Prediction of anthracene solubility in alcohol + alkane solvent mixtures using binary alcohol + alkane VLE data. Comparison of Kretschmer-Wiebe and mobile order models

Powell, Joyce R.; McHale, Mary E. R.; Kauppila, Ann-Sofi M.; Acree, William E.; Flanders, Patrick H.; Varanasi, Venu; Campbell, Scott W.

doi:10.1016/s0378-3812(97)00039-3

Cited by 27 publications

(18 citation statements)

References 39 publications

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“…Subsequent studies will interpret the measured pyrene solubilities using both Mobile Order Theory and the Kretschmer-Wiebe association model. Powell et al 4 and McHale et al 5 showed that these latter two solution models provided reasonably accurate descriptions for the solubility behavior of pyrene and anthracene in binary alkane + alcohol and alcohol + alcohol solvent mixtures. Neither model has been used to describe solubility in ternary solvent systems.…”

Section: Introductionmentioning

confidence: 99%

Solubility of Pyrene in Ternary Propanol + Butanol + 2,2,4-Trimethylpentane Solvent Mixtures at 299.15 K

Debase

Acree

2001

J. Chem. Eng. Data

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Experimental solubilities are reported for pyrene dissolved in ternary 1-propanol + 1-butanol + 2,2,4-trimethylpentane, 2-propanol + 1-butanol + 2,2,4-trimethylpentane, 1-propanol + 2-butanol + 2,2,4-trimethylpentane, and 2-propanol + 2-butanol + 2,2,4-trimethylpentane solvent mixtures at 26°C and atmospheric pressure. Nineteen compositions were studied for each of the four solvent systems. Also measured were the solubilities of pyrene in binary 1-butanol + 2,2,4-trimethylpentane mixtures. Results of these measurements are used to test the predictive ability of the ternary solvent form of the Combined NIBS/Redlich-Kister equation. Computations showed that the model predicted the observed solubility behavior to within an overall average absolute deviation of ∼1.6%, which is comparable to the experimental uncertainty of (1.5%.

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Section: Introductionmentioning

confidence: 99%

Solubility of Pyrene in Ternary Propanol + Butanol + 2,2,4-Trimethylpentane Solvent Mixtures at 299.15 K

Debase

Acree

2001

J. Chem. Eng. Data

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“…Deviations from ideality arise from the selfassociation of each alcohol cosolvent and, in mixtures containing two alcohol cosolvents, from the formation of heterogeneous hydrogen-bonded chains between dissimilar alcohol molecules. Powell et al (1997b) and McHale et al (1996) showed that the aforementioned thermodynamic models provided reasonably accurate descriptions for the solubility behavior of pyrene and anthracene in binary alkane + alcohol and alcohol + alcohol solvent mixtures.…”

Section: Introductionmentioning

confidence: 99%

Solubility of Anthracene in Ternary Dibutyl Ether + Alcohol + Cyclohexane Solvent Mixtures

Pribyla

Acree

1999

J. Chem. Eng. Data

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Experimental solubilities are reported for anthracene dissolved in ternary dibutyl ether + 1-propanol + cyclohexane, dibutyl ether + 2-propanol + cyclohexane, dibutyl ether + 1-butanol + cyclohexane, dibutyl ether + 2-butanol + cyclohexane, and dibutyl ether + 2-methyl-1-propanol + cyclohexane solvent mixtures at 25°C and atmospheric pressure. Nineteen compositions were studied for each of the five solvent systems. Results of these measurements are used to test the predictive ability of the ternary solvent form of the combined NIMS/Redlich-Kister equation. Computations showed that the model predicted the observed solubility behavior to within an overall average absolute deviation of about 1.5%, which is comparable to the experimental uncertainty of (1.5%.

