Toward molecular modeling of thiophene distribution between the ionic liquid and hydrocarbon phases: Effect of hydrocarbon structure

Gorji, Ali Ebrahimpoor; Sobati, Mohammad Amin

doi:10.1016/j.molliq.2019.110976

Cited by 15 publications

(17 citation statements)

References 37 publications

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“…For datasets 4 and 5, as observed in Tables 4 and 5, the addition of Pol descriptor which reflects the effect of variation of hydrocarbon, improved the ability of models to predict Y 2 as expected, and the reason why the addition Pol descriptor can boost the prediction ability of QSPR models reported in Gorji et al study [29]. By adding hydrocarbon descriptor in equations ( 12) and ( 15), there is an increase in the R 2 value and a reduction of F-value for both datasets.…”

Section: Resultssupporting

confidence: 61%

“…Therefore, the effect of each hydrocarbon on the mole fraction of thiophene in the IL-rich phase (Y2) should be investigated. Gorji et al [29], used the Wiener polarity number (Pol) as the molecular characteristic of hydrocarbon for this purpose, as following:…”

Section: Methodsmentioning

confidence: 99%

“…Holbrey et al [16], investigated extraction of sulfur compound from dodecane using ionic liquids and used QSPR analysis of solvent group contributions to extraction. Gorji et al [29], employed QSPR methodology to propose models for the prediction of thiophene distribution between the IL-and hydrocarbon-rich phases in ternary systems containing IL, thiophene, and hydrocarbon solvent. Moreover, they investigated the effects of different anion and cation structures on the thiophene distribution between ionic liquid and hydrocarbon phases in the ternary systems using QSPR approach [30,31].…”

Section: Number Of Published Papersmentioning

confidence: 99%

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Investigation the effects of cation/anion structure on distribution of Thiophene between IL-rich and Hydrocarbon-rich phases by QSPR approach

Moheb-Aleaba

Khosravi‐Nikou

2021

Preprint

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Selecting an appropriate ionic liquid as extraction solvent for extracting sulfur compounds from fuel, is a promising way to reduce SOx emissions and to prevent environmental pollution. In this regard, the best structural descriptors of different cation and anion, which play an important role on the thiophene distribution between ionic liquid (IL) and hydrocarbon phases in the ternary systems, that is helpful for selecting a proper IL, have been investigated using quantitative structure − property relationship (QSPR) approach. Five different datasets were collected from the literature containing {(Cation/[NTf2] − thiophene − n-heptane), (Cation/[NTf2] − thiophene − n-hexane), (Cation/[FAP] − thiophene − n-heptane), (Cation/[TCM] − thiophene − n-heptane), ([C2MIM]/Anion − thiophene − hydrocarbon), ([C8MIM]/Anion–thiophene − hydrocarbon)} with 664 data points. By investigating the various kinds of molecular descriptors of 1D, 2D and 3D, it was found that the increment of Spanning Tree Number (STN) descriptor as cation structure descriptor, causes a decrease in mole fraction of thiophene in IL-rich phase due to the increase in steric hindrance. STN descriptor reflects the complexity of structure of cation and the information about steric hindrance. Also, it was found that an increase in E1p value as anion structure descriptor leads to the decrement of mole fraction of thiophene in IL-rich phase, in order to increase the interaction between cation and anion in ionic liquid, that reduced the available space of cation to interact with thiophene. The E1p descriptor represents the density of atoms projected along the length or unfilled space of the anion, thus it is informative of the accessibility of them by thiophene.

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Section: Resultssupporting

confidence: 61%

Section: Methodsmentioning

confidence: 99%

Section: Number Of Published Papersmentioning

confidence: 99%

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Investigation the effects of cation/anion structure on distribution of Thiophene between IL-rich and Hydrocarbon-rich phases by QSPR approach

Moheb-Aleaba

Khosravi‐Nikou

2021

Preprint

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“…Liquid–liquid extraction is a widely used separation technology in many fields of chemical industry, for example, removal of aromatic sulfurs and nitrogens from fuel oil, 1‐9 separation of phenols or cresols from coal tar oil or water, 10‐15 recovery of organic acids and metal ions from aqueous solution, 16‐20 and so forth. Between two solvent phases (α and β), the distribution of solute (A) equilibrium concentrations ( C A ) is crucial for liquid–liquid equilibrium (LLE) systems 21,22 . And the distribution coefficient ( D ) is an indicator for extraction performance, as expressed by C A (β)/ C A (α).…”

