- Activity coefficients at infinite dilution for organic solutes dissolved in three 1-alkyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide ionic liquids bearing short linear alkyl side chains of three to five carbons
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In this work, we report the infinite dilution activity coefficients (γ1,2∞) of 39 to 43 diverse organic solutes dissolved in three 1-alkyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide ionic liquids (IL) homologues bearing propyl, butyl, and pentyl n-alkyl side chains, respectively, as determined by inverse gas chromatography at temperatures from 323 K to 343 K. The organic solutes include various (cyclo)alkanes, alkenes, alkynes, aromatic hydrocarbons, alcohols, thiophene, ethers, nitroalkanes, and ketones. The measured retention data were further transformed to gas-to-IL and water-to-IL partition coefficients using established thermodynamic approaches based upon the corresponding gas-to-water partition coefficients of the test solutes. Both sets of partition coefficients were interpreted with a modified form of the basic Abraham general solvation parameter model. The mathematical correlations obtained by regression analysis back-calculated the observed gas-to-IL and water-to-IL partition coefficient data to within average standard deviations of 0.104 and 0.136 log units, respectively.
- Mutelet, Fabrice,Hassan, El-Sayed R. E.,Stephens, Timothy W.,Acree, William E.,Baker, Gary A.
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Read Online
- Low-melting, low-viscous, hydrophobic ionic liquids: N-alkyl(alkyl ether)-N-methylpyrrolidinium perfluoroethyltrifluoroborate
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A series of new hydrophobic ionic liquids comprising N-alkyl (alkyl ether)-N-methylpyrrolidinium and perfluoroethyltrifluoroborate were prepared and characterized. The new [C2F5BF3] --based salts show lower melting points than the corresponding [BF4]--based ones. Of these new salts, five are liquids at room temperature and show very low viscosities (37-71 cP at 25°C), high ionic conductivities (3.0-6.8 mScm-1) and wide electrochemical windows. Copyright
- Zhou, Zhi-Bin,Matsumoto, Hajime,Tatsumi, Kuniaki
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- Electrochemical investigations of ionic liquids with vinylene carbonate for applications in rechargeable lithium ion batteries
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Ionic liquids based on methylpropylpyrrolidinium (MPPY) and methylpropylpiperidinium (MPPI) cations and bis(trifluoromethanesulfonyl)imide (TFSI) anion have been synthesized and characterized by thermal analysis, cyclic voltammetry, impedance spectroscopy as well as galvanostatic charge/discharge tests. 10 wt% of vinylene carbonate (VC) was added to the electrolytes of 0.5 M LiTFSI/MPPY.TFSI and 0.5 M LiTFSI/MPPI.TFSI, which were evaluated in Li || natural graphite (NG) half cells at 25 °C and 50 °C under different current densities. At 25 °C, due to their intrinsic high viscosities, the charge/discharge capacities under the current density of 80 μA cm-2 were much lower than those under the current density of 40 μA cm-2. At 50 °C, with reduced viscosities, the charge/discharge capacities under both current densities were almost indistinguishable, which were also close to the typical values obtained using conventional carbonate electrolytes. In addition, the discharge capacities of the half cells were very stable with cycling, due to the effective formation of solid electrolyte interphase (SEI) on the graphite electrode. On the contrary, the charge/discharge capacities of the Li || LiCoO2 cells using both ionic liquid electrolytes under the current density of 40 μA cm-2 decreased continually with cycling, which were primarily due to the low oxidative stability of VC on the surface of LiCoO2.
- Sun, Xiao-Guang,Dai, Sheng
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Read Online
- Electrolyte and a battery with said electrolyte
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An electrolyte for a lithium-ion battery, and a battery incorporating the electrolyte. The electrolyte includes a lithium salt, a non-aqueous organic solvent which includes a carbonate-based solvent, a flame retardant, a film former, and a stabilizing medium. The flame retardant includes PYR1RPF6 (N-Methyl-N-alkylpyrrolidinium Hexafluorophosphate Salt).
