Dearomatization Insights with Phosphonium-Based Deep Eutectic Solvent: Liquid–Liquid Equilibria Experiments and Predictions

Kumar, Nikhil; Banerjee, Tamal

doi:10.1021/acs.jced.1c00241

Cited by 16 publications

(7 citation statements)

References 41 publications

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“…The term “pseudo” has been introduced to indicate that the DES was treated as a pseudo-pure species instead of a mixture of the HBA and HBD, as demonstrated by Kumar and Banerjee . The composition of pure DES was verified using 1 H NMR, as shown in the Supporting Information.…”

Section: Experimental Sectionmentioning

confidence: 99%

“…For pseudoternary LLE experiments, different amounts of toluene, n -heptane, and DES were measured and added into a temperature-controlled glass vessel under vigorous mixing for a few hours. As several research groups have done, − we integrate the respective peak areas for the number of hydrogen atoms present within each functional group of a component.…”

Section: Experimental Sectionmentioning

confidence: 99%

“…The term "pseudo" has been introduced to indicate that the DES was treated as a pseudo-pure species instead of a mixture of the HBA and HBD, as demonstrated by Kumar and Banerjee. 15 The composition of pure DES was verified using 1 H NMR, as shown in the Supporting Information. Several different mole fractions of each of the compound mixtures were prepared using toluene and DES and n-heptane and DES to conduct pseudobinary LLE experiments.…”

Section: Measurements Of Physicalmentioning

confidence: 99%

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Thermophysical Properties and Liquid–Liquid Equilibria of Pseudoternary Systems {Toluene + n-Heptane + Deep Eutectic Solvents Based on Levulinic Acid}

Jung

Park

2022

J. Chem. Eng. Data

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Three deep eutectic solvents (DESs), DES1−DES3, were prepared using levulinic acid and choline chloride with molar ratios of 3:1, 4:1, and 5:1, respectively. Another three DESs, DES4−DES6, were prepared using levulinic acid and acetylcholine chloride with the same molar ratio. The density and viscosity of all six DESs were experimentally measured at temperatures ranging from 293.2 to 323.2 K. Both the density and logarithmic value of viscosity of all DESs follow a linear tendency with respect to temperature and reciprocal temperature, respectively. The liquid−liquid equilibria (LLE) for the pseudobinary systems of both toluene and the DES and n-heptane and the DES were performed over a temperature range from 298.2 to 318.2 K with a 10 K interval. The solubilities of toluene in DESs were higher than those of n-heptane in DESs. The LLE of the pseudoternary systems of toluene, n-heptane, and DESs were obtained over a temperature range of 298.2−318.2 K with a 10 K interval. The distribution coefficient of toluene and selectivity were determined. The values of selectivity of toluene with DESs measured in this study were higher than those of other conventional solvents. Not only the mole fraction of toluene in the raffinate phase and temperature but also the mole ratio between the hydrogen bond acceptor and the hydrogen bond donor plays a role in determining both the distribution coefficient of toluene and selectivity.

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Section: Experimental Sectionmentioning

confidence: 99%

Section: Experimental Sectionmentioning

confidence: 99%

Section: Measurements Of Physicalmentioning

confidence: 99%

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Thermophysical Properties and Liquid–Liquid Equilibria of Pseudoternary Systems {Toluene + n-Heptane + Deep Eutectic Solvents Based on Levulinic Acid}

Jung

Park

2022

J. Chem. Eng. Data

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“…Jung et al synthesized DES using choline chloride as the HBA and levulinic acid (LA) as the HBD for the separation of toluene/ n -heptane, and the selectivity of toluene reached 52.9. At present, ammonium/phosphonium salts as HBAs and alcohols/acids as HBDs are mainly used to design and synthesize DESs, which have achieved good extraction effects in the separation of aromatic/alkane. , Nevertheless, it is difficult to further improve the separation performance by adjusting the HBA/HBD structure for common DESs. Therefore, we propose the design and development of novel IL-based DESs by using IL as the HBA and selecting suitable HBDs, which can combine the advantages of both ILs and DESs and improve the designability and extraction performance of IL-based DESs. , …”

Section: Introductionmentioning

confidence: 99%

Pyridine Ionic Liquid-Based Deep Eutectic Solvents Selectively Separating Toluene from Alkanes

