- Physical and electrochemical properties of 1-alkyl-3-methylimidazolium tetrafluoroborate for electrolyte
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Three kinds of ionic liquids, 1-alkyl-3-methylimidazolium tetrafluoroborate (n = 2-4), were prepared and fundamental properties of ionic liquids and those mixed with industrially used organic solvents (PC, GBL and AN) were investigated compared to solid salts, TEMABF4. It was found that degree of ionization of the ionic liquids were almost same as that of TEMABF4 from the conductivity measurement in diluted system of PC. The ionic liquids and the organic solvents intermingle with each other. Some enhancement in conductivity was observed compared to TEMABF4.
- Nishida, Tetsou,Tashiro, Yasutaka,Yamamoto, Masashi
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- Photoreduction of benzophenones by amines in room-temperature ionic liquids
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(equation presented) The amine-mediated photoreduction of benzophenones in room temperature ionic liquids was investigated. Unlike the analogous reaction in organic solvents, the photoreduction produces mainly the corresponding benzhydrol in most cases. Because the reaction consumes only 1 equiv of amine and the solvent can be easily recycled, the photoreduction allows a very clean method for the conversion of benzophenones to benzhydrols.
- Reynolds, John L.,Erdner, Kimberly R.,Jones, Paul B.
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- Conductivities of binary mixtures of ionic liquids with polar solvents
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Data for the conductivity, κ, of selected binary mixtures of the ionic liquids [emim][BF4], [bmim][BF4], [bmim][PF 6], [brmm][DCA], and [hmim][BF4] with polar solvents (water, propylene carbonate, dimethyl-sulfoxide, methanol, dichloromethane) at 25 °C are reported. Additionally, mixture densities, p, were determined to convert κ into molar conductivity, A. The obtained results were fitted by appropriate interpolation formulas. Where possible, data were compared with information from the literature. Electrode polarization and sample purity, including [BF4-] hydrolysis, were considered as possible sources of errors in κ. The effect of viscosity on the accuracy of p and thus A was checked.
- Stoppa, Alexander,Hunger, Johannes,Buchner, Richard
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- Synthesis of High-Purity Imidazolium Tetrafluoroborates and Bis(oxalato)borates
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The synthesis and purification of imidazolium-based ionic liquids (ILs) with boron-containing anions is reported. The scope was the optimization of the meta thesis reaction and on the purification of the synthesized ILs. It was possible to reduce the reac
- Schmitz, Paulo,Jakelski, Rene,Jalkanen, Kirsi,Winter, Martin,Bieker, Peter
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- Water-assisted stability of carbene: cyclic voltammetric investigation of 1-ethyl-3-methylimidazolium ethylsulfate ionic liquid
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In this work, we report electrochemical studies on imidazolium-based ionic liquids with an objective to explore the possibility of carbene formation in their dilute aqueous solutions. Conventionally, water plays a detrimental role during investigations involving ionic liquids, and this role has been investigated via electrochemical studies in aqueous ionic liquid solutions. There are varying opinions regarding the influence of water on the physicochemical behaviour of ionic liquids that require an in-depth understanding. To eludicate the role of water, we attempted to evaluate the electrochemical performance of ionic liquids in water as a solvent, and the influence of water on ionic liquids was explored through feasibility and stability studies on carbene formed in an aqueous imidazolium-based ionic liquid solution. The electrochemical investigation of an aqueous solution of 1-ethyl-3-methylimidazolium ethylsulfate ([EMIM][EtSO4]) revealed a redox couple. Detailed investigations suggest that reduction of the imidazolium cation occurs at the C2 position, with subsequent formation of carbene. Furthermore, an anodic peak was found to be associated with the oxidation of carbene. The coulometric process associated with the anodic peaks indicated that the two-electron oxidation of carbene occurred. The stability of carbene in water was evaluated through the use of different protic and aprotic solvents. The hydrogen bond-forming ability of carbene with water seems to be responsible for its improved stability in water.
- Jain, Preeti,Chaudhari, Vijay R.,Kumar, Anil
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- Efficient absorption of ammonia with hydroxyl-functionalized ionic liquids
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Ammonia (NH3) emitted from the ammonia synthesis process is a kind of waste chemical resource and a major environmental pollutant. The traditional water scrubbing method suffers from high energy consumption due to the concentrated NH3 from aqueous ammonia. Therefore, it is desirable to develop novel absorbents for the efficient, reversible and environmentally-friendly recovery of NH3. In this paper, a series of hydroxyl-functionalized imidazolium ILs ([EtOHmim]X, X = [NTf2], [PF6], [BF4], [DCA], [SCN] and [NO3]) were designed and prepared. Their physical properties and NH3 absorption capacities under different temperatures and pressures were systematically investigated. The effects of hydroxyl cation, anionic structures, pressure and temperature on absorption performance were sufficiently studied. In addition, the absorption mechanism was investigated in detail by spectral analysis and quantum chemistry calculations. Compared with conventional IL [Emim]X, a higher absorption capacity was achieved by introducing the hydroxyl group on the imidazolium cation. The mechanism results showed the fascinating absorption performance of the task-specific ILs was attributed to the stronger hydrogen bonding interaction between NH3 and the H atom of the hydroxyl group. Considering the excellent absorption performance, high thermal stability, and super reversibility, this type of IL provides great improvement over conventional IL and shows their enormous potential in NH3 recovery.
