- Aggregation behavior of 1-dodecyl-3-methylimidazolium bromide in aqueous solution: Effect of ionic liquids with aromatic anions
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The effects of ionic liquids (ILs), 1-butyl-3-methylimidazolium methylsulfonate (bmimMsa), 1-butyl-3-methylimidazolium benzenesulfonate (bmimBsa), and 1-butyl-3-methylimidazolium 2-naphthalenesulfonate (bmimNsa), on the aggregation behavior of 1-dodecyl-3-methylimidazolium bromide (C 12mimBr) in aqueous solution were investigated by surface tension, dynamic light scattering measurements, and 1H NMR spectroscopy. The ability to promote the surfactant aggregation is in the order bmimNsa > bmimBsa > bmimMsa. Nevertheless, only bmimNsa distinctly reduces both the CMC value and the surface tension at CMC. Due to the penetration of C 10H7SO3-anions into the surfactant aggregate, bmimNsa is found to induce a phase transition from micelles to vesicles, whereas the other ILs only slightly increase the sizes of micelles. The combined effect of intermolecular interactions, such as hydrophobic effect, electrostatic attractions, and π-π stacking interactions, is supposed to be responsible for this structural transformation, in which π-π stacking plays an important role.
- Gu, Yingqiu,Shi, Lijuan,Cheng, Xiyuan,Lu, Fei,Zheng, Liqiang
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- Synergistic interplay of ionic liquid and dodecyl sulphate driving the oxidation state of polypyrrole based electrodes
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Herein, polypyrrole (PPy) films are prepared via electrochemical deposition in a mixture of 1-n-butyl-3-methylimidazolium methanesulfonate (BMI·CH3SO3) ionic liquid (IL) and dodecyl sulfate (DS). The physico-chemical properties of the films have been investigated by a wide range of characterization techniques. PPy films synthesized in DS or IL have shown larger and irregular granules as compared to PPy films prepared in the mixture of DS and IL. This result is related to the preferential dissolution of pyrrole monomers in micelle templates formed by the IL and a co-assembly of IL and dodecyl-sulfate (DS), thereby decreasing the granule size and affecting the structural arrangement of the polymer chain. The template behavior of the IL in combination with DS promotes the selective formation of polaron and bipolaron states in the PPy films. This effect has been investigated by UV-Vis spectrophotometry, Raman spectroscopy, electrochemical impedance spectroscopy (EIS), cyclic voltammetry, scanning electron microscopy, transmission electron microscopy, and electrical conductivity measurements. The synergy of IL-DS has helped to decrease the resistivity of the PPy film from 2.17 × 102 Ω cm for PPy-IL to 2.44 Ω for PPy-IL-DS. EIS has also shown a decreased interfacial charge transfer resistance for PPy-IL-DS when compared to PPy-IL. The cyclic voltammetry curves have shown that the PPy films are electrocatalytically active for the I-/I3- redox reaction, and therefore, can be applied as a counter electrode (CE) in dye sensitised solar cells. The PPy based CEs resulted in nearly the same photocurrent and energy conversion efficiencies as that obtained from a conventional Pt CE.
- Loguercio, Lara F.,De Matos, Carolina F.,De Oliveira, Matheus C.,Marin, Graciane,Khan, Sherdil,Balzaretti, Naira M.,Dupont, Jairton,Leite Santos, Marcos J.,Leite Santos, Jacqueline F.
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- SN2 Fluorination reactions in ionic liquids: A mechanistic study towards solvent engineering
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In the catalysis of SN2 fluorination reactions, the ionic liquid anion plays a key role as a Lewis base by binding to the counterion Cs + and thereby reducing the retarding Coulombic influence of Cs + on the nucleophile F-. The reaction rates also depend critically on the structures of ionic liquid cation, for example, n-butyl imidazolium gives no SN2 products, whereas n-butylmethyl imidazolium works well. The origin of the observed phenomenal synergetic effects by the ionic liquid [mim-tOH][OMs], in which t-butanol is bonded covalently to the cation [mim], is that the t-butanol moiety binds to the leaving group of the substrate, moderating the retarding interactions between the acidic hydrogen and F-. This work is a significant step toward designing and engineering solvents for promoting specific chemical reactions.
