Building blocks for ionic liquids: Vapor pressures and vaporization enthalpies of 1-(n-alkyl)-imidazoles

Emel′yanenko, Vladimir N.; Portnova, S. V.; Verevkin, Sergey P.; Skrzypczak, Andrzej; Schubert, Thomas

doi:10.1016/j.jct.2011.05.004

Cited by 47 publications

(48 citation statements)

References 7 publications

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“…These compounds served as precursors for the synthesis of TAAILs with a common anion [NTf 2 ] presented in this work. To extend our systematic studies of vaporization thermodynamics of substituted imidazoles and imidazolium based ILs[15d], [15e] we report results of vaporization enthalpy measurements for a group of five TAAILs ( 1 – 5 ) based on 2‐ and 4‐phenyl‐1 H ‐imidazoles derivatives containing methyl‐ and methoxy‐substituents with the bis(trifluoromethylsulfonyl)imide ([NTf 2 ]) anion (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Thermochemical Properties of Tunable Aryl Alkyl Ionic Liquids (TAAILs) based on Phenyl‐1H‐imidazoles

Zaitsau

Kaliner

Lerch

et al. 2016

Zeitschrift anorg allge chemie

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Vaporization enthalpies of five different imidazolium based Tunable Aryl Alkyl Ionic Liquids (TAAILs) with a common bis(trifluoromethylsulfonyl)imide ([NTf2]) anion were measured using a Quartz Crystalline Microbalance (QCM) and by Thermogravimetric Analysis (TGA). The counter anion and the alkyl chain of these imidazolium‐based ionic liquids with one N‐aryl and one N‐alkyl substituent were kept constant to study the influence of the ortho‐ and para‐substituted aryl moieties on the vaporization enthalpies of these ionic liquids. For comparison, enthalpies of vaporization measured at elevated temperatures were adjusted to the reference temperature 298 K. Structure‐property relations between TAAILs and similarly shaped corresponding 1‐(R‐phenyl)‐imidazoles were analyzed. An incremental approach to predict vaporization enthalpies of ionic liquids by group contributions was suggested. The procedure is based on vaporization enthalpy of a starting IL and group contributions well established from molecular compounds.

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Section: Introductionmentioning

confidence: 99%

Thermochemical Properties of Tunable Aryl Alkyl Ionic Liquids (TAAILs) based on Phenyl‐1H‐imidazoles

Zaitsau

Kaliner

Lerch

et al. 2016

Zeitschrift anorg allge chemie

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“…monoethanolamine (MEA) and Nmethylethanolamine (NMEA)) are capable of direct reaction with CO 2 in a 1:2 (CO 2 :amine) stoichiometry in which one amine and CO 2 first react to form a zwitterion which is then deprotonated by a second amine to form an ammonium-carbamate salt. [24][25][26] In two collaborative studies, [27,28] we have shown that although imidazoles certainly have a measurable vapor pressure compared to ILs, the volatility of imidazoles is significantly reduced compared to other organic solvents and amines such as MEA. We demonstrated that a solution containing both an alkylimidazole and an amine could exceed the conventional 1:2 (CO 2 :amine) stoichiometry as the alkylimidazole could serve as a H + acceptor, and increase the overall CO 2 capacity per volume of solvent.…”

Section: Experimental and Computational Resultsmentioning

confidence: 98%

Imidazole-Based Solvents and Membranes for CO₂ Capture Applications

et al. 2014

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Imidazoles present a tunable, versatile and economical platform for the development of novel liquid solvents and polymer membranes for CO 2 capture. An overview of our studies in this area is presented, with emphasis on characterization of structure-property relationships in imidazole-based materials through both experimental and computational studies. To this end, a growing library of systematically varied imidazole compounds has been synthesized using only commercial available starting materials and straightforward reactions. Using this library of compounds, we have sought to understand and develop predictive models for thermophysical properties relating to process design, including: density, viscosity, vapor pressure, pK a and CO 2 absorption capacity. Furthermore, we have discovered that imidazoles are stable in the presence of SO 2 and can form reversible 1:1 adducts, which can be beneficial as SO 2 is typically present at ppm levels alongside CO 2 in flue gas from coal-fired power plants.

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“…where Δ r H m 0 (liq) is the enthalpy ascribed to the reaction (1) and measured in this work by the DSC, values of vaporization enthalpies of precursors

{normalΔ}_{1}^{normalg}

H m 0 (1‐C n Im) and

{normalΔ}_{1}^{normalg}

H m 0 (C n Br) are available from our previous work or from the literature (see Table S1, Supporting Information). The Δ r H m 0 (gas) value is referred to the following gas‐phase reaction:

1 - C_{n} normalI normalm (normalg normala normals) + C_{n} normalB normalr (normalg normala normals) = [C_{n} C_{n} normalI normalm] [normalB normalr] (normalg normala normals)

…”

Section: Resultsmentioning

confidence: 99%

Imidazolium Based Ionic Liquids: Impact of the Cation Symmetry and Alkyl Chain Length on the Enthalpy of Vaporization

Yermalayeu

Zaitsau

Loor

et al. 2016

Zeitschrift anorg allge chemie

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The vaporization thermodynamics of symmetric imidazolium based ionic liquids of the general formula [CnCnIm][Br] with the chains length n = 4, 5, 6, and 8 were investigated using a combination of DSC, TGA, and QCM methods with quantum chemical calculations. Comparison of vaporization enthalpies for the symmetric ([CnCnIm][Br]) and asymmetric imidazolium based ILs ([Cnmim][Br]) revealed a general trend with the lower vaporization enthalpies of the symmetric species indicating a significant decrease of the Coulombic interactions affecting energetics of vaporization.

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Building blocks for ionic liquids: Vapor pressures and vaporization enthalpies of 1-(n-alkyl)-imidazoles

Cited by 47 publications

References 7 publications

Thermochemical Properties of Tunable Aryl Alkyl Ionic Liquids (TAAILs) based on Phenyl‐1H‐imidazoles

Thermochemical Properties of Tunable Aryl Alkyl Ionic Liquids (TAAILs) based on Phenyl‐1H‐imidazoles

Imidazole-Based Solvents and Membranes for CO₂ Capture Applications

Imidazolium Based Ionic Liquids: Impact of the Cation Symmetry and Alkyl Chain Length on the Enthalpy of Vaporization

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Building blocks for ionic liquids: Vapor pressures and vaporization enthalpies of 1-(n-alkyl)-imidazoles

Cited by 47 publications

References 7 publications

Thermochemical Properties of Tunable Aryl Alkyl Ionic Liquids (TAAILs) based on Phenyl‐1H‐imidazoles

Thermochemical Properties of Tunable Aryl Alkyl Ionic Liquids (TAAILs) based on Phenyl‐1H‐imidazoles

Imidazole-Based Solvents and Membranes for CO2 Capture Applications

Imidazolium Based Ionic Liquids: Impact of the Cation Symmetry and Alkyl Chain Length on the Enthalpy of Vaporization

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Imidazole-Based Solvents and Membranes for CO₂ Capture Applications