- Concentration-dependent apparent partition coefficients of ionic liquids possessing ethyl- and bi-sulphate anions
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This study deals with the concentration dependent apparent partition coefficients log P of the ethyl and bisulfate-based ionic liquids. It is observed that the bisulfate-based ionic liquids show different behaviour with respect to concentration as compared to ethyl sulphate-based ionic liquids. It is significant and useful analysis for the further implementation of alkyl sulfate based ionic liquids as solvents in extraction processes. The log P values of the ethyl sulphate-based ionic liquids were noted to vary linearly with the concentration of the ionic liquid, whereas a flip-flop trend with the concentration for the log P values of the bisulphate-based ionic liquids was observed due to the difference in hydrogen bond accepting basicity and possibility of aggregate formation of these anions. The π-π interactions between the imidazolium and pyridinium rings were seen to affect the log P values. The alkyl chain length of anions was also observed to influence the log P values. The hydrophobicity of ionic liquid changes with the alkyl chain in the anion in the order; [HSO4]- 4]- 4]-.
- Jain, Preeti,Kumar, Anil
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- Fine tuning the ionic liquid-vacuum outer atomic surface using ion mixtures
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Ionic liquid-vacuum outer atomic surfaces can be created that are remarkably different from the bulk composition. In this communication we demonstrate, using low-energy ion scattering (LEIS), that for ionic liquid mixtures the outer atomic surface shows s
- Villar-Garcia, Ignacio J.,Fearn, Sarah,Ismail, Nur L.,McIntosh, Alastair J. S.,Lovelock, Kevin R. J.
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- Choline chloride-thiourea, a deep eutectic solvent for the production of chitin nanofibers
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Deep eutectic solvents (DESs) consisting of the mixtures of choline halide (chloride/bromide)-urea and choline chloride-thiourea were used as solvents to prepare α-chitin nanofibers (CNFs). CNFs of diameter 20-30 nm could be obtained using the DESs comprising of the mixture of choline chloride and thiourea (CCT 1:2); however, NFs could not be obtained using the DESs having urea (CCU 1:2) as hydrogen bond donor. The physicochemical properties of thus obtained NFs were compared with those obtained using a couple of imidazolium based ionic liquids namely, 1-butyl-3-methylimidazolium hydrogen sulphate [(Bmim)HSO4] and 1-methylimidazolium hydrogen sulphate [(Hmim)HSO4] as well as choline based bio-ILs namely, choline hydrogen sulphate [(Chol)HSO4] and choline acrylate. The CNFs obtained using the DES as a solvent were used to prepare calcium alginate bio-nanocomposite gel beads having enhanced elasticity in comparison to Ca-alginate beads. The bio-nanocomposite gel beads thus obtained were used to study slow release of 5-fluorouracil, an anticancer drug.
- Mukesh, Chandrakant,Mondal, Dibyendu,Sharma, Mukesh,Prasad, Kamalesh
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- Are alkyl sulfate-based protic and aprotic ionic liquids stable with water and alcohols? A thermodynamic approach
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The knowledge of the chemical stability as a function of the temperature of ionic liquids (ILs) in the presence of other molecules such as water is crucial prior to developing any industrial application and process involving these novel materials. Fluid phase equilibria and density over a large range of temperature and composition can give basic information on IL purity and chemical stability. The IL scientific community requires accurate measurements accessed from reference data. In this work, the stability of different alkyl sulfate-based ILs in the presence of water and various alcohols (methanol, ethanol, 1-butanol, and 1-octanol) was investigated to understand their stability as a function of temperature up to 423.15 K over the hydrolysis and transesterification reactions, respectively. From this investigation, it was clear that methyl sulfate- and ethyl sulfate-based ILs are not stable in the presence of water, since hydrolysis of the methyl sulfate or ethyl sulfate anions to methanol or ethanol and hydrogenate anion is undoubtedly observed. Such observations could help to explain the differences observed for the physical properties published in the literature by various groups. Furthermore, it appears that a thermodynamic equilibrium process drives these hydrolysis reactions. In other words, these hydrolysis reactions are in fact reversible, providing the possibility to re-form the desired alkyl sulfate anions by a simple transesterification reaction between hydrogen sulfate-based ILs and the corresponding alcohol (methanol or ethanol). Additionally, butyl sulfate- and octyl sulfate-based ILs appear to follow this pattern but under more drastic conditions. In these systems, hydrolysis is observed in both cases after several months for temperatures up to 423 K in the presence of water. Therein, the partial miscibility of hydrogen sulfate-based ILs with long chain alcohols (1-butanol and 1-octanol) can help to explain the enhanced hydrolytic stability of the butyl sulfate- and octyl sulfate-based ILs compared with the methyl or ethyl sulfate systems. Additionally, rapid transesterification reactions are observed during liquid-liquid equilibrium studies as a function of temperature for binary systems of (hydrogen sulfate-based ionic liquids + 1-butanol) and of (hydrogen sulfate-based ionic liquids + 1-octanol). Finally, this atom-efficient catalyst-free transesterification reaction between hydrogen sulfate-based ILs and alcohol was then tested to provide a novel way to synthesize new ILs with various anion structures containing the alkyl sulfate group. ? 2013 American Chemical Society.
