Solubility Measurement and Modeling of 1-(3-nitrophenyl)Ethanone and 1-(4-nitrophenyl)Ethenone in Nine Pure Organic Solvents from T = (278.15 to 318.15) K and Mixing Properties of Solutions

Abstract

The knowledge of solubility and solution thermodynamics for 1-(3-nitrophenyl)ethanone and 1-(4-nitrophenyl)ethenone in different solvents is essential for their purification and further theoretical study. In this work, the solid−liquid equilibrium for 1-(3-nitrophenyl)ethanone and 1-(4-nitrophenyl)ethenone in nine pure solvents (methanol, ethanol, n-propanol, isopropanol, acetone, acetonitrile, ethyl acetate, toluene, and cyclohexane) was established with the isothermal saturation method at temperatures T = (278.15 to 318.15) K under pressure of 101.2 kPa. The mole fraction solubility of 1-(3-nitrophenyl)ethanone obeys the following order from high to low in different solvents: acetone > acetonitrile, ethyl acetate > toluene > methanol > ethanol > n-propanol, isopropanol > cyclohexane. While in 1-(4-nitrophenyl)ethanone + solvents, the order of the data from high to low is acetone > acetonitrile > ethyl acetate > toluene > methanol > ethanol > n-propanol > isopropanol > cyclohexane. The modified Apelblat equation, λh equation, Wilson model, and nonrandom two-liquid model were employed to correlate the measured solubility data of 1-(3-nitrophenyl)ethanone and 1-(4-nitrophenyl)ethanone in the selected solvents. Results showed that the largest values of relative average deviation and root-mean-square deviation obtained with the four models were no greater than 2.78% and 7.59 × 10 −3 , respectively. The modified Apelblat equation provided better results than the other three models. Furthermore, the mixing properties, including Gibbs energy, mixing enthalpy, mixing entropy, activity coefficient at infinitesimal concentration (γ 1 ∞ ), and reduced excess enthalpy (H 1 E,∞ ) were computed. The mixing processes of 1-(3-nitrophenyl)ethanone and 1-(4-nitrophenyl)ethenone in the studied solvents are all spontaneous and endothermic. The obtained solubility and thermodynamic studies are very helpful for optimizing the purification process of 1-(3-nitrophenyl)ethanone and 1-(4-nitrophenyl)ethenone.

Solubility Measurement and Correlation of Probenecid in 12 Pure Organic Solvents and Thermodynamic Properties of Mixing of Solutions

“…The thermodynamic properties of mixing are commonly characterized by the changes in Gibbs energy, enthalpy, and entropy in the mixing process of the solute and solvent. For a real solution obtained from the nonideal mixing process, the thermodynamic properties of mixing consist of the ideal mixing properties and the excess thermodynamic properties. , These are expressed as follows where Δ mix G °, Δ mix S °, and Δ mix H ° refer to the Gibbs energy change, the entropy change, and the enthalpy change of the mixing process, respectively. Δ mix G id , Δ mix S id , and Δ mix H id refer to the ideal Gibbs energy of mixing change, the ideal mixing entropy change, and the ideal enthalpy change, respectively.…”

“…For a real solution obtained from the nonideal mixing process, the thermodynamic properties of mixing consist of the ideal mixing properties and the excess thermodynamic properties. 31,32 These are expressed as follows…”

Solubility Determination and Thermodynamic Mixing Properties of 5-Methyl-2-pyrazinecarboxylic Acid in Different Solvents

“…Based on the Lewis–Randall rule, the mixing properties of solutions could be obtained by the Wilson model. Moreover, for an ideal binary solution, the mixing properties including the mixing Gibbs energy, mixing enthalpy, and mixing entropy could be described as eqs – where x 1 is the mole fraction of the solute, and x 2 the corresponding solvent.…”

“…For the nonideal solution, the three mixing properties can be described as eqs and . for In eq , Δ mix M , M E , and Δ mix M id are the mixing property in practical solutions, excess property in nonideal solutions, and mixing property at the ideal state, respectively. Moreover, the excess mixing property could be calculated by eqs – …”

Solid–Liquid Phase Equilibrium for Ternary Systems of p-Nitroacetophenone plus m-Nitroacetophenone plus Methanol/Toluene/Ethyl Acetate

“…Apparently, the separation procedure of p -nitroacetophenone or m -nitroacetophenone via solvent crystallization is based on the mutual solubility for the ternary p -nitroacetophenone + m -nitroacetophenone + solvent system. The solubilities of pure p -nitroacetophenone and pure m -nitroacetophenone in several neat solvents, for example, methanol, ethanol, n -propanol, isopropanol, acetone, acetonitrile, ethyl acetate, toluene, cyclohexane, N , N -dimethylformamide, and tetrahydrofuran, and in the ternary system of p -nitroacetophenone + m -nitroacetophenone + methanol have been reported; − nevertheless, the obtainable solubility is not adequate for the purification of p -nitroacetophenone or m -nitroacetophenone from the mixture. A study of the ternary liquid–solid equilibrium of p -nitroacetophenone and m -nitroacetophenone in aprotic solvents has not been performed yet.…”