Abraham model correlations for describing dissolution of organic solutes and inorganic gases in dimethyl carbonate

Strickland, Sara E.; Ocon, Libby; Zhang, Alex; Wang, Shang; Eddula, Shrika; Liu, Grace; Tirumala, Priya; Huang, Jennifer; Dai, Jingyi; Jiang, Carina; Acree, William E.; Abraham, Michael H.

doi:10.1080/00319104.2019.1698044

Cited by 14 publications

(7 citation statements)

References 92 publications

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“…This can be seen in Figure 4 for 1-chloroanthraquinone, phenothiazine, benzoin, and 4-nitrobenzoic acid. The experimental data for those solutes originate from the publications by Dai et al, 32 Flanagan et al, 33 Grubbs et al, 34 Hoover et al, 35,36 Saifullah et al, 37 Stephens et al, 38 Strickland et al, 39 Yang et al, 40 and Zhu et al 41 In the Supporting Information (Figure S6), the same analysis is made for the 40 solutes that are most common in the database at 298 K. As can be seen in Figure 4 (blue), the solid solubility of some solutes is predicted very well, while a constant deviation from the parity line is observed for others. In the latter case, the absolute value of the predicted solid solubility is off, but the relative solid solubility between various organic solvents is well captured by the model.…”

Section: S Dtmentioning

confidence: 99%

“…This is demonstrated in Figure 6 for nacetylglycine, benzoin, bezafibrate, and chlorpropamide. The experimental data for these solvents originate from the publications by Dai et al, 32 Guo et al, 42 Guo et al, 43 Liu et al, 44 Liu et al, 45 Stephens et al, 38 Strickland et al, 39 Yang et al, 46 Yang et al, 40 and Zhu et al 41 For the 40 most common solutes in the CombiSolu-Exp database, the same analysis is added to the Supporting Information (Figure S10). Replacing log(S aq,model,298 K ) with experimental data log(S EtOH,exp,298 K ) for the calculation of log(S X,298 K ) shifts the prediction results to the parity line, which is in line with the results for log(S X,298 K ).…”

Section: S Dtmentioning

confidence: 99%

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Predicting Solubility Limits of Organic Solutes for a Wide Range of Solvents and Temperatures

2022

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The solubility of organic molecules is crucial in organic synthesis and industrial chemistry; it is important in the design of many phase separation and purification units, and it controls the migration of many species into the environment. To decide which solvents and temperatures can be used in the design of new processes, trial and error is often used, as the choice is restricted by unknown solid solubility limits. Here, we present a fast and convenient computational method for estimating the solubility of solid neutral organic molecules in water and many organic solvents for a broad range of temperatures. The model is developed by combining fundamental thermodynamic equations with machine learning models for solvation free energy, solvation enthalpy, Abraham solute parameters, and aqueous solid solubility at 298 K. We provide free open-source and online tools for the prediction of solid solubility limits and a curated data collection (SolProp) that includes more than 5000 experimental solid solubility values for validation of the model. The model predictions are accurate for aqueous systems and for a huge range of organic solvents up to 550 K or higher. Methods to further improve solid solubility predictions by providing experimental data on the solute of interest in another solvent, or on the solute’s sublimation enthalpy, are also presented.

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Section: S Dtmentioning

confidence: 99%

Section: S Dtmentioning

confidence: 99%

Predicting Solubility Limits of Organic Solutes for a Wide Range of Solvents and Temperatures

2022

View full text Add to dashboard Cite

show abstract

“…This can be seen in Figure 4 for 1-chloroanthraquinone, phenothiazine, benzoin, and 4-nitrobenzoic acid. The experimental data for those solutes originate from the publications by Dai et al, 32 Flanagan et al, 33 Grubbs et al, 34 Hoover et al, 35,36 Saifullah et al, 37 Stephens et al, 38 Strickland et al, 39 Yang et al, 40 and Zhu et al 41 In the supporting information (Figure S6), the same analysis is made for the 40 solutes that are most common in the database at 298K. As can be seen in Figure 4 (blue), the solid solubility of some solutes is predicted very well, whilst a constant deviation from the parity line is observed for others.…”