- Jacquemin, Johan,Goodrich, Peter,Jiang, Wei,Rooney, David W.,Hardacre, Christopher
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- A quick, simple, robust method to measure the acidity of ionic liquids
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Introduced here is a quick, simple, robust method to measure acidity in ionic liquid (IL) systems by the use of the NMR-probe mesityl oxide. Acidity corresponding to a Hammett acidity of -1 to -9 can be measured reliably using this technique, a range that vastly exceeds that of any single UV-vis probe.
- Gr?svik, John,Hallett, Jason P.,To, Trang Quynh,Welton, Tom
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- Oxidative desulfurization of gasoline by ionic liquids coupled with extraction by organic solvents
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In this work, desulfurization of real fluidized catalytic cracking (FCC) gasoline was investigated in dual steps; first in oxidative desulfurization (ODS) using imidazolium and pyrrolidonium based Br?nsted acidic ionic liquids (ILs) as solvent and catalyst and hydrogen peroxide as oxidant. In second step, extractive desulfurization took place using organic solvents of furfural, furfural alcohol and ethylene glycol. Variety of factors such as temperature, time, mass ratio of oil/ILs and regeneration and recycling of ILs, multiple-step desulfurization of ILs and organic solvents and solvent/oil ratio were also investigated. The S-content was significantly decreased to ca. 18 ppm from initial S-content of 260 ppm with a total S-removal of ca. 95percent in one-step ODS using pyrrolidonium based ILs coupled with five-step extraction desulfurization (EDS) using furfural alcohol as extractant. This work shows that oxidative desulfurization using ionic liquids coupled with extractive desulfurization using organic solvents is a potential method to produce clean gasoline.
- Abro, Rashid,Gao, Shurong,Chen, Xiaochun,Yu, Guangren,Abdeltawab Salem, Ahmed A.,Al-Deyabb
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- Efficient combination of recyclable task specific ionic liquid and microwave dielectric heating for the synthesis of lipophilic esters
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Mild and efficient esterification reactions of carboxylic acids with neo-pentanol were carried out using task-specific ionic liquids with hydrogen sulphate counteranion under microwave irradiation. The latent acidity of the ionic liquid was introduced by
- Arfan, Atef,Bazureau, Jean Pierre
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- Influence of anions of imidazole ionic liquids on dissolution of cellulose
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[Bmim]Cl, [Bmim]Br, [Bmim]HSO4, [Bmim]BF4 and [Bmim]PF6 were synthesized to study the influence of anions on the dissolution of cellulose. Experimental studies showed that the dissolution of cellulose was related to the formation of hydrogen bonds between the anions and cellulose, which is attributed to the charge density on the anion. The sequence of solubility of cellulose in six ionic liquids tested was [Bmim]Cl > [Bmim]Br > [Bmim]HSO4 > [Bmim]BF4, [Bmim]PF 6. Thermogravimetric method was employed to investigate the stability of ionic liquids. The dissolution process was monitored with polarizing microscope. The results showed that dissolution of cellulose was related to stability of the ionic liquids. For similar ionic liquids, poorer stability led to higher solubility. Both the original and regenerated cellulose samples were characterized with wide-angle X-ray diffraction and FTIR. It was shown that the structures of original cellulose and regenerated cellulose were similar; however, the crystalline structure of cellulose was converted to cellulose II from cellulose I of the original cellulose.
