- Syntheses and physicochemical properties of new ionic liquids based on the hexafluorouranate anion
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The first syntheses of a series of ionic liquids based on the hexafluorouranate(V) anion are described along with their physicochemical and electrochemical properties. The green roomtemperature ionic liquid, 1-ethyl-3-methylimidazolium hexafluorouranate (EMImUF6), exhibits a conductivity of 7.9 mS cm-1, viscosity of 59 cP, and electrochemical window of 2.3 V at 298 K. Copyright
- Kanatani, Takatsugu,Matsumoto, Kazuhiko,Hagiwara, Rika
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- Broensted Superacidity of HCl in a Liquid Chloroaluminate. AlCl3-1-Ethyl-3-methyl-1H-imidazolium Chloride
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The system HCl (0.1 - 1 atm)/AlCl3-EMIC (55.0 mol percent AlCl3)(EMIC = 1-ethyl-3-methyl-1H-imidazolium chloride) at 23 deg C is a Broensted superacid capable of protonating arenes to a degree similar to that of liquid HF at 0 deg C (H0=-15.1).Arenes used in this investigation were biphenyl (I), naphthalene (II), 9H-fluorene (III), chrysene (IV), 2-methylnaphthalene (V), mesitylene (VI), pentamethylbenzene (VII), hexamethylbenzene (VIII), anthracene (IX), and 9,10-dimethylanthracene (X).In both the chloroaluminate melt and HF I is a weak base while VIII-X are strong bases.In between these extremes the order of basicities in both media is II arene*H(1+) + 2AlCl4(1-) and is reversible.The degree of protonation was measured by optical absorption spectrophotometry.The arenes are stable in the liquid chloroaluminate for many hours, and their protonated forms (arenium ions) are stable for 1 h or more.A new procedure for the preparation of EMIC was developed that yields exceptionally clean AlCl3-EMIC melts with very low concentrations of protic and oxidizing impurities.
- Smith, G. P.,Dworkin, A. S.,Pagni, R. M.,Zingg, S. P.
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- Preparation of nanocellulose using ionic liquids: 1-propyl-3-methylimidazolium chloride and 1-ethyl-3-methylimidazolium chloride
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Cellulose nanocrystals were prepared using ionic liquids (ILs), 1-ethyl-3-methylimidazolium chloride [EMIM][Cl] and 1-propyl-3-methylimidazolium chloride [PMIM][Cl], from microcrystalline cellulose. The resultant samples were characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), dynamic light scattering (DLS), scanning electron microscopy (SEM), and transmission electron microscopy (TEM). The XRD results showed that nanocellulose obtained by treatment with both ILs preserved basic cellulose I structure, but crystallinity index of samples (except for Sigmacell treated with [EMIM][Cl]) was lower in comparison to the starting microcrystalline cellulose. The DLS results indicated noticeably smaller particle sizes of prepared cellulose for material treated with [PMIM][Cl] compared to cellulose samples hydrolyzed with [EMIM][Cl], which were prone to agglomeration. The obtained nanocellulose had a rod-like structure that was confirmed by electron microscopy analyses. Moreover, the results described in this paper indicate that cation type of ILs influences particle size and morphology of cellulose after treatment with ionic liquids.
- Babicka, Marta,Borysiak, S?awomir,Dwiecki, Krzysztof,Ratajczak, Izabela,Wo?niak, Magdalena
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- Four fluoroborates ion liquid synthetic method of the (by machine translation)
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The invention discloses a four-tetrafluoroborate ionic liquid synthetic method, comprises the following steps: the molar ratio of 1:1 - 7 of the quaternized substrate with the alkyl halide dispersed in a solvent, in the 30 - 50 °C lower, by UV-irradiation, the illumination intensity for 10 - 1000 W/m2 , Irradiation time is 8 - 12 is H, to obtain the quaternary ammonium salt solution; the quaternary ammonium salt solution with four fluoroborates mix, in the 35 - 45 °C lower, by UV-irradiation, the illumination intensity for 10 - 1000 W/m2 , Irradiation time is 16 - 20 the H, get mixed solution; filtering the mixed solution, to obtain the filtrate, the filtrate is heated and concentrated, to remove the solvent, to obtain four tetrafluoroborate ionic liquid. The invention by UV-irradiation and heating way to synthesize four tetrafluoroborate ionic liquid, yield and the reaction rate is high. (by machine translation)
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Page/Page column 9-10
(2019/05/22)
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- Ionic Liquids Catalyzed Friedel–Crafts Alkylation of Substituted Benzenes with CCl4 Toward Trichloromethylarenes
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Abstract: An ionic liquid catalyzed Friedel–Crafts alkylation reaction of substituted benzenes with CCl4 was developed. The reaction proceeded efficiently under mild conditions, gave corresponding trichloromethylarenes with diversity functional groups in moderate to good yields. The influence of Lewis acidity of ionic liquids on the conversion of the alkylation reaction has been investigated. Notably, the probable mechanism of this reaction has been proposed with the assistance of 27Al NMR spectroscopy. It was noteworthy that the predominance of [Al2Cl7]? species in EmimCl–AlCl3, N = 0.67 could be detected by 27Al NMR spectral analysis, and [AlCl4]? was generated at the beginning of reaction. Additionally, it was found that [AlCl4]? could be transformed into [Al2Cl7]? when the reaction finished. Some control experiments confirmed that the interaction between Lewis acidic species [Al2Cl7]? of the ionic liquid and CCl4 led to the change in speciation of aluminum during the alkylation reactions. Graphical Abstract: [Figure not available: see fulltext.].