Section: Aqueous Solid Solubility At 298kmentioning

confidence: 99%

“…This is demonstrated in Figure 6 for n-acetylglycine, benzoin, bezafibrate, and chlorpropamide. The experimental data for these solvents originate from the publications by Dai et al, 32 Guo et al, 42 Guo et al, 43 Liu et al, 44 Liu et al, 45 Stephens et al, 38 Strickland et al, 39 Yang et al, 46 Yang et al, 40 and Zhu et al 41 For the 40 most common solutes in the CombiSolu-Exp database, the same analysis is added to the supporting information (Figure S10). Replacing log(S aq,model,298K ) with experimental data log(S EtOH,exp,298K ) for the calculation of log(S X,298K ) shifts the prediction results to the parity line, which is in line with the results for log(S X,298K ).…”

Section: Predicting Temperature-dependent Solid Solubilitymentioning

confidence: 99%

Predicting Solubility Limits of Organic Solutes for a Wide Range of Solvents and Temperatures

Vermeire

Chung

Green

2022

Preprint

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The solubility of organic molecules is crucial in organic synthesis and industrial chemistry, it is important in the design of many phase separation and purification units, and it controls the migration of many species into the environment. Solubility limits force chemists and engineers to change the solvent or adjust the temperature of their process, often by trial and error. Here we present a fast and convenient computational method for estimating the solubility of any neutral organic molecule in water and any organic solvent at any temperature. The model is developed by combining fundamental thermodynamic equations with machine learning models for solvation free energy, solvation enthalpy, Abraham solute parameters, and aqueous solubility at 298K. We provide free open-source and online tools for the prediction of solubility limits and a curated data collection (SolProp) that includes more than 5,000 experimental solubility values for validation of the model. The model predictions are accurate for aqueous systems and for a huge range of organic solvents up to 550K or higher. Methods to further improve solubility predictions by providing experimental data on the solute of interest in any solvent at any temperature, or on the solute’s sublimation enthalpy, are also presented.

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“…Our recent efforts pertaining to solubility have focused on experimental measurements for crystalline nonelectrolyte solutes dissolved in select organic mono-solvents [14][15][16][17] and in binary aqueous-organic solvent mixtures [18][19][20][21][22]. The measured solubility data has been used in the calculation of the Abraham model solute descriptors [14][15][16][17] and in developing the Abraham model correlations for predicting the solubilities of pharmaceutical compounds in organic solvents used in recrystallization purifications and in co-solvency solubility enhancements [23][24][25][26][27]. Transcutol was one the recent organic solvents for which the predictive Abraham model expressions were reported [23].…”

Section: Introductionmentioning

confidence: 99%

Abraham Model Descriptors for Vitamin K4: Prediction of Solution, Biological and Thermodynamic Properties

Motati,

Kandi

et al. 2023

Liquids

Self Cite

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Spectrophotometric measurements were used to determine the mole fraction solubilities of vitamin K4 dissolved in cyclohexane, methylcyclohexane, 1-heptanol, 2-butanol, 2-pentanol, 2-methyl-1-butanol, 4-methyl-2-pentanol, and cyclopentanol at 298.15 K. Results from our experimental measurements, combined with the published solubility data, are used to calculate the solute descriptors of the vitamin K4 solute. The calculated solute descriptors describe the observed solubility data to within an overall standard deviation of 0.110 log units. The calculated solute descriptors were also used to estimate the several blood-to-rat tissue partition coefficients of vitamin K4, as well as the equilibrium vapor pressure above the solid vitamin at 298 K, and the vitamin’s enthalpy of solvation in both water and in 1,4-dioxane organic mono-solvent.

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Abraham model correlations for describing dissolution of organic solutes and inorganic gases in dimethyl carbonate

Cited by 14 publications

References 92 publications

Predicting Solubility Limits of Organic Solutes for a Wide Range of Solvents and Temperatures

Predicting Solubility Limits of Organic Solutes for a Wide Range of Solvents and Temperatures

Predicting Solubility Limits of Organic Solutes for a Wide Range of Solvents and Temperatures

Abraham Model Descriptors for Vitamin K4: Prediction of Solution, Biological and Thermodynamic Properties

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