- Liu,Yu,Zhou,Zhang,Zhang
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- Development of Acidic Imidazolium Ionic Liquids for Activation of Kraft Lignin by Controlled Oxidation: Comprehensive Evaluation and Practical Utility
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A novel, eco-friendly method for the activation of lignin by controlled oxidation was studied. The results obtained for six acidic imidazolium ionic liquids containing the hydrogen sulfate anion were compared. The key goal of this research was to increase the content of carbonyl groups in the lignin structure because these may play the main role in the transport of protons and electrons in active materials for electrochemical applications. By means of a variety of analytical techniques (FTIR, 13C CP/MAS NMR, and X-ray photoelectron spectroscopy; selected reactions to determine the presence of carbonyl groups; SEM; zeta-potential analysis; thermogravimetric analysis/differential thermogravimetric analysis; and porous structure analysis), it was determined that the product obtained after treatment with 3-cyclohexyloxymethy-1-methylimidazolium hydrogen sulfate had favorable properties, in terms of the target application. Electrochemical tests proved that the obtained materials could be used as anodes in lithium batteries. The results show that the activation of lignin with ionic liquids can increase its capacity and maintain stability.
- Klapiszewski, ?ukasz,Szalaty, Tadeusz J.,Kurc, Beata,Stanisz, Ma?gorzata,Zawadzki, Bartosz,Skrzypczak, Andrzej,Jesionowski, Teofil
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- The efficient hydroxyalkylation of phenol with formaldehyde to bisphenol F over a thermoregulated phase-separable reaction system containing a water-soluble Bronsted acidic ionic liquid
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The efficient hydroxyalkylation of phenol with formaldehyde to bisphenol F over a thermoregulated phase-separable reaction system containing a water-soluble Bronsted acidic ionic liquid was studied. The reaction system containing the water-soluble IL showed thermoregulated biphasic behavior with change of the alkyl chain length of IL, temperature and water amount. Four types of imidazolium-, ammonium-, phosphonium- and pyridinium-based water-soluble ionic liquids with different anions of dihydrogen phosphate [H2PO4]-, acetate [CH3COO] - and hydrogen sulfate [HSO4]- were used as both Bronsted acidic catalysts and thermoregulated solvents. Among them, [C6MIM][HSO4] gave a high yield of 80.5% and a selectivity of 96.9% for bisphenol F, and the optimal reaction conditions were stirring speed 450 rpm, phenol-formaldehyde ratio 6:1, IL catalyst molar concentration 12.5%, reaction temperature 90 °C and reaction time 1 h. [C 6MIM][HSO4] could be recovered by simple decantation and could retain its original activity even after six recycling-uses [C nMIM][HSO4] with the alkyl chain length n = 6 found to be the most suitable for the synthesis of bisphenol F because of both the formation of a thermoregulated monophasic reaction system at 90 °C to enhance the reaction efficiency and as a thermoregulated phase-transition solvent to facilitate its recovery from the reaction system. the Partner Organisations 2014.
- Wang, Qing,Wu, Zhi Min,Li, Yongfei,Tan, Ying,Liu, Ning,Liu, Yuejin
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- Kinetics and quantum chemical study for cyclotrimerization of propanal catalyzed by Br?nsted acidic ionic liquids
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Several Br?nsted acidic ionic liquids (BAILs) were synthesized and used as catalysts for the cyclotrimerization of propanal. The acidity of different BAILs was explored and a preliminarily study of the relationship between catalytic activity and acidity was performed. The kinetics for the BAILs-catalyzed cyclotrimerization of propanal was studied systemically to determine the kinetic model and the kinetic parameters by taking [BSTMG][HSO4] as the representative catalyst. The effects of various parameters such as catalyst loading, reaction temperature on the kinetics were examined in detail. Besides, the structures of three representative BAILs and the interactions between propanal molecule and ionic pairs of BAILs were studied by means of quantum chemistry calculations.