Section: Introductionmentioning

confidence: 99%

A simple model for precisely describing liquid–liquid equilibrium and better understanding extraction mechanism

et al. 2020

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Describing distribution of solute equilibrium concentrations between two solvents is important for liquid–liquid equilibrium (LLE). Due to non‐ideality of solutions, the distribution usually possesses non‐linear characteristic. In this work, the non‐ideality was simply represented by pseudo reaction (or chemical interaction) between the solute and the solvent without recourse to the complicated activity coefficient models. On this basis, a simple model, which combined physical partition and pseudo reaction equilibriums, was proposed and can precisely correlate various LLE systems, for example, the immiscible, the partially miscible, the organic, and even the electrolyte. More interestingly, the model can accurately reflect intrinsic mechanism by fitted parameters, that is, stoichiometric ratio of the pseudo reaction and total equilibrium constant for the interaction intensity. Besides, influence of the solute, the extractant, and temperature on the parameters was discussed deeply. This simple model is promising for precisely describing the LLE systems and better understanding their intrinsic extraction mechanism.

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“…Quantitative structure− property relationship (QSPR) is a methodology in which a macroscopic property can be interpreted at the molecular level. 43,44 Recently, this method has been used in our work 45 to investigate the effect of hydrocarbon structures on the thiophene distribution coefficient between IL-and hydrocarbon-rich phases successfully. It was found that the "Pol" descriptor of hydrocarbons, as a predictive and descriptive variable, can be used to take into account the effect of changing hydrocarbon structures on the thiophene distribution coefficient.…”

Section: Introductionmentioning

confidence: 99%

How Anion Structures Can Affect the Thiophene Distribution between Imidazolium-Based Ionic Liquid and Hydrocarbon Phases? A Theoretical QSPR Study

Gorji

Sobati

2019

Energy Fuels

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In this study, the effects of different anion structures have been investigated on the thiophene distribution between ionic liquid (IL) and hydrocarbon phases in the ternary systems using quantitative structure−property relationship. The role of anion structures was investigated in the presence of different cations and hydrocarbons. In this regard, three different datasets were selected from the literature containing {([C n MIM/anion]−thiophene−different hydrocarbon solvents): n = 2, 4, and 8} with 445 data points. It was found that the "E1v" descriptor of anions, belonging to the WHIM descriptor category, can take into account the effect of anion structures on the thiophene distribution for the systems containing the IL with the [C 2 MIM] cation and different hydrocarbons. It was found that increasing the E1v values of anion structures leads to a decrease in the thiophene distribution coefficients. E1v reflects the unfilled space of the anion structure, which in turn affects the interactions of the anion and cation in the IL structure. More unfilled spaces of the anion structure lead to more powerful interaction with the cation, which in turn limit the cation interaction with thiophene and decrease the thiophene distribution coefficient. It was also found that the effect of the anion on the thiophene distribution is decreased by increasing the length of alkyl chains in the cation from [C 2 MIM] to [C 4 MIM] and [C 8 MIM]. This finding can be attributed to the higher free volumes of [C 4 MIM] and [C 8 MIM] cations in comparison with that of [C 2 MIM], which allows more efficient packing of thiophene in the IL structure.

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Toward molecular modeling of thiophene distribution between the ionic liquid and hydrocarbon phases: Effect of hydrocarbon structure

Cited by 15 publications

References 37 publications

Investigation the effects of cation/anion structure on distribution of Thiophene between IL-rich and Hydrocarbon-rich phases by QSPR approach

Investigation the effects of cation/anion structure on distribution of Thiophene between IL-rich and Hydrocarbon-rich phases by QSPR approach

A simple model for precisely describing liquid–liquid equilibrium and better understanding extraction mechanism

How Anion Structures Can Affect the Thiophene Distribution between Imidazolium-Based Ionic Liquid and Hydrocarbon Phases? A Theoretical QSPR Study

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