Solubility and Preferential Solvation of Carbazochrome in Solvent Mixtures of <i>N</i>,<i>N</i>‑Dimethylformamide Plus Methanol/Ethanol/<i>n</i>‑Propanol and Dimethyl Sulfoxide Plus Water

The carbazochrome (3) solubility in solvent mixtures of DMF (<i>N</i>,<i>N</i>-dimethylformamide, 1) + methanol (2), DMF (1) + ethanol (2), DMF (1) + <i>n</i>-propanol (2), and dimethyl sulfoxide (DMSO, 1) + water (2) was measured by the static method within the temperature range from (278.15 to 318.15) K under atmospheric pressure, <i>p</i> = 101.0 kPa. The solubility of carbazochrome increased with rising mass fraction of DMF or DMSO and temperature. The Jouyban–Acree, van’t Hoff–Jouyban–Acree, and Apelblat–Jouyban–Acree models were used to correlate the obtained solubility, and the Apelblat–Jouyban–Acree model provided better correlation results. The parameters of preferential solvation (<i>δx</i>_1,3) were acquired from the mixture properties with the method of inverse Kirkwood–Buff integrals. The values of <i>δx</i>_1,3 changed nonlinearly with the DMF/DMSO (1) proportion in the studied mixed solvents. The carbazochrome was solvated preferentially by alcohol or water in alcohol or water-rich solutions and preferentially solvated by DMF/DMSO in DMF/DMSO-rich mixtures. It could be speculated that in DMF/DMSO-rich mixtures the interaction by acidic hydrogen bonding with the basic sites of carbazochrome played a significant role in carbazochrome solvation

Solubility Modeling and Mixing Properties for Benzoin in Different Monosolvents and Solvent Mixtures at the Temperature Range from 273.15 to 313.15 K

In the present work, the benzoin solubility in ethanol, methanol, <i>n</i>-propanol, isopropyl alcohol, <i>n</i>-butanol, acetone, ethyl acetate, acetonitrile, cyclohexane, butyl acetate, isobutyl alcohol, and toluene and ethyl acetate + ethanol solvent mixtures was measured by using the static method at the temperature range from 273.15 to 313.15 K under atmospheric pressure (101.1 kPa). The solubilities in mole fraction increased with increasing temperature and followed the order from high to low in the selected monosolvents: ethyl acetate > acetone > butyl acetate > (acetonitrile, toluene) > methanol > ethanol > <i>n</i>-propanol > <i>n</i>-butanol > isobutyl alcohol > isopropyl alcohol > cyclohexane; and for the ethyl acetate + ethanol mixture, the mole fraction solubilities of benzoin increased with the increase in temperature and ethyl acetate mass fraction. The obtained solubility of benzoin in neat solvents was correlated with the Apelblat equation, <i>λh</i> equation, and Wilson and NRTL models; and in solvent mixtures of ethyl acetate (<i>w</i>) + ethanol (1 – <i>w</i>), with the Jouyban–Acree, van’t Hoff–Jouyban–Acree and Apelblat–Jouyban–Acree models. The largest value of root-mean-square deviation was 4.02 × 10^–4, and relative average deviation was 2.36 × 10^–2. Furthermore, the mixing enthalpy, mixing Gibbs energy, mixing entropy, activity coefficients under infinitesimal concentration (γ₁^∞), and reduced excess enthalpy (<i>H</i>₁^E,∞) were deduced

Thermodynamic Functions for the Solubility of 3‑Nitrobenzonitrile in 12 Organic Solvents from <i>T</i>/K = (278.15 to 318.15)

The solubilities of 3-nitrobenzonitrile in 12 organic solvents including methanol, ethanol, <i>n</i>-propanol, isopropanol, acetone, <i>n</i>-butanol, 2-methyl-1-propanol, acetonitrile, acetic acid, ethyl acetate, cyclohexane, and toluene were measured by the static method within the temperature range from (278.15 to 318.15) K under atmospheric pressure of 101.1 kPa. The mole fraction solubility of 3-nitrobenzonitrile in the selected solvents increased with a rise in temperature. In general, they ranked as acetone > (acetonitrile, ethyl acetate) > toluene > acetic acid > methanol > ethanol > <i>n</i>-propanol > <i>n</i>-butanol > isopropanol >2-methyl-1-propanol > cyclohexane. The achieved solubilities of 3-nitrobenzonitrile were correlated via the <i>λh</i> equation, modified Apelblat equation, NRTL model, and Wilson model. The maximum relative average deviation and root-mean-square deviation were 1.87% and 2.399 × 10^–3, respectively. Finally, the mixing properties, e.g., change in Gibbs energy, enthalpy, entropy, activity coefficient at infinitesimal concentration, and reduced excess enthalpy, were also derived on the basis of the Wilson model. The mixing process of 3-nitrobenzonitrile in these solvents was endothermic and spontaneous