- Oh, Young-Ho,Jang, Hyeong Bin,Im, Suk,Song, Myoung Jong,Kim, So-Yeon,Park, Sung-Woo,Chi, Dae Yoon,Song, Choong Eui,Lee, Sungyul
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- Electrochemical and spectroscopic study of vanadyl acetylacetonate–ionic liquids interactions
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A panel of ionic liquids has been synthesized and their effect on the vanadyl acetylacetonate solubility in acetonitrile has been firstly assessed. 1-Butyl-3-methylimidazolium acetate showed an unprecedented result, increasing the VO(acac)2 solubility in acetonitrile of more than one magnitude order (from 0.06 M to 1.1 M) opening new interesting horizons for the possible applications of this vanadium complex. The electrochemical effect of the considered ionic liquids has been subsequently investigated through cyclic voltammetry and linear sweep voltammetry with rotating disk electrode, determining diffusion coefficient and kinetic current of VO(acac)2 in the considered media. In order to achieve a deeper understanding on the examined systems, VO(acac)2 solutions in acetonitrile ILs were eventually studied through IR, UV–vis, and EPR spectroscopies, finding evidences, corroborated by DFT studies, of the formation of strong adducts between VO(acac)2 and ILs.
- Guglielmero,Langroudi, Mo. Meskinfam,Khatib, M. Al,de Oliveira, M. Aysla Costa,Mecheri,De Leo,Mezzetta,Guazzelli,Giglioli,Epifanio, A. D',Pogni,Chiappe,Pomelli
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- Convenient synthesis of long alkyl-chain triazolylglycosides using ionic liquid as dual promoter-solvent: Readily access to non-ionic triazolylglycoside surfactants for evaluation of cytotoxic activity
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A convenient method for the one-pot synthesis of long alkyl-chain triazolylglycosides using ionic liquid as dual promoter and solvent is described via a sequential one-pot two-step glycosidation-CuAAc click reaction. The reaction was carried out using commercially available substrates, including glycosyl bromides, sodium azide and various long alkyl-chain alkynes to achieve the corresponding products in moderate to high yields. Furthermore, this approach was successfully applied for the preparation of non-ionic monocatenary triazolylglycoside surfactants in excellent yields through simple deacetylation. Subsequently, these surfactants were further evaluated for their cytotoxic activity.
- Ketsomboon, Nutthanicha,Saeeng, Rungnapha,Srisook, Klaokwan,Sirion, Uthaiwan
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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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- IONIC LIQUID CONTAINING ALLYLSULFONATE ANION
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PROBLEM: Providing a novel ionic liquid, which is low-cost, environment-friendly, and has low viscosity and melting point. MEANS FOR SOLVING THE PROBLEM: The present invention is the invention of the ionic liquid represented by the general formula [1]: {wherein, R1 to R3 and n pieces of R4 each independently represent hydrogen atom or alkyl group having 1 to 4 carbon atoms, R5 to R7 each independently represent alkyl group, aralkyl group, or aryl group, R8 represents alkyl group, aralkyl group, aryl group, or the one represented by the general formula [2]: (wherein T represents alkylene chain having 1 to 8 carbon atoms, n represents 1 or 2, and R1 to R7 are the same as the above-described), X represents nitrogen atom or phosphorus atom, n represents 1 or 2. When n is 1, R3 and R4 are bound and may form cyclohexene ring together with the adjacent carbon atoms. In addition, when X is nitrogen atom, R5 to R7 or R5 to R6 may form hetero ring with nitrogen atom binding thereto}.
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Page/Page column 19
(2012/06/30)
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- A simple halide-to-anion exchange method for heteroaromatic salts and ionic liquids
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A broad and simple method permitted halide ions in quaternary heteroaromatic and ammonium salts to be exchanged for a variety of anions using an anion exchange resin (A- form) in non-aqueous media. The anion loading of the AER (OH- form) was examined using two different anion sources, acids or ammonium salts, and changing the polarity of the solvents. The AER (A- form) method in organic solvents was then applied to several quaternary heteroaromatic salts and ILs, and the anion exchange proceeded in excellent to quantitative yields, concomitantly removing halide impurities. Relying on the hydrophobicity of the targeted ion pair for the counteranion swap, organic solvents with variable polarity were used, such as CH3OH, CH3CN and the dipolar nonhydroxylic solvent mixture CH3CN:CH2Cl 2 (3:7) and the anion exchange was equally successful with both lipophilic cations and anions.
