Synthesis and properties of novel ammonium-based room-temperature gemini ionic liquids

Yang, Xu-Zhao; Fang, Yun

doi:10.1039/c8ra04127j

Cited by 12 publications

(4 citation statements)

References 52 publications

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“…28,29 Similar to MOFs, almost infinite numbers of ILs can be designed with different physical and chemical properties, such as solubility, melting point, density, thermal stability, 30 and viscosity. 31,32 Thermal stability is one of the major properties that should be determined because most of the industrial processes are carried out at high temperatures and structures of the materials used for these applications should remain intact during the operation. 33−35 There have been several studies focusing on investigating the structural factors controlling the thermal stability limits of MOFs and ILs in their bulk states.…”

Section: Introductionmentioning

confidence: 99%

“…Ionic liquids (ILs), on the other hand, are novel solvents with many unique properties, such as very low vapor pressure, nonflammability, and high chemical and thermal stability. These properties make them perfect solvents/modifiers/reaction mediums for various applications, such as synthesis, catalysis, − fuel cells, , batteries, and gas separation. , Similar to MOFs, almost infinite numbers of ILs can be designed with different physical and chemical properties, such as solubility, melting point, density, thermal stability, and viscosity. , …”

Section: Introductionmentioning

confidence: 99%

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Structural Factors Determining Thermal Stability Limits of Ionic Liquid/MOF Composites: Imidazolium Ionic Liquids Combined with CuBTC and ZIF-8

Zeeshan

Nozari

Keskın

et al. 2019

Ind. Eng. Chem. Res.

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Twenty-nine different imidazolium ionic liquids (ILs) were combined with two different metal−organic frameworks (MOFs), ZIF-8 and CuBTC, and the resulting IL/MOF composites were characterized in detail by combining X-ray diffraction (XRD), scanning electron microscopy (SEM), Brunauer−Emmett−Teller (BET), and Fourier transform infrared (FTIR) spectroscopy. Characterization data illustrated that MOFs remained structurally intact upon combining them with ILs. Thermogravimetric analysis performed on IL/MOF composites showed that most of the composites have lower thermal stabilities compared to the bulk ILs and pristine MOFs, whereas composites with ILs having a functional group in their anions showed thermal stability limits higher than those of bulk ILs. The derivative onset temperatures representing the maximum tolerable temperatures of the composites were analyzed based on the structural differences in MOFs and ILs, such as the changes in the alkyl chain length, methylation on the C2 site, and functionalization of the cation and the size/electronic changes on the anion. Data illustrated that the maximum tolerable temperatures of IL/MOF composites decrease with an increase in the alkyl chain length on the IL's imidazolium ring. Substitution of the alkyl group with functionalized groups in the IL's imidazolium ring also led to a decrease in the maximum tolerable temperatures of the composites. Whereas, fluorination of the anion resulted in an increase in the thermal stability limits of the corresponding IL/MOF composites. Furthermore, ILs having a dicyanamide, acetate, and phosphate anion also showed an increase in their maximum tolerable temperatures when combined with CuBTC compared to their bulk counterparts. Moreover, simple structural descriptors for each cation and anion were defined by means of the density functional theory (DFT) calculations and used in the quantitative structure−property relationship (QSPR) analysis to correlate the maximum tolerable temperatures of IL/MOF composites to the IL's cation and anion structure. Results presented in this study will provide a guideline for the selection of proper IL−MOF pairs according to the application temperature of IL/MOF composites in various fields.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structural Factors Determining Thermal Stability Limits of Ionic Liquid/MOF Composites: Imidazolium Ionic Liquids Combined with CuBTC and ZIF-8

Zeeshan

Nozari

Keskın

et al. 2019

Ind. Eng. Chem. Res.

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“…All materials were kept in a controlled environment to prevent moisture and any contamination and used directly without further purification. The studied GILs, [N 111 C 3 Py][DCA] 2 and [N 111 C 3 MPi][DCA] 2 , were obtained according to our previous work, and their chemical structures are shown in Figure . The water content of [N 111 C 3 Py][DCA] 2 and [N 111 C 3 MPi][DCA] 2 was determined by Karl Fischer titration technique (Aquastar V-200 Titrator, EM Science) to be less than 50 ppm.…”

Section: Methodsmentioning

confidence: 99%

A Volumetric and Viscosity Study for the Binary Mixtures of Ammonium-Based Asymmetrical Gemini Ionic Liquids with Alcohols at T = 293.15–333.15 K