Thermodynamic Functions for Solubility of 1‑Hydroxybenzotriazole in Sixteen Solvents at Temperatures from (278.15 to 313.15) K and Mixing Property of Mixtures

Solubility of 1-hydroxybenzotriazole in 16 neat solvents including methanol, ethanol, <i>n</i>-propanol, isopropanol, acetone, butanone, isoamyl alcohol, <i>n</i>-hexanol, <i>n</i>-heptanol, isooctyl alcohol, <i>N</i>,<i>N</i>-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), ethyl acetate, acetonitrile, 1,4-dioxane, and toluene was measured using the method of isothermal saturation over a temperature range from (278.15 to 313.15) K under atmospheric pressure (101.1 kPa). The mole fraction solubility of 1-hydroxybenzotriazole in the selected solvents increased with an increase of temperature. They followed the order from high to low in studied neat solvents: DMF > DMSO > ethanol > <i>n</i>-propanol > isopropanol > methanol > butanone > acetone >1,4-dioxane > <i>n</i>-heptanol > <i>n</i>-hexanol > isoamyl alcohol > isooctyl alcohol > ethyl acetate > acetonitrile > toluene. The obtained solubility data of 1-hydroxybenzotriazole in the studied solvents were correlated with the <i>λh</i> equation, modified Apelblat equation, and NRTL and Wilson models. The largest value of root-mean-square deviation was 7.65 × 10^–4, and relative average deviation, 4.21%. The values of root-mean-square deviation obtained with the modified Apelblat equation were smaller than those with the other equations for a given solvent. By and large, the four thermodynamic models all provided acceptable results for 1-hydroxybenzotriazole in the studied solvents. Moreover, the apparent dissolution enthalpy and the mixing enthalpy, mixing Gibbs energy, mixing entropy, reduced excess enthalpy, and activity coefficient at infinitesimal concentration were derived. The obtained solubility and thermodynamic studies could provide the fundamental data for optimizing the reaction and purification procedure of 1-hydroxybenzotriazole

Solubility and Preferential Solvation of 3‑Nitrobenzonitrile in Binary Solvent Mixtures of Ethyl Acetate Plus (Methanol, Ethanol, <i>n</i>‑Propanol, and Isopropyl Alcohol)

The solubilities of 3-nitrobenzonitrile in solvent mixtures of ethyl acetate (1) + methanol (ethanol, <i>n</i>-propanol or isopropyl alcohol) (2) determined over the temperature range from 278.15 to 318.15 K under atmospheric pressure (101.1 kPa) with the isothermal dissolution equilibrium method were reported. They increased with a rise of temperature and mass fraction of ethyl acetate, and the largest solubility value was observed in neat ethyl acetate for all the binary mixtures investigated. The temperature and solvent composition dependence of 3-nitrobenzonitrile solubility was analyzed through the Jouyban–Acree, van’t Hoff–Jouyban–Acree, and Apelblat–Jouyban–Acree models acquiring average relative deviations lower than 1.57% and root-mean-square deviation lower than 11.52 × 10^–4 for correlative investigations. In addition, the preferential solvation parameters (δ<i>x</i>_1,3) of 3-nitrobenzonitrile by ethyl acetate were determined from experimental solubility values by using the inverse Kirkwood–Buff integrals. It was found that alcohol preferentially solvated 3-nitrobenzonitrile in alcohol-rich mixtures while ethyl acetate forms local solvation shells in compositions from intermediate composition up to neat ethyl acetate. The former case was possibly due to the ordered structure of alcohol molecules around the apolar group of 3-nitrobenzonitrile, which was formed via hydrophobic hydration in alcohol-rich solutions

