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Development of an Infinite Dilution Activity Coefficient Prediction Model for Organic Solutes in Ionic Liquids with Modified Partial Equalization Orbital Electronegativity Method Derived Descriptors.

ABSTRACT: The objective of this study was to develop a robust prediction model for the infinite dilution activity coefficients (γ ^∞) of organic molecules in diverse ionic liquid (IL) solvents. Electrostatic, hydrogen bond, polarizability, molecular structure, and temperature terms were used in model development. A feed-forward model based on artificial neural networks was developed with 34,754 experimental activity coefficients, a combination of 195 IL solvents (88 cations and 38 anions), and 147 organic solutes at a temperature range of 298 to 408 K. The root mean squared error (RMSE) of the training set and test set was 0.219 and 0.235, respectively. The R ² of the training set and the test set was 0.984 and 0.981, respectively. The applicability domain was determined through a Williams plot, which implied that water and halogenated compounds were outside of the applicability domain. The robustness test shows that the developed model is robust. The web server supports using the developed prediction model and is freely available at https://preadmet.bmdrc.kr/activitycoefficient_mainpage/prediction/.

SUBMITTER: Jeon HN

PROVIDER: S-EPMC8210453 | biostudies-literature |

REPOSITORIES: biostudies-literature

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QSPR modeling of selectivity at infinite dilution of ionic liquids.

Project description:The intelligent choice of extractants and entrainers can improve current mixture separation techniques allowing better efficiency and sustainability of chemical processes that are both used in industry and laboratory practice. The most promising approach is a straightforward comparison of selectivity at infinite dilution between potential candidates. However, selectivity at infinite dilution values are rarely available for most compounds so a theoretical estimation is highly desired. In this study, we suggest a Quantitative Structure-Property Relationship (QSPR) approach to the modelling of the selectivity at infinite dilution of ionic liquids. Additionally, auxiliary models were developed to overcome the potential bias from big activity coefficient at infinite dilution from the solute. Data from SelinfDB database was used as training and internal validation sets in QSPR model development. External validation was done with the data from literature. The selection of the best models was done using decision functions that aim to diminish bias in prediction of the data points associated with the underrepresented ionic liquids or extreme temperatures. The best models were used for the virtual screening for potential azeotrope breakers of aniline + n-dodecane mixture. The subject of screening was a combinatorial library of ionic liquids, created based on the previously unused combinations of cations and anions from SelinfDB and the test set extractants. Both selectivity at infinite dilution and auxiliary models show good performance in the validation. Our models' predictions were compared to the ones of the COSMO-RS, where applicable, displaying smaller prediction error. The best ionic liquid to extract aniline from n-dodecane was suggested.

| S-EPMC8549394 | biostudies-literature

Imidazolium Based Ionic Liquids: Unbiased Recovering of Vaporization Enthalpies from Infinite-Dilution Activity Coefficients.

Project description:We propose and test an efficient approach for the assessment of the enthalpies of vaporization of ionic liquids at the reference temperature 298.15 K. The approach is based on activity coefficients at infinite dilution of volatile organic solutes in ionic liquids bearing the imidazolium cation of the general formula [Cnmim][Anion].

| S-EPMC8510351 | biostudies-literature

Measurements of Activity Coefficients at Infinite Dilution for Organic Solutes in the Ionic Liquids N-Ethyl- and N-Octyl-N-methylmorpholinium Bis(trifluoromethanesulfonyl)imide. A Useful Tool for Solvent Selection.

Project description:In recent years, many papers describing ionic liquids (IL) as promising solvents in separation techniques have been published. The conscious choice of appropriate ionic liquid as absorption media in effective extraction of selected types of analytes requires deeper understanding of the analyte-IL interactions. Therefore, intensive research is conducted to determine the values of activity coefficient at infinite dilution, which allows us to characterize the nature of these interactions. Based on the inverse gas chromatography retention data, activity coefficients at infinite dilution γ 13 ∞ of 48 different organic compounds in the ionic liquids N-ethyl-N-methylmorpholinium bis(trifluoromethanesulfonyl)imide [C2C1Mor][TFSI] and N-octyl-N-methylmorpholinium bis(trifluoromethanesulfonyl)imide [C8C1Mor][TFSI] were determined. The measurements covered a broad range of volatile organic compounds, including n-alkanes, n-alkenes, n-alkynes, alcohols, aldehydes, ketones, aromatic compounds and common polar solvents, representing different types of interactions. Activity coefficients at infinite dilution were measured in the temperature range from 313.15 to 363.15 K. The excess partial molar enthalpies and entropies at infinite dilution were determined. Selectivity at infinite dilution was also calculated for exemplary separation processes in the hexane/benzene system. The obtained results were analyzed and compared with literature data for ionic liquids containing the same anion [TFSI]¯ and different cations. The study results indicate that some potential applications of the investigated ionic liquids in separation problems exist.