Shi

et al. 2023

Energy Fuels

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Naphtha is an important raw material for ethylene cracking, and the aromatics in it can affect the ethylene yield due to the easy coking during the cracking process. Therefore, it is important to separate the aromatics from naphtha to increase the alkane content and improve the ethylene cracking production. Liquid−liquid extraction separation of the aromatic/alkane mixture is one of the effective pathways, and the key is the design and synthesis of new efficient extractants. In this work, a novel pyridine ionic liquid-based deep eutectic solvent (DES) for the separation of aromatics from alkanes was proposed and successfully synthesized. 1-Ethylpyridinium chloride (EpyCl) was used as the hydrogen bond acceptor and levulinic acid (LA) as the hydrogen bond donor. Among them, the π−π interactions between pyridine ring, C�O, and aromatic ring can enhance the interactions with aromatic compounds. In contrast, the introduction of acidic groups can increase the polarity of DES, enhance the induced polarization of unsaturated bonds in aromatic rings by DES, and thus increase the non-bonding force with aromatics. Toluene/n-heptane and toluene/cyclohexane were used as simulated oil systems. The optimal ratio of EpyCl/LA is 2:1, which has the best extraction efficiency, stability, and reusability; the selectivity of toluene was up to 69.57 for the toluene-n-heptane system, while it was 24.41 for the toluene-cyclohexane system. The reliability of the liquid−liquid equilibrium data was verified by using the Othmer−Tobias correlation equations, and the basic system physical property data were obtained by fitting with the NRTL thermodynamic model. The interaction mechanism between DES and toluene/alkanes was revealed by AIM topology analysis, IGMH analysis, and symmetry-adapted perturbation theory energy decomposition. The interaction between DES and toluene/alkanes is a van der Waals force, dominated by dispersion forces.

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“…Rogošić et al discovered that the most significant mass ratio of DES/model fuel of 1.00 kg·kg –1 yielded the maximum extraction efficiency. Our earlier work reported dearomatization of benzene from model diesel fuel consisting of long-chain hydrocarbons in the range of C 10 –C 16 using phosphonium-based deep eutectic solvents. It reveals that the noncovalent interaction between the DES and benzene is mainly responsible for the higher selectivity and distribution coefficient at a minimal concentration.…”

Section: Introductionmentioning

confidence: 99%

Molecular Mechanism and Solubility Performance Evaluation for Separation of Benzothiophene and Model Diesel Compounds through Deep Eutectic Solvents as Extractants

Kumar

Banerjee

2022

Ind. Eng. Chem. Res.

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During combustion, sulfur compounds in fuels are oxidized to SO x , poisoning automatic catalytic converters and posing severe environmental risks (e.g., acid rain). As an outcome, effective liquid fuel desulphurization is a vital step in reducing SO x emissions and their inherent ecological impacts. The extraction of ultralow benzothiophene from n-decane as representative model diesel fuel was analyzed using phosphonium-based deep eutectic solvents (DESs) at 308.15 K and 1 bar pressure. Liquid−liquid equilibrium (LLE) studies were conducted on a ternary system of DES− benzothiophene−n-decane for all six feed point concentrations. 1 H NMR analysis was used to determine the molar composition of each raffinate and extract phase. The LLE experimental findings were examined using a conductor-like screening model for segment activity coefficient (COSMO-SAC) based on quantum calculations. The average root-mean-square deviation (RMSD) of the studied LLE ternary system was 1.07%, which was suitable considering the prior nature of the approach. The σ-profile calculations using the COSMO-SAC model and Hansen solubility parameters (HSPs) using different predicted models were used to provide insights into the molecular mechanism of benzothiophene extraction efficacy using DES. We observed higher extraction of benzothiophene due to the higher proportion of hydrogen-bonding and dispersion-type interactions. Charge transfer analysis using the density functional theory (DFT) calculation of the DES cluster suggested that bromide (Br − ) ions can act as a charge transfer bridge between the methyltriphenylphosphonium (MTP) cation and the hydrogen bond donor. The MTP cation and ethylene glycol also aided in the extraction of benzothiophene by dislocating charge from the aromatic sulfur compound. The bromide (Br − ) ion is essentially noninteractive with benzothiophene due to retention of the conventional hydrogen bond network existing within the initial components of DES, mainly hydrogen bond donors and hydrogen bond acceptors.

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Dearomatization Insights with Phosphonium-Based Deep Eutectic Solvent: Liquid–Liquid Equilibria Experiments and Predictions

Cited by 16 publications

References 41 publications

Thermophysical Properties and Liquid–Liquid Equilibria of Pseudoternary Systems {Toluene + n-Heptane + Deep Eutectic Solvents Based on Levulinic Acid}

Thermophysical Properties and Liquid–Liquid Equilibria of Pseudoternary Systems {Toluene + n-Heptane + Deep Eutectic Solvents Based on Levulinic Acid}

Pyridine Ionic Liquid-Based Deep Eutectic Solvents Selectively Separating Toluene from Alkanes

Molecular Mechanism and Solubility Performance Evaluation for Separation of Benzothiophene and Model Diesel Compounds through Deep Eutectic Solvents as Extractants

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