- Lyu, Xinyu,Wang, Wencheng,Sun, Yiqun,Zhao, Qian,Qiu, Tao
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p. 665 - 671
(2019/01/04)
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- Ionothermal synthesis, structures, properties of cobalt-1,4-benzenedicarboxylate metal-organic frameworks
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Eight kinds of 1-methyl-3-alkylimidazolium halide [RMI]X (R=ethyl (E), propyl (P), butyl (B) and amyl (A); MI = imidazolium; X= Cl-, I-) ionic liquids (ILs) were used as reaction media and obtained a series of 2D [RMI]2[Co3(BDC)3X2] frameworks through the ionothermal reactions of 1,4-benzenedicarboxylic acid (H2BDC) with Co(NO3)2·6H2O. The 2D [RMI]2[Co3(BDC)3X2] frameworks exhibit a same (3,6) topology network with [RMI]+ cations locating in the interlayer space. [RMI]+ cations play a template role in the structure constructions, whose influence combining with the effect of X- anions pass to the TG behaviors. The decomposition temperatures of the [RMI]2[Co3(BDC)3X2] frameworks decrease with the alkyl chains in [RMI]+ cations, and the compounds containing Cl- show higher thermal stabilities than those with I-. However, compounds 1-8 exhibit two similar broad emissions at ca. 380 and 390 nm, assigned to ILCT. The RMI+ templates and the X- anions do not exert their influence on the fluorescence.
- Zhang, Zong-Hui,Xu, Ling,Jiao, Huan
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p. 217 - 222
(2016/04/06)
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- Combination effect of ionic liquid components on the structure and properties in 1,4-benzenedicarboxylate based zinc metal-organic frameworks
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Two types of 2D [RMI]2[Zn3(BDC)3X2] (Type A) and 3D [Zn(BDC)(H2O)] (Type B) (H2BDC = 1,4-benzenedicarboxylate acid) compounds were synthesized with three kinds of 1-alkyl-3-methyl imidazolium halide ([RMI]X) ionic liquids. Type A is the primary structure model showing a (3,6) network. Type B can be obtained from [BMI]Cl, [AMI]Cl and [AMI]Br media, showing a 4,4-connected {42·84} network. The structure, TG, and fluorescence analyses demonstrate the combination effect of the RMI+ templating effect and X- controlling the structure types. The boundary between Types A and B is from [PMI]Cl, via [BMI]Br, to [AMI]I as the reaction media. The decomposition temperatures of the compounds in Type A decrease with increased RMI+, while X- anions exert the influence that compounds containing Br- supply the highest thermal stability. Similarly, with increased RMI+, or X = I-, the compounds show red shifts compared to the emissions of the ligand.
- Zhang, Zong-Hui,Liu, Bing,Xu, Ling,Jiao, Huan
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p. 17980 - 17989
(2015/10/28)
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- Process for preparing esters and organic halides
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A process for preparing esters and organic halides, which comprises reacting - a salt having a melting point of less than 100°C (at 1 bar) and of the formula ???????? (K+)n X (COO-)n, in which K+ is an organic cation, X (COO-)n is an organic anion having an n-valent organic group X which is substituted by n carboxylate groups COO-, and n is 1, 2 or 3, - with an organic halogen compound (Hal)mY, in which Hal is a halogen atom, Y is an m-valent organic group, and m is 1, 2 or 3, to give an ester and a halide K+ Hal-.