- Li, Zhijie,Zhang, Xiangping,Dong, Haifeng,Zhang, Xiaochun,Gao, Hongshuai,Zhang, Suojiang,Li, Jianwei,Wang, Congmin
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- Deciphering the anthelmintic activity of benzimidazolium salts by experimental and in-silico studies
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Inspired from the facts that majority of the drug administrated in the form of salts and “poison is in the dose”; herein, we have synthesized and characterized 1-methyl-3-alkylbenzimidazolium and 1-methyl-3-alkylimidazolium derived ionic salts with varying N-alkyl chains and different anions. These ionic salts were evaluated for their vermicidal activity (VA) and cell viability test against the Pheretima posthuma and A549 cell lines (human alveolar basal epithelial cells), respectively. The morphological changes in the test organism were visualized by the Scanning Electron Spectroscopy (SEM) to get the mechanistic insight. Furthermore, results were compared with VA of 1-methyl-3-alkylimidazolium derivatives to establish their structure-activity-relationship (SAR) of the fused benzene ring in 1-methyl-3-alkylimidazolium. The current findings suggested that the activity of these salts depends on the nature of N-alkyl side-chain, anionic moieties, varying partial charge on quaternary nitrogen (due to different anions) lipophilicity and types of cationic core fused with imidazolium ring. These findings were complemented by the quantitative-structure-activity-relationship (QSAR), molecular docking approaches to unfold the features accountable for their activities and binding patterns of the ligand-receptor complex respectively. ADME/T assessment of the ionic salts shows that twelve compounds qualified the ADMET profiling test & encompasses the drug-likeness features.
- Ranjan, Prabodh,Athar, Mohd,Vijayakrishna, Kari,Meena, Lalit K.,Vasita, Rajesh,Jha, Prakash C.
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- Weakly-basic anion exchange resin scavenges impurities in ionic liquid synthesized from trialkyloxonium salt
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A new purification method of ionic liquids made from trialkyloxonium salts (Meerwein reagents) has been established. 1H and 19F NMR spectroscopy clarified the presence of 1-methylimidazolium ([Hmim]+) and trifluoro(1-methylimidazole)boron ([BF3(mim)]) as impurities occurring in the crude ionic liquid, 1-ethyl-3-methylimidazolium tetrafluoroborate ([emim]BF4). The Lewis acidic parts of these impurities, that is, H+ and BF3, were demonstrated to be able to transfer to dimethylamino groups of the weakly basic anion exchange resin (DOWEX MARATHON WBA) in aqueous solutions, releasing 1-methylimidazole (mim). The adsorption isotherms of [Hmim]BF4 and [BF 3(mim)] resulted in the equilibrium constants (K) of the reactions with the resin ([Hmim]BF4: log K ≈ 1.7, [BF3(mim)]: log K = -0.17 ± 0.03), indicating that the impurities show a difference in the reactivity with the resin. The volatiles (mim and water) are possible to be removed by evaporation under reduced pressure. Although intense reddish brown color was given to the residual oil of [emim]BF4, further purification and decolorization have been achieved by using silica-gel column chromatography (eluent: acetone) and treatment with activated carbon in water. Finally, the purified [emim]BF4 was successfully obtained as an almost colorless oil. The resin after use can be regenerated simply by washing with 1 M NaOH aq and deionized water.
- Takao, Koichiro,Tsubomura, Taro
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- Lewis Acid Catalyzed Synthesis of Cyanidoborates
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The reactions of [BF4]- salts with Me3SiCN were studied at different temperatures and in the presence of several different Lewis acids, which led to the generation of the well-known [BF4-n(CN)n]- (n = 1-4) salts. Depending on the catalyst and the reaction conditions, the whole series of [BF4-n(CN)n]- salts is now accessible under ambient conditions, and long preparation times and the excessive production of waste materials can be avoided. The best results were obtained when the F-/CN- substitution reactions were performed in ionic liquids.
