Assessment of Pyrrolidinium-Based Ionic Liquid for the Separation of Binary Mixtures Based on Activity Coefficients at Infinite Dilution

Kabane, Bakusele; Arumugam, Vasanthakumar; Chokkareddy, Rajasekhar; Redhi, Gan G.

doi:10.1021/acs.jced.9b00341

Cited by 22 publications

(7 citation statements)

References 45 publications

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“…By combining cations and anions, large numbers of ILs can be synthesized, and thus, the physiochemical properties can be tuned. Wide liquidus temperature, low vapor pressure, nonflammability, and ability to dissolve various solutes attract their use in organic and inorganic synthesis, catalysis, extraction medium, , and so forth. The physiochemical properties further vary depending upon the intermolecular interactions of solute and IL .…”

Section: Introductionmentioning

confidence: 99%

Low- to Room-Temperature Dehydrogenation of Dimethylamine Borane Facilitated by Ionic Liquids: Molecular Modeling and Experimental Studies

2020

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A novel low-and room-temperature dehydrogenation of dimethylamine borane (DMAB) is being reported using hydrogen sulfate-based ionic liquids (ILs), namely, 1-ethyl-3-methylimidazolium hydrogen sulfate ([EMIM][HSO 4 ]) and 1-butyl-3methylimidazolium hydrogen sulfate ([BMIM][HSO 4 ]). The ILs are selected from a pool of potential ILs using a conductor-like screening model-segment activity coefficient (COSMO-SAC) model, and the dehydrogenation is performed at 0, 15, and 25 °C and a high vacuum of 4 × 10 −2 mbar gauge pressure. The dehydrogenated products are characterized with 1 H and 11 B NMR. 1 H NMR characterization reveals the structural integrity of ILs after the dehydrogenation. The 11 B NMR characterization reveals the evolution of −BH 2 and BN moieties during dehydrogenation. Based on the 11 B NMR study, the IL-assisted intramolecular and intermolecular dehydrogenation mechanism has been proposed. The intramolecular dehydrogenation pathway of dehydrogenation is proposed at 0 °C, and the intermolecular dehydrogenation pathway is at 15 and 25 °C. Formation of DMAB dimers has been confirmed for the intermolecular dehydrogenation pathway; on the contrary, DMAB does not oligomerize as other amine boranes. The interaction energy calculations reveal a greater stability of DMAB in [EMIM][HSO 4 ] than in [BMIM][HSO 4 ] IL. The anionic moiety of ILs is found to be the prominent pathway for the hydrogen bond interaction with protic and hydridic moieties of DMAB. It confirms the dominant role with respect to the selection of anion in hydrogen production.

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Section: Introductionmentioning

confidence: 99%

Low- to Room-Temperature Dehydrogenation of Dimethylamine Borane Facilitated by Ionic Liquids: Molecular Modeling and Experimental Studies

2020

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“…When compared to other solvents, such as deep eutectic solvents, the hexane/benzene mixture gave S ij ∞ = 3.645 for [(EMPYR) + Gly], S ij ∞ = 1.832 for [(EMPYR) + EG], S ij ∞ = 91.35 for [(TMAM) + EG], and S ij ∞ = 5.870 for [(BMIM) + Gly] . The same mixture with ionic liquids produced [HMPYR] + [Tf 2 N] − ( S ij ∞ = 9.584), [(OH) 2 C 3 MPYR][Cl] ( S ij ∞ = 8.455), and [BMIM] + [Tf 2 N] − ( S ij ∞ = 13.05) …”

Section: Data and Discussionmentioning

confidence: 99%

“…When compared to other separating solvents, such as deep eutectic solvents, benzene gave k ij ∞ = 0.032 for [(EMPYR) + Gly], k ij ∞ = 0.990 for [(EMPYR) + EG], k ij ∞ = 0.059 for [(TMAM) + EG], and k ij ∞ = 0.052 for [(BMIM) + Gly] . Ionic liquid [HMPYR] + [Tf 2 N] − resulted in k ij ∞ = 1.299, [(OH) 2 C 3 MPYR][Cl] resulted in k ij ∞ = 0.576, and [BMIM] + [Tf 2 N] − resulted in k ij ∞ = 1.087. Thus, ionic liquids produced better capacity values compared with the deep eutectic solvents for this separation.…”

