Influence of the alkyl chain length on densities and volumetric properties of 1,3-dialkylimidazolium bromide ionic liquids and their aqueous solutions

Zec, Nebojša; Bešter‐Rogač, Marija; Trtić-Petrović, Tatjana; Dimitrijević, Aleksandra; Čobanov, Isidora; Gadžurić, Slobodan

doi:10.1016/j.jct.2018.02.001

Cited by 20 publications

(27 citation statements)

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“…On the other hand, for [diBIm][Br], the trend and densities fit better with the experimental reference [1]. The increased accuracy for the bulk properties may be due to the symmetry of the cation, which exhibits a more evenly distributed electronic charge density around the molecule.…”

Section: Spatial Distribution Function (Sdf) Analyses For [5mim][br] ...mentioning

confidence: 73%

“…Ionic Liquids (IL's) are mixtures of cations and anions forming salts that are liquid at room temperature, remaining in that phase even at high temperatures [1,2]. The first ionic liquid was reported in 1914 by Paul Walden, synthesized by neutralization of ethylamine with concentrated nitric acid, resulting in ethylamonium nitrate salt [3], [EtNH 3 ][NO 3 ].…”

Section: Introductionmentioning

confidence: 99%

“…This means that, having a single cation, it is possible to combine it with one of the numerous anions available, forming a different ionic liquid with each combination. One of the most investigated cations is imidazolium [Im + ] due to its particular properties such as the ease with which the alkyl chain length can be modified on the nitrogen atoms of the [Im + ] ring, being an interesting option for the development of more solvents by combining it with different anions, using the same basic structure for the cation [1]. The versatility of [Im + ] cation is one of the reasons why [Im + ]-based IL's are some of the most employed IL's in industrial applications [13].…”

Section: Introductionmentioning

confidence: 99%

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Development of Imidazolium-Based Parameters for AMOEBA–IL

CERVANTES

Cisneros

2022

Preprint

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A new approach for the efficient parametrization of the polarizable ionic liquid potential AMOEBA–IL, and its application to develop parameters for imidazolium– based cations is presented. The new approach relies on the development of parameters for fragments that can be transferred to generate new molecules. The parametrization uses the original AMOEBA–IL parametrization approach, in- cluding the use of Gaussian Electrostatic Model-Distributed Multipoles (GEM-DM) for the permanent multipoles and approximation of the Van der Waals parameters using quantum mechanics energy decomposition analysis (QM-EDA) data. Based on this, functional groups of the selected initial structures are employed as building blocks to develop parameters for new imidazolium-based cations (symmetric or asymmetric) with longer alkyl chains. The parameters obtained with this proposed method were compared with inter-molecular interactions from QM references via energy decomposition analysis using Symmetry Adapted Perturbation Theory (SAPT) and counterpoise corrected total inter-molecular interactions. The validation of the new parametrized cations was carried out by running molecular dynamics simulations on a series of imidazolium-based IL’s with different anions to compare selected thermodynamic and transport properties, including density ρ, enthalpy of vaporization ∆H vap , radial distribution function g(r), and diffusion coefficients D±, with experimental data. Overall, the calculated gas–phase and bulk properties show agreement with the reference data. The new procedure provides a straightforward approach to generate the required AMOEBA–IL parameters for any imidazolium-based cation.

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Section: Spatial Distribution Function (Sdf) Analyses For [5mim][br] ...mentioning

confidence: 73%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Development of Imidazolium-Based Parameters for AMOEBA–IL

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Cisneros

2022

Preprint

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“…PILs with [BEHA] cation has higher α p than that of PILs with [EHA] cation. This indicates that the thermal expansion coefficient does not only depend on the cation symmetry but is also related to the length of the alkyl substituent [ 57 ]. Meanwhile, the behavior of the thermal expansion coefficient is almost similar for all PILs with common cations.…”

