Experimental determination of the LLE data of systems consisting of {hexane + benzene + deep eutectic solvent} and prediction using the Conductor-like Screening Model for Real Solvents

Rodriguez, N Nerea Rodriguez; Gerlach, Thomas; Scheepers, Daniëlle; Kroon, MC Maaike; Смирнова, Ирина

doi:10.1016/j.jct.2016.09.021

Cited by 51 publications

(28 citation statements)

References 50 publications

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“…Table S8 in the supporting material presents a comparative analysis of solvent performance in extracting benzene from n-hexane using distribution coefficient and selectivity as metrics. Three categories of solvent are compared namely organic solvent [19,20], ionic liquids [3] and deep eutectic solvents [12,16,26]. Considering the fact that organic solvent is the state-of-the art in industrial practice, it is appropriate to make one of them (sulfolane) the reference for comparison.…”

Section: Selectivity (S)mentioning

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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Section: Selectivity (S)mentioning

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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“…This method of first modeling electron density on the surface of a molecule and then examining electrostatic interactions better fits the complex ways that DES components interact with themselves and solutes. The maximum solubility of benzene and hexane have been accurately predicted in DES using COSMO, with an average root mean square deviation (RMSD) of 5% [17,18]. Though this is not complete LLE data, it is promising.…”

Section: Introductionmentioning

confidence: 99%

Liquid-Liquid Equilibrium of Deep Eutectic Solvent-Aromatic-Aliphatic Ternary Systems: Experimental Study with COSMO Model Predictions

McGaughy

Reza

2021

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Common solvents used for aromatic extraction from aliphatics typically degrade into toxic compounds, while green alternatives perform poorly compared to the state-of-the-art solvents. Deep eutectic solvents (DES) are a novel solvent type made of hydrogen bond donors (HBD) and hydrogen bond acceptors (HBA). DES have been applied in various applications, including advanced separations. In this study, DES were studied experimentally and using the Conductor-like Screening Model (COSMO) to separate benzene from cyclohexane as model compounds for an aromatic:aliphatic system. Both equilibrium and kinetic studies were performed to determine the liquid liquid equilibrium (LLE) and mass transfer rate for the DES-based separation. Selected HBAs including tetrabutylammonium bromide (N4444Br), tetrahexylammonium bromide (N6666Br), choline chloride (ChCl), and methyltriphenylphosphonium bromide (METPB) were paired with HBDs including ethylene glycol (EG) and glycerol (Gly). COSMO was used, with adjustments to reflect DES specific interactions, to predict the liquid-liquid equilibrium (LLE). COSMO results showed that ChCl and N6666Br-based DES extracted too little benzene or too much cyclohexane, respectively, to be considered for experimental evaluation. Overall, the COSMO model predictions for LLE of EG-based DES were very accurate, with root-mean-square deviations (RMSD) below 1% for both N4444Br:EG and METPB:EG. The glycerol systems were less accurately modeled, with RMSD’s of 4% for N4444Br:Gly and 6% for METPB:Gly. The lower accuracy of glycerol system predictions fmay be due to limitations in COSMO for handling glycerol’s influence on polarizability in the DES that is not seen in EG-based DES. Mass transfer kinetics were determined experimentally for DES and the results were fit to a first order kinetics model. METPB:Gly had the highest mass transfer coefficient at 0.180 min−1, followed by N4444Br:EG at 0.143 min−1. N4444Br:Gly and METPB:EG had the lowest mass transfer coefficients at 0.096 min−1 and 0.084 min−1, respectively. It was found that mass transfer rate was not directly related to maximum benzene solubility, as N4444Br:EG and METPB:Gly had the highest and lowest benzene removal, respectively, but had similar mass transfer coefficients.

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“…Their suggested DESs demonstrated lower selectivities in comparison to those of some ILs, while having comparable distribution ratios. 33 The feasibility of separation of benzene from hexane using the DESs made of one tetramethylammonium chloride, tetraethylammonium chloride, tetrabutylammonium chloride, or tetrahexylammonium chloride with either two ethylene glycol or glycerol was also probed by Rodriguez et al 34 Their results revealed that the increase of the alkyl chain length in the HBA led to an increase in the distribution ratio of benzene, while it reduced the selectivity. By comparing their studied DESs at the same HBA−HBD molar ratio, they also found that the ethylene glycol-based DESs show higher solubilities for both aromatics and aliphatics.…”

Section: Introductionmentioning

confidence: 99%

“…By comparing their studied DESs at the same HBA−HBD molar ratio, they also found that the ethylene glycol-based DESs show higher solubilities for both aromatics and aliphatics. 34 Based on the literature to date, only a limited number of DESs have been investigated for the separation of aromatics from aliphatics. In this manner, the potential of other DESs for separation of aromatics from aliphatics still remains an interesting topic to be investigated by researchers and scientists.…”

Section: Introductionmentioning

confidence: 99%

Experimental Investigation of Liquid–Liquid Extraction of Toluene + Heptane or Toluene + Hexane Using Deep Eutectic Solvents

2019

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In this work, the selective separation of toluene from mixtures of toluene + heptane or toluene + hexane was investigated using the newly emerging family of solvents, namely, deep eutectic solvents (DESs), as the extracting agent. The liquid–liquid equilibria (LLE) of these systems were measured at a temperature of 303.2 K and a pressure of 85 kPa. The DESs considered were made of choline chloride as the hydrogen bond acceptor (HBA) and phenol as the hydrogen bond donor (HBD), at the two different HBA–HBD molar ratios of 1:3 and 1:4. The experimental liquid–liquid equilibrium data, along with the selectivities and distribution coefficients, were reported for each set of equilibrium data and also compared with other ternary systems in the literature containing toluene + heptane or toluene + hexane and various solvents. The experimental results revealed that the studied DESs in this work have the potential to be utilized in the separation of toluene from either hexane or heptane at low concentrations of toluene. The experimental LLE data was also modeled using the nonrandom two-liquid (NRTL) model. The values of the root-mean-square deviations of the NRTL results with respect to experimental values indicated acceptable agreement, suggesting NRTL as a potential model for such systems.

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Experimental determination of the LLE data of systems consisting of {hexane + benzene + deep eutectic solvent} and prediction using the Conductor-like Screening Model for Real Solvents

Cited by 51 publications

References 50 publications

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

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

Liquid-Liquid Equilibrium of Deep Eutectic Solvent-Aromatic-Aliphatic Ternary Systems: Experimental Study with COSMO Model Predictions

Experimental Investigation of Liquid–Liquid Extraction of Toluene + Heptane or Toluene + Hexane Using Deep Eutectic Solvents

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