- Alcalde, Ermitas,Dinares, Immaculada,Ibanez, Anna,Mesquida, Neus
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experimental part
p. 4007 - 4027
(2012/07/28)
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- Ionic liquid protected heteropoly acids for methanol dehydration
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We report herein the synthesis of an organic-inorganic hybrid composed by the ionic liquid protected Keggin structure, as a precursor for acid catalyst and its subsequent application in the methanol dehydration reaction. Special attention was paid to the thermal stability of the resulted hybrids as a function of the Keggin anion. The catalytic behaviour of these new materials are also studied and compared to the metal salt Cs2HPW 12O40. The prepared hybrids are less thermally stable than the metal salt, but their partial decomposition results in very active and selective catalysts for the dehydration of methanol to dimethyl ether.
- Ivanova, Svetlana,Nitsch, Xavier,Romero-Sarria, Francisca,Louis, Beno?t,Centeno, Miguel Angel,Roger, Anne Cecile,Odriozola, Jose Antonio
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experimental part
p. 236 - 241
(2011/11/07)
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- PROCESS FOR PREPARING IONIC LIQUIDS BY ANION EXCHANGE
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Process for preparing salts of the formula I [in-line-formulae](B+)nxAy?[/in-line-formulae] where B is a cation comprising at least one nitrogen atom, A is an anion and n is an integer from 1 to 3, x and y are each an integer from 1 to 3 and the product of x and y is equal to n, by reacting salts of the formula II [in-line-formulae](B+)nxAy?[/in-line-formulae] where B and n, x and y are as defined above and C is a compound which has one or more carboxylate groups (referred to as carboxylate for short) and is different from A, with the ammonium salt of the anion A or with the protic acid of the anion A in the presence of ammonia.
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(2010/09/05)
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- Convenient synthesis of various ionic liquids from onium hydroxides and ammonium salts
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Hydroxide ionic liquids, such as 1-alkyl-3-methylimidazolium hydroxides, undergo smooth anion metathesis with ammonium salts to produce a variety of ionic liquids in excellent yields. It is a practical supplement of traditional neutralization method due to the broader range of starting materials containing desired anions.
- Peng, Yanqing,Li, Guiyun,Li, Jianguo,Yu, Shaojun
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experimental part
p. 4286 - 4288
(2009/10/26)
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- Imidazolium ionic liquids: A simple anion exchange protocol
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An efficient and simple protocol was developed to obtain quantitative iodide or bromide exchange for a broad range of anions in imidazolium ionic liquids. Selected anions were loaded in an anion exchange resin using two different procedures and were then used to provide a pure convenient ion pair. The Royal Society of Chemistry 2009.
- Dinares, Immaculada,Garcia De Miguel, Cristina,Ibanez, Anna,Mesquida, Neus,Alcalde, Ermitas
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supporting information; experimental part
p. 1507 - 1510
(2010/06/11)
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- Further investigation of the biodegradability of imidazolium ionic liquids
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In continuation of our earlier investigations, this report presents a rationale behind the design of a series of imidazolium based ionic liquids and their biodegradation using the CO2 headspace test (ISO 14593 method, OECD 310). The effect on biodegradability of these salts through variation of the N-substituted side chains of imidazolium ions was examined further through incorporation of various functional groups and increased alkyl chain lengths. A series of anions containing moieties known to be biodegradable were also incorporated into a number of imidazolium based salts and examined in a similar fashion.
- Harjani, Jitendra R.,Farrell, Jeff,Garcia, M. Teresa,Singer, Robert D.,Scammells, Peter J.
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experimental part
p. 821 - 829
(2010/04/23)
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- 1-Alkyl-3-methylimidazolium alkanesulfonate ionic liquids, [C nH2n+1mim][CkH 2k+1SO3]: Synthesis and physicochemical properties
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A set of 1-alkyl-3-methylimidazolium alkanesulfonate ionic liquids, [C nmim][CkSO3], formed by the variation of the alkyl chain lengths both in the cation and the anion (n = 1-6, 8, or 10; k = 1-4, or 6), was synthesised, with sixteen of them being novel. The ionic liquids were characterised by 1H and 13C NMR spectroscopy, and mass spectrometry. Their viscosities and densities as a function of temperature, as well as melting points and decomposition temperatures, were determined. The molecular volumes, both experimental and calculated, were found to depend linearly on the sum (n + k). the Owner Societies 2009.