Section: Resultsmentioning

confidence: 99%

Experimental Investigation on Thermophysical Properties of Ammonium-Based Protic Ionic Liquids and Their Potential Ability towards CO2 Capture

et al. 2022

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Ionic liquids, which are extensively known as low-melting-point salts, have received significant attention as the promising solvent for CO2 capture. This work presents the synthesis, thermophysical properties and the CO2 absorption of a series of ammonium cations coupled with carboxylate anions producing ammonium-based protic ionic liquids (PILs), namely 2-ethylhexylammonium pentanoate ([EHA][C5]), 2-ethylhexylammonium hexanoate ([EHA][C6]), 2-ethylhexylammonium heptanoate ([EHA][C7]), bis-(2-ethylhexyl)ammonium pentanoate ([BEHA][C5]), bis-(2-ethylhexyl)ammonium hexanoate ([BEHA][C6]) and bis-(2-ethylhexyl)ammonium heptanoate ([BEHA][C7]). The chemical structures of the PILs were confirmed by using Nuclear Magnetic Resonance (NMR) spectroscopy while the density (ρ) and the dynamic viscosity (η) of the PILs were determined and analyzed in a range from 293.15K up to 363.15K. The refractive index (nD) was also measured at T = (293.15 to 333.15) K. Thermal analyses conducted via a thermogravimetric analyzer (TGA) and differential scanning calorimeter (DSC) indicated that all PILs have the thermal decomposition temperature, Td of greater than 416K and the presence of glass transition, Tg was detected in each PIL. The CO2 absorption of the PILs was studied up to 29 bar at 298.15 K and the experimental results showed that [BEHA][C7] had the highest CO2 absorption with 0.78 mol at 29 bar. The CO2 absorption values increase in the order of [C5] < [C6] < [C7] anion regardless of the nature of the cation.

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“…Wang et al, 2016;Y. Wang et al, 2014;Xiao et al, 2010;Yan et al, 2015;Zec et al, 2018;Zicmanis & Anteina, 2014). These solvents are relatively inert and tolerate a large variety of chemical substances, but they are generally good for the nucleophilic substitution reaction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of the ionic liquid 1-methyl-3-(2,6-(S)-dimethyloct-2-ene)-imidazol tetrafluoroborate

Oliveira

Melo

Macedo

et al. 2021

RSD

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Ionic liquids (ILs) are good electrical conductors and organic liquid compounds at room temperature, with potential applicability in water electrolysis for H2 generation. The objective of this work is to describe the synthesis, characterization and study of the feasibility of ionic liquid 1-methyl-3-(2,6-(S)-dimethyloct-2-ene)-imidazolium tetrafluoroborate (MDI-BF4) as electrolyte to produce hydrogen through electrolysis of water. The synthesized MDI-BF4 was characterized by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC), mid-infrared spectroscopy with Fourier Transform by method of attenuated total reflectance (FTIR-ATR), nuclear magnetic resonance spectroscopy of hydrogen (NMR 1H) and cyclic voltammetry (CV). The yield of the synthesis were calculate by the TGA and DSC. From the results: The infrared spectroscopy identified the functional groups of the compound and the B-F bond at 1053 cm-1. The NMR 1H analyzed and compared with literature data confirms the structure of MDI-BF4. The yield of the synthesis of MDI-BF4 which was 88.84%. The current density achieved by MDI-BF4 in the voltammogram shows that the IL can conduct electrical current regardless the concentration of water, indicating that the MDI-BF4 is a potential electrolyte for hydrogen production from water electrolysis.

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Influence of the alkyl chain length on densities and volumetric properties of 1,3-dialkylimidazolium bromide ionic liquids and their aqueous solutions

Cited by 20 publications

References 50 publications

Development of Imidazolium-Based Parameters for AMOEBA–IL

Development of Imidazolium-Based Parameters for AMOEBA–IL

Experimental Investigation on Thermophysical Properties of Ammonium-Based Protic Ionic Liquids and Their Potential Ability towards CO2 Capture

Synthesis and characterization of the ionic liquid 1-methyl-3-(2,6-(S)-dimethyloct-2-ene)-imidazol tetrafluoroborate

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