well as in the solvent mixtures (methanol + water, ethanol + water, acetone + water), were measured by an isothermal method at temperatures ranging from (293.15 to 313.15) K. The measured data in pure and mixed solvents were then modelled using the modified Apelblat equation, van’t Hoff equation, λh equation, ideal model and the Wilson model. The modified Apelblat equation showed the best modelling results, and it was therefore used to predict the mixing Gibbs free energies, enthalpies, and entropies of 5′-IMPNa₂in pure and binary solvents. The positive values of the calculated partial molar Gibbs free energies indicated the variations in the solubility trends of 5′-IMPNa₂. Water and ethanol (in the binary mixture with water) were found to be the most effective solvent and anti-solvent, respectively.     

Solubility and solution thermodynamics of sorbic acid in eight pure organic solvents

By the gravimetric method, the solubility of sorbic acid in eight solvents including ethanol, 2-propanol, methanol, 1-butanol, ethyl acetate, methyl tert-butyl ether, acetone and acetonitrile was determined over a temperature range from 285.15 to K at atmospheric pressure. For the temperature range investigated, the solubility of sorbic acid in the solvents increased with increasing temperature. The experimental values were correlated with the linear solvation energy relationship, modified Apelblat equation, λh equation, non-random two-liquid (NRTL) model, and Wilson model. On the other hand, the enthalpy, entropy and Gibbs free energy of dissolution were obtained from these solubility values by using the van’t Hoff and Gibbs equations. The excess enthalpy of solution was estimated on the basis of λh equation. Furthermore, the a priori predictive model COSMO-RS was employed to predict the solubility of sorbic acid in selected solvents and reasonable agreement with experimental values is achieved.     

Determination and correlation of the solubility for diosgenin in alcohol solvents

Using a laser monitoring technique, the solubility of diosgenin in ethanol, 1-propanol, 1-butanol, isobutyl alcohol, tert-butanol, 1-pentanol, and iso-octyl alcohol was measured over the temperature range from (290.15 to 330.15) K at atmospheric pressure. Its corresponding (solid + liquid) equilibrium data will provide essential support for industrial design and further theoretical studies. From the experimental results, the solubility of diosgenin in ethanol, 1-propanol, 1-butanol, isobutyl alcohol, tert-butanol, 1-pentanol, and iso-octyl alcohol was found to increase with increasing temperature and decrease with the increase of the polarity of the alcohols solvents. The Apelblat equation, the ideal model and the λh equation were used to correlate the solubility values. The results showed that the three models mentioned above agreed well with the experimental data.     

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.     

Measurement and Correlation of the Solubility of N-Acetylglycine in Different Solvents at Temperatures from 278.15 to 319.15 K

The solubility of N-acetylglycine was measured in methanol, ethanol, propanol, isopropanol, n-butanol and ethyl formate in the temperature range between 278.15 and 319.15 K under atmospheric pressure by a gravimetric method. The solubility of N-acetylglycine in those selected solvents increases with increasing temperature. The solubility data were correlated with the van’t Hoff equation, the modified Apelblat equation and the λh equation to obtain the corresponding model parameters. The experimental results could be useful for optimizing the industrial process of purification of N-acetylglycine.     

Solubility of Omeprazole Sulfide in Different Solvents at the Range of 280.35–319.65 K

Solubility data were measured for omeprazole sulfide in ethanol, 95 mass-% ethanol, ethyl acetate, isopropanol, methanol, acetone, n-butanol and n-propanol in the temperature range from 280.35 to 319.65 K by employing the gravimetric method. The solubilities increase with temperature and they are in good agreement with the calculated solubility of the modified Apelblat equation and the λh equation. The experimental solubility and correlation equation in this work can be used as essential data and model in the purification process of omeprazole sulfide. The thermodynamic properties of the solution process, including the Gibbs energy, enthalpy, and entropy were calculated using the van’t Hoff equation.     

Measurement and correlation of the solubility of genistin in eleven organic solvents from T = (283.2 to 323.2) K

The solubilities of genistin in pure solvents including tetrahydrofuran, acetone, ethyl acetate, acetonitrile, isopropanol, n-butyl alcohol, methanol, cyclohexane, n-hexane, chloroform and ethanol were determined by the high performance liquid chromatography (HPLC) analysis method at T = (283.2, 293.2, 303.2, 313.2 and 323.2) K. The fusion enthalpy of genistin was estimated by the group contribution method. The solubility data of genistin were correlated by the simplified thermodynamic model, the modified Apelblat model, λh model and NRTL (Non-Random Two-Liquid) model. The calculated values by all models were in good agreement with the experimental values and however, the NRTL model could give better correlation results than other three models.     

