Solubility Determination and Modeling of p-Nitrobenzamide Dissolved in Twelve Neat Solvents from 283.15 to 328.15 K

Abstract

Through the shake-flask method, the solubility of p-nitrobenzamide in 12 pure solvents including n-propanol, ethanol, isopropanol, n-butanol, water, isobutanol, ethyl acetate, acetonitrile, dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), N-methyl-2-pyrrolidinone (NMP), and ethylene glycol (EG) was acquired over a temperature range from 283.15 to 328.15 K at ambient pressure p = 101.2 kPa. The mole fractions of p-nitrobenzamide in the equilibrium liquid phase increased as the temperature increased and had the following order in various solvents: DMSO > DMF > NMP > EG > ethyl acetate > ethanol > isopropanol > n-propanol > isobutanol > acetonitrile > n-butanol > water. They were fitted through the Wilson model, modified Apelblat equation, λh equation, and NRTL model. The maximum root-mean-square deviation value and relative average deviation value gained through the four models were, respectively, 56.69 × 10–4 and 6.55 × 10–2. The relative average deviation values achieved were smaller through the modified Apelblat equation than through the other equations for a given solvent. The mixing properties, infinitesimal concentration activity coefficient, and reduced excess enthalpy were derived. Additionally, using the relationship analysis of the Kamlet and Taft linear solvation energy of the solvent effect, the degree and type of interactions of solute–solvent and solvent–solvent were recognized.

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

“…This semi-empirical equation is expressed as eq , which can accurately describe the dependence of mole fraction solubility data on experiment temperature. − This equation is very suitable for nonpolar and polar solvent systems. Here, x represents the mole fraction solubility data of 3,3′-diaminodiphenyl sulfone in solvents at the experimental temperature T /K. The parameters of this equation are signified as A , B , and C .…”

“…It is a nonactivity coefficient model with two parameters employed to examine the solvent activity in hydrogen-bonding saturated solutions. This equation, described as eq , − has been extensively utilized to mathematically describe the solid solubility behavior. The λ h equation is an alternative one to mathematically describe the equilibrium solubility behavior of 3,3′-diaminodiphenyl sulfone in the 14 solvents selected. where T m is the melting point temperature of 3,3′-diaminodiphenyl sulfone; two adjustable parameters are denoted as λ and h .…”

“…For a binary solid–liquid system under equilibrium state, the Wilson model gives the natural logarithm of activity coefficient as eqs –. − Here, V 1 and V 2 stand for, respectively, the molar volume of the solute and solvent in equilibrium systems. Δλ ij denote the interaction energy parameters (J·mol –1 ) of i and j molecules.…”

“…As a result, the expressions of the activity coefficient can be described by − wherein x 1 and x 2 = 1 – x 1 are the mole fraction concentrations of the solute and solvent in the saturated solutions, respectively, τ 12 and τ 21 are energy parameters related to intermolecular interactions, and α ij refer to empirical constants that represent the solution nonrandomness and usually range from 0.2 to 0.47. In this contribution, α 12 = 0.2 or 0.3 is selected for correlating the 3,3′-diaminodiphenyl sulfone solubility in different neat solvents.…”

“…Several interaction modes of solvent and solute are put forward in the publications. The Kamlet–Taft linear solvation energy relationships, named as KAT-LSER hereinafter, utilize the solvent and solute molecule characteristics to define the Gibbs energy of solvents for equilibrated solutions by the use of linear contributions of different molecule interactions of the solute and solvent by − wherein c 0 is a constant that signifies the influence of solvent descriptors excluding α, β, π*, and δ H upon solid solubility, ln­( x ), α indicates the acidity of a solvent, and β indicates the basicity. The solvent descriptor π* denotes the dipolarity/polarizability.…”