- Thermally stable bis(trifluoromethylsulfonyl)imide salts and their mixtures
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We show that both tetraphenylphosphonium bis(trifluoromethylsulfonyl)imide ([PPh4][NTf2]) and Cs[NTf2] are low melting salts of exceptionally high and also very similar thermal stability. This similarity indicates that the thermal stability is dominated by the anion. Moreover, eutectic mixtures of [PPh4][NTf2] and Cs[NTf2] with melting points below 100 °C are presented. Surface analysis of the latter in the liquid state reveals a surprising depletion of [PPh4]+ ions from the surface.
- Scheuermeyer, Marlene,Kusche, Matthias,Agel, Friederike,Schreiber, Patrick,Maier, Florian,Steinrück, Hans-Peter,Davis, James H.,Heym, Florian,Jess, Andreas,Wasserscheid, Peter
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- N-FLUORO-BIS(TRIFLUOROMETHANESULFONYL)IMIDE AN IMPROVED SYNTHESIS
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An improved synthesis of (CF3SO2)2NH and its conversion to the very useful fluorination reagent (CF3SO2)2NF is described.The five-step synthesis yields (CF3SO2)NF in 76percent yield based on the starting CF3SO2F.
- Desmarteau, Darryl D.,Witz, Michael
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- A one-pot synthesis of a ternary nanocomposite based on mesoporous silica, polyaniline and silver
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The research on hybrid materials composed of inorganic and organic species in the nanometer range is motivated by the synergic combination of their native properties in a unique material. In this paper, we report a new one-pot synthesis of a ternary nanocomposite based on a conducting polymer (polyaniline-PANI) and silver, using mesoporous silica (MCM-41) as a hard template to promote the controlled growth of both polymer chains and silver nanoparticles. The presence of these reaction products was proved by the appearance of the characteristic diffraction peaks of face-centered cubic metallic silver phase in the X-ray diffractogram and by the presence of typical bands of polyaniline as emeraldine salt in the FTIR and UV-Vis spectra. The preservation of the ordered MCM-41 mesostructure after the polymerization reaction was also attested by XRD and TEM analysis and it was accompanied by a decreasing of the particle size as observed in the SEM images. N2 adsorption-desorption isotherms support the statement that PANI chains and AgNP have been incorporated mainly into the channel of MCM-41, a fact also attested by TEM images. The electrical conductivity of this nanocomposite is on the order of 10-3 S cm-1, which is one million times higher than the value obtained for a MCM-41/polyaniline composite. Although some reports about the isolated incorporation of polyaniline or silver nanoparticles into the MCM-41 pores are found in the literature, to our knowledge this is the first time that such nanocomposite preparation is reported.
- Rosa, Ana Claudia De Abreu,Correa, Cintia Marques,Faez, Roselena,Bizeto, Marcos Augusto,Camilo, Fernanda Ferraz
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- PERFLUOROALKYL SULFONAMIDE AND METHOD FOR PRODUCING THE SAME
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PROBLEM TO BE SOLVED: To simply provide high-purity perfluoroalkyl sulfonamide by efficiently reducing bis(perfluoroalkyl sulfone)imide, an impurity to be generated in a production process. SOLUTION: High-purity perfluoroalkyl sulfonamide is obtained by reducing bis(perfluoroalkyl sulfone)imide by washing perfluoroalkyl sulfonamide expressed by the following formula (1), which contains the bis(perfluoroalkyl sulfone)imide, with a chlorinated solvent: RfSO2 NH2, provided that, in the formula (1), Rf is a straight or branched 1-4C perfluoroalkyl group. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0070-0074
(2018/06/05)
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- Silylium-Catalyzed Carbon–Carbon Coupling of Alkynylsilanes with (2-Bromo-1-methoxyethyl)arenes: Alternative Approaches
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The catalytic activation of alkynylsilanes towards 2-halo-1-alkoxyalkyl arenes gives β-halo-substituted alkynes. It involves the chemoselective substitution of an alkoxide by an alkyne in the presence of a neighboring C(sp3)–Br bond in a cationic C–C bond-forming event. Two complementary protocols to accomplish this new transformation are reported. The outcome of a direct approach based on mixing the precursors with a freshly prepared solution of the active catalytic species (TMSNTf2) is compared with an alternative based on smooth release of the required silylium ions upon selective activation of the alkyne by gold(I) (JohnPhosAuNTf2). The two approaches gave satisfactory results to access this otherwise elusive alkynylation process, which furnishes 4-bromo-substituted alkynes and tolerates various functional groups.
- Rubial, Belén,Ballesteros, Alfredo,González, José M.