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Activity Coefficients at Infinite Dilution and Physicochemical Properties for Organic Solutes and Water in the Ionic Liquid 1-Ethyl-3-methylimidazolium trifluorotris(perfluoroethyl)phosphate.

Project description:New data of activity coefficients at infinite dilution, γ13∞, for 65 different solutes including alkanes, alkenes, alkynes, cycloalkanes, aromatic hydrocarbons, alcohols, thiophene, ethers, ketones, aldehydes, esters and water in the ionic liquid 1-ethyl-3-methylimidazolium trifluorotris(perfluoroethyl)phosphate, were determined using inverse gas chromatography within the temperature range from 318.15 to 368.15 K. This is a continuation of our study of ionic liquids based on this anion. The results are compared with the other trifluorotris(perfluoroethyl)phosphate ionic liquids. The γ13∞ values were used to calculate thermodynamic functions such as partial molar excess Gibbs energies [Formula: see text], enthalpies [Formula: see text] and entropies [Formula: see text] as well as gas-liquid partition coefficients of the solutes, KL. These values were used to determine the linear free energy relationship (LFER) system constants as a function of temperature. The selectivities at infinite dilution needed for some extraction problems were calculated and compared with literature data of ionic liquids based on the trifluorotris(perfluoroethyl)phosphate anion and the 1-ethyl-3-methylimidazolium cation. Additionally, the density and viscosity of the investigated ionic liquid at temperatures from 298.15 to 348.15 K were measured.

| S-EPMC4412692 | biostudies-literature

Predictive Models for the Binary Diffusion Coefficient at Infinite Dilution in Polar and Nonpolar Fluids.

Project description:Experimental diffusivities are scarcely available, though their knowledge is essential to model rate-controlled processes. In this work various machine learning models to estimate diffusivities in polar and nonpolar solvents (except water and supercritical CO2) were developed. Such models were trained on a database of 90 polar systems (1431 points) and 154 nonpolar systems (1129 points) with data on 20 properties. Five machine learning algorithms were evaluated: multilinear regression, k-nearest neighbors, decision tree, and two ensemble methods (random forest and gradient boosted). For both polar and nonpolar data, the best results were found using the gradient boosted algorithm. The model for polar systems contains 6 variables/parameters (temperature, solvent viscosity, solute molar mass, solute critical pressure, solvent molar mass, and solvent Lennard-Jones energy constant) and showed an average deviation (AARD) of 5.07%. The nonpolar model requires five variables/parameters (the same of polar systems except the Lennard-Jones constant) and presents AARD = 5.86%. These results were compared with four classic models, including the 2-parameter correlation of Magalhães et al. (AARD = 5.19/6.19% for polar/nonpolar) and the predictive Wilke-Chang equation (AARD = 40.92/29.19%). Nonetheless Magalhães et al. requires two parameters per system that must be previously fitted to data. The developed models are coded and provided as command line program.

| S-EPMC7866074 | biostudies-literature

Application of a General Computer Algorithm Based on the Group-Additivity Method for the Calculation of Two Molecular Descriptors at Both Ends of Dilution: Liquid Viscosity and Activity Coefficient in Water at Infinite Dilution.

Project description:The application of a commonly used computer algorithm based on the group-additivity method for the calculation of the liquid viscosity coefficient at 293.15 K and the activity coefficient at infinite dilution in water at 298.15 K of organic molecules is presented. The method is based on the complete breakdown of the molecules into their constituting atoms, further subdividing them by their immediate neighborhood. A fast Gauss-Seidel fitting method using experimental data from literature is applied for the calculation of the atom groups' contributions. Plausibility tests have been carried out on each of the calculations using a ten-fold cross-validation procedure which confirms the excellent predictive quality of the method. The goodness of fit (Q²) and the standard deviation (σ) of the cross-validation calculations for the viscosity coefficient, expressed as log(η), was 0.9728 and 0.11, respectively, for 413 test molecules, and for the activity coefficient log(γ)∞ the corresponding values were 0.9736 and 0.31, respectively, for 621 test compounds. The present approach has proven its versatility in that it enabled the simultaneous evaluation of the liquid viscosity of normal organic compounds as well as of ionic liquids.

| S-EPMC5943952 | biostudies-literature

Mechanisms ruling the partition of solutes in ionic-liquid-based aqueous biphasic systems - the multiple effects of ionic liquids.