Solubility Modeling, Solvent Effect, and Preferential Solvation of Thiamphenicol in Cosolvent Mixtures of Methanol, Ethanol, <i>N,N</i>-Dimethylformamide, and 1,4-Dioxane with Water

The thiamphenicol solubility in aqueous cosolvent solutions of ethanol (1), methanol (1), 1,4-dioxane (1), and <i>N,N</i>-dimethylformamide (DMF, 1) was measured via the isothermal dissolution equilibrium method at temperatures ranging from 278.15 to 318.15 K under local pressure (101.1 kPa). At fixed composition of ethanol (methanol, 1,4-dioxane, or DMF) and temperature, the solubility of thiamphenicol was larger in DMF + water mixtures than in the ethanol/methanol/1,4-dioxane mixtures. The local solvent proportions were acquired with the method of inverse Kirkwood–Buff integrals. The absolute value of these preferential solvation parameters were all lower than 1.0 × 10^–2 for ethanol (1) + water (2) and 1,4-dioxane (1) + water (2) solutions in water-rich compositions and for methanol (1) + water (2) solutions in whole compositions. In the former two cosolvent mixtures in intermediate compositions and cosolvent-rich regions, thiamphenicol was preferentially solvated by cosolvent. However, for the DMF (1) + water (2) solutions, water solvated preferentially thiamphenicol in water-rich compositions and by DMF in intermediate and DMF-rich compositions. This case by cosolvent might be illustrated based on higher basic behavior of water, which interacted with Lewis acidic groups of thiamphenicol. In addition, the solubility of thiamphenicol was described with the van’t Hoff–Jouyban–Acree, Jouyban–Acree, and Apelblat–Jouyban–Acree models. The obtained average relative deviations were no greater than 1.85%. Furthermore, the solvent effect treatment through the KAT-LSER model indicated that the solubility variation was significantly affected by the cavity term

Solubility and Modeling of Hesperidin in Cosolvent Mixtures of Ethanol, Isopropanol, Propylene Glycol, and <i>n</i>‑Propanol + Water

Equilibrium solubility of hesperidin in aqueous solutions of ethanol, isopropanol, propylene glycol, and <i>n</i>-propanol was determined by static technique at temperatures ranging from 293.15 to 333.15 K under <i>p</i> = 101.1 kPa. The hesperidin solubility increased monotonously with the increase in mass fraction of ethanol isopropanol, propylene glycol, and <i>n</i>-propanol and temperature. At the same composition of alcohol and temperature, the mole fraction solubility of hesperidin was largest in propylene glycol + water among the four cosolvent mixtures. The solubilities of hesperidin were correlated with Jouyban–Acree model, Apelblat–Jouyban–Acree model, and van’t Hoff–Jouyban–Acree model. The obtained average relative deviations were less than 2.38%

Solubility Measurement and Thermodynamic Modeling of 4‑Nitrophthalimide in Twelve Pure Solvents at Elevated Temperatures Ranging from (273.15 to 323.15) K

The solubility of 4-nitrophthalimide in different solvents are of great importance for the design of its purification process via crystallization. The work reported new solubility data for 4-nitrophthalimide in 12 pure solvents of methanol, ethanol, isopropanol, cyclohexanone, acetone, acetonitrile, ethyl acetate, 2-butanone, chloroform, 1,4-dioxane benzyl alcohol and <i>N</i>,<i>N</i>-dimethylformamide. They were determined by a high-performance liquid chromatography at <i>T</i> = (273.15 to 323.15) K under pressure of 0.1 MPa. The 4-nitrophthalimide solubility in the selected solvents increased with the temperature increase. At a given temperature, the solubility of 4-nitrophthalimide is largest in <i>N</i>,<i>N</i>-dimethylformamide and lowest in chloroform. The solubility data in the these solvents ranked as <i>N</i>,<i>N</i>-dimethylformamide > cyclohexanone > (1,4-dioxane, acetone, 2-butanone, benzyl alcohol) > ethyl acetate > acetonitrile > methanol > ethanol > isopropanol > chloroform. The experimental solubility data were correlated by modified Apelblat equation, <i>λh</i> equation, Wilson model, and NRTL model. The obtained values of root-mean-square deviation and relative average deviation are all less than 16.17 × 10^–4 and 1.58%, respectively. The modified Apelblat equation achieved the best correlating results in totally