Electrodialytic Universal Synthesis of Highly Pure and Mixed Ionic Liquids.
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ABSTRACT:
SUBMITTER: Haque MA
PROVIDER: S-EPMC9245113 | biostudies-literature |
REPOSITORIES: biostudies-literature
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Project description:A series of highly-fluorinated triaminocyclopropenium salts, with up to six fluorous groups, were prepared and their properties as ionic liquids investigated. Reaction of pentachlorocyclopropane or tetrachlorocyclopropene with bis(2,2,2-trifluoroethyl)amine, HN(CH2 CF3 )2 , occurs in the presence of a trialkylamine, NR3 , to give cations with two fluorinated amino groups, [C3 (N(CH2 CF3 )2 )2 (NR2 )]+ (R=Et, Pr, Bu, Hex), with traces of [C3 (N(CH2 CF3 )2 )3 ]+ . Use of appropriate reagent ratios and reaction times and subsequent addition of a dialkylamine, HNR'R", gives cations with one fluorinated amino group, [C3 (N(CH2 CF3 )2 )(NR2 )(NR'R")]+ ((NR2 )(NR'R")=(NBu2 )2 , (NEt2 )(NPr2 ), (NBu2 )(NBuMe)). These cations were isolated as chloride salts and some of these were converted to bistriflamide, dicyanamide and triflate salts to provide ionic liquids. These salts were characterised by thermal (DSC and TGA) measurements and miscibility/solubility properties (determined in a range of solvents). Ionic liquids (ILs) were also characterised by density, viscosity and conductivity measurements where possible. X-ray diffraction studies of chloride salts showed the formation of fluorous regions and more hydrophilic ionic regions in the solid state.
| S-EPMC9314049 | biostudies-literature
Project description:Because of the appealing properties, ionic liquids (ILs) are believed to be promising alternatives for the CO2 absorption in the flue gas. Several ILs, such as [NH2emim][BF4], [C4mim][OAc], and [NH2emim[OAc], have been used to capture CO2 of the simulated flue gas in this work. The structural changes of the ILs before and after absorption were also investigated by quantum chemical methods, FTIR, and NMR technologies. However, the experimental results and theoretical calculation showed that the flue gas component SO2 would significantly weaken the CO2 absorption performance of the ILs. SO2 was more likely to react with the active sites of the ILs than CO2. To improve the absorption capacity, the ionic liquid (IL) mixture [C4mim][OAc]/ [NH2emim][BF4] were employed for the CO2 absorption of the flue gas. It is found that the CO2 absorption capacity would be increased by about 25%, even in the presence of SO2. The calculation results suggested that CO2 could not compete with SO2 for reacting with the IL during the absorption process. Nevertheless, SO2 might be first captured by the [NH2emim][BF4] of the IL mixture, and then the [C4mim][OAc] ionic liquid could absorb more CO2 without the interference of SO2.
| S-EPMC7179232 | biostudies-literature
Project description:S-alkyltetrahydrothiophenium, [Cn THT]+ bis(trifluorosulfonyl)imide, [NTf2 ]- room temperature ionic liquids (ILs) and tetraphenylborate, [BPh4 ]- salts with alkyl chain lengths from C4 to C10 have been prepared. The ILs and salts were characterized and their purity verified by 1 H- and 13 C-nuclear magnetic resonance, elemental analysis, ion chromatography, Karl-Fischer titration, single crystal X-ray diffraction as well as thermogravimetric analysis. The experimentally determined density and viscosity decrease with increasing temperature. The experimental solubility of the [Cn THT][NTf2 ]-ILs in water (75 to 2.2 mg/L for C4 to C10 ) was modelled with very good agreement by Perturbed Chain Statistical Associating Fluid Theory (PC-SAFT), based on the extremely low vapor pressures for the [Cn THT][NTf2 ]-ILs measured in this work (4.15 to 0.037 ⋅ 10-7 ×psat for C4 to C10 ). PC-SAFT is able to predict and correlate different thermodynamic properties by estimating the Helmholtz residual energy.
| S-EPMC7874261 | biostudies-literature
Project description:Ionic Liquids are a broad group of salts with low melting points that can be specifically tuned for a broad range of applications. Despite being initially considered “green” solvents, their better environmental friendliness compared to traditional solvents has been increasingly challenged. In this study, we aimed to investigate the molecular effects of ILs exposure by using RNA-sequencing to study differential gene expression patterns. Thus, we exposed Daphnia magna to 1-ethyl-3-methylimidazolium chloride ([C2mim]Cl), 1-dodecyl chloride-3-methylimidazolium ([C12mim]Cl) and cholinium chloride ([Chol]Cl). Results suggest that the three ILs share several mechanisms of toxicity, including cellular membrane and cytoskeleton damage, oxidative stress, inhibition of antioxidant enzymes, mitochondrial affectation, changes in protein biosynthesis and energy production, DNA damage, and ultimately, programmed cell death and disease initiation. Overall, the dataset revealed that [C2mim]Cl and [C12mim]Cl were, respectively, the least and the most toxic ILs at the transcriptional level. Also, it is reinforced that [Chol]Cl is not devoid of environmental hazardous potential. Unique gene expression signatures could also be identified for each IL.