- Bl?sing, Kevin,Ellinger, Stefan,Harloff, J?rg,Schulz, Axel,Sievert, Katharina,T?schler, Christoph,Villinger, Alexander,Zur T?schler, Cornelia
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- Steady-state and time-resolved fluorescence behavior of C153 and PRODAN in room-temperature ionic liquids
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Room temperature ionic liquids have emerged as nature-friendly media suitable for various applications. In this work, steady-state and time-resolved fluorescence behavior of coumarin 153 (C153) and 6-propionyl-2-dimethylaminonaphthalene (PRODAN) have been reported in two room-temperature sonic liquids based on substituted imidazolium salts. The steady-state fluorescence behavior of the two probe molecules suggests that these liquids are more polar than acetonitrile. The polarity of these media is found to be comparable to that of 2-propanol. No significant difference in the polarity of the two media could be observed although the cationic components of the two liquids contain alkyl substitutents of different chain length. Both the probe molecules display a wavelength-dependent fluorescence decay behavior. The decay profile at the red edge of the spectrum consists of an initial rise followed by a slow decay, while no rise could be observed at the blue edge of the spectrum. The solvation dynamics of the two probe molecules in the two room-temperature ionic liquids have been studied from the time-dependence of the spectral shift function constructed from the wavelength-dependent fluorescence decay profiles. The solvation of the probe molecules occurs on two different time scales with the absolute values strongly dependent on the cationic component of the ionic liquids. The average solvation time is found to be fairly long and dependent on the probe molecule used.
- Karmakar, Rana,Samanta, Anunay
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- Interactions of CO2 with the homologous series of СnMIMBF4 ionic liquids studied in situ ATR-FTIR spectroscopy: spectral characteristics, thermodynamic parameters and their correlation
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In this work, in situ ATR-FTIR spectroscopy was used to study the interaction of CO2 and a series of 1-alkyl-3-methylimidazolium tetrafluoroborate СnMIMBF4 (n = 2, 4, 6, 8, 10) ionic liquids. A detailed analysis of the infrared spectra acquired from ionic liquids and sorbed СО2 was performed as ionic liquids with different the alkyl chain lengths were subjected to changing pressures of СО2 and temperature. With a longer alkyl chain length, an increase in the shift of the CH stretching vibrations bands of alkyl groups and BF stretching vibrations of BF4? anions is observed during CO2 sorption. This indicates the disaggregation of alkyl chains and anions. There is a correlation with the position of the wavenumber of the ν3 asymmetric stretching CO2 band and the length of the alkyl chain. It was found that some of the CO2 adsorbed by ionic liquids does not interact with the ionic liquid but is “free” in the bulk of the alkyl chains. For the first time, ATR-FTIR spectroscopy was used to determine the thermodynamic parameters of CO2 sorption in ionic liquids. It was demonstrated that the values of enthalpy and entropy obtained by analysis of the ATR-FTIR spectra are consistent the data obtained by other methods. A correlation was found between the enthalpy of sorption of CO2 and the wavenumber of the ν3 band. This opens up the possibility of using CO2 as an IR-sensitive probe molecule to characterize the acid-base properties of ionic liquids and determine the enthalpy of CO2 sorption.
- Adonin, Nikolai Y.,Kazarian, Sergei G.,Martyanov, Oleg N.,Nesterov, Nikolai S.,Prikhod'ko, Sergei A.,Shalygin, Anton S.
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- Improved preparation and use of room-temperature ionic liquids in lipase-catalyzed enantio- and regioselective acylations
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Polar organic solvents such as methanol or N-methylformamide inactivate lipases. Although ionic liquids such as 3-alkyl-1-methylimidazolium tetrafluoroborates have polarities similar to these polar organic solvents, they do not inactivate lipases. To get reliable lipase-catalyzed reactions in ionic liquids, we modified their preparation by adding a wash with aqueous sodium carbonate. Lipase-catalyzed reactions that previously did not occur in untreated ionic liquids now occur at rates comparable to those in nonpolar organic solvents such as toluene. Acetylation of 1-phenylethanol catalyzed by lipase from Pseudomonas cepacia (PCL) was as fast and as enantioselective in ionic liquids as in toluene. Ionic liquids permit reactions in a more polar solvent than previously possible. Acetylation of glucose catalyzed by lipase B from Candida antarctica (CAL-B) was more regioselective in ionic liquids because glucose is up to one hundred times more soluble in ionic liquids. Acetylation of insoluble glucose in organic solvents yielded the more soluble 6-O-acetyl glucose, which underwent further acetylation to give 3,6-O-diacetyl glucose (2-3:1 mixture). However, acetylation of glucose in ionic liquids yielded only 6-O-acetyl glucose (> 13:1 and up to > 50:1).