- Blesic, Marijana,Swadzba-Kwasny, Malgorzata,Belhocine, Tayeb,Gunaratne, H. Q. Nimal,Lopes, Jose N. Canongia,Gomes, Margarida F. Costa,Padua, Agilio A. H.,Seddon, Kenneth R.,Rebelo, Luis Paulo N.
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experimental part
p. 8939 - 8948
(2010/06/20)
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- Method for Producing Ionic Liquids
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The present invention describes a process for preparing ionic liquids (I) by reacting ionic liquids (II) whose anion is a halide with an acid (III), with the resulting hydrogen halide being scavenged by means of an amine and the resulting ammonium halide being able to be separated off.
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Page/Page column 11
(2008/12/09)
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- Method of preparation of halogen-free ionic liquids and ionic liquids prepared in this manner
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The reaction of N-alkylimidazol with alkyl sulfonates, at room temperature, favors the production of 1,3-dialkylimidazolium alkane-sulfonates as crystalline solids at high yields. The alkane-sulfonate anions may be easily substituted by a series of other anions [BF4, PF6, PF3(CF2CF3)3, CF3SO3 and (CF3SO2)2N] through simple anion, salt, or acid reactions in water at room temperature. The extraction with dichloromethane, filtration, and evaporation of the solvent, allows the production of the desired ionic liquids at a yield of 80-95%. The purity of these ionic liquids (in some cases >99.4%) is performed using the intensity of 13C satellite signals from the magnetic resonance spectrums of the N-methyl imidazolium group as an internal standard.
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Page/Page column 3
(2008/06/13)
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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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- METHOD FOR PRODUCING ONIUM SALTS COMPRISING ALKYL ANIONS OR ARYL SULFONATE ANIONS OR ALKYL ANIONS OR ARYL CARBOXYLATE ANIONS HAVING A LOW HALIDE CONTENT
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The invention relates to a method for producing onium salts comprising alkyl anions or aryl sulfonate anions or alkyl carboxylate anions or acryl carboxylate anions by reacting an onium halide with an alkyl silyl ester or trialkyl silyl ester of an alkyl sulfonic acid or aryl sulfonic acid or an alkyl carboxylic acid or aryl carboxylic acid or the anhydrides thereof.
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Page/Page column 30
(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 26-27
(2008/06/13)
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- METHOD FOR THE PRODUCTION OF HETEROCYCLIC QUATERNARY AMMONIUM COMPOUNDS AND/OR GUANIDINE COMPOUNDS HAVING HIGH PURITY
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A method for the production of heterocylic quaternary ammonium compounds and/or guanidine compounds, wherein the carboxylate of the corresponding heterocyclic quaternary ammonium cation and/or guanidine cation containing the carboxylate anion of general formula R'-COO- (I), wherein R' represents hydrogen; C1- C7-alkyl; -OOC-(CH2)n- wherein n is equal to 0, 1 or 2; R"OOC-(CH2)n- wherein n is equal to 0, 1 or 2; -OOC-CH=CH-; R"OOC-CH=CH-; ethenyl; 2-propenyl; or a phenyl group which is unsubstituted or substituted by one to five independently selected groups from the series of C1- C6-alkyl, hydroxy, carboxylate (-COO-), carboxy (-COOH) and C1- C6- alkyloxy carbonyl (-COOR# wherein R# equals C1 - C6-alkyl) and R" equals hyrogen or C1- C6-alkyl; is reacted with an inorganic or organic protonic acid with a pKa-value of von 14 measured at 25 °C in an aqueous solution.
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Page/Page column 31
(2008/06/13)
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- METHOD FOR PRODUCING HIGH-PURITY QUATERNARY AMMONIUM COMPOUNDS
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The invention relates to a method for producing high-purity quaternary ammonium compounds by reacting the corresponding tertiary sp3-hybridized amine or sp2-hybridized imine with dimethyl sulfite. According to said method, the reaction is carried out (i) in the presence of an inorganic or organic Bronsted acid having a pKa value of 1.8 to 14, measured at 25 °C in an aqueous solution; and (ii) at a temperature of 10 to 100 °C.