- Wu, Li,Li, Zhen,Wang, Fang,Lei, Min,Chen, Jing
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- Theoretical and experimental comparative study of nonlinear properties of imidazolium cation based ionic liquids
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This work describes the experimental and theoretical investigation of the nonlinear optical properties of the imidazolium cation based ionic liquids and the corresponding thermo-optical parameters. The experimental results of nonlinear optical properties, such as nonlinear refractive index and thermo-optical properties are determined by Z-scan and EZ-scan techniques with a femtosecond laser source. Theoretical simulations of linear and nonlinear optical properties performed by density functional theory (DFT) are discussed in terms of polarizabilities and hyperpolarizabilities. A correlation between the theoretical and experimental results is presented, where the variation of the experimental signals of each ionic liquid can be compared with their calculated nonlinear optical properties.
- Ferreira, Vinícius Castro,Zanchet, Letícia,Monteiro, Wesley Formentin,da Trindade, Letícia Guerreiro,de Souza, Michèle Oberson,Correia, Ricardo Rego Bordalo
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- Bismuth mediated barbier synthesis of α-homoallylic alcohols via a sigmatropic rearrangement in [bmim][HSO4]
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A novel protocol for the Bismuth metal mediated regioselctive crotylation of aldehydes yielding α-homoallylic alcohols has been developed using 20mol% [bmim][HSO4] as a metal activator, as well as a mediator for regioconversion from the initially formed γ-regiomer. The present protocol minimizes the use of conventional solvents and proceeds with good yields and excellent regioselectivities.
- Chatterjee, Sucheta,Dey, Papiya,Kanojia, Seema V.,Chattopadhyay, Subrata,Goswami, Dibakar
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supporting information
p. 765 - 775
(2020/12/13)
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- Insights on the catalytic behaviour of sulfonic acid-functionalized ionic liquids (ILs) in transesterification reactions - voltammetric characterization of sulfonic task-specific ILs with bisulfate anions
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This work shows for the first time the link between the amount of free sulfuric acid (as detected by cyclic voltammetry) and the activity of sulfonic-acid-functionalized ionic liquids (ILs) as acid catalysts for a transesterification reaction, and demonstrates that sulfonic acid groups, while are not directly involved in the catalysis, release the free acid during the reaction. Two imidazolic ILs with bisulfate as the counterion and their corresponding task-specific ILs (TSILs) that resulted from the addition of a sulfonic acid group inside the imidazolic-base structure were studied. The outstanding catalytic activity at room temperature of the TSILs 1-(4-sulfonic acid)-butyl-3-methylimidazolium bisulfate ([bsmim]HSO4) and 1-(4-sulfonic acid)-butyl-imidazolium bisulfate ([bsHim]HSO4) for the transesterification ofp-nitrophenyl acetate with methanol was associated to the significant amounts of free sulfuric acid in equilibria with the ionic pairs. It was concluded that these TSILs function as reservoirs for releasing the free acid, which is the actual acid catalyst. In contrast, the corresponding non-sulfonic ILs supply very little amounts of free acid and consequently present low catalytic activities at room temperature, which in fact can be improved by increasing the reaction temperature up to 100 °C.
- Martini, María B.,Fernández, José L.,Adam, Claudia G.
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p. 2731 - 2741
(2021/02/12)
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- Preparation method of low-molecular olefin polymer
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The invention provides a preparation method of a low-molecular olefin polymer. The preparation method comprises the following steps: low-molecular olefin is subjected to a polymerization reaction under the action of a catalyst, and a product is collected; the catalyst is prepared from ionic liquid, polyphosphoric acid and heteropolyacid by mixing at 30-100 DEG C for 1-12 h. The preparation methodhas the advantages of mild reaction conditions, high conversion rate and good selectivity, and the catalyst is easy to recover and can be recycled; the preparation method is green and pollution-free.
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Paragraph 0053
(2018/06/26)
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- Preparation method of alkylsalicylic acid and/or alkylsalicylate
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The invention provides a preparation method of alkylsalicylic acid and/or alkylsalicylate. The preparation method of alkylsalicylic acid and/or alkylsalicylate comprises the following steps: alpha-olefin, salicylic acid and/or salicylate are subjected to an alkylation reaction under the action of a catalyst, and a product is collected, wherein the catalyst is prepared from an ionic liquid, polyphosphoric acid and organic acid salt by mixing at 30-100 DEG C for 1-12 h. The method has the advantages of high conversion rate, good product selectivity, relatively mild reaction conditions, easily recovered catalyst and the like, and is a green and pollution-free preparation process.