- Park,Kazlauskas
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- Heteronuclear NOE spectroscopy of ionic liquids
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19F,1H HOESY experiments with three ionic liquids ([bmim]BF4, [bmim]PF6 and [emim]BF4) were run in two different solvents and neat. The results give preferred probabilities of presence and enable us to systematically study interactions between the cations and the anions in the ionic liquid phase by NMR spectroscopy. The influence of different solvents and of the presence or absence of air (i.e. oxygen) is discussed. This enabled us to substantially speed up the NMR experiments and to develop a more precise method for the investigation of liquid-phase structures in ionic liquids. Copyright
- Lingscheid, Yves,Arenz, Sven,Giernoth, Ralf
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- Greatly enhanced fluorescence of dicyanamide anion based ionic liquids confined into mesoporous silica gel
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1-Ethyl-3-methylimidazolium dicyanamide EMImN(CN)2 and S-ethyltetrahydrothiophene dicyanamide EThN(CN)2 physically confined into mesoporous silica gel with pore sizes of 6-8 nm (IL-sg) were synthesized according to a proper sol-gel process. Greatly enhanced fluorescence emissions of dicyanamide based ILs after being confined were exhibited.
- Zhang, Juan,Zhang, Qinghua,Shi, Feng,Zhang, Shiguo,Qiao, Botao,Liu, Lequan,Ma, Yubo,Deng, Youquan
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- Correlation between hydrogen bond basicity and acetylene solubility in room temperature ionic liquids
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Room temperature ionic liquids (RTILs) are proposed as the alternative solvents for the acetylene separation in ethylene generated from the naphtha cracking process. The solubility behavior of acetylene in RTILs was examined using a linear solvation energy relationship based on Kamlet-Taft solvent parameters including the hydrogen-bond acidity or donor ability (α), the hydrogen-bond basicity or acceptor ability (β), and the polarity/polarizability (π*). It is found that the solubility of acetylene linearly correlates with β value and is almost independent of α or π*. The solubility of acetylene in RTILs increases with increasing hydrogen-bond acceptor (HBA) ability of the anion, but is little affected by the nature of the cation. Quantum mechanical calculations demonstrate that the acidic proton of acetylene specifically forms hydrogen bond with a basic oxygen atom on the anion of a RTIL. On the other hand, although C-H???π interaction is plausible, all optimized structures indicate that the acidic protons on the cation do not specifically associate with the π cloud of acetylene. Thermodynamic analysis agrees well with the proposed correlation: the higher the β value of a RTIL is, the more negative the enthalpy of acetylene absorption in the RTIL is.
- Palgunadi, Jelliarko,Hong, Sung Yun,Lee, Jin Kyu,Lee, Hyunjoo,Lee, Sang Deuk,Cheong, Minserk,Kim, Hoon Sik
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- Voltammetric study and electrodeposition of tellurium, lead, and lead telluride in room-temperature ionic liquid 1-ethyl-3-methylimidazolium tetrafluoroborate
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Room-temperature ionic liquid 1-ethyl-3-methylimidazolium tetrafluoroborate (RTIL EMI-BF4) was used as the electrolyte to study the voltammetric behavior of Te(IV), Pb(II), and their mixtures. Te(IV) and Pb(II) were introduced into the IL by the addition of TeCl4 and PbCl2, respectively, with sufficient 1-ethyl-3-methylimidazolium chloride (EMIC). The electrodeposition of Te, Pb, and PbTe was achieved under constant applied potential at nickel electrodes. The nucleation mechanisms of Te and Pb were determined to be three-dimensional instantaneous nucleation with diffusion-controlled growth. Crystalline stoichiometric PbTe electrodeposits were obtained via Pb under-potential deposition at the continuously growing surface of Te. They exhibited an energy bandgap of 0.22 eV.
- Tsai, Ren-Wei,Hsieh, Yi-Ting,Chen, Po-Yu,Sun, I-Wen
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- A novel method for preparation of imidazolium tetrafluoroborate ionic liquids
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A new method for the preparation of substituted imidazolium tetrafluoroborate salt, some of which are known as versatile room temperature ionic liquids, is proposed. The new method based on N-methylation of imidazole provided tetrafluoroborate derivatives containing no counterions, with shorter time and lower cost than conventional ion-exchange method.
- Egashira, Minato,Yamamoto, Yuji,Fukutake, Tsubasa,Yoshimoto, Nobuko,Morita, Masayuki
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- Lewis Acid Catalyzed Synthesis of Cyanidophosphates
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Salts containing new cyanido(fluorido)phosphate anions of the general formula [PF6-n(CN)n]- (n=1-4) were synthesized by a very mild Lewis-acid-catalyzed synthetic protocol and fully characterized. All [PF6-n(CN)n]- (n=1-4) salts could be isolated on a preparative scale. It was also possible to detect the [PF(CN)5]- but not the [P(CN)6]- anion. The best results with respect to purity, yield, and low cost were obtained when the F-/CN- substitution reactions were carried out in ionic liquids. Cyanido(fluorido)phosphates: Salts containing [PF6-n(CN)n]- (n=1-4) ions were isolated on a preparative scale by utilizing Lewis acids (LA) catalysts under mild conditions (see equation). The best results with respect to purity, yield, and low cost were obtained when the F-/CN- substitution reactions were carried out in ionic liquids.