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supporting information
p. 6194 - 6198
(2018/07/31)
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- Preparation method of LiN(CF3SO2)2 salt
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The invention discloses a preparation method of LiN(CF3SO2)2 salt. The preparation method comprises the following steps: benzene methanamine is dissolved in an organic solvent and subjected to a sulfonamide reaction with trifluoromethyl sulfonyl chloride or trifluoromethyl sulfonyl fluoride, benzyl bis(trifluoromethyl sulfamide) is obtained and reduced, and bis(trifluoromethyl sulfamide) is obtained; the obtained bis(trifluoromethyl sulfamide) and resin lithium are subjected to ion exchange in an anhydrous solvent, and a final product LiN(CF3SO2)2 salt is obtained. According to the method, raw materials are low in price and easy to obtain, reaction procedures are simple, the yield is high, nearly no pollution is caused, rigid and dangerous reaction conditions are avoided, the product is easy to purify, and the method is suitable for large-scale production in China.
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Paragraph 0044; 0046; 0049; 0052; 0054
(2018/02/04)
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- METHOD FOR PRODUCING TRIFLUOROMETHANESULFONYL IMIDE OR ITS SALT
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The present invention relates to trifluoromethanesulfonyl imide or a method of producing salt thereof. More specifically, the method comprises: a first process in which the organosilicon nitrogen compound is dissolved in an organic solvent, and chlorosulfonic acid (ClSO_3H) or dichlorosulfone (ClSO_2Cl) is added and reaction is conducted; and a second process in which the compound obtained through the first process is dissolved in an organic solvent, an inorganic base containing lithium, sodium, potassium or cesium or an organic base is added and reaction is conducted, and tetrahalogen methane (CX_4) is added thereto and reaction is conducted. According to the present invention, the method has effects of: producing stable and high-quality trifluoromethanesulfonyl imide and the salt thereof by using the safe organosilicon nitrogen compound without amine gas or inorganic amine; and being capable of mass producing industrially high-purity products.
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Paragraph 0154; 0155
(2017/02/28)
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- The method for manufacturing the same and sulfoneimido compd. (by machine translation)
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The present invention relates to a method for preparing an aqueous sulfonimide compound of the formula (Rf1—SO2) (Rf2—SO2)NH, wherein Rf1et Rf2 are independently selected from the group comprising: a fluorine atom and groups having 1 to 10 carbon atoms selected from the perfluoroalkyl, fluoroalkyl, fluoroalkenyl and fluoroallyl groups, from a mixture M1 including (Rf1—SO2)(Rf2—SO2)NH, Rf1SO2H and/or Rf2SO2H, Rf1SO2NH2 and/or Rf2SO2NH2, characterized in that said method includes an oxidation step of said mixture M1 using an oxidizing agent in order to obtain a mixture M2 including (Rf1—SO2)(Rf2—SO2)NH, Rf1SO3H and/or Rf2SO3H, and Rf1SO2NH2 and/or Rf2SO2NH2.
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Paragraph 0311; 0312; 0313
(2017/01/02)
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- METHOD FOR PREPARING A SULFONIMIDE COMPOUND AND SALTS THEREOF
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The present invention relates to a method for preparing an aqueous sulfonimide compound of the formula (Rf1—SO2) (Rf2—SO2)NH, wherein Rf1et Rf2 are independently selected from the group comprising: a fluorine atom and groups having 1 to 10 carbon atoms selected from the perfluoroalkyl, fluoroalkyl, fluoroalkenyl and fluoroallyl groups, from a mixture M1 including (Rf1—SO2)(Rf2—SO2)NH, Rf1SO2H and/or Rf2SO2H, Rf1SO2NH2 and/or Rf2SO2NH2, characterized in that said method includes an oxidation step of said mixture M1 using an oxidizing agent in order to obtain a mixture M2 including (Rf1—SO2)(Rf2—SO2)NH, Rf1SO3H and/or Rf2SO3H, and Rf1SO2NH2 and/or Rf2SO2NH2.