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Page/Page column 7
(2020/09/13)
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- Ultrafast dynamics in nonaromatic cation based ionic liquids: A femtosecond raman-induced kerr effect spectroscopic study
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Herein, the data of the intermolecular vibrations of forty nonaromatic cation based ionic liquids (ILs) at 293 K measured by femtosecond Raman-induced Kerr effect spectroscopy are reported. The low-frequency spectra in the frequency range of 0.3700 cm11 were obtained by Fourier transform deconvolution analysis. The line shapes of the low-frequency spectra below 3200 cm11 were discussed on the basis of the ion species. The spectral intensity in nonaromatic cation based ILs was much lower than that in aromatic cation based ILs owing to the absence of the aromatic ring, i.e., the libration of the aromatic species had a strong spectral intensity in the low-frequency region. However, nonaromatic cation based ILs with a flat anion, such as dicyanamide and tricyanomethanide, showed stronger spectral intensity because of the libration of the anion. Other unique spectral features were also discussed in the context of the structure of the ion species. Liquid properties, such as density, viscosity, electrical conductivity, and surface tension, were also estimated. On comparing the low-frequency spectra with the bulk liquid properties of the nonaromatic cation based ILs, a mild linear relationship between the first moment of the low-frequency spectrum and a bulk parameter comprised of surface tension and density was observed.
- Shirota, Hideaki,Ando, Masatoshi,Kakinuma, Shohei,Takahashi, Kotaro
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supporting information
p. 1520 - 1539
(2020/12/29)
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- N, N - dialkyl pyrrolidine pressure concentrated water ion liquid preparation method and its application (by machine translation)
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The invention relates to a N, N - dialkyl pyrrolidine pressure concentrated water ion liquid preparation method and its application, the method to N - alkyl pyrrolidine and alkyl alcohol as raw material through the electrolysis mode, in the electrolytic cell is provided with a cation exchange membrane, cation exchange membrane into the cathode with the anode compartment of the electrolytic aluminum, electrolytic taken out after completion of the cathode electrolyte, separation and purification, to obtain N, N - dialkyl pyrrolidines pressure concentrated water ionic liquid, the preparation method is simple, mild condition, purity and high yield. The N, N - dialkyl pyrrolidine pressure concentrated water ionic liquid as solvent, in order to chlorine methyl pyridine hydrochloride and ammonia as raw material, synthetic three-pyridine methyl amine compound, the preparation of yield and high purity, without follow-up separation, low cost, environmental protection, the ionic liquid can be used repeatedly, is suitable for industrial production. (by machine translation)
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Paragraph 0024-0026
(2019/10/29)
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- PROCESS FOR PRODUCING QUATERNARY AMMONIUM CATIONS AND IONIC LIQUIDS
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The present invention provides a process and a method for producing a quaternary ammonium cation in an aqueous solution while reducing or preventing formation of a protonated ammonium cation. In particular, the quaternary ammonium cation is produced by adding a base to an aqueous reaction mixture comprising a tertiary amine compound and an alkylating agent.
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Paragraph 0044
(2017/08/01)
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- Comprehensive Insights into the Thermal Stability, Biodegradability, and Combustion Chemistry of Pyrrolidinium-Based Ionic Liquids
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The use of ionic liquids (ILs) as advanced electrolyte components in electrochemical energy-storage devices is one of the most appealing and emerging options. However, although ILs are hailed as safer and eco-friendly electrolytes, to overcome the limitations imposed by the highly volatile/combustible carbonate-based electrolytes, full-scale and precise appraisal of their overall safety levels under abuse conditions still needs to be fully addressed. With the aim of providing this level of information on the thermal and chemical stabilities, as well as actual fire hazards, herein, a detailed investigation of the short- and long-term thermal stabilities, biodegradability, and combustion behavior of various pyrrolidinium-based ILs, with different alkyl chain lengths, counteranions, and cations, as well as the effect of doping with lithium salts, is described.
