1-Butyl-3-methylimidazolium Tosylate Ionic Liquid:  Heat Capacity, Thermal Stability, and Phase Equilibrium of Its Binary Mixtures with Water and Caprolactam

Strechan, A.A.; Paulechka, Yauheni U.; Kabo, Andrey G.; Blokhin, Andrey V.; Kabo, Gennady J.

doi:10.1021/je700152c

Cited by 47 publications

(42 citation statements)

References 10 publications

(22 reference statements)

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“…[21] Such a melting point depression may originate from impurities introduced during synthesis and/or moisture uptake during storage or measurement. Organic salts can be very hygroscopic, [20,22] suggesting that even short exposure to air may lead to significant water uptake. If water or solvent molecules form stoichiometric or non-stoichiometric co-crystals with the salt, this may be overlooked, especially if the crystal structure was not determined.…”

Section: Contaminationmentioning

confidence: 99%

Is Universal, Simple Melting Point Prediction Possible?

et al. 2011

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An investigation of the melting points of 520 organic 1:1 salts is presented with the aim of developing a universal, simple, physically well-founded prediction scheme. The general reliability and reproducibility of the recorded experimental data are discussed with respect to purity, phase behavior, disorder and thermal history of a given substance. Additionally, mistakes, systematic errors, or lack of conventions can lead to considerable differences in the experimental measurements. A rough error bar for the reproducibility of the melting points of organic salts of ±5 to ±15 °C can be assigned. With this restraint, we developed two simple, semiempirical, five- and nine-parameter schemes with easy-to-calculate quantities. With these, we could predict the melting temperature of a given organic salt in the temperature range of -25 to +300 °C with an average error of 33.5 °C and a relative error of 9.3%. All calculated quantities are assessed with the help of conventional DFT, COSMO and COSMO-RS calculations, and are currently implemented into the IL-Prop module of the upcoming version of COSMOtherm. These prediction schemes are suitable for high-throughput computational screening of substances in the context of "computer-aided synthesis". Therefore, they are valuable tools to find a compound with a suitable melting point before its first synthesis.

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Section: Contaminationmentioning

confidence: 99%

Is Universal, Simple Melting Point Prediction Possible?

et al. 2011

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“…The C vib values were calculated in a harmonic approximation using these frequencies. The set of frequencies for the most stable conformers of [bmim] + and anions [7,10] and in this work were used. The equation C p ðliqÞ=J Á K À1 Á mol À1 ¼ ½7:71 À 2:12 Á 10 À2 T À 1:17 Á 10 À2 M þ 2:27 Á 10 À5 T 2 þ 1:11 Á 10 À5 TM þ 9:77…”

Section: Calculationmentioning

confidence: 99%

“…Especially, this concerns dependence of thermal properties on the nature of the anion. Earlier, the authors investigated a series of 1-butyl-3-methylimidazolium ([bmim] + ) ILs [6][7][8][9][10]. It was found that thermal behavior of ILs is strongly dependent on the nature of the anion.…”

Section: Introductionmentioning

confidence: 99%

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Low-temperature heat capacity of hydrophilic ionic liquids [BMIM][CF3COO] and [BMIM][CH3COO] and a correlation scheme for estimation of heat capacity of ionic liquids

Strechan

Paulechka

Blokhin

et al. 2008

The Journal of Chemical Thermodynamics

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“…Aprerequisitefor the suitability of asalttoact as ionic liquid is its low melting pointthat is conveniently achieved by the introduction of long perfluoroalkylalkyl chainsinto simple nitrogen-containing organic moieties and crystallizing theresulting cations by means of bulkier anions suchastosylate [1]. In our continued interest in creating simplerd erivatives of nitrogen compounds that might act as ionicliquids [2] motivated us to synthesize the title compound andelucidateits crystal structure by means of adiffraction study.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of bis(imidazolium) para-toluenesulfonate, C20H22N4O6S2

Moleko

Tshentu

Hosten

et al. 2015

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThecompoundwas prepared upon reacting the neutral nitrogencontaining compound with iron(III)-para-toluenesulfonatehexahydrate in methanol. Crystals suitable for the diffraction study were obtained upon evaporation of the solvent at ambient conditions. Experimental detailsCarbon-bound Hatomswere placed in calculated positions (C-H 0.95 Å) and were included in the refinementinthe riding model approximation, with U iso (H) setto1.2U eq (C). The Hatoms of the methyl group were allowed to rotate with afixed angle around the C-C bond to best fit the experimental electron density (HFIX 137 in the SHELX program suite [10]), with U iso (H) setto1.5U eq (C). Nitrogen-bound Ha tomsw ere placed in calculated positions (N-H 0.88 Å) and were included in the refinement in the riding model approximation, with U iso (H) setto1.2U eq (N). DiscussionPerfluorinated hydrocarbons ionic liquids have attracted much attention as versatilereactionmedia over thepast decades. Aprerequisitefor the suitability of asalttoact as ionic liquid is its low melting pointthat is conveniently achieved by the introduction of long perfluoroalkylalkyl chainsinto simple nitrogen-containing organic moieties and crystallizing theresulting cations by means of bulkier anions suchastosylate [1]. In our continued interest in creating simplerd erivatives of nitrogen compounds that might act as ionicliquids [2] motivated us to synthesize the title compound andelucidateits crystal structure by means of adiffraction study. Exampleso fi midazolium-baseds ulfonates haveb een characterized structurallybefore [3][4][5].The title compoundisthe para-toluene-sulfonatesalt of bisimidazole.The asymmetric unit contains half ac ation and ac omplete anion. Thel east-squares planes as defined by the non-hydrogen atomso ft he two heterocyclic moieties, respectively the phenylgroup on the one hand and one of the heterocy-clic rings on the other hand, intersect at an angle of 84.48(4)°. Intracyclic angles in the cation span arange of 106.93(11)-108.99(11)°with the smallest angle found on one of the "terminal" carbon atomsand the largest angle on one of the nitrogen atoms. The S-O bond lengths are measured in between 1.4355(10)-1.4738(11) Åw ith the shortest bond length observed for the oxygen atom that does not participate in any intermolecu-larc ontacts( videi nfra). In comparisont oo ther tosylateswhose metricalparameters have been deposited with the Cambridge Structural Database [6],t hese values are in good agreementwiththe most commonones observed. In the crystal, classical hydrogen bonds of the N-H×××Otype are observed next to C-H×××Ocontacts whose range invariably falls below the sum of van-der-Waals radii of the atomsparticipating in them [7].The classical hydrogen bonds involve all NH groups as donors and are directed towards two different oxygen atomsofthe tosylate anion as acceptors.The C-H×××Ocontacts are supported by one of the CH groups of the cation and -exclusively -only have one of the two oxygen atomsasacceptors that is also engaged in the clas...

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1-Butyl-3-methylimidazolium Tosylate Ionic Liquid: Heat Capacity, Thermal Stability, and Phase Equilibrium of Its Binary Mixtures with Water and Caprolactam

Cited by 47 publications

References 10 publications

Is Universal, Simple Melting Point Prediction Possible?

Is Universal, Simple Melting Point Prediction Possible?

Low-temperature heat capacity of hydrophilic ionic liquids [BMIM][CF3COO] and [BMIM][CH3COO] and a correlation scheme for estimation of heat capacity of ionic liquids

Crystal structure of bis(imidazolium) para-toluenesulfonate, C20H22N4O6S2

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