2021-08-13 | GSE156769 | GEO
Project description:Bio-based ionic liquids (ILs) are being increasingly sought after, as they are more sustainable and eco-friendly. Purines are the most widely distributed, naturally occurring N-heterocycles, but their low water-solubility limits their application. In this work, four purines (theobromine, theophylline, xanthine, and uric acid) were combined with the cation tetrabutylammonium to synthesize bio-based ILs. The physico-chemical properties of the purine-based ILs were characterized, including their melting and decomposition temperatures and water-solubility. The ecotoxicity against the microalgae Raphidocelis subcapitata was also determined. The ILs show good thermal stability (>457 K) and an aqueous solubility enhancement ranging from 53- to 870-fold, in comparison to their respective purine percursors, unlocking new prospects for their application where aqueous solutions are demanded. The ecotoxicity of these ILs seems to be dominated by the cation, and it is similar to chloride-based IL, emphasizing that the use of natural anions does not necessarily translate to more benign ILs. The application of the novel ILs in the formation of aqueous biphasic systems (ABS), and as solubility enhancers, was also evaluated. The ILs were able to form ABS with sodium sulfate and tripotassium citrate salts. The development of thermoresponsive ABS, using sodium sulfate as a salting-out agent, was accomplished, with the ILs having different thermosensitivities. In addition, the purine-based ILs acted as solubility enhancers of ferulic acid in aqueous solution.
| S-EPMC8620494 | biostudies-literature
Project description:Titanium is a strong, corrosion-resistant light-weight metal which is poised to replace steel in automobiles, aircraft, and watercraft. However, the titanium oxide (titania) layer that forms on the surface of titanium in air is notoriously difficult to lubricate with conventional lubricants, which restricts its use in moving parts such as bearings. Ionic liquids (ILs) are potentially excellent lubricants for titania but the relationship between IL molecular structure and lubricity for titania remains poorly understood. Here, three-ball-on-disk macrotribology and atomic force microscopy (AFM) nanotribology measurements reveal the lubricity of four IL lubricants: trioctyl(2-ethylhexyl)phosphonium bis(2-ethylhexyl)phosphate (P8,8,8,6(2) BEHP), trihexyl(tetradecyl)phosphonium bis(2-ethylhexyl)phosphate (P6,6,6,14 BEHP), trihexyl(tetradecyl)phosphonium bis(2,4,4-trimethylpentyl)phosphinate (P6,6,6,14 ( i C8)2PO2), and trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide (P6,6,6,14 TFSI). The macrotribology measurements demonstrated that friction decreased in P6,6,6,14 TFSI by four times (μ = 0.13) compared to in hexadecane, even at 60°C and loads up to 10 N. On the other hand, P8,8,8,6(2) BEHP reduced friction most effectively in the AFM nanotribology measurements. The results were interpreted in terms of the lubrication regime. The lower viscosity of P6,6,6,14 TFSI coupled with its good boundary lubrication made it the most effective IL for the macrotribology measurements, which were in the mixed lubrication regime. Conversely, the cation structure of P8,8,8,6(2) BEHP allowed it to adsorb strongly to the surface and minimized energy dissipation in the nanotribology measurements, although its high bulk viscosity inhibited its performance in the mixed regime. These results reinforce the importance of carefully selecting IL lubricants based on the lubrication regime of the sliding surfaces.