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Page/Page column 7-8
(2013/02/27)
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- Monitoring of liquid-phase organic reactions by photoelectron spectroscopy
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There are strings attached: After linking the reacting groups to head groups of ionic liquids to drastically lower the vapour pressures of the reactants, ordinary liquid-phase organic reactions can be monitored by in situ X-ray photoelectron spectroscopy. This approach is demonstrated for the nucleophilic substitution of an alkyl amine and an alkyl chloride moiety, which are attached to the cation and anion of ionic liquids, respectively. Copyright
- Kolbeck, Claudia,Niedermaier, Inga,Taccardi, Nicola,Schulz, Peter S.,Maier, Florian,Wasserscheid, Peter,Steinrueck, Hans-Peter
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scheme or table
p. 2610 - 2613
(2012/04/17)
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- Synthesis, structure, and physico-optical properties of manganate(II)-based ionic liquids
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Several ionic liquids (ILs) based on complex manganate(II) anions with chloro, bromo, and bis(trifluoromethanesulfonyl)amido (Tf2N) ligands have been synthesized. As counterions, n-alkyl-methylimidazolium (C nmin) cations of different chain length (alkyl = ethyl (C 2), propyl (C3), butyl (C4), hexyl (C 6)) were chosen. Except for the 1-hexyl-3-methylimidazolium ILs, all of the prepared compounds could be obtained in a crystalline state at room temperature. However, each of the compounds displayed a strong tendency to form a supercooled liquid. Generally, solidification via a glass transition took place below -40°C. Consequently, all of these compounds can be regarded as ionic liquids. Depending on the local coordination environment of Mn 2+, green (tetrahedrally coordinated Mn2+) or red (octahedrally coordinated Mn2+) luminescence emission from the 4T(G) level is observed.[1] The local coordination of the luminescent Mn2+ centre has been unequivocally established by UV/Vis as well as Raman and IR vibrational spectroscopies. Emission decay times measured at room temperature in the solid state (crystalline or powder) were generally a few ms, although, depending on the ligand, values of up to 25 ms were obtained. For the bromo compounds, the luminescence decay times proved to be almost independent of the physical state and the temperature. However, for the chloro- and bis(trifluoromethanesulfonyl)amido ILs, the emission decay times were found to be dependent on the temperature even in the solid state, indicating that the measured values are strongly influenced by nuclear motion and the vibration of the atoms. In the liquid state, the luminescence of tetrahedrally coordinated Mn2+ could only be observed when the tetrachloromanganate ILs were diluted with the respective halide ILs. However, for [C3mim][Mn(Tf2N)3], in which Mn 2+ is in an octahedral coordination environment, a weak red emission from the pure compound was found even in the liquid state at elevated temperatures.
- Pitula, Slawomir,Mudring, Anja-Verena
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experimental part
p. 3355 - 3365
(2010/06/21)
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- A novel and green method for the synthesis of ionic liquids using the corresponding acidic ionic liquid precursors and dialkyl carbonate
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A novel and green method for the synthesis of dialkylimidazolium ionic liquids (ILs) has been developed. It was through a one-step alkylation of dialkyl carbonate with the corresponding acidic ionic liquid precursors (AILPs) prepared from the neutralization of imidazole derivatives with acids.
- Xiao, Wenjun,Wang, Xiaoxing,Chen, Qin,Wu, Tinghua,Wu, Ying,Dai, Lizong,Song, Chunshan
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supporting information; experimental part
p. 1112 - 1113
(2011/08/08)
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- High conversion, solvent free, continuous synthesis of imidazolium ionic liquids in spinning tube-in-tube reactors
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A spinning tube-in-tube (STT) reactor has been used for the accelerated solvent-free synthesis of a number of l-methylimidazole-based ionic liquids with excellent conversions (>99%) and high throughputs (tens of kg/day).
- Gonzalez, Michael A.,Ciszewski, James T.
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experimental part
p. 64 - 66
(2010/04/22)
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- Characterisation and properties of new ionic liquids with the difluoromono[1,2-oxalato(2-)-O,O′]borate anion
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Three ionic liquids with borate anions of low symmetry, tetraethylammonium difluoromono[1,2-oxalato(2-)-O,O′]borate, 1-ethyl-3-methylimidazolium difluoromono[1,2-oxalato(2-)-O,O′]borate, and 1-butyl-3-methylimidazolium difluoromono[1,2-oxalato(2-)-O,O′]borate were synthesised and characterised by physicochemical and electrochemical measurements including thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), cyclic voltammetry (CV), viscosity and conductivity measurements.
- Herzig, Tobias,Schreiner, Christian,Gerhard, Dirk,Wasserscheid, Peter,Gores, Heiner Jakob
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p. 612 - 618
(2007/12/29)
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- Method for producing haloalkanes from alcohols
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The invention relates to a process for preparing haloalkanes by reaction of alcohol with hydrogen halide, wherein the reaction of the alcohol with the hydrogen halide occurs in the presence of an ionic liquid at a temperature which is above 100° C. for at least part of the time and, at least at the time of the commencement of the reaction, the water content is not more than 25 mol % based on the amount of liquid, where the ionic liquid is not octyltrimethylammonium chloride.