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Paragraph 0040; 0043
(2018/05/30)
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- Fragrance Compositions Comprising Ionic Liquids
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The present invention relates to a fragrance composition comprising ionic liquids for delayed evaporation of the perfume raw materials. The invention also relates to methods of use of the fragrance compositions for perfuming suitable substrates, particularly skin and hair.
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Paragraph 0245
(2017/05/20)
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- Experimental study on CO2 sorption capacity of the neat and porous silica supported ionic liquids and the effect of water content of flue gas
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In this research, absorption of CO2 in different ionic liquids (ILs) is studied. Thus four ILs were synthesized containing 1-butyl-3-methylimidazolium as the cation and nitrate [NO3]?, thiocyanate [SCN]?, dicyanamide [N(CN)2]? and hydrogen sulfate [HSO4]? as the anions, respectively. The resulting ILs were then immobilized into activated silica support in a 1/1 IL/SiO2 weight ratio via the impregnation-vaporization method. CO2 sorption behavior of both neat and silica supported ILs (ILs-SiO2) were investigated at different temperatures and flow rates under atmospheric pressure, while their desorption process were carried out under 20?mm?Hg at 70?°C. In both sorbents, the best results were obtained at 25?°C with a flow rate of 12?mL/min, where [bmim][N(CN)2] with 1.85 (wt%) or 0.42?mmol CO2 per gram of sorbent and [bmim][HSO4]-SiO2 with 2.33 (wt%) or 0.53?mmol CO2 per gram of sorbent showed the highest sorption capacities. The effect of water on CO2 absorption capacity of the neat and silica supported ILs were also studied by transmission of CO2 gas flue containing 400?ppm water. The results indicated that the mass gain was higher when wet CO2 was passed through the sorbents, opposed to passing dry CO2. Because of the existence of a weak coulombic intraction between the sorbents and CO2, desorption occurs rapidly and a readily reuse of the sorbents is therefore provided.
- Mirzaei, Mojtaba,Badiei, Ali Reza,Mokhtarani, Babak,Sharifi, Ali
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p. 462 - 470
(2017/03/10)
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- Treatment of biomass to dissolve lignin with ionic liquid composition
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The present invention relates to a method for treating a lignocellulose biomass in order to dissolve the lignin therein, while the cellulose does not dissolve. The cellulose pulp obtained can be used to produce glucose. In addition the lignin can be isolated for subsequent use in the renewable chemical industry as a source for aromatic platform chemicals.
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Page/Page column 11
(2017/10/05)
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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 synthesizing triformol (by machine translation)
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The present invention provides a method of synthesizing triformol. The method comprises use of an ionic liquid as a solvent and catalyst, the use of a solid poly-formaldehyde as raw materials, in the 30 °C -150 ° C reaction 0.1h -5h the step of synthesizing triformol, wherein the amount of the solid poly-formaldehyde into the ionic liquid and solid paraformaldehyde of the total mass of the 80% the following. The method provided by the invention is the use of a solid poly-formaldehyde as raw materials, ionic liquid as the solvent and the catalyst, will not produce by-products methyl formate, such as methanol and METHYLAL, can significantly improve the yield of balance trioxymethylene , the energy consumption can be reduced, and the ionic liquid can be repeatedly used, so as to reduce the production cost. (by machine translation)
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Paragraph 0081-0083
(2017/01/26)
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- Ion liquid in the application in the preparation of bromoethane
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The invention discloses application of an ionic liquid in bromoethane preparation, belonging to the fields of green chemistry and new materials. Under the action of the ionic liquid, hydrobromic acid and ethanol are subjected to substitution reaction; and after the reaction finishes, after-treatment is performed to obtain the bromoethane. The ionic liquid is composed of cations X and anions Y, wherein the cations are imidazole, pyridine, pyrrolidone and other cations containing nitrogen heterocyclic ring, and the anions are various functionalized anions with catalytic action. The ionic liquid is used for preparing the bromoethane, thereby avoiding using the traditional concentrated sulfuric acid, enhancing the reaction efficiency, avoiding generating waste acid and being beneficial to environmental protection. The ionic liquid can be recovered, and is a high-efficiency green synthesis means.
