Solubility Modeling, Solute–Solvent Interactions, and Thermodynamic Dissolution Properties of <i>p</i>-Nitrophenylacetonitrile in Sixteen Monosolvents at Temperatures Ranging from 278.15 to 333.15 K

Chen, Gaoquan; Liang, Jieying; Han, Jingchao; Zhao, Hongkun

doi:10.1021/acs.jced.8b00811

Cited by 125 publications

(175 citation statements)

References 41 publications

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“…The masses of neat solvents, saturated solutions, and solute o -nitroacetanilide were determined by an analytical balance having a type of CPA225D and an absolute error of 0.0001 g that was acquired from the Satorius Scientific Instrument (Beijing). The experimental determination of o -nitroacetanilide equilibrium solubility in the selected 15 monosolvents was conducted by means of the shake-flask technique broadly used in previous works. − The apparatus utilized in this work was produced by Tianjin Ounuo Instrument Co. Ltd., China. Validation of apparatus reliability was previously made by the use of the solubility data of benzoic acid in pure toluene …”

Section: Methodsmentioning

confidence: 99%

“…The experimental determination of o -nitroacetanilide equilibrium solubility in the selected 15 monosolvents was conducted by means of the shake-flask technique broadly used in previous works. − The apparatus utilized in this work was produced by Tianjin Ounuo Instrument Co. Ltd., China. Validation of apparatus reliability was previously made by the use of the solubility data of benzoic acid in pure toluene …”

Section: Methodsmentioning

confidence: 99%

“…Validation of apparatus reliability was previously made by the use of the solubility data of benzoic acid in pure toluene. 32 All solubility experiments were conducted under local ambient pressure (around 101.2 kPa). Each system was measured three times in parallel.…”

Section: ■ Data Correlation Modelsmentioning

confidence: 99%

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o-Nitroacetanilide Equilibrium Solubility in 15 Monosolvents: Experimental Determination, Mathematical Correlation, and Solvent Effect Examination

et al. 2021

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Equilibrium solubility of o-nitroacetanilide in 15 monosolvents (ethylene glycol, n-propanol, methanol, ethyl acetate, N,N-dimethylformamide, ethanol, isopropanol, acetonitrile, 1,4-dioxane, n-butanol, isobutanol, n-heptanol, water, cyclohexane, and N-methyl pyrrolidone) was acquired through experiments that were conducted by a shake-flask method under a local pressure of 101.2 kPa at elevated temperatures from 278.15 to 323.15 K. The decreasing tendency of solubility magnitudes in the 15 monosolvents was N-methyl pyrrolidone > N,N-dimethylformamide > 1,4-dioxane > ethyl acetate > methanol (acetonitrile) > ethanol > n-propanol > n-butanol > isobutanol > isopropanol > n-heptanol > ethylene glycol > cyclohexane > water. No polymorphic transformation or solvation phenomenon happened after equilibration in the 15 solvents. Solubility correlations were made through two semiempirical equations (Apelblat equation and λh equation) and two activity coefficient models (NRTL model and Wilson model). The maximum root-mean-square and relative average deviations acquired through back-calculation were 87.57 × 10–4 and 8.95%, respectively. The correlating result was better through Apelblat equation than through the other models and equations. Examination was made for the molecular interactions between solvent–solvent and solute–solvent species by the linear solvation energy relationships. In addition, this work reported the thermodynamic mixing properties, infinite dilution activity coefficient, and reduced excess enthalpy achieved through the Wilson model.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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o-Nitroacetanilide Equilibrium Solubility in 15 Monosolvents: Experimental Determination, Mathematical Correlation, and Solvent Effect Examination

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“…The equilibrium systems of 1-(2-bromophenyl)-pyrrole-2,5-dione in aqueous isopropanol/ethanol/NMP/methanol solutions were constructed by the well-known shake-flask method. ,− Before experiments, the mole fraction solubility of benzoic acid in neat toluene was determined through the apparatus. The obtained data is summarized in Table S1 and plotted in Figure S1 with the intention of comparison with those in the literature. − Examination of Table S1 specified that the mole fraction solubility determined by us well agreed with those reported in the publication. As a result, the experimental apparatus used this work was reliable.…”

Section: Methodsmentioning

confidence: 99%

Solubility Determination, Modeling, and Preferential Solvation of 1-(2-Bromophenyl)-pyrrole-2,5-dione in Aqueous Binary Mixtures of Isopropanol, Ethanol, N-Methyl-2-pyrrolidinone and Methanol