- Bl?sing, Kevin,Ellinger, Stefan,Harloff, J?rg,Schulz, Axel,Sievert, Katharina,T?schler, Christoph,Villinger, Alexander,Zurt?schler, Cornelia
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- Alternative route to metal halide free ionic liquids
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An alternative synthetic route to metal halide free ionic liquids using trialkyloxonium salt is proposed. Utility of this synthetic route has been demonstrated by preparing 1-ethyl-3-methylimidazolium tetrafluoroborate ionic liquid through the reaction be
- Takao, Koichiro,Ikeda, Yasuhisa
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- Self-assembly and lower critical solution temperature properties of supramolecular block copolymer/ionic liquid complexes depending on the alkyl chain length of imidazolium rings
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We report the liquid crystalline (LC) assembly and lower critical solution temperature (LCST) properties of wedge-shaped block copolymer (BCP)/1-alkyl-3-methylimidazolium tetrafluoroborate ([CnMIM][BF4], n = 2, 4, 6) complexes (1–3) depending on the alkyl chain length of the ionic liquids (ILs). In contrast to the crystalline BCP, all of the ionic samples showed LC phases. 1 with [C2MIM][BF4] exhibited a hexagonal columnar phase, and 3 with [C6MIM][BF4] exhibited a gyroid phase. Interestingly, a temperature-dependent transformation from columnar phase to gyroid phase was revealed for 2 with [C4MIM][BF4]. The phase difference may be explained by the supramolecular shape change that was dependent on the alkyl chain length of the ILs. The LCST behavior was characterized using the differential scanning calorimetry, turbidity observations, and the X-ray diffraction techniques. Notably, the primary d-spacing began to decrease at the clouding temperature (Tc). 3 showed the highest Tc at 130 °C, which is greater than the temperature of the order-to-disorder transition. The results demonstrate that the subtle variation in the IL structure affects the morphological and LCST properties.
- Noh, Minjoo,Cho, Byoung-Ki
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- Separation of ethyl acetate and ethanol by room temperature ionic liquids with the tetrafluoroborate anion
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Liquid-liquid equilibrium data are presented for mixtures of 1-ethyl-3-methylimidazolium tetrafluoroborate ([emim]BF4) or 1-(2-hydroxyethyl)-3-methylimidazolium tetrafluoroborate ([C2OHmim] BF4) or 1-ethyl-2,3-dimethylimidazolium tetrafluoroborate ([edmim]BF4) or 1-(2-hydroxyethyl)-2,3-dimethylimidazolium tetrafluoroborate ([C2OHdmim]BF4) + ethanol + ethyl acetate at 298.15 K. The distribution ratio and selectivity values, derived from the tie line data, show that [C2OHmim]BF4 has better extraction capacity than other studied ionic liquids and that a hydroxyl group on the cation and a CH3 group at the 2-position can obviously affect the interaction between the ionic liquid and ethanol. The experimental results show that [C2OHmim]BF4 is potentially a candidate to separate ethyl acetate and ethanol by liquid-liquid extraction. The experimental tie lines were correlated with the NRTL equation.
- Hu, Xuesheng,Li, Yingxia,Cui, Dannan,Chen, Biaohua
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- A quick and green approach to prepare [Rmim]OH and its application in hydrophilic ionic liquid synthesis
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A quick and green process to prepare [Rmim]OH solutions is developed based on fast ion exchange between OH- and halide ions (halide = Cl - or Br-) in ethanol. Five ionic liquids were synthesized by neutralizing the obtained [Rmim]OH solution with acids to verify the feasibility of the whole process. The halogen content in the finally obtained ionic liquids and the experimental factors influencing the content are mainly discussed. Moreover, two other alcohols besides ethanol, propanol and iso-propanol, were further examined as solvents. The results show that this process, together with the alkylation and hydroxide anion route, is simple and efficient for preparing various ionic liquids, and that the process is a complementary synthetic route to existing strategies to prepare various ILs.
- Gao, Jian,Liu, Jianguo,Li, Bo,Liu, Wenming,Xie, Yun,Xin, Yuchen,Yin, Ying,Jie, Xiao,Gu, Jun,Zou, Zhigang
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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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- Preparation method of high-purity supercapacitor electrolyte quaternary ammonium salt
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The invention provides a preparation method of a high-purity supercapacitor electrolyte quaternary ammonium salt. The preparation steps comprise: (1) carrying out a quaternization reaction on amine and alkyl silicate in an organic solvent to generate a quaternary ammonium silicate; (2) carrying out a reaction on the quaternary ammonium silicate and an acid to generate a quaternary ammonium salt, filtering out the solid from the reaction liquid, dewatering, and removing solvent to obtain a solid product; and (3) re-crystallizing the solid product obtained in the step (2) to obtain the high-purity quaternary ammonium salt. According to the present invention, the method does not use the halide, the purity of the product is high, and the supercapacitor electrolyte prepared by using the quaternary ammonium salt has low halogen ion content and good electrochemical performance.