Yang

Fang

2019

J. Chem. Eng. Data

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In this work, the experimental densities and dynamic viscosities of binary mixtures of ammonium-based roomtemperature asymmetrical Gemini ionic liquids (GILs) 1-trimethylammonium-3-(pyridinium) propane bisdicyanamide ([N 111 C 3 Py][DCA] 2 ) and 1-trimethylammonium-3-(1-methylpiperidinium) propane bisdicyanamide ([N 111 C 3 MPi][DCA] 2 ) with methanol (MeOH) or ethanol (EtOH) over the entire concentration range were, respectively, determined experimentally at temperatures of (293.15, 303.15, 313.15, 323.15, and 333.15) K in the atmospheric pressure of 0.1 MPa. The excess molar volumes (V m E ), excess dynamic viscosities (Δη), and excess Gibbs energy of activation (ΔG* E ) of the mixtures were evaluated according to the experimental ρ and η values of pure [N 111 C 3 Py][DCA] 2 , [N 111 C 3 MPi][DCA] 2 , MeOH, EtOH, and their binary solutions at the investigated temperatures and pressure. The change of V mE and Δη were correlated with the Redlich− Kister-type expression and optimal fitting parameters were evaluated. It was observed that values of V m E and Δη are negative deviations from ideal behaviors for the four binary systems. With the mole fraction of alcohol decreasing, these excess properties for these mixtures exist as more negative deviations from ideal solutions, until minimum excess values are reached. Negative values of V m E and Δη for the four binary solutions indicate stronger interactions between GIL and alcohol molecules compared to the pure components and better packing owing to the differences in size and shape of the investigated molecules. Positive values of ΔG* E can be ascribed to the size effect of mixing components. Meanwhile, the dependence of these excess properties on temperature for all binary systems indicates that the temperature has a great influence on intermolecular interactions in the studied mixtures.

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“…EILs containing different anions did not exhibit the same thermal decomposition. Figure 4a Then the weight loss process of [Fcmim][N(CN) 2 ] at 245 and 383 C could be attributed to the dissociation of anion and cation [32] through the cleavage of C-N and N-B bonds, respectively. Finally, the decomposed products continued to crack at around 688 C. The TG-DTG curves of [Fcbemim][BH 3 CN] and [Fcbemim][N(CN) 2 ] shown in Figure 5 were the same as those of the imidazolyl EILs.…”

Section: Thermal Stabilitymentioning

confidence: 99%

Synthesis and properties of borane‐containing ionic liquids based on biferrocene

Liu

Zhou

Lin

et al. 2021

Applied Organom Chemis

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To develop a new type of energetic ionic liquid (EIL) that has a catalytic effect on the thermal decomposition of ammonium perchlorate (AP) and can be ignited in white fuming nitric acid (WFNA), six borane-containing ionic liquids based on biferrocene were successfully synthesized, and their structures were determined by x-ray crystallography. Except for iodized salts, four EILs with high thermal stability burned rapidly in WFNA, one of which, bis [1-(ferrocenylmethyl)imidazole-3-yl] dihydroboronium cyanoborohydride, [Fcmim][BH 3 CN], produced the shortest ignition delay (ID) time of 5 ms. However, iodized salts demonstrated a better catalytic effect on AP than did BH 3 CN À -or N(CN) 2 À -based EILs and bis[1-(ferrocenylmethyl)benzimidazole-3-yl] dihydroboronium iodide, [Fcbemim][I], could advance the final thermal decomposition temperature of AP by 50 C. Anions have a significant effect on the structures and performances of ionic liquids.

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Synthesis and properties of novel ammonium-based room-temperature gemini ionic liquids

Abstract: Ammonium-based asymmetrical gemini ionic liquids, 1-trimethylammonium-3-(pyridinium)propane bisdicyanamide and 1-trimethylammonium-3-(1-methylpiperidinium)propane bisdicyanamide were respectively synthesized and characterized by 1H NMR and 13C NMR.

Cited by 12 publications

References 52 publications

Structural Factors Determining Thermal Stability Limits of Ionic Liquid/MOF Composites: Imidazolium Ionic Liquids Combined with CuBTC and ZIF-8

Structural Factors Determining Thermal Stability Limits of Ionic Liquid/MOF Composites: Imidazolium Ionic Liquids Combined with CuBTC and ZIF-8

A Volumetric and Viscosity Study for the Binary Mixtures of Ammonium-Based Asymmetrical Gemini Ionic Liquids with Alcohols at T = 293.15–333.15 K

Synthesis and properties of borane‐containing ionic liquids based on biferrocene

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