Synthesis and properties of symmetric glycerol-derived 1,2,3-triethers and 1,3-diether-2-ketones for CO2 absorption

Qian, Shuai; Liu, Xiaoyang; Turner, C. Heath; Bara, Jason E.

doi:10.1016/j.ces.2021.117150

Cited by 10 publications

(22 citation statements)

References 44 publications

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“…The H CO2 values obtained at different temperatures in Table can be used for the calculation of enthalpy of absorption using the Van’t Hoff equation: and the fitting parameters are shown in Table . The enthalpy of absorption was calculated as −9.72 kJ·mol –1 , which, apart from the x –P plot, is another evidence of the physical (i.e., nonreactive) nature of [(ME,F)-mim][Tf 2 N] in CO 2 absorption as it falls within the typical range of −8.0 to −15.0 kJ·mol –1 as other physical absorbents including ILs and small neutral molecules. − The R 2 value being 0.9989 and maximum deviation <0.68% indicate good reliability for predictions of H CO2 values in a reasonably broader temperature range when these parameters are incorporated into eq . As a result, the temperature dependence of H CO2 is predicted consecutively for [(ME,F)-mim][Tf 2 N] in Figure over 273.15–353.15 K with scattered data for other physical solvents in the literature for comparison purposes including ILs ([C 2 mim][BF 4 ], [C 4 mim][PF 6 ], [C 2 mim][Tf 2 N], [C 6 mim][Tf 2 N], [Bnmim][Tf 2 N]), neutral molecules such as the IL precursor [ME, O, F] and its analogues [ME, K, F], [ME, ME, F] along with dimethyl ethers of polyethylene glycol (DMPEG) as a widely used industrial CO 2 absorbent.…”

Section: Resultsmentioning

confidence: 93%

Properties of Imidazolium Ionic Liquids with Glycerol-Derived Functional Groups

et al. 2022

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The selection of functional groups at the N(1) and N(3) sites of the imidazolium cation provides versatile opportunities for the design and synthesis of novel ionic liquids (ILs). Here, we show how glycerol-derived ethers provide new possibilities for the introduction of highly tailored, branched functional groups and how the selection of symmetric or asymmetric branches influences the properties of the resultant 1-R-3-methylimidazolium bistriflimide ILs. The densities and viscosities of these ILs were measured in the temperature range of 293.15−353.15 K and compared with those of the analogous 1-n-alkyl-3-methylimidazolium ILs. The temperature dependence of corresponding properties was elucidated using either linear or exponential models. Furthermore, CO 2 absorption isotherms were obtained for one of the ILs, 1-(1-(2-methoxyethoxy)-3-(2,2,2-trifluoroethoxy)propan-2-yl)-3-methyl-imidazolium bistriflimide ([(ME, F)-mim]-[Tf 2 N]). This IL had a higher CO 2 capacity than most physical solvents considered including its associated precursor, other imidazolium ILs, and DMPEG.

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Section: Resultsmentioning

confidence: 93%

Properties of Imidazolium Ionic Liquids with Glycerol-Derived Functional Groups

et al. 2022

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“…Unlike density, viscosity followed a non-linear trend. Among several empirical equations that can be used to model viscosity-temperature relationship, the Andrade Equation [41], in the form of η = a•exp•(b•T −1 ), was chosen first, for its simplicity and effectiveness in our prior work [42][43][44]. Parameters for the Andrade equation are presented in Table 6, coefficients of determination (R 2 ) for all equations derived for branched and cycloalkyl imidazoles considered in this work are >0.99 while the broad residual deviations indicated by the maximium absolute residual and SSR values call for model improvement.…”

Section: Viscosity Of Branched and Cycloalkyl Imidazole Compoundsmentioning

confidence: 99%

Experimental and Computational Study of the Properties of Imidazole Compounds with Branched and Cycloalkyl Substituents

Qian

Mileski

Irvin

et al. 2022

Liquids

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N-functionalized imidazole compounds with linear alkyl groups have been widely utilized precursors for imidazolium ionic liquids (ILs) while the effects of branched and cycloalkyl substituents on properties of imidazole compounds have not been studied; however, such compounds are just as synthetically accessible as those with linear alkyl groups. In this work, two fundamental properties, density and viscosity, of selected N-functionalized imidazoles bearing iso-propyl, iso-butyl, sec-butyl methylcyclopropyl, cyclopentyl, and methylcyclohexyl groups have been measured in the temperature range of 293.15–353.15 K for the guidance of molecular design for future applications. A linear and parabolic model were used for temperature-density correlation while temperature dependence of viscosity was summarized using the Andrade Equation and the Vogel-Fulcher-Tammann equation. In addition to experimental data, density, viscosity, vapor pressure and vaporization of enthalpies of target imidazole compounds were predicted using COSMOtherm calculations and compared with experimental data. It was found that the calculated densities were quite close to the experimental data, while viscosity data, obtained from COSMOtherm, underestimated experimental measurements and a scaling factor provided agreement with experiments. Predictions of vapor pressure were relatively reliable at low temperature, although the difference between experiment and prediction tended to expand with increasing temperature. Variances of vaporization enthalpies were small upon temperature change and a maximum error of ~12.3% was observed for all compounds studied.

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“…21 Thus, there is an opportunity to convert this low-cost feedstock into a higher value solvent, due to its chemical versatility and wide availability. [23][24][25] Very recently, Qian et al 26,27 used a combination of experiments and simulations to show that different glycerolderived compounds (e.g., triethers) have promising performance for CO 2 absorption; other applications of glycerol-derived solvents have been previously proposed in the literature. 24,28,29 Despite the similarities in the chemical structure of glycerol derived triethers and glymes, to the best of our knowledge, there are no experimental or computational studies of the solvation of Li + cations by glycerol-derived triethers.…”

Section: Introductionmentioning

confidence: 99%

“…21 Thus, there is an opportunity to convert this low-cost feedstock into a higher value solvent, due to its chemical versatility and wide availability. 23–25 Very recently, Qian et al 26,27 used a combination of experiments and simulations to show that different glycerol-derived compounds ( e.g. , triethers) have promising performance for CO 2 absorption; other applications of glycerol-derived solvents have been previously proposed in the literature.…”

Section: Introductionmentioning

confidence: 99%