Section: Data and Discussionmentioning

confidence: 99%

“…This indicates good solubility for these mixtures. 17,20 For the separation of cyclohexane (i)/hexane (j) and ethanol (i)/toluene (j) mixtures, ethaline gave relatively low selectivity values of 0.843 42 The same mixture with ionic liquids produced 48 and [BMIM] + [Tf 2 N] − (S ij ∞ = 13.05). 49 Table 7 shows that the capacity values matched the selectivity values, indicating that ethaline could not be a useful deep eutectic solvent for the separation of benzene, methanol, and toluene.…”

Section: Journal Ofmentioning

confidence: 99%

“…TMAM) + EG],24 and k ij ∞ = 0.052 for [(BMIM) + Gly] 42. Ionic liquid[HMPYR] + [Tf 2 N] −47 resulted in k ij ∞ = 1.299, [(OH) 2 C 3 MPYR][Cl]48 resulted in k ij ∞ = 0.576, and [BMIM] + [Tf 2 N] −49 resulted in k ij ∞ = 1.087. Thus, ionic liquids produced better capacity values compared with the deep eutectic solvents for this separation.…”

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Separation Performance of Ethaline: Infinite Dilution Activity Coefficients and the Excess Thermodynamic Properties

Manyoni

Redhi

2023

J. Chem. Eng. Data

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This paper presents excess thermodynamic data of a mixture of choline chloride, a hydrogen bond acceptor (HBA), and ethylene glycol, a hydrogen bond donor (HBD), with a molar ratio of 1:2, correspondingly. This mixture is popularly known as ethaline. A gas−liquid chromatograph (GLC) fitted with a thermal conductivity detector (TCD) was used to determine infinite dilution activity coefficient (IDAC) values of different functional groups (e.g., alkanes, alkenes, alkynes, cycloalkanes, aromatics, alcohols, ketones, and water) for 32 different organic solutes at different temperatures (T = 313.15−343.15 K) and air pressures. The partial excess molar properties, including Gibbs free energy, enthalpy, and entropy, were computed from the infinite dilution activity coefficient measurements at T = 323.15 K. Furthermore, the separation performance of common separation problems, i.e., hexane/ benzene, cyclohexane/hexane, ethanol/toluene, and acetone/methanol, was evaluated through the selectivity and capacity values, and this was also computed from the infinite dilution activity coefficient values. It was found that ethaline could not be suitable for prospective separation issues, as a result of the poor thermodynamic data that were measured.

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Thermodynamic Properties, Activity Coefficients at Infinite Dilution and Cosmo‐SAC Modelling of Deep Eutectic Solvents at Different Temperatures

et al. 2023

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A deep understanding of the solute‐ deep eutectic solvent (DESs) interactions is required for an appropriate selection of DESs as absorption media in the extraction of binary mixtures. As a result, these studies are done to evaluate the values of the activity coefficients at infinite dilution ( ), allowing us to define and understand the nature of these intermolecular interactions comprising DES mixtures with volatile organic solvents at different temperatures using gas liquid chromatography technique to determine the for 34 solutes in DESs [zinc chloride+acetic or phosphoric acid] prepared at 1 : 2 molar ratio for the temperature range (313.15–353.15) K. The thermal stability of the prepared DESs was determined by a thermogravimetric analyser. Excess thermodynamic parameters [partial molar excess enthalpies and Gibbs free energies ] were derived from the data. The selectivity and capacity values for the industrial separations were calculated and compared with the literature values of other DESs, ionic liquids, and sulfolane to assess the suitability of the investigated DESs for possible applications as extracting solvents. The selectivity and capacity values are high and therefore, [zinc chloride+acetic or phosphoric acid] can be used as a potential solvent to replace the currently used conventional solvents in the separation of the selected azeotropes. COSMO‐SAC predictions were qualitatively in very good agreement with the experimental data.

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Assessment of Pyrrolidinium-Based Ionic Liquid for the Separation of Binary Mixtures Based on Activity Coefficients at Infinite Dilution

Cited by 22 publications

References 45 publications

Low- to Room-Temperature Dehydrogenation of Dimethylamine Borane Facilitated by Ionic Liquids: Molecular Modeling and Experimental Studies

Low- to Room-Temperature Dehydrogenation of Dimethylamine Borane Facilitated by Ionic Liquids: Molecular Modeling and Experimental Studies

Separation Performance of Ethaline: Infinite Dilution Activity Coefficients and the Excess Thermodynamic Properties

Thermodynamic Properties, Activity Coefficients at Infinite Dilution and Cosmo‐SAC Modelling of Deep Eutectic Solvents at Different Temperatures

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