Synthesis and characterization of dicationic ionic liquids that contain both hydrophilic and hydrophobic anions

Chang, Jui-Chi; Ho, Wen-Yueh; Sun, I‐Wen; Tung, Yung-Liang; Tsui, Meng-Chin; Wu, Tzi‐Yi; Liang, Shih‐Shin

doi:10.1016/j.tet.2010.05.105

Cited by 63 publications

(41 citation statements)

References 25 publications

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“…1,2 Room temperature ionic liquids with dipositive cations are rare, hence their physical behaviour is not well understood. [3][4][5][6][7][8][9] Tripositive cations are even scarcer. [10][11][12] The interest in dicationic ionic liquids is largely due to their high thermal stability, higher than that normally characterising the corresponding monocationic ionic liquids.…”

Section: Introductionmentioning

confidence: 99%

Solution and thermal behaviour of novel dicationic imidazolium ionic liquids

et al. 2013

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A new class of functionalised dicationic ionic liquids, containing a central cationic unit capped by a basic functionality (imidazole), has been synthesised. These salts have been characterised in isotropic solution using proton and 2D-NMR spectroscopy, and their thermal stability has been studied by DSC and TGA. All these novel salts contain the 1-(1-imidazolylmethyl)-3,5-di{1-(3'-octylimidazolylmethyl)}-benzene cation as a defining structural motif. Salts of both singly and doubly charged anions were prepared and, in particular, the selected monoanions (Br − , [BF 4 ] − , or [NTf 2 ] − ) differ in size, shape and hydrogenbonding ability, whereas the dianions differ in the nature of the spacer, such as 1,4-benzenedicarboxylate, 2,6-naphthalenedicarboxylate, 1,5-and 2,6-naphthalenedisulfonate, 1,4-butanedicarboxylate, and 1,6-hexanedicarboxylate. These ionic liquids exhibit the presence of different conformers in solution, whose distribution is affected by the nature of the anion. The nature of the anion also affects their thermal stability.

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Section: Introductionmentioning

confidence: 99%

Solution and thermal behaviour of novel dicationic imidazolium ionic liquids

et al. 2013

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“…The structures of the dicationic IL (IL2-di) and its monocationic analogue (IL2), which was used as a benchmark in this study, are shown in Figure 1. connecting chain [28][29][30][31] that was associated with better tribological properties, higher stability, lower toxicity and corrosiveness of the dicationic ILs [14,[31][32][33][34][35][36][37][38][39][40][41]. In the literature, there is a consensus of opinions that the good friction-reduction and wearresistant properties of ILs are owed to their ability to form stable adsorbed layers and protective tribofilms [4,27,[42][43][44].…”

Section: Methodsmentioning

confidence: 99%

“…Another approach relies on bridging two cationic head groups by PEG chain. Molecular dynamics simulation and advanced spectroscopy have revealed significant differences in structural heterogeneity and nano-organization between monocationic and geminal dicationic ILs with a long connecting chain [28][29][30][31] that was associated with better tribological properties, higher stability, lower toxicity and corrosiveness of the dicationic ILs [14,[31][32][33][34][35][36][37][38][39][40][41].…”

Section: Introductionmentioning

confidence: 99%

Time-Resolved Characterization of Dynamic Tribochemical Processes for Dicationic Imidazolium Ionic Liquid

et al. 2017

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Dynamic tribochemical processes for dicationic ionic liquid containing a geminal imidazolium cation head group bridged by a poly(ethylene glycol) and a bis(trifluoromethylsulfonyl)imide anion were studied using time-resolved mechanically stimulated gas emission mass-spectrometry (MSGE-MS). In comparison with similar monocationic imidazolium ionic liquids with short alkyl or long polyether side chains, the dicationic ionic liquid had a lower coefficient of friction on Ti6Al4V alloy and smoother behavior. The analysis of volatile decomposition products suggested multiple tribochemical reactions in which both anionic and cationic moieties are involved. The tribochemical degradation of cations was mainly through the detachment of the side and bridging chains from the imidazolium head groups. The absence of volatile products containing nitrogen implies that the imidazole group remained unchanged. Hydrogen and water desorption were attributed to the reactions of hydrogen fluoride being a product of anion degradation with titanium and titanium oxide, respectively.

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“…Laboratory-made SPME device was applied using a modified version of a procedure presented by Jiang et al [24]. Prior to coating, polyimide was removed from the last 1 cm segment of the fiber using a flame torch, which was then dipped into 1 mol L -1 NaOH for 3 h. After washing with water and 0.1 mol L -1 HCl, the fiber was washed with methanol and water, and then air-dried at room temperature.…”

Section: Preparation Of Il-linked Fibermentioning

confidence: 99%

“…Several unique IL properties, such as tunable viscosity, thermal stability, selectivity, low vapor pressure, and water or solvent solubility [22][23][24], are useful for extraction processes. They also exhibit a good extractability for various organic compounds [25,26] and pesticides [27,28].…”

Section: Introductionmentioning

confidence: 99%

A Novel SPME Fiber Chemically Linked with 1-Vinyl-3-hexadecylimidazolium hexafluorophosphate Ionic Liquid Coupled with GC for the Simultaneous Determination of Pyrethroids in Vegetables

et al. 2012

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A solid-phase microextraction (SPME) fiber chemically linked with ionic liquid (IL), coupled to gas chromatography-electron capture detector (GC-ECD) technique for the simultaneous sampling and determination of pyrethroids has been developed. A novel ionic liquid, 1-vinyl-3-hexadecylimidazolium hexafluorophosphate (ViHDIm ? PF 6 -), was synthesized and used as SPME fiber material. The IL-linked fiber was applied to the determination of seven pyrethroids in vegetables by direct immersion extraction, followed by gas chromatographic separation and electron capture detection. Important extraction parameters, including extraction temperature, extraction time, stirring rate, desorption temperature and time were carefully optimized. Several experiments were carried out to evaluate the analytical characteristics of the SPME-GC-ECD method under optimum conditions. The limits of detection (LODs) for the seven pyrethroids were between 0.07 and 0.29 lg L -1 . The linearity was from 0.1 to 100 lg L -1 for fenpropathrin, from 0.25 to 100 lg L -1 for cypermethrin, permethrin and deltamethrin, and from 0.5 to 100 lg L -1 for flucythrinate, fenvalerate and fluvalinate. Single fiber and fiber-to-fiber reproducibility, expressed as relative standard deviation, were less than 8.10 and 13.27 %, respectively. Compared with the commercial polydimethyl siloxane (PDMS) fiber, the extraction efficiency of the prepared IL-linked fiber for seven pyrethroids was about 20 % higher than that of PDMS fiber. The established SPME-GC-ECD was successfully applied in the detection of pyrethroids in cabbage and cucumber, with LODs of the seven pyrethroids between 0.21 and 0.49 lg kg -1 and recoveries of between 67.40 and 90.38 % in vegetables.

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Synthesis and characterization of dicationic ionic liquids that contain both hydrophilic and hydrophobic anions

Cited by 63 publications

References 25 publications

Solution and thermal behaviour of novel dicationic imidazolium ionic liquids

Solution and thermal behaviour of novel dicationic imidazolium ionic liquids

Time-Resolved Characterization of Dynamic Tribochemical Processes for Dicationic Imidazolium Ionic Liquid

A Novel SPME Fiber Chemically Linked with 1-Vinyl-3-hexadecylimidazolium hexafluorophosphate Ionic Liquid Coupled with GC for the Simultaneous Determination of Pyrethroids in Vegetables

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