Solubilities of oleanolic acid and ursolic acid in (ethanol + water) mixed solvents from T = (292.2 to 328.2) K

The solubility of oleanolic acid and of ursolic acid in (ethanol + water) mixed solvents was measured over the temperature range of (292.2 to 328.2) K. The solubility of oleanolic acid and of ursolic acid in the (ethanol + water) mixed solvent systems increase with increasing the mole fraction of ethanol in mixed solvents. The experimental solubility data are correlated by a simplified thermodynamic equation and the modified Apelblat equation.     

Solubility of l-tartaric Acid in Ethanol, Propanol, Isopropanol, n-Butanol, Acetone and Acetonitrile

The solubility of l-tartaric acid was measured in ethanol, propanol, isopropanol, n-butanol, acetone and acetonitrile in the temperature range 281.15 and 324.25 K under atmospheric pressure by a gravimetric method. The solubility of l-tartaric acid in those selected solvents increases with increasing temperature. The apparent molar enthalpies of solution of l-tartaric acid in the selected solvents were estimated from the solubility data. The solubility results were correlated with the van’t Hoff equation, the modified Apelblat equation, and the λh equation. Agreement with the experimental data was very good in all cases. The experimental results could be useful for optimizing the purification process of l-tartaric acid in industry.     

Solubility of diosgenin in different solvents

The solubility of diosgenin in methanol, ethanol (95%), isopropanol, acetone, acetic ether, and propyl acetate were measured at temperatures from (295.15 to 330.15) K using the synthetic method by a laser monitoring observation technique at atmospheric pressure. Its corresponding (solid + liquid) equilibrium data will provide essential support for industrial design and further theoretical studies. The solubility data of diosgenin in isopropanol, acetone, ethanol (95%), and acetic ether were correlated with Apelblat equation, and the experimental data of diosgenin in methanol and propyl acetate were also correlated with the λh model. The calculated values were good in agreement with the experimental values.     

Determination and correlation of the solubility of tricin in water and ethanol mixtures

The solubility of tricin in water and ethanol mixtures was measured over the temperature range of (288.15 to 328.15) K. The concentrations of tricin in the aqueous mixtures were assayed by the ultraviolet spectrophotometric method. The experimental solubility data indicated that the solubility of tricin increases with an increase in temperature and an enrichment in ethanol content. The two models, including the modified Apelblat equation and λh equation were used to correlate the experimental solubility data. The calculated solubility of tricin shows good agreement with the experimental results. Additionally, the estimation of thermodynamic properties including the activity coefficients, dissolution enthalpy, and entropy were obtained from the experimental data. Within the studied temperature range the dissolution process of tricin is endothermic, and the driving force is the entropy.     

Solubility measurement and modelling of 1,8-dinitronaphthalene in nine organic solvents from T = (273.15 to 308.15) K and mixing properties of solutions

The solubility of 1,8-dinitronaphthalene in acetonitrile, methanol, ethanol, trichloromethane, isopropanol, acetone, toluene, ethyl acetate and butyl alcohol were obtained experimentally at temperatures ranging from (273.15 to 308.15) K under 0.1 MPa by using a gravimetric method. The solubility of 1,8-dinitronaphthalene in those solvents increases with an increase in temperature. The solubility values decrease according to the following order: acetone > (acetonitrile, ethyl acetate) > trichloromethane > toluene > methanol > ethanol > isopropanol > butyl alcohol. Three models, the modified Apelblat equation, Wilson and NRTL were used to correlate the solubility of 1,8-dinitronaphthalene in the solvents studied. The calculated solubility by the modified Apelblat equation provides better agreement than those evaluated by the other two models. The regressed results via the three models are all acceptable for the solubility of 1,8-dinitronaphthalene in the selected solvents. Furthermore, the mixing Gibbs energy, mixing enthalpy, and mixing entropy for per 1 mol of mixture of 1,8-dinitronaphthalene and solvents were calculated based on the Wilson model. The dissolution process of 1,8-dinitronaphthalene in the selected solvents is spontaneous and exothermic.     

Solubility and dissolution thermodynamics of phthalic anhydride in organic solvents at 283–313 K

The solubility of phthalic anhydride was measured at 283–313 K under atmospheric pressure in ethyl acetate, n-propyl acetate, methyl acetate, acetone, 1,4-dioxane, n-hexane, n-butyl acetate, cyclohexane, and dichloromethane. The solubility of phthalic anhydride in all solvents increased with the increasing temperature. The Van’t Hoff equation, modified Apelblat equation, λh equation, and Wilson model were used to correlate the experimental solubility data. The standard dissolution enthalpy, the standard entropy, and the standard Gibbs energy were evaluated based on the Van’t Hoff analysis. The experimental data and model parameters would be useful for optimizing of the separation processes involving phthalic anhydride.     