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Paragraph 0042-0044
(2018/08/28)
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- Quaternary ammonium salt preparation method
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The invention provides a quaternary ammonium salt preparation method which comprises the preparation steps: (1) making amine and acid react to generate amine salt; (2) making the amine salt and alkylcarbonate react in an organic solvent to generate quaternary ammonium salt; (3) purifying a product in the step (2) by a crystallizing method to obtain corresponding quaternary ammonium salt. No halide takes part in a reaction process of the method, so that a content of halide ions in the quaternary ammonium salt is smaller than 5ppm; super capacitor electrolyte prepared from the quaternary ammonium salt has excellent cycling performance.
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Paragraph 0043; 0044; 0045
(2018/07/15)
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- A potential greener protocol for peptide coupling reactions using recyclable/reusable ionic liquid [ C 4-DABCO ] [ N(CN) 2 ]
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Abstract : Development of greener methodologies in synthetic organic chemistry has brought awareness in recent decades due to the ecological performance of green solvent media and catalytic systems. Here, we carried out the peptide bond formation reaction in one of the environmentally secure solvents, ‘ionic liquids’ in the presence of coupling reagent and in the absence of external base at room temperature, affording dipeptides in good to excellent yields. GRAPHICAL ABSTRACT: SYNOPSIS We carried out the peptide bond formation reaction in ionic liquids in the presence of a coupling reagent at room temperature, in the absence of an external base, affording dipeptides in good to excellent yields.
- Konwar, Manashjyoti,Khupse, Nageshwar D,Saikia, Prakash J,Sarma, Diganta
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- Redox Reaction: A New Route for the Synthesis of Water-Miscible Imidazolium Ionic Liquids
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A novel chemical redox route was developed for the preparation of water-miscible imidazolium ionic liquids (ILs). In this method, the reaction between 1-alkyl-3-methylimidazolium bromides or 3-butyl-1-phenylimidazolium bromide and the appropriate acid reactant was promoted by the redox reaction between the bromide ion and aqueous hydrogen peroxide, with hex-1-ene as both solvent and bromine scavenger. The residual bromide ion and water contents of the prepared ILs were determined by ion chromatography and the Karl-Fischer test, respectively. This method not only produces water-miscible ILs in high purity and high yield, but also simplifies the reaction conditions in comparison with previous routes.
- Li, Wenxiu,Dai, Shangwu,Li, Dong,Zhang, Qinqin,Fan, Hongtao,Zhang, Tao,Zhang, Zhigang
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p. 1065 - 1072
(2017/02/23)
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- A method of manufacturing a quaternary salt solution
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PROBLEM TO BE SOLVED: To provide a method of industrially efficiently manufacturing a solution where low moisture quaternary salt is dissolved into a specific solvent without special facilities.SOLUTION: The method of manufacturing includes the following processes 1 to 3. Process 1: A process of alkylating amines and/or phosphines in a solvent (b1) having a boiling point of 35 to 260°C to obtaining a solution (S1) of a quaternary ammonium salt and/or a quaternary phosphonium salt (a1), then conducting an acid exchange treatment of (S1) with an inorganic acid aqueous solution or an organic acid aqueous solution to obtain a solution (S2) of a quaternary salt (a2). Process 2: A process of removing the solvent (b1) and water in (S2) to obtain a quaternary salt solution (S3) having a concentration of 50 to 90 wt.%. Process 3: A process of removing the solvent (b1) and water after adding a solvent (b2) having a boiling point of 101 to 300°C and higher than the boiling point of the solvent (b1) for dissolving the quaternary salt (a2) to obtain a quaternary salt solution (S).
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Paragraph 0054
(2017/02/24)
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- Method for Preparation of Cyano Compounds of the 13th Group with a Lewis Acid
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The invention discloses a method for preparation of cyano compounds of the 13th group of the periodic table with 1, 2, 3 or 4 cyano residues, represented by formula (I): [Catn+][(Z1F4-m(CN)m)?]n by a reaction of [(Z1F4)?] with trimethylsilylcyanide in the presence of a Lewis acid and in the presence of the cation Catn+; Catn+ is a cation, Z1 is B, Al, Ga, In or Tl, m is 1, 2, 3 or 4 and n is 1, 2, 3 or 4.