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“…[5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21]), a number of studies have developed quantitative structure-property relationships (QSPRs) and employed associated software programs (see, e.g., ref. [22][23][24][25][26][27][28]) for predicting the solubility of these compounds in a wide range of solvent systems.To date, despite its broad applications towards predicting the partitioning behavior and reactivity of various organic compounds, the SPARC software program [29][30][31][32][33][34][35][36] has not been previously benchmarked for its capacity to estimate the solubility of representative PAHs in organic solvents. Consequently, in the current work we investigate the ability of SPARC to predict the solubilities of naphthalene (1) and anthracene (2) (Figure 1) in a range of organic solvents at various temperatures.…”

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Benchmarking the SPARC software program for estimating solubilities of naphthalene and anthracene in organic solvents

Rayne¹,

Forest²

2011

Nature Precedings

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The solubility of polyaromatic hydrocarbons (PAHs) and their derivatives in organic solvents is of substantial interest for the upstream and downstream petroleum sectors [1][2][3][4]. Knowledge of this physico-chemical property helps guide the development and optimization of existing and proposed extraction and processing operations. In addition to extensive experimental work determining the solubilities of various PAHs (see, e.g., ref. [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21]), a number of studies have developed quantitative structure-property relationships (QSPRs) and employed associated software programs (see, e.g., ref. [22][23][24][25][26][27][28]) for predicting the solubility of these compounds in a wide range of solvent systems.To date, despite its broad applications towards predicting the partitioning behavior and reactivity of various organic compounds, the SPARC software program [29][30][31][32][33][34][35][36] has not been previously benchmarked for its capacity to estimate the solubility of representative PAHs in organic solvents. Consequently, in the current work we investigate the ability of SPARC to predict the solubilities of naphthalene (1) and anthracene (2) (Figure 1) in a range of organic solvents at various temperatures. Mole fraction solubilities (log10 ΧA sat ) of 1 and 2 were estimated using SPARC (August 2011 release w4.6.1646-s4.6.1646; http://ibmlc2.chem.uga.edu/sparc/) with the default settings and solvent profiles. We have previously examined the ability of this program to estimate the pKa values, hydrolysis rate constants, and partitioning behavior of several classes of organic compounds [37][38][39][40][41][42][43][44][45][46]. We began our studies using the ΧA sat of naphthalene obtained in chloroform, t-butanol, cyclohexanol, 2-propanol, 1-propanol, and ethanol at 40°C under atmospheric pressure (Table 1). Poor agreement between the experimental and SPARC predicted ΧA sat was found for t-butanol, cyclohexanol, and 2-propanol (errors of +0.78, +0.41, and +0.45 log10 units, respectively), with reasonable ΧA sat agreement for chloroform, 1-propanol, and ethanol (errors of +0.11, -0.15, and -0.02 log10 units, respectively). We then considered the solubility behavior of naphthalene in a suite of additional organic solvents of varying polarity and for which broad temperature range specific ΧA sat values were available (Table 2). With the single exception of methanol, SPARC overestimates the solubility of naphthalene in all solvents (i.e., log10 ΧA,SPARC sat >log10 ΧA,expt sat ). Similarly, with the exception of methanol, the SPARC prediction performance improves with increasing temperature, as the solute becomes more soluble in the solvent. While the errors in predicted versus experimental log10 ΧA sat are typically on the order of several tenths of a log10 unit at low temperatures, at higher temperatures the error is reduced (with the exception of methanol) to <0.1 log10 units.

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Prediction of anthracene solubility in alcohol + alkane solvent mixtures using binary alcohol + alkane VLE data. Comparison of Kretschmer-Wiebe and mobile order models

Cited by 27 publications

References 39 publications

Solubility of Pyrene in Ternary Propanol + Butanol + 2,2,4-Trimethylpentane Solvent Mixtures at 299.15 K

Solubility of Pyrene in Ternary Propanol + Butanol + 2,2,4-Trimethylpentane Solvent Mixtures at 299.15 K

Solubility of Anthracene in Ternary Dibutyl Ether + Alcohol + Cyclohexane Solvent Mixtures

Benchmarking the SPARC software program for estimating solubilities of naphthalene and anthracene in organic solvents

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