Experimental and predicted solubilities of 3,4-dichlorobenzoic acid in select organic solvents and in binary aqueous–ethanol mixtures

Abstract

Experimental solubilities are reported for 3,4-dichlorobenzoic acid dissolved in methyl butyrate, and in 16 alcohol, 5 alkyl acetate, 5 alkoxyalcohol and 6 ether solvents. Solubilities were also measured in nine binary aqueous-ethanol solvent mixtures at 298.15 K. The measured solubility data were correlated with the Abraham solvation parameter model. Mathematical expressions based on the Abraham model predicted the observed molar solubilities to within 0.12 log units.

Abraham model correlations for describing solute transfer into 2-butoxyethanol from both water and the gas phase at 298K

“…An arithmetic average of the equation coefficients for ethyl acetate and butyl acetate provided a fairly reasonable estimate of the solubility behavior of 3,4-dichlorobenzoic acid in propyl acetate [57].…”

“…6 and 7 are the logarithm of the water-to-organic solvent partition coefficient (log P), the logarithm of the gas-to-organic solvent partition coefficient (log K), and the two logarithms of the molar solubility ratios (log (CS,organic/CS,water) and log (CS,organic/CS,gas)). The published mole fraction solubility data [57][58][59] and mole fraction solubility data in Table 2 …”

“…As part of this study solubilities were also measured for 2-hydroxybenzoic acid, acetylsalicylic acid, 3,5-dinitro-2-methylbenzoic acid, acenaphthene, fluoranthene, trans-stilbene, xanthene, phenothiazine, 3,5-dinitrobenzoic acid, 3-chlorobenzoic acid, 2-methylbenzoic acid, 4-chloro-3-nitrobenzoic acid, 2-chloro-5-nitrobenzoic acid, benzoic acid, 4-aminobenzoic acid, benzil, thioxanthen-9-one, 3-nitrobenzoic acid, and diphenyl sulfone dissolved in 2-butoxyethanol at 298.15 K. The measured partition coefficients and solubilities, combined with published gas solubility data for carbon dioxide [52] and hydrogen gas [53], and our previously reported solubility data for anthracene [54], pyrene [55], benzoin [56], 3,4-dichlorobenzoic acid [57], 3,4-dimethoxybenzoic acid [58], 3-methylbenzoic acid [59], salicylamide [59], 4-nitrobenzoic acid [59], 2-methoxybenzoic acid [59], 4-methoxybenzoic acid [59], 4-chlorobenzoic acid [59], biphenyl [59] and 4-hydroxyacetanilide [59] dissolved in 2-butoxyethanol, were used to derive Abraham model correlations for both water-to-2-butoxyethanol partition coefficients (as log P) and gas-to-2-butoxyethanol partition coefficients (as log K).…”

Abraham model correlations for solute transfer into 2-methoxyethanol from water and from the gas phase

“…Molar concentrations of the diluted solutions were determined from a Beer-Lambert law absorbance versus concentration working curve for nine standard solutions of known concentration. The analysis wavelengths and concentration ranges used for each solute have been reported in earlier solubility publications [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38].…”

Abraham model correlations for solute transfer into 2-ethoxyethanol from water and from the gas phase

“…As part of this study solubilities were also measured for xanthene, phenothiazine, acenaphthene, diphenyl sulfone, 3,5-dinitro-2-methylbenzoic acid, 3-chlorobenzoic acid, 2-methylbenzoic acid, 4-chloro-3-nitrobenzoic acid, 3,5-dinitrobenzoic acid, benzil, and thioxanthen-9-one dissolved in 2-ethoxyethanol at 298 K. The measured partition coefficients, combined with published infinite dilution activity coefficient data for liquid organic compounds [40][41][42][43][44][45][46][47][48][49][50][51][52], gas solubility data for 2-methylpropane [53] and hydrogen gas [54], and solubility data for crystalline nonelectrolyte organic compounds [55][56][57][58][59][60][61][62][63][64][65][66] dissolved in 2-ethoxyethanol, were used to derive Abraham model correlations for both water-to-2-ethoxyethanol partition coefficients (as log P) and gas-to-2-ethoxyethanol partition coefficients (as log K).…”