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Paragraph 0352; 0353; 0354; 0355; 0356; 0357; 0358-0360
(2016/09/12)
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- Alkali metal oligoether carboxylates - A new class of ionic liquids
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A new group of ionic liquids (IL) based on small inorganic cations and oligoether carboxylate anions were synthesized. The physicochemical properties of the salts were also investigated, and possible reasons for the formation of ionic liquids with alkali metal ions were proposed. It was found that complexation of the alkali metal cations by their combined oligoether- carboxylate counter-ion was sufficient to generate room-temperature liquid salts. It was also found that the use of simple tri- and tetraalkylammonium instead of alkali metal ions could also yielded ionic liquids at ambient temperature that appear to display additional desirable properties such as low viscosity. The result also showed that the combination of the 2,5,8,1 l-tetraoxatridecan-13-oate (TOTO) anion with biological cations such as choline could also lead to the development of even greener ILs.
- Zech, Oliver,Kellermeier, Matthias,Thomaier, Stefan,Maurer, Eva,Klein, Regina,Schreiner, Christian,Kunz, Werner
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experimental part
p. 1341 - 1345
(2009/09/04)
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- Multiple cobalt phosphate ring system from l-alkyl-3-methylimidazolium tetrafluoroborate ionic liquids
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Open-framework phosphate Co7(PO4) 2(HPO4)4 with a multiple ring system was ionothermally synthesized by using 1-alkyl -3-methylimidazolium tetrafiuoroborates as solvent. The crystals of Co7(PO 4)2(HPO4)4 were large enough to do single crystal X-ray diffraction analysis, which crystallize in the space group P-1 (No.2), with cell parameters of α = 6.471(3) A, b = 7.881(3) A, c = 9.488(4) A, α = 104.288(6)°, β = 109.062(5)° and γ = 101.345(5)°. The systematic increase in alkyl chain length from 2 to 4 carbon atoms in l-alkyl-3-methylimidazolium tetrafluoroborates was investigated in this ionothermal synthesis system. The effect of different anions, such as Cl - , Br - and BF4 - , on the synthesis result will also be presented in this paper.
- Yang, Miao,Liu, Qingshan,Yan, Peifang,Liu, Xiumei,Welz-Biermann, Urs
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experimental part
p. 97 - 104
(2010/06/19)
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- An efficient protocol for the preparation of pyridinium and imidazolium salts based on the Mitsunobu reaction
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We report herein that, in the absence of any nucleophilic counterions, tertiary nitrogen nucleophiles such as pyridines and imidazoles can be alkylated with alcohols, by simply using their ammonium form as the acidic component of the Mitsunobu reaction. This led to efficient preparation of ionic liquids under mild conditions, avoiding the usual anion exchange step.
- Petit, Sylvain,Azzouz, Rabah,Fruit, Corinne,Bischoff, Laurent,Marsais, Francis
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p. 3663 - 3665
(2008/09/20)
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- A green and novel procedure for the preparation of ionic liquid
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A green and novel procedure is described for the preparation of a series of ionic liquid containing alkylimidazolium-based or N-alkylpyridinium-based cations and hexafluorophosphate-based or tetrafluoroborate-based anions in one-pot solvent-free conditions to give excellent yields with shortened time.
- Fang, Dong,Cheng, Jian,Gong, Kai,Shi, Qun-Rong,Zhou, Xin-Li,Liu, Zu-Liang
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p. 108 - 111
(2008/09/21)
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- PROCESS FOR PRODUCING BORON TETRAFLUORIDE, BORON TETRAFLUORIDE PRODUCED BY SAID PROCESS, ELECTROLYSIS SOLUTION FOR ELECTRIC DOUBLE LAYER CAPACITOR USING SAID BORON TETRAFLUORIDE, AND PROCESS FOR PRODUCING SAID ELECTROLYSIS SOLUTION
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This invention provides a process for producing boron tetrafluoride represented by Q+BF4-. The production process is characterized by comprising reacting (A) a salt compound represented by Q+X- wherein Q+ represents an onium ion or a metal ion, X- represents an inorganic acid ion except for BF4-, an organic acid ion, or a hydroxide ion, (B) at least one boron compound selected from the group consisting of orthoboric acid, metaboric acid, tetraboric acid, boron oxide, and a boric ester represented by B(OR1)(OR2)(OR3) wherein R1 represents an alkyl group having 1 to 10 carbon atoms and R2 and R3 represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, provided that R1, R2, and R3 may be the same or different, and (C) hydrogen fluoride. There are also provided a boron tetrafluoride produced by the above process, an electrolysis solution for an electric double layer capacitor using said boron tetrafluoride, and a process for producing the electrolysis solution. The production process can produce high-purity boron tetrafluoride for use in an electrolysis solution for an electric double layer capacitor without using an expensive and highly toxic BF3 gas in an industrially advantageous manner. In particular, boron tetrafluoride having good properties as a nonaqueous electrolysis solution for an electric double layer capacitor can be produced in an industrially very advantageous manner, and, thus, a high-performance nonaqueous electrolysis solution for an electric double layer capacitor can be produced in a cost-effective manner.