Measurement and correlation of solubility of dodecanedioic acid in different pure solvents from T = (288.15 to 323.15) K

The solubility of dodecanedioic acid in ethanol, acetic acid, acetone, butanone, 3-pentanone and ethyl acetate has been measured at temperatures ranging from (288.15 to 323.15) K by a static analytic method at atmospheric pressure. At a given temperature, the order of solubility is ethanol > acetic acid > acetone > butanone > 3-pentanone > ethyl acetate. Molecular modeling study using Materials Studio DMol³ (Accelrys Software Inc.) indicated that the solubility of dodecanedioic acid depends not only on the polarities of the solvents but also on the interactions between dodecanedioic acid and solvent molecules. Furthermore, the modified Apelblat equation was used to represent the temperature dependence of the mole fraction solubility. Finally, the molar Gibbs energy, enthalpy, and entropy of the solution were calculated using the fitting parameters of the modified Apelblat equation.     

Study of equilibrium solution and thermodynamic models in correlation with solubility data of rivastigmine tartrate in (H2O + isopropanol), (H2O + ethanol), and (H2O + acetonitrile) binary solvent mixtures

Millions of people around the world have been suffering from Alzheimer’s disease (AD) everyday. Rivastigmine tartrate is a potential AD drug. A crystallization process can enhance purities of rivastigmine tartrate properly. Predictive models for solubilities of rivastigmine tartrate will improve subsequent industrial crystallization process design. In this work, the solubility of rivastigmine tartrate in (H₂O?+?isopropanol), (H₂O?+?ethanol), and (H₂O?+?acetonitrile) binary solvent systems in the temperature range of 278.15–333.15 K under atmospheric pressure was measured and investigated by employing the analytical stirred-flask method. Binary solvent systems of rivastigmine tartrate overcame drawbacks of mono-solvent crystallization systems, such as high viscosity. Three thermodynamic models, including modified Apelblat equation, the general cosolvency model, and the Jouyban–Acree model, were employed to correlate with the obtained experimental solubility data. Moreover, the calculations of apparent thermodynamic properties of rivastigmine tartrate dissolution process involving the Gibbs free energy, enthalpy, and entropy were accomplished by using the van’t Hoff analysis. Among the three models, the modified Apelblat equation is the most suitable one for predicting the solubility behavior of rivastigmine tartrate in binary solvent systems. Based on the data from modified Apelblat equation, a crystallization process of (H₂O?+?ethanol) binary solvent mixture was developed.

     

Solubility and Solution Thermodynamic Properties of 4-(4-Hydroxyphenyl)-2-butanone (Raspberry Ketone) in Different Pure Solvents

The solubility of 4-(4-hydroxyphenyl)-2-butanone (raspberry ketone) in six pure solvents was experimentally determined at temperatures ranging from 283.15 to 313.15 K under the pressure 0.10 MPa by employing a gravimetrical method. The experimental results indicate that the solubility of raspberry ketone in all studied solvents is temperature dependent, a rise in temperature brings about an increase in solubility. The experimental solubility data of raspberry ketone in six pure solvents (acetone, ethanol, ethyl acetate, n-propyl alcohol, n-butyl alcohol, and distilled water) was correlated by using several commonly used thermodynamic models, including the Apelblat, van’t Hoff and λh equations. The results of the error analysis indicate that the van’t Hoff equation was able to give more accurate and reliable predictions of solubility with root-mean-square deviation less than 0.56%. Furthermore, the changes of dissolution enthalpies (Δ_diss H°), dissolution entropies (Δ_diss S°) and dissolution Gibbs energies (Δ_diss G°) of raspberry ketone in the solvents studied were estimated by the van’t Hoff equation. The positive value of Δ_diss H°, Δ_diss S°, and Δ_diss G° indicated that these dissolution processes of raspberry ketone in the solvents studied were all endothermic and enthalpy-driven.     

Application of the NRTL method to correlate solubility of diosgenin

Using the synthetic method, the solubility of diosgenin in 1-hexanol and 1-heptanol was measured at temperatures from 300 K to 329 K by a laser monitoring observation technique at atmospheric pressure. The solubility data were correlated by semi-empirical equations, such as the Apelblat equation, λh model and the ideal model, which agreed well with experimental results. The fusion enthalpy and the melting point determined by differential scanning calorimeter (DSC), are −34064.2 J · mol⁻¹ and 207.09 °C for diosgenin. With collection of over 14 solvents from different references, the NRTL thermodynamic model as one of the activity coefficient models was used to correlate and predict the solubility of diosgenin. The solubility calculated for all solvents showed good agreement with the experimental results within the temperature range studied. Additionally, the solubility of diosgenin in 14 solvents is also investigated at T = 308.15 K, the results of which indicated that solubility of diosgenin in n-alkanols tends to increase with increasing alkanol chain length from methanol to 1-heptanol and n-alkanols presented higher solubility than heterogeneous alcohols for diosgenin, such as 1-butanol > isobutyl alcohol > tert-butanol and 1-propanol > isopropanol. It also shows that solubility of diosgenin decreases with the increasing polarity of solvents. Its corresponding (solid + liquid) equilibrium data will provide essential support for industrial design and further detailed theoretical studies.