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Paragraph 0365; 0366
(2015/07/27)
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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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- Bronsted acids in ionic liquids: How acidity depends on the liquid structure
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Gutmann Acceptor Number (AN) values have been determined for Bronsted acid-ionic liquid mixtures, over a wide compositional range. Four systems of general formula [C2mim][A]-HA (A- = bistriflamide, [NTf2]-; triflate, [OTf]-; mesylate, [OMs]-; or acetate, [OAc]-, [C2mim]+ = 1-ethyl-3-methylimidazolium cation) were studied. A library of Bronsted acidic systems of varying acidity was constructed and the AN parameter was found to be a convenient approach for quantifying their acidity. HOAc, HOMs and HOTf, when dissolved in ionic liquids, were found to associate with the respective anions to form hydrogen-bonded anionic clusters, [A(HA)x]-. In contrast, HNTf2 was solubilised as a discrete, undissociated molecule. AN values were sensitive to the presence of anionic clusters; acidity could be buffered to a particular AN by binding the solubilised acid in the anionic cluster form. Overall, a simple way to manipulate and quantify the Bronsted acidity of acid-ionic liquid mixtures was demonstrated, and measured AN values were related to liquid speciation. This journal is
- McCune, Jade A.,He, Peizhao,Petkovic, Marina,Coleman, Fergal,Estager, Julien,Holbrey, John D.,Seddon, Kenneth R.,Swadba-Kwasny, Malgorzata
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p. 23233 - 23243
(2015/01/08)
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- Ionic liquid silver salt complexes for propene/propane separation
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Properties of the room-temperature liquid complex salt [Ag(propene) x][Tf2N] have been studied to probe its suitability for acting as active separation layer in immobilised liquid membrane (ILM) concepts for propane/propene separation. The pressure/temperature range of complex formation has been determined and the thermal properties of Ag[Tf2N] and [Ag(propene)x][Tf2N] have been studied by DSC (differential scanning calorimetry) and TGA (thermogravimetric analysis) measurements. Pressure dependent measurements of solubility and diffusivity showed that the observed membrane selectivity is dominated by the solubility selectivity. The self-diffusion coefficient of propene is always smaller compared to propane as propene is temporarily bound to the silver ion in the [Ag(propene)x][Tf2N] ionic liquid.
- Agel, Friederike,Pitsch, Fee,Krull, Florian Felix,Schulz, Peter,Wessling, Matthias,Melin, Thomas,Wasserscheid, Peter
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p. 725 - 731
(2014/03/21)
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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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- Syntheses and lipophilicity measurement of Nα/N-terminus-1,1-dihydroperfluoroalkylated α-amino acids and small peptides
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(1,1-Dihydroperfluoroalkyl)phenyliodonium N,N-bis(trifluoromethylsulfonyl)imides (4, n = 0-2) were synthesized and used to transfer the corresponding 1,1-dihydroperfluoroalkyl groups to the α-amino group of (l)tyrosine. The obtained Nα-2,2,2-trifluoroethylated (l)tyrosine (6, n = 0) was further used as the N-terminus in the solid phase peptide synthesis of leucine enkephalin analogue. The lipophilicity of the Nα-1,1-dihydroperfluoroalkylated (l)tyrosines (6, n = 0-2) and N-terminus-2,2,2-trifluoroethylated leucine enkephalin analogue (7), as well as the corresponding parent compounds, was measured.
- DesMarteau, Darryl D.,Lu, Changqing
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p. 1326 - 1334
(2008/02/08)
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- Electrochemically stable onium salts and electrolytes containing such for electrochemical capacitors
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Based on the discovery that the melting point and solubility of onium salts are affected by the asymmetry of the substitution on cation, and that the branched substituents effectively shield onium cations from electrochemical reduction, new onium salts are synthesized and high performance electrolytes based on these salts for electrochemical capacitor are provided. The composition of the new electrolyte comprises an onium salt or mixture of such onium salts dissolved in aprotic, non-aqueous solvents or mixture of such solvents. The electrolyte is able to perform at high rate of charge/discharge, at low ambient temperatures, and within wide operating voltage, due to the high solubility, low melting temperature, and the improved reduction stability of the new onium cations, respectively.
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Page column 8
(2008/06/13)
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- Perfluorinated bronsted 'superacids': Powerful catalysts for the preparation of vitamin E
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The key-step in the industrial synthesis of (all-rac)-α-tocopherol (synthetic vitamin E) is the condensation reaction of trimethylhydroquinone with the C20 building block isophytol. For this Friedel-Crafts-type reaction, perfluorinated NH- and CH-acidic compounds (perfluoroalkyl(aryl) sulfonyl imides and methides) have been applied as excellent catalysts, preferably in biphasic solvent systems.
- Netscher, Thomas,Bonrath, Werner,Haas, Alois,Hoppmann, Eike,Pauling, Horst
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p. 153 - 155
(2007/10/03)
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- Highly reactive trialkylsilylation reagents derived from bis(trifluoromethanesulfonyl)imide - Silylation of functional groups, alkines and reactive aromatics
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The synthesis of trialkylsilyl-bis(trifluormethanesulfonyl)imides 3 is described. Compounds 3 with bulky trialkylsilyl groups 3a,b only exist in the silatautomeric form 3a′,b′ under usual conditions, 3c in the N-trimethylsilyl structure. Despite of the bulky silyl substituents in 3a′,b′ their reactivity is higher than that of trimethylsilyltriflate. Alcohols, carbonyl compounds, nitroalkanes and carboxylic acid esters are silylated in good yields, especially by the more reactive triisopropylsilyl derivative 3b′ in presence of tertiary amines, tert.-Butyl carboxylates and benzylcarboxylates are cleaved. Monosubstituted alkines and electron-rich (hetero) aromatics are carbosilylated in presence of N-ethyl-diisopropylamine.
- Simchen, Gerhard,Jonas, Simon
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experimental part
p. 506 - 512
(2011/10/17)
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