Ionic liquids based on S-alkylthiolanium cations and TFSI anion as potential electrolytes

Zhang, Huanqi; Yang, Li; Fang, Shaohua; Peng, Chengxin; Luo, HongJun

doi:10.1007/s11434-009-0038-1

Cited by 7 publications

(4 citation statements)

References 31 publications

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“…The S‐alkyl chains varied from n‐butyl (C 4 ) to n‐decyl (C 10 ) (Scheme 1). First, the [C n THT] + iodide intermediates were prepared from tetrahydrothiophene, THT and iodoalkanes, based on the synthesis of Zhang et al [27] . The second step involved the iodide anion exchange with either Li[NTf 2 ] or Na[BPh 4 ] (for further information see experimental section).…”

Section: Resultsmentioning

confidence: 99%

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Tetrahydrothiophene‐Based Ionic Liquids: Synthesis and Thermodynamic Characterizations

et al. 2020

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S‐alkyltetrahydrothiophenium, [CnTHT]+ bis(trifluorosulfonyl)imide, [NTf2]− room temperature ionic liquids (ILs) and tetraphenylborate, [BPh4]− salts with alkyl chain lengths from C4 to C10 have been prepared. The ILs and salts were characterized and their purity verified by 1H‐ and 13C‐nuclear magnetic resonance, elemental analysis, ion chromatography, Karl‐Fischer titration, single crystal X‐ray diffraction as well as thermogravimetric analysis. The experimentally determined density and viscosity decrease with increasing temperature. The experimental solubility of the [CnTHT][NTf2]‐ILs in water (75 to 2.2 mg/L for C4 to C10) was modelled with very good agreement by Perturbed Chain Statistical Associating Fluid Theory (PC‐SAFT), based on the extremely low vapor pressures for the [CnTHT][NTf2]‐ILs measured in this work (4.15 to 0.037 ⋅ 10−7×psat for C4 to C10). PC‐SAFT is able to predict and correlate different thermodynamic properties by estimating the Helmholtz residual energy.

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Section: Resultsmentioning

confidence: 99%

“…Additionally, PC-SAFT was applied to model the solubility in water for [C n THT][NTf 2 ]-ILs based on parametrization including the extremely low vapor pressures measured in this work. [27] The second step involved the iodide anion exchange with either Li[NTf 2 ] or Na[BPh 4 ] (for further information see experimental section).…”

Section: Introductionmentioning

confidence: 99%

Tetrahydrothiophene‐Based Ionic Liquids: Synthesis and Thermodynamic Characterizations

et al. 2020

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“…A limited ionic conductivity is a disadvantage in the use of ILs as electrolytes and in electrochemical devices including lithium ion batteries, supercapacitors, − fuel cells, and photoelectrochemical cells . Angel and co-workers have described a qualitative approach based on the Walden plot to identify the degree of ion association with respect to KCl, which is fully dissociated. , On the basis of the Walden rule, the product of ionic conductivity and viscosity is a constant at a specific temperature .…”

Section: Relating Ionic Association Conductivity and Viscositymentioning

confidence: 99%

Imidazolium Triflate Ionic Liquids’ Capacitance–Potential Relationships and Transport Properties Affected by Cation Chain Lengths

Pitawela

Shaw

2021

ACS Meas. Sci. Au

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In this paper we report the effects of five imidazolium cations with varying alkyl chain lengths to study the effects of cation size on capacitance versus voltage behavior. The cations include ethyl-, butyl-, hexyl-, octyl-, and decyl-3methylimidazolium, all paired with a triflate anion. We analyze the capacitance with respect to the cation alkyl chain length qualitatively and quantitatively by analyzing changes in the capacitance−potential curvature shape and magnitude across several standard scanning protocols and electrochemical techniques. Further, three transport properties (viscosity, diffusion coefficient, and electrical conductivity) are experimentally determined and integrated into the outcomes. Ultimately, we find higher viscosities, lower diffusion coefficients, and lower electrical conductivities when the alkyl chain length is increased. Also, capacitance values increase with cation size, except 1-octyl-3methylimidazolium, which does not follow an otherwise linear trend. This capacitive increase is most pronounced when sweeping the potential in the cathodic direction. These findings challenge the conventional hypothesis that increasing the length of the alkyl chain of imidazolium cations diminishes the capacitance and ionic liquid performance in charge storage.

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“…The cations were 1- n -hexyl-3-methylimidazolium ([hmim] + ) to compare to the literature, 1- n -hexyl-3-methylpyridinium ([hmpy] + ), triethyl- n -octylphosphonium ([P 2228 ] + ), and 1- n -butylthiolanium ([bthiol] + ) for its structural similarity to sulfolane. Thermophysical properties of these ILs have been previously characterized, and all have densities significantly greater than n -heptane and toluene and decomposition temperatures above 550 K. − Systems of [bthiol][Tf 2 N] and n -heptane with o , m , and p -xylene were also measured to test the behavior of different aromatics. One reason ILs are of great interest is that the IL mole fraction in the n -heptane-rich phase is reported as negligible; − ,− however, to assess the feasibility of a commercial process, it is important to know this composition, no matter how small.…”

Section: Introductionmentioning

confidence: 99%

Promising Thiolanium Ionic Liquid for Extraction of Aromatics from Aliphatics: Experiments and Modeling

Lübben

Canales

Lyu

et al. 2020

Ind. Eng. Chem. Res.

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Four ionic liquids (ILs) consisting of the bis(trifluoromethylsulfonyl)imide anion paired with a phosphonium, pyridinium, imidazolium, or thiolanium cation were investigated as potential solvents to separate aromatic from aliphatic compounds in a liquid–liquid extraction process. The thiolanium IL was chosen due to its structural similarity to sulfolane, which is the most widely used organic solvent for aromatic/aliphatic separation in the industry. Interestingly, ternary liquid–liquid equilibrium data shows that 1-n-butylthiolanium bis(trifluoromethylsulfonyl)imide performs as well as the equivalent imidazolium IL despite the fact that it is not aromatic and cannot use π–π interactions (which are available to imidazolium ILs) to enhance aromatic solubility and selectivity. Moreover, we provide quantification of the IL solubility in the organic-rich phase, which is on the order of 10–4 mole fraction. This quantity is important because it would represent IL loss and product contamination in a real extraction process; however, it is commonly reported to be nondetectable. The nonrandom two-liquid (NRTL), perturbed-chain statistical associating fluid theory (PC-SAFT), COSMO-RS, and COSMO-SAC models are appropriate for the mixtures explored, and each model’s strengths and weaknesses are discussed.

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Ionic liquids based on S-alkylthiolanium cations and TFSI anion as potential electrolytes

Cited by 7 publications

References 31 publications

Tetrahydrothiophene‐Based Ionic Liquids: Synthesis and Thermodynamic Characterizations

Tetrahydrothiophene‐Based Ionic Liquids: Synthesis and Thermodynamic Characterizations

Imidazolium Triflate Ionic Liquids’ Capacitance–Potential Relationships and Transport Properties Affected by Cation Chain Lengths

Promising Thiolanium Ionic Liquid for Extraction of Aromatics from Aliphatics: Experiments and Modeling

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