| S-EPMC6498968 | biostudies-literature
Project description:Bi2 S3 was dissolved in the presence of either AuCl/PtCl2 or AgCl in the ionic liquids [BMIm]Cl ⋅ xAlCl3 (BMIm=1-n-butyl-3-methylimidazolium; x=4-4.3) through annealing the mixtures at 180 or 200 °C. Upon cooling to room temperature, orange, air-sensitive crystals of [BMIm](Bi4 S4 )[AlCl4 ]5 (1) or Ag(Bi7 S8 )[S(AlCl3 )3 ]2 [AlCl4 ]2 (2) precipitated, respectively. 1 did not form in the absence of AuCl/PtCl2 , suggesting an essential role of the metal cations. X-ray diffraction on single-crystals of 1 revealed a monoclinic crystal structure that contains (Bi4 S4 )4+ heterocubanes and [AlCl4 ]- tetrahedra as well as [BMIm]+ cations. The intercalation of the ionic liquid was confirmed via solid state NMR spectroscopy, revealing unusual coupling behavior. The crystal structure of 2 consists of (Bi7 S8 )5+ spiro-dicubanes, [S(AlCl3 )3 ]2- tetrahedra triples, isolated [AlCl4 ]- tetrahedra, and heavily disordered silver(I) cations. No cation ordering took place in 2 upon slow cooling to 100 K.
| S-EPMC7874255 | biostudies-literature
Project description:A facile synthetic route for tetra-branched tetraimidazolium and tetrapyrrolidinium ionic liquids was developed. In contrast to the previous synthetic scheme, the new synthetic route requires only three reaction steps instead of seven. The total yield of tetracation was also improved from 17-21 to 39-41%. Using the new synthetic scheme, four kinds of tetracations were synthesized from the combination of two cationic units (imidazolium and pyrrolidinium) and two counteranions [bis(fluorosulfonyl)imide (FSI) and bis(trifluoromethanesulfonyl)imide (TFSI)]. Basic physical properties including glass transition temperature, thermal decomposition temperature, density, viscosity, and ionic conductivity were determined. The counterion exchange from TFSI to FSI resulted in lower glass transition temperature and higher ionic conductivity. Tetrapyrrolidinium exhibited higher viscosity and lower ionic conductivity than tetraimidazolium. The counterion exchange from TFSI to FSI resulted in lower viscosity in the case of tetraimidazolium, while the opposite result was obtained in the case of tetrapyrrolidinium. Tetracations composed of ethyl imidazolium units, diethylene glycol spacers, and FSI counterions exhibited the highest ionic conductivity of 3.5 × 10-4 S cm-1 at 25 °C under anhydrous conditions. This is the best ionic conductivity in the tetracations ever reported.
| S-EPMC8340402 | biostudies-literature
Project description:As the development of novel antibiotics has been at a halt for several decades, chemically enhancing existing drugs is a very promising approach to drug development. Herein, we report the preparation of twelve organic salts and ionic liquids (OSILs) from ciprofloxacin and norfloxacin as anions with enhanced antimicrobial activity. Each one of the fluoroquinolones (FQs) was combined with six different organic hydroxide cations in 93-100% yield through a buffer-assisted neutralization methodology. Six of those were isomorphous salts while the remaining six were ionic liquids, with four of them being room temperature ionic liquids. The prepared compounds were not toxic to healthy cell lines and displayed between 47- and 1416-fold more solubility in water at 25 and 37 °C than the original drugs, with the exception of the ones containing the cetylpyridinium cation. In general, the antimicrobial activity against Klebsiella pneumoniae was particularly enhanced for the ciprofloxacin-based OSILs, with up to ca. 20-fold decreases of the inhibitory concentrations in relation to the parent drug, while activity against Staphylococcus aureus and the commensal Bacillus subtilis strain was often reduced. Depending on the cation-drug combination, broad-spectrum or strain-specific antibiotic salts were achieved, potentially leading to the future development of highly bioavailable and safe antimicrobial ionic formulations.
| S-EPMC7464485 | biostudies-literature
Project description:The development of ionic liquids based on active pharmaceutical ingredients (API-ILs) is a possible solution to some of the problems of solid and/or hydrophobic drugs such as low solubility and bioavailability, polymorphism and an alternative route of administration could be suggested as compared to the classical drug. Here, we report for the first time the synthesis and detailed characterization of a series of ILs containing a cation amino acid esters and anion ketoprofen (KETO-ILs). The affinity and the binding mode of the KETO-ILs to bovine serum albumin (BSA) were assessed using fluorescence spectroscopy. All compounds bind in a distance not longer than 6.14 nm to the BSA fluorophores. The estimated binding constants (KA) are in order of 105 L mol-1, which is indicative of strong drug or IL-BSA interactions. With respect to the ketoprofen-BSA system, a stronger affinity of the ILs containing l-LeuOEt, l-ValOBu, and l-ValOEt cation towards BSA is clearly seen. Fourier transformed infrared spectroscopy experiments have shown that all studied compounds induced a rearrangement of the protein molecule upon binding, which is consistent with the suggested static mechanism of BSA fluorescence quenching and formation of complexes between BSA and the drugs. All tested compounds were safe for macrophages.
| S-EPMC6983093 | biostudies-literature