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- Ionic liquid droplet as e-microreactor
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A powerful approach combining a droplet-based, open digital microfluidic lab-on-a-chip using task-specific ionic liquids as soluble supports to perform solution-phase synthesis is reported as a new tool for chemical applications. The negligible volatility of ionic liquids enables their use as stable droplet reactors on a chip surface under air. The concept was validated with different ionic liquids and with a multicomponent reaction. Indeed, we showed that different ionic liquids can be moved by electrowetting on dielectric (EWOD), and their displacement was compared with aqueous solutions. Furthermore, we showed that mixing ionic liquids droplets, each containing a different reagent, in "open" systems is an efficient way of carrying supported organic synthesis. This was applied to Grieco's tetrahydroquinolines synthesis with different reagents. Analysis of the final product was performed off-line and on-line, and the results were compared with those obtained in a conventional reaction flask. This technology opens the way to easy synthesis of minute amounts of compounds ad libitum without the use of complex, expensive, and bulky robots and allows complete automation of the process for embedded chemistry in a portable device. It offers several advantages, including simplicity of use, flexibility, and scalability, and appears to be complementary to conventional microfluidic lab-on-a-chip devices usually based on continuous-flow in microchannels.
- Dubois, Philippe,Marchand, Gilles,Fouillet, Yves,Berthier, Jean,Douki, Thierry,Hassine, Fatima,Gmouh, Said,Vaultier, Michel
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p. 4909 - 4917
(2008/02/12)
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- Lonization state and ion migration mechanism of room temperature molten dialkylimidazolium fluorohydrogenates
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The ionization state of room temperature molten salts, alkylimidazolium fluorohydrogenates (RMIm-(HF)2.3F: R = alkyl group, M =methyl group), was evaluated from the observed diffusion coefficient and viscosity, using the Stokes-Einstein relation. Assuming that the dissociation degree of the salt is acceptable for representation of the ionic state of the molten salts, the larger the cation size with elongation of the alkyl chain was, the higher the dissociation degree of the salt Further, we proposed that an idea of the "degree of ordering of cations and anions" was more suitable to represent the ionization state without solvent species. On the basis of this idea, the smaller the cation size of RMIm(HF)2.3F salt was, the higher the ordering of the ion, indicating formation of domain particles of aggregated ions as a unit of mobile species such as A(AX)m + and X(AX)n- for A+X- salt. It was found that highly ordered particles, with large numbers for m and n, showed a high diffusion coefficient. ? 2005 American Chemical Society.
- Saito, Yuria,Hirai, Kenichi,Matsumoto, Kazuhiko,Hagiwara, Rika,Minamizaki, Yoshihiro
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p. 2942 - 2948
(2007/10/03)
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- Organic salt conditioner, organic salt-containing composition, and uses thereof
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The present invention relates to the use of, and a composition containing, at least one non-polymeric organic salt with a melting point of less than 60° C. These organic salts may be imidazolium, pyrazolium, pyridinium, pyrimidinium or tetraalkylphosphonium salts. The inventinon composition may be used for washing (cleaning) and/or conditioning keratin materials, and especially the hair.
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- Alkylation process
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This invention relates to a process for the alkylation of aromatics by reacting an aromatic hydrocarbon with an olefin in the presence of an ionic liquid comprising (a) a compound of the formula Rn MX3-n wherein R is a C1-C6 alkyl radical, M is aluminium or gallium, X is a halogen atom and n is 0, 1 or 2 and, (b) a hydrocarbyl substituted imidazolium halide or a hydrocarbyl substituted pyridinium halide wherein at least one of the said hydrocarbyl substituents in the imidazolium halide is an alkyl group having 1-18 carbon atoms. The process allows ready separation of reaction products from the ionic liquid and improves selectivity to alkylated products.
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- Evidence for Hydrogen Bonding in Solution of 1-Ethyl-3-methylimidazolium Halides, and its Implications for Room-temperature Halogenoaluminate(III) Ionic Ligands
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Multinuclear NMR spectroscopy and conductivity measurements showed that the 1-ethyl-3-methylimidazolium cation, (1+), not only forms strong hydrogen bonds (using all three ring protons H2, H4 and H5) with halide ions in polar molecular solvents (e.g. ethanenitrile) and ionic liquids, but that it exists in a quasi-molecular state, X, in non-polar solvents (e.g. trichloro- and dichloromethane), showing a conventional aromatic stacking phenomenon.
- Avent, Anthony G.,Chaloner, Penelope A.,Day, Martin P.,Seddon, Kenneth R.,Welton, Thomas
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p. 3405 - 3414
(2007/10/02)
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