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Page/Page column 17-18
(2008/06/13)
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- METHOD FOR PRODUCING ONIUM SALTS WITH A LOW CHLORIDE CONTENT
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The invention relates to a method for producing onium salts with a low chloride content by reacting an onium chloride with an acid. According to the invention, the hydrochloric acid that is produced can be removed by co-ordination with an organic solvent, which forms an azeotropic mixture with water, and by subsequent azeotropic distillation.
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Page/Page column 21-22
(2008/06/13)
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- METHOD FOR THE PRODUCTION OF ONIUM SALTS WITH TETRAFLUOROBORATE ANION HAVING A REDUCED HALIDE CONTENT
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The invention relates to a method for producing onium salts with tetrafluoroborate anion by reacting an onium halide with an oxonium tetrafluoroborate, sulfonium tetrafluoroborate, or triphenylcarbonium tetrafluoroborate.
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Page/Page column 21
(2008/06/13)
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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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- A PURIFICATION METHOD OF IONIC LIQUIDS TO OBTAIN THEIR HIGH PURITY
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Disclosed is an ionic liquid purification method for preparing high purity ionic liquids which can be used as solvents for organic, inorganic and biochemical reactions or as electrolytic solutions of storage batteries, secondary batteries, or fuel batteries, by removing organic halide salts, organic salts, halide residues, acid residues, excess alkali metals and so on, from unpurified ionic liquids using liquid/liquid continuous extraction.
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- Process for preparing ambient temperature ionic liquids
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A process for preparing an ionic liquid or salt, preferably in which the cation comprises an N-alkylated base and the anion is a carboxylate, formed by reaction between an organic base and an alkylating agent, wherein the alkylating agent is a fluorinated ester or an alkyl sulfonate, is described. Suitable organic bases include imizadoles, substituted imidazoles, pyridines and substituted pyridines. The so-formed products can be subsequently transformed into different ionic liquids or salts by metathesis.
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- Single step preparation of ionic fluids
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Preparation of ionic liquids (I) involves alkylating an amine, phosphine, imidazole, pyridine, triazole or pyrazole, corresponding to the cation of (I), with a halide (II) then replacing the sulfate anion by the anion of (I), the process is carried out without isolation of the intermediate. In the preparation of ionic liquids of formula (I) involves alkylating the amine, phosphine, imidazole, pyridine, triazole or pyrazole, corresponding to the cation A with a halide of formula (II) then replacing the sulfate anion X by the anion Yn-, the process is carried out without isolation of the intermediate. (A)n.(Yn-) (I) RX (II) n = 1 or 2; Yn- = BF4, BCl4, PF6, SbF6, AsF6, AlCl4, ZnCl3, CuCl2, SO4, CO3, R'COO, R'SO3 or (R'SO2)2N; R' = 1-12C linear, branched or cyclic alkyl, 5-18C aryl, (5-18C) aryl-(1-6C) alkyl or (1-6C) alkyl-(5-18C) aryl (all optionally halo-substituted); A = NR1R2R3R or PR1R2R3R; or 1-(R)-3-(R1)-imidazolium, (R1)-substituted 1-(R)-pyridinium, 1-(R)-2-(R1)-pyrazolium or 1-(R)-1,3,5-triazolium (all optionally ring-substituted by one or more of 1-6C alkyl, 1-6C alkoxy, 1-6C aminoalkyl, 5-12C aryl or (5-12C) aryl-(1-6C) alkyl); R1-R3 = H; 1-20C linear, branched or cyclic alkyl; Het or Het-(1-6C) alkyl; or Ar or Ar-(1-6C) alkyl; R = 1-20C linear, branched or cyclic alkyl; Het-(1-6C) alkyl; or Ar-(1-6C) alkyl; Het = heteroaryl containing 3-8C and at least one of N, O and S (optionally substituted by one or more of 1-6C alkyl and halo); Ar = 5-12C aryl (optionally substituted by one or more of 1-6C alkyl and halo); and X = halogen.
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- The phase behaviour of 1-alkyl-3-methylimidazolium tetrafluoroborates; ionic liquids and ionic liquid crystals
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Air- and water-stable 1-alkyl-3-methylimidazolium tetrafluoroborate salts with the general formula [Cn-mim][BF4] (n = 0-18) have been prepared by metathesis from the corresponding chloride or bromide salts. The salts have been characterised by 1H NMR and IR spectroscopy, microanalysis, polarising optical microscopy and differential scanning calorimetry. Those with short alkyl chains (n = 2-10) are isotropic ionic liquids at room temperature and exhibit a wide liquid range, whereas the longer chain analogues are low melting mesomorphic crystalline solids which display an enantiotropic smectic A mesophase. The thermal range of the mesophase increases with increasing chain length and in the case of the longest chain salt prepared, [C18-mim][BF4], the mesophase range is ca. 150°C.
- Holbrey, John D.,Seddon, Kenneth R.
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p. 2133 - 2139
(2007/10/03)
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