- Eshetu, Gebrekidan Gebresilassie,Jeong, Sangsik,Pandard, Pascal,Lecocq, Amandine,Marlair, Guy,Passerini, Stefano
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p. 3146 - 3159
(2017/08/18)
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- METHOD FOR PRODUCING IONIC LIQUID AND METHOD FOR PRODUCING INTERMEDIATE BODY FOR PRODUCTION OF IONIC LIQUID
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PROBLEM TO BE SOLVED: To provide a method for producing an ionic liquid for synthesizing a desired ionic liquid with high purity, and to provide a method for producing an intermediate body for synthesizing the ionic liquid. SOLUTION: A method for producing an ionic liquid which produces a desired ionic liquid Q+Z- formed from cation Q+ and anion Z- includes: a step of purifying a high-melting point intermediate body Q+Y- that is formed from the cation Q+ and the anion Z- and has such a melting point as to be recrystallized, by recrystallization; and a step of obtaining the ionic liquid Q+Z- directly or indirectly from the purified high-melting point intermediate body Q+Y-. A method for producing a strongly acidic intermediate body and a super-hydrophilic intermediate body includes: a step of obtaining a strongly acidic intermediate body or a super-hydrophilic intermediate body from the purified high-melting point intermediate body Q+Y- by a double decomposition precipitation method or obtaining the strongly acidic intermediate body from the purified high-melting point intermediate body Q+Y- by a double decomposition precipitation method, or a step of obtaining the super-hydrophilic intermediate body from the strongly acidic intermediate body by a neutralization method. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0094
(2018/02/22)
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- FIVE-MEMBERED CYCLIC ANION USE THEREOF AS AN ELECTROLYTE
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A pentacyclic anion salt is provided for use thereof in electrolyte compositions. The compound has an inorganic, organic or organometallic cation M of valency m (1≦m≦3) and m anions corresponding to the formula (I) in which Rf is a —CFZ′Z″ group in which Z′ is F or a perflouroalkyl group having from 1 to 3 carbon atoms, and Z″ is an H, F or Cl group, an optionally fluorinated or perfluorinated alkoxy group having from 1 to 5 carbon atoms, an optionally fluorinated or perfluorinated oxaalkoxy group having 1 to 5 carbon atoms or an optionally fluorinated or perfluorinated alkyl group having from 1 to 5 carbon atoms; Z″ being other than F when Z′ is F. An electrolyte composition comprises said salt in solution in a liquid solvent or a polymer solvent.
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Paragraph 0095
(2015/11/28)
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- Eu3 + as a dual probe for the determination of IL anion donor power: A combined luminescence spectroscopic and electrochemical approach
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This work is aimed at giving proof that Eu(Tf2N)3 (Tf2N = bis(trifluoromethanesulfonyl)amide) can act as both an optical and electrochemical probe for the determination of the Lewis acidity of an ionic liquid anion. For that reason the luminescence spectra and cyclic voltammograms of dilute solutions of Eu(Tf2N)3 in various ionic liquids were investigated. The Eu2 +/3 + redox potential in the investigated ILs can be related to the Lewis basicity of the IL anion. The IL cation had little influence. The lower the determined halfwave potential, the higher the IL anion basicity. The obtained ranking can be confirmed by luminescence spectroscopy where a bathochromic shift of the 5D 0 → 7F4 transition indicates a stronger Lewis basicity of the IL anion.
- Babai, Arash,Kopiec, Gabriel,Lackmann, Anastasia,Mallick, Bert,Pitula, Slawomir,Tang, Sifu,Mudring, Anja-Verena
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p. 191 - 198
(2014/05/20)
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- Cucurbit[7]uril host-guest complexes and [2]pseudorotaxanes with N-methylpiperidinium, N-methylpyrrolidinium, and N-methylmorpholinium cations in aqueous solution
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The formations of host-guest complexes between cucurbit[7]uril and a series of N-substituted N-methylpiperidinium, N-methylpyrrolidinium, and N-methylmorpholinium cations in aqueous solution have been investigated using 1H NMR spectroscopy and electrospray ionization mass spectrometry. Dications comprising the N-methylheterocyclic head groups, bridged by a decamethylene chain, form sequential 1:1 ([2]pseudorotaxanes) and 2:1 host-guest complexes with cucurbit[7]uril. The cucurbituril initially resides over the decamethylene chain, however with further additions of the host molecule a translocation of the hosts to the cationic N-heterocyclic head groups occurs. The order of the magnitude of the cucurbituril host-guest stability constants, determined by competitive 1H NMR binding experiments, follows the trend in the hydrophobicity of the quaternary ammonium cations.
- Gamal-Eldin, Mona A.,MacArtney, Donal H.