Project description:In the past decade, the remarkable potential of ionic-liquid-based aqueous biphasic systems (IL-based ABSs) to extract and purify a large range of valued-added biocompounds has been demonstrated. However, the translation of lab-scale experiments to an industrial scale has been precluded by a poor understanding of the molecular-level mechanisms ruling the separation or partition of target compounds between the coexisting phases. To overcome this limitation, we carried out a systematic evaluation of specific interactions, induced by ILs and several salts used as phase-forming components, and their impact on the partition of several solutes in IL-based ABSs. To this end, the physicochemical characterization of ABSs composed of imidazolium-based ILs, three salts (Na2SO4, K2CO3 and K3C6H5O7) and water was performed. The ability of the coexisting phases to participate in different solute-solvent interactions (where "solvent" corresponds to each ABS phase) was estimated based on the Gibbs free energy of transfer of a methylene group between the phases in equilibrium, ΔG(CH2), and on the Kamlet-Taft parameters - dipolarity/polarizability (π*), hydrogen-bonding donor acidity (α) and hydrogen-bonding acceptor basicity (β) - of the coexisting phases. Relationships between the partition coefficients, the phase properties expressed as Kamlet-Taft parameters and COSMO-RS descriptors were established, highlighting the ability of ILs to establish specific interactions with given solutes. The assembled results clearly support the idea that the partition of solutes in IL-based ABSs is due to multiple effects resulting from both global solute-solvent and specific solute-IL interactions. Solute-IL specific interactions are often dominant in IL-based ABSs, explaining the higher partition coefficients, extraction efficiencies and selectivities observed with these systems when compared to more traditional ones majorly composed of polymers.

| S-EPMC6161819 | biostudies-literature

Stability of cellulase in ionic liquids: correlations between enzyme activity and COSMO-RS descriptors.

Project description:Ionic liquids (ILs) are effective in pretreating cellulose for enhanced enzymatic saccharification, however ILs can inactivate cellulases. To guide the selection of ILs, the activity of cellulase was correlated with COSMO-RS calculations and descriptors of ILs including hydrogen bond (H-bond) basicity/acidity, polarity and ion size. Trends were deduced using an anion-series and a cation-series of ionic liquids in aqueous solutions. The activity in the cation-series was best correlated with the size of varied cations, whereas the activity in the anion-series showed a pronounced correlation to H-bond basicity and polarity of different anions. COSMO-RS was further used to predict the solubility of cellulose in ILs, which was correlated with cellulase activity on IL-pretreated cellulose. The best correlations were found between the enzyme activity in the anion-series ILs and the logarithmic activity coefficients, the H-bond energy, H-bond basicity and polarizability, underlining that the anion plays a crucial role in cellulose dissolution.

| S-EPMC6877754 | biostudies-literature

Transcriptional toxicity of imidazolium- and cholinium-based ionic liquids

Project description:Ionic Liquids are a broad group of salts with low melting points that can be specifically tuned for a broad range of applications. Despite being initially considered “green” solvents, their better environmental friendliness compared to traditional solvents has been increasingly challenged. In this study, we aimed to investigate the molecular effects of ILs exposure by using RNA-sequencing to study differential gene expression patterns. Thus, we exposed Daphnia magna to 1-ethyl-3-methylimidazolium chloride ([C2mim]Cl), 1-dodecyl chloride-3-methylimidazolium ([C12mim]Cl) and cholinium chloride ([Chol]Cl). Results suggest that the three ILs share several mechanisms of toxicity, including cellular membrane and cytoskeleton damage, oxidative stress, inhibition of antioxidant enzymes, mitochondrial affectation, changes in protein biosynthesis and energy production, DNA damage, and ultimately, programmed cell death and disease initiation. Overall, the dataset revealed that [C2mim]Cl and [C12mim]Cl were, respectively, the least and the most toxic ILs at the transcriptional level. Also, it is reinforced that [Chol]Cl is not devoid of environmental hazardous potential. Unique gene expression signatures could also be identified for each IL.

2021-08-13 | GSE156769 | GEO

Comprehensive approach for predicting toxicological effects of ionic liquids on several biological systems using unified descriptors.

Project description:The challenge and opportunity for design of environmentally-benign ionic liquids (ILs) would start from prediction of their toxicological effects on several endpoints solely based on the structural formulas. Especially, a comprehensive yet simple equation able to predict several biological responses to IL toxicity is of much advantage. Therefore, based on 50 toxicity testing systems on ILs a comprehensively approachable prediction method was developed. For the modelling, approximately 1600 toxicity values measured by several biological systems and an amended linear free energy relationship (LFER) model were used. Since the toxicological activities of an IL could be differently described according to sensitivity of toxicity testing systems, the sensitivity of each of toxicity testing systems was also estimated in the modelling. By statistical analysis with the calculated descriptors, a LFER model was built. Also the sensitivity value of each system on the basis of the comprehensively approachable model was numerically estimated. In results, it was observed that the combination of single model and sensitivity terms was able to predict each of 50 toxicological effects of ILs with R(2) of 0.593~0.978, and SE of 0.098~0.699 log unit, and the total data set with R(2) of 0.901 and SE of 0.426 log unit.

| S-EPMC5022054 | biostudies-literature

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