Abraham model correlations for solute partitioning into o-xylene, m-xylene and p-xylene from both water and the gas phase

Abstract

Experimental data have been compiled from the published literature on the partition coefficients of solutes and vapors into o-xylene, m-xylene and p-xylene at 298 K. The logarithms of the water-to-xylene partition coefficients, log P, and gas-to-xylene partition coefficients, log K, were correlated with the Abraham solvation parameter model. The derived mathematical expressions described the observed log P and log K data for the three xylene isomers to within average deviations of 0.14 log units or less. Key words and phrasesPartition coefficients, xylene solvents, Abraham model correlations ________________________________________________________________________ *To whom correspondence should be addressed. (E-mail: acree@unt.edu) 2 IntroductionLiquid-liquid extraction affords a convenient experimental means for separating synthesized organic materials from reaction solvent media, and for pre-concentrating chemicals in unknown liquid samples prior to quantitative analyses. Extraction methods are based on solute partitioning in a biphasic liquid system containing two or more solvents having limited mutual solubility. Molecular interactions between the dissolved solute(s) and surrounding extraction solvents determine the solute recovery factor and separation efficiency. Considerable attention has been given in recent years to developing methods for selecting the best biphasic partitioning system to achieve a desired chemical separation.In many previous studies [1-8], we have shown that two general linear free energy Abraham model correlations, equations 1 and 2, can be used to mathematically describe the transfer of neutral solutes from water to organic solvents and from the gas phase to organic solvents log P = c p + e p ·E + s p ·S + a p ·A + b p ·B + v p ·Vlog K = c k + e k ·E + s k ·S + a k ·A + bk·B + l k ·LThe dependent variables in eqns. 1 and 2 are the logarithm of the water-to-organic solvent partition coefficient, log P, and the logarithm of the gas-to-organic solvent partition coefficient, log K, for a series of solutes. The independent variables, or solute descriptors, are properties of the neutral solutes as follows: [9,10] E is the solute excess molar refraction in cm 3 mol -1 /10, S is the solute dipolarity/polarizability, A is the overall solute hydrogen bond acidity, B is the overall solute hydrogen bond basicity, V is McGowan's characteristic molecular volume in cm 3 mol -1 /100 and L is the logarithm of the gas to hexadecane partition coefficient measured at 298 K.

IUPAC-NIST Solubility Data Series. 102. Solubility of Nonsteroidal Anti-inflammatory Drugs (NSAIDs) in Neat Organic Solvents and Organic Solvent Mixtures

“…(10) and (11) are obtained by multiple linear regression analysis of experimental partition coefficient data and solubility ratios for a specific biphasic system. To date, Abraham model correlations have been developed for predicting the solubility of crystalline nonelectrolytes in more than 70 different organic solvents, [28][29][30][31][32][33][34][35] for predicting the water-toorganic solvent and gas-to-organic solvent partition coefficient for more than 70 different biphasic systems, [28][29][30][31][32][33][34][35][36][37] and for predicting the partition coefficients of organic vapors and gaseous solutes into aqueous micellar solvent media, 38,39 into humic acid, 40 and into various body tissues and fluids. [41][42][43][44][45][46][47] Each of the aforementioned predictions requires a priori knowledge of the compound's solute descriptors as input parameters.…”

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

“…The model that we have been using in our studies has been the Abraham solvation parameter model [2,[21][22][23][24][25][26], which allows one to describe solute transfer between two condensed phases (a biphasic aqueous-organic or organic-organic system) or solute transfer to a condensed phase from the vapor phase. During the past five years we have published Abraham model correlations for 11 additional organic solvents (e.g., diisopropyl ether [27], tributyl phosphate [28], 2-hexadecene [29,30], 1,9-decadiene [29,30], sulfolane [31], benzonitrile [32], ethylbenzene [33], o-xylene [34], m-xylene [34], p-xylene [34], 2-ethoxyethanol [35], and propylene glycol [36]) and several ionic liquids [37][38][39][40][41][42][43][44][45][46][47], as well as updating our existing correlations for hexane [48], heptane [48], octane [48], decane [48], isooctane [49], toluene [33], tetrahydrofuran [50], and 1,4-dioxane [50].…”

Correlation of the Solubilizing Abilities of 1-Butyl-1-methyl-pyrrolidinium Tris(pentafluoroethyl)trifluorophosphate, 1-Butyl-1-methylpyrrolidinium Triflate and 1-Methoxyethyl-1-methylmorpholinium Tris(pentafluoroethyl)trifluorophosphate

“…The solvation parameter model, developed by Abraham and coworkers [10,11], has been successfully employed to evaluate the solubilizing properties of a large number of traditional organic solvents [12][13][14][15][16][17] and several classes of ILs [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33]. The solvation parameter model is based on two liner free energy relationships (LFERs), the first relationship describes solute transfer between two condensed phases: log 10 P = c p + e p ·E + s p ·S + a p ·A + b p ·B + v p ·V (1) and the second relationship involves solute transfer from the gas phase to a condensed phase log 10 K = c k + e k ·E + s k ·S + a k ·A + b k ·B + l k ·L (2) where P and K refer to the solute's condensed phase-to-condensed phase partition coefficient (often water-to-organic solvent partition coefficient) and gas-to-condensed phase partition coefficient, respectively.…”