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p. 1234 - 1241
(2013/03/29)
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- Fluorosulfonyl-(trifluoromethanesulfonyl)imide ionic liquids with enhanced asymmetry
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New ionic liquids with an asymmetric anion, fluorosulfonyl- (trifluoromethanesulfonyl)imide (FTFSI), were prepared and their chemical-physical properties were investigated. The ionic liquids based on N-methyl-N-propylpyrrolidinium, PYR13, N-but
- Reiter, Jakub,Jeremias, Sebastian,Paillard, Elie,Winter, Martin,Passerini, Stefano
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p. 2565 - 2571
(2013/04/10)
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- BORON OR ALUMINUM COMPLEXES
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The present invention relates to boron and aluminum complexes, to the preparation thereof, and to the use thereof for solubilizing ionic compounds. The complexes have one of the following formulae: in which D represents B or Al; R1 represents R, RF, NO2, CN, C(═O)OR, RSO2, or RFSO2; —X1—, —X2—, —X3— and X4 each represent a divalent group >C═O, >C═NC≡N, >C═C(C≡N)2, >CR2R3 or >SO2; —Y1—, —Y2— and —Y3— each represent a divalent group —O—, >N(C≡N), >N(CORF), >N(SO2R4), >NR4, >N(COR4) or >N(SO2RF); R, R2 and R3 each represent H, an alkyl group, an aryl group, an alkylaryl group, an arylalkyl group, an oxaalkyl group or an alkenyl group; R4 represents an alkyl group, an aryl group, an alkylaryl group, a heteroaryl group, an arylalkyl group, an oxaalkyl group, an alkenyl group or an RFCH2— group; RF is a perfluoroalkyl group, a partially fluorinated alkyl group, or a partially or totally fluorinated phenyl group; each of the R′2 and R′3 groups represents R or F.
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Page/Page column 25
(2011/08/02)
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- Manganese acetate in pyrrolidinium ionic liquid as a robust and efficient catalytic system for epoxidation of aliphatic terminal alkenes
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Green epoxides! A novel and simple ionic liquid/manganese acetate catalytic system has been developed for the rapid and selective oxidation of aliphatic terminal alkenes to epoxides. It provides an efficient, reusable, and scalable protocol for the green synthesis of epoxides from various aliphatic terminal alkenes.
- Ho, Kam-Piu,Wong, Wing-Leung,Lee, Lawrence Yoon Suk,Lam, Kin-Ming,Chan, Tak Hang,Wong, Kwok-Yin
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supporting information; experimental part
p. 1970 - 1973
(2011/04/15)
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- Melting behavior and ionic conductivity in hydrophobic ionic liquids
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Four room-temperature ionic liquids (RTILs) based on the N-butyl-N-methyl pyrrolidinium (Pyr14 +) and N-methyl-N-propyl pyrrolidinium cations (Pyr13 +) and bis(trifluoromethanesulfonyl)imide (TFSI-) and bis(fluorosulfonyl) imide (FSI-) anions were intensively investigated during their melting. The diffusion coefficients of 1H and 19F were determined using pulsed field gradient (PFG) NMR to study the dynamics of the cations, anions, and ion pairs. The AC conductivities were measured to detect only the motion of the charged particles. The melting points of these ionic liquids were measured by DSC and verified by the temperature-dependent full width at half-maximum (FWHM) of the 1H and 19F NMR peaks. The diffusion and conductivity data at low temperatures gave information about the dynamics at the melting point and allowed specifying the way of melting. In addition, the diffusion coefficients of 1H (DH) and 19F (DF) and conductivity were correlated using the Nernst-Einstein equation with respect to the existence of ion pairs. Our results show that in dependence on the cation different melting behaviors were identified. In the Pyr14based ILs, ion pairs exist, which collapse above the melting point of the sample. This is in contrast to the Pyr 13-based ILs where the present ion pairs in the crystal dissociate during the melting. Furthermore, the anions do not influence the melting behavior of the investigated Pyr14 systems but affect the Pyr 13 ILs. This becomes apparent in species with a higher mobility during the breakup of the crystalline IL.
- Kunze, Miriam,Montanino, Maria,Appetecchi, Giovanni B.,Jeong, Sangsik,Schoenhoff, Monika,Winter, Martin,Passerini, Stefano
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experimental part
p. 1776 - 1782
(2010/08/04)
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- IONIC LIQUID, METHOD FOR PRODUCING SAME, DOUBLE LAYER CAPACITOR COMPRISING SAME, AND LITHIUM BATTERY
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The present invention relates to ionic liquids comprising at least one organic ammonium ion and at least one member selected from the group consisting of anions represented by [BF3(CnF2n+1)]- wherein n represents 2, 3 or 4.
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Page/Page column 7-8
(2008/06/13)
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