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Page/Page column 22-23
(2008/06/13)
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- METHOD FOR HIGH-PURITY QUATERNARY AMMONIUM COMPOUNDS
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The invention relates to a method for producing quaternary ammonium compounds by reacting the corresponding tertiary sp3-hybridized amine or sp2-hybridized imine with dimethyl sulfite. The inventive method is characterized by carrying out the reaction (i) in the presence of a solvent selected from the group including aromatic hydrocarbons having 6 to 10 carbon atoms, symmetrical or unsymmetrical dialkyl ethers having a total of 5 to 10 carbon atoms, cycloalkane having 5 to 8 carbon atoms and C5 to C10 alkane; and (ii) at a temperature of 10 to 100 °C.
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Page/Page column 24-25
(2008/06/13)
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- IMIDAZOLIUM-METHYL SULFITES FOR USE AS STARTING COMPOUNDS FOR PRODUCING IONIC LIQUIDS
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The invention relates to the imidazolium-methyl sulfites of general formula (I), wherein the groups have the following independent meanings: R1 to R3 represent hydrogen, halogen, hydroxy, amine, aminocarbonyl, sulfo, cyano, nitro; C1 to C20 alkyl, C2 to C20alkenyl, C2 to C20 alkinyl, C1 to C20alkyloxy, C2 to C20 alkenyloxy, C2to C20 alkinyloxy, C1 to C20 alkylcarbonyl, C1 to C20 alkyloxycarbonyl, C1 to C20 acyloxy, C1 to C20 alkylaminocarbonyl, di-(C1 to C20 alkyl)amino-carbonyl, C1 to C20alkylamino, di-(C1 to C20 alkyl)amino, C1 to C20 alkylsulfonyl, C3 to C8 cycloalkyl, wherein the above-mentioned alkyl, alkenyl, alkinyl and cycloalkyl groups may be substituted and/or CH2 groups may be replaced by oxygen; phenyl, phenoxy, which may be substituted themselves; R4 represents sulfo; C1 to C20 alkyl, C2 to C20 alkenyl, C2 to C20alkinyl, C3 to C8 cycloalkyl, wherein the mentioned alkyl, alkenyl, alkinyl and cycloalkyl groups may be substituted and/or CH2 groups may be replaced by oxygen; phenyl, which may be substituted; or R1 together with R4, and/or R2 together with R3, or R4 together with R2 represent alkylene-(CH2)n-, wherein n = 4, 5 or 6 or butadienylene -CH=CH-CH=CH-, which may be substituted and/or CH2 groups may be replaced by oxygen and CH groups may be replaced by NR5.
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Page/Page column 34
(2008/06/13)
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- A simple and practical method for the preparation and purity determination of halide-free imidazolium ionic liquids
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The reaction of N-alkylimidazole with alkyl sulfonates at room temperature affords 1,3-dialkylimidazolium alkanesulfonates as crystalline solids in high yields. The alkanesulfonate anions can be easily substituted by a series of other anions [BF4, PF6, PF3(CF 2CF3)3, CF3SO3 and N(CF3SO2)2] by simple reaction of anions, salts, or acids in water at room temperature. Extraction with dichloromethane, filtration through a short basic alumina column and solvent evaporation affords the desired ionic liquids in 80-95% yield. The purity (> 99.4%) of these ionic liquids can be determined by 1H NMR spectra using the intensity of the 13C satellites of the imidazolium N-methyl group as internal standard.
- Cassol, Claudia C.,Ebeling, Guenter,Ferrera, Bauer,Dupont, Jairton
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p. 243 - 248
(2007/10/03)
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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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- Ionic liquids as reaction media for esterification of carboxylate sodium salts with alkyl halides
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Ionic liquids based on 1,3-dialkylimidazolinium methanesulfonate have been used as effective reusable reaction media in the esterification of several carboxylate sodium salts with different alkyl halides. Products are easily isolated by extraction with ether, and the protocol is mild and green, compared to the existing methods based on toxic solvents. Proper 'design' of the ionic liquid allows us to obtain esters always in quantitative yields.
- Brinchi,Germani,Savelli
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p. 2027 - 2029
(2007/10/03)
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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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