Effective extraction of benzene and thiophene by novel deep eutectic solvents from hexane / aromatic mixture at different temperatures

Shekaari, Hemayat; Zafarani-Moattar, Mohammed Taghi; Mohammadi, Behrouz

doi:10.1016/j.fluid.2018.11.025

Cited by 26 publications

(11 citation statements)

References 30 publications

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“…According to the latest review of DES applications published in 2020, the challenge and future direction are to use molecular simulation, response surface analysis, and process simulation to understand the nature of such solvents that can help develop these neoteric solvents . Prior research has used experimental methods to determine the extraction of aromatics and the solubility of DESs . At the same time, only a few studies have focused on the microscopic behavior of DESs mixtures and the solubility of aromatic and aliphatic compounds in solvents.…”

Section: Introductionmentioning

confidence: 99%

Molecular Dynamic Insights into the Distinct Solvation Structures of Aromatic and Aliphatic Compounds in Monoethanolamine-Based Deep Eutectic Solvents

2022

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Deep eutectic solvents (DESs) are developing as an alternate medium for aromatic extraction, especially benzene and thiophene from aliphatic hydrocarbon mixtures. In this work, molecular dynamics (MD) simulations were first used to investigate the solvation structure of benzene, thiophene, and n-hexane in monoethanolamine-based DESs. It reveals the liquid structures in the adjacent neighbor shells, which is a function of electron-withdrawing sulfur attached to thiophene and the π-electron cloud of benzene. The intermolecular forces between aromatic, aliphatic, and DES components are analyzed in van der Waals and hydrogen bond interactions. The chloride ions serve as a charge carrier bridge between choline and monoethanolamine precursors. The solvation of benzene, thiophene, and n-hexane in the DESs depends on volume expansion and minor solvent structural changes. Density functional theory results provided information on the mechanism of short-range interactions between organic solutes and studied DES. It aids in understanding the structural orientations of a DES with the addition of solutes, essential to the formation of DES. The solvation shell structure and characteristics were investigated in tandem with the possibility of benzene and thiophene clustering. The 1H NMR and 2D 1H–1H-NOESY were used to investigate the intermolecular interactions between benzene, thiophene, and n-hexane with monoethanolamine-based solvents. It concludes that high-ordered DES1 is more inclined to higher solubility than lower-ordered ones with a higher molar ratio of monoethanolamine. The solvation was reduced because the entropy gain was not maximized in the lower ordered DESs.

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Section: Introductionmentioning

confidence: 99%

Molecular Dynamic Insights into the Distinct Solvation Structures of Aromatic and Aliphatic Compounds in Monoethanolamine-Based Deep Eutectic Solvents

2022

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“…Shekaari et al [29] investigated the use of DESs, synthesized from choline chloride (HBA) and several HBDs, ethanolamines (mono-, di-and tri-) and ethylene glycol (mono-, di-and tri-), in the extraction of benzene from n-hexane. Their results show high selectivity for benzene, with ethanolamine based DES outperforming the ethylene glycol based DES.…”

Section: Introductionmentioning

confidence: 99%

Ternary liquid–liquid equilibrium data for n-Hexane-Benzene-DES (choline chloride/ethylene glycol, choline chloride/glycerol, choline chloride/urea) at 303 K and 101.3 kPa

et al. 2020

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In this study, deep eutectic solvents (DESs) were prepared using choline chloride as hydrogen bond acceptor (HBA) and ethylene glycol (EG) or glycerol (GLY) or urea (U) as hydrogen bond donor (HBD) and were evaluated as solvents in the extraction of benzene from n-hexane. Six of such solvents were prepared using different molar ratios of HBA: HBD and code named DES1, DES2, DES3, DES4, DES5 and DES6. Liquid–liquid equilibria (LLE) data for the ternary systems of n-hexane-benzene-DESs were measured at 303 K and 101.3 kPa. Solubility data and mutual solubilities between n-hexane and DES were measured using the traditional cloud point method. The tie lines were obtained using titration and refractive index measurements on both phases (n-hexane phase and DES-phases). The ternary systems exhibit type-1 phase behavior. The Othmer-Tobias and Hands equations were applied to examine the reliability of the LLE data. The tie-line data were correlated using the nonrandom two-liquid (NRTL) and universal quasichemical (UNIQUAC) thermodynamic models, and their corresponding binary interaction parameters were determined. The results show that the maximum separation factors were 31.24, 462.00, 15.24, 37.83, 174.60 and 126.00 for DES1, DES2, DES3, DES4, DES5 and DES6, respectively. The glycerol based DES (DES2 and DES5) show the highest separation factors and thus considered the most suitable for separating benzene from hexane. The regression coefficient for both Othmer-Tobias and Hand equations are higher than 0.99 for all DESs, indicating the reliability and consistency of the data. Both NRTL and UNIQUAC models adequately capture the experimental data.

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“…Aromatic-based solvents are widely used in many chemical and petrochemical engineering applications, , despite the increasing restrictions imposed by environmental legislations and chemical processes’ safety organizations . Among these solvents, toluene (methylbenzene) is used in several processes, including surfactant production, extraction solvent, and painting production processes.…”

Section: Introductionmentioning

confidence: 99%

Viscosity and Density of Binary Mixtures of Toluene + Igepal (CO-520, CO-630, CO-720, and CA-720) at T = 293.15–333.15 K and Atmospheric Pressure

et al. 2020

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Surfactants are widely used in industrial applications associated with several solvents. Therefore, it is worthy to know the nature of the molecular interactions present in surfactants and cosurfactant mixtures, whose thermodynamic and physical properties can provide important information from an academic and industrial viewpoint. In this work, density and viscosity data of binary mixtures of toluene + Igepal series (Igepal CO-520, Igepal CO-630, Igepal CO-720, or Igepal CA-720) were experimentally determined within a range of temperature T = 293.15–333.15 K and at an atmospheric pressure of 101.325 kPa. From these data, the following derivative properties have been evaluated: excess molar volume, viscosity deviation, thermal expansion coefficient, partial molar volume, and excess thermal expansion coefficient. It was observed that all these mixtures showed the prevalence of dispersion intermolecular forces.

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Effective extraction of benzene and thiophene by novel deep eutectic solvents from hexane / aromatic mixture at different temperatures

Cited by 26 publications

References 30 publications

Molecular Dynamic Insights into the Distinct Solvation Structures of Aromatic and Aliphatic Compounds in Monoethanolamine-Based Deep Eutectic Solvents

Molecular Dynamic Insights into the Distinct Solvation Structures of Aromatic and Aliphatic Compounds in Monoethanolamine-Based Deep Eutectic Solvents

Ternary liquid–liquid equilibrium data for n-Hexane-Benzene-DES (choline chloride/ethylene glycol, choline chloride/glycerol, choline chloride/urea) at 303 K and 101.3 kPa

Viscosity and Density of Binary Mixtures of Toluene + Igepal (CO-520, CO-630, CO-720, and CA-720) at T = 293.15–333.15 K and Atmospheric Pressure

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