Gao

et al. 2021

J. Chem. Eng. Data

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Experimental determination of equilibrium solubility of 1-(2-bromophenyl)-pyrrole-2,5-dione in binary aqueous solutions containing a co-solvent of isopropanol, ethanol, N-methyl-2-pyrrolidinone (NMP) or methanol over temperatures from 278.15 to 323.15 K was made by the shake-flask technique under local pressure of 101.2 kPa. At the identical experimental conditions (temperature and mass fraction compositions of co-solvents), the maximum equilibrium solubility magnitude in a mole fraction of 1-(2-bromophenyl)-pyrrole-2,5-dione was recorded in the NMP (1) + water (2) system; and the minimum one, in the isopropanol (1) + water (2) system. The solvent effect was quantitatively analyzed by employing the KAT-LSER model, representing the solubility parameter and dipolarity–polarizability had main contributions to the solubility variation at 298.15 K. Four relationships, such as the Jouyban–Acree model, modified Wilson model, Jouyban–Acree–van’t Hoff model, and mixture response surface (MRS) model, were employed to correlate the determined solubility magnitudes, attaining the root-mean-square deviations of no higher than 493.0 × 10–5 and relative average deviations of no higher than 5.59%. The molecule interactions of solute–solvent and solvent–solvent were investigated through the extended Hildebrand solubility approach. In water-rich composition regions, there was some association between 1-(2-bromophenyl)-pyrrole-2,5-dione and solution. Furthermore, the local mole fractions of isopropanol (ethanol, NMP, or methanol) and water nearby 1-(2-bromophenyl)-pyrrole-2,5-dione were quantitatively evaluated by the inverse Kirkwood–Buff integrals. 1-(2-Bromophenyl)-pyrrole-2,5-dione was preferentially solvated by water in water-rich proportions; while in co-solvent-rich proportions for the solutions studied, it was preferentially solvated by isopropanol (ethanol, NMP, or methanol). In water-rich ranges, 1-(2-bromophenyl)-pyrrole-2,5-dione could be predominantly serving as a Lewis base in front of water molecules.

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“…The equilibrated systems for 3,3′-diaminodiphenyl sulfone dissolved in different monosolvents were constructed by the saturation shake-flask method that was broadly applied in solid solubility measurement. − The experiment apparatus was provided by Tianjin Ounuo Instrument Co. Ltd., China. The reliability was validated previously through the equilibrium solubility data of benzoic acid in toluene …”

Section: Experimental Partmentioning

confidence: 99%

Solubility, Three-Dimensional Hansen Solubility Parameters, and Solution Thermodynamics of 3,3′-Diaminodiphenyl Sulfone in 14 Neat Solvents from 283.15 to 328.15 K

et al. 2021

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By means of the saturation shake-flask technique, the saturation solubility data of 3,3′-diaminodiphenyl sulfone in 14 monosolvents (n-propanol, N,N-dimethylformamide, methanol, ethanol, ethylene glycol, cyclohexane, acetonitrile, isopropanol, water, n-butanol, ethyl acetate, 1,4-dioxane, isobutanol, and 1-heptanol) was achieved at temperatures from 283.15 to 328.15 K and ambient pressure (p = 101.2 kPa). No phenomenon of crystalline form transformation or solvation occurred after dissolution of 3,3′-diaminodiphenyl sulfone in different solvents. The solubility values (mole fraction) of 3,3′-diaminodiphenyl sulfone in above 14 solvents increased as the temperature elevated and obeyed the decreasing tendency in different monosolvents as follows: N,N-dimethylformamide > ethyl acetate > acetonitrile > ethylene glycol > 1,4-dioxane > methanol > ethanol > isobutanol > n-propanol > n-butanol > isopropanol > 1-heptanol > water > cyclohexane. The mutual miscibility of solvent and 3,3′-diaminodiphenyl sulfone was explained through the three-dimensional Hansen solubility parameter. Examination was carried out for molecular interactions between the solute–solvent and solvent–solvent species by means of the linear solvation energy relationships. The solubility data obtained through experiments was correlated by the use of four models/equations, namely, the NRTL model, Apelblat equation, λh equation, and Wilson model. Correlation resulted in the maximum root-mean-square and relative average deviation values of, respectively, 397.1 × 10–5 and 7.57 × 10–2. The Apelblat equation gave lower relative average deviations than the other models/equations for a certain neat solvent. Also, the mixing thermodynamic properties, infinite-dilution activity coefficient, and reduced excess enthalpy were obtained in terms of the Wilson model.

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Solubility Modeling, Solute–Solvent Interactions, and Thermodynamic Dissolution Properties of p-Nitrophenylacetonitrile in Sixteen Monosolvents at Temperatures Ranging from 278.15 to 333.15 K

Cited by 125 publications

References 41 publications

o-Nitroacetanilide Equilibrium Solubility in 15 Monosolvents: Experimental Determination, Mathematical Correlation, and Solvent Effect Examination

o-Nitroacetanilide Equilibrium Solubility in 15 Monosolvents: Experimental Determination, Mathematical Correlation, and Solvent Effect Examination

Solubility Determination, Modeling, and Preferential Solvation of 1-(2-Bromophenyl)-pyrrole-2,5-dione in Aqueous Binary Mixtures of Isopropanol, Ethanol, N-Methyl-2-pyrrolidinone and Methanol

Solubility, Three-Dimensional Hansen Solubility Parameters, and Solution Thermodynamics of 3,3′-Diaminodiphenyl Sulfone in 14 Neat Solvents from 283.15 to 328.15 K

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