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Paragraph 0048; 0049; 0052-0054
(2017/05/02)
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- Ionic liquid catalyzed synthesis of 2-(indole-3-yl)-thiochroman-4-ones and their novel antifungal activities
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2-(Indole-3-yl)-thiochroman-4-ones were synthesized via ionic liquid and tested for in vitro antifungal activity. The contribution of ionic liquid to Michael addition reaction is significant. Structures of all compounds are elucidated by 1H NMR, 13C NMR and HRMS. Most of these compounds showed better antifungal activity than fluconazole. The results suggest that 2-(indole-3-yl)-thiochroman-4-ones would be efficient antifungal agents.
- Song, Ya-Li,Wu, Fan,Zhang, Chao-Chao,Liang, Guo-Chao,Zhou, Guan,Yu, Jiao-Jiao
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supporting information
p. 259 - 261
(2015/04/13)
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- Brosted acidic ionic liquid ([Bmim]Hso4) promoted cyclocodensation reaction: Synthesis of 3,4,5-substituted furan-2(5h)-ones
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1-Butyl-3-methylimidazolium hydrogen sulfate [bmim]HSO4: an acidic ionic liquid was used as a catalyst for the synthesis of heterocyclic compounds 3,4,5-substituted furan-2(5H)-ones from aniline derivatives, dialkyl acetylenedicarboxylates and aromatic aldehydes at 75 °C. Solventfree conditions, shorter reaction time, and good yields (71-94%) are some of advantages.
- Salahi, Sajjad,Maghsoodlou, Malek Taher,Hazeri, Nourallah
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p. 2047 - 2052
(2016/02/27)
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- Activity investigation of imidazolium-based ionic liquid as catalyst for friedel-crafts alkylation of aromatic compounds
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N-Methylimidazolium ionic liquids were synthesised from N-methylimidazole and 1-bromobutane by two-step method. The alkylation of benzene and other aromatic compounds through improved Friedel-Crafts reaction was investigated in these ionic liquids. The imidazolium-based ionic liquids showed both high activity and high selectivity for this reaction. In particular, remarkable enhancement of the catalytic effect of the imidazolium-based ionic liquids was observed for the ionic liquids containing the PF6- anion. The effects of various types of anions, ionic liquid dosage, reaction temperature and molar ratio of aromatic compound to 1-bromobutane/tertbutyl alcohol were explored using [Bmim]PF6 or its mixture with AlCl3 as catalyst. The synthesis yielded improved results over those obtained using either neat AlCl3 or other imidazolium-based ionic liquids as catalyst. The ionic liquids can also be recycled and reused in contrast to traditional solvent-catalyst systems.
- Cai, Mingjian,Wang, Xiuge
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p. 649 - 653
(2015/01/30)
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- SO3H-functionalized Bronsted acidic ionic liquids as efficient catalysts for the synthesis of isoamyl salicylate
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Six Bronsted acidic ionic liquids (BAILs) composed of [HSO 4] were prepared, characterized, and used as catalysts of low dosage in the synthesis of isoamyl salicylate. The effects of various parameters such as the kind of BAILs, temperature, catalyst loading, and molar ratio of the reactants on the conversion of salicylic acid were also examined in detail. The results suggested that the catalytic performances of BAILs were of close relevance to their Hammett acidities. The SO3H-functionalized BAILs 1-(4-sulfonic acid) butyl-3-methylimidazolium hydrogen sulfate ([BSmim][HSO 4]) and N-(4-sulfonic acid) butyl triethylammonium hydrogen sulfate ([BSEt3N][HSO4]) of strong acidities exhibited excellently catalytic activities and selectivities in the esterification of salicylic acid with isoamyl alcohol. The fully optimized geometries of [BSmim][HSO4] and [BSEt3N][HSO4] further manifest that their strong acidities are derived from the strong interactions between the anion with the sulfonic acid group. In addition, it was found that [BSmim][HSO4] could be also recovered easily and used repetitively at least six times without obvious decline in activity and quantity.
- Tao, Duan-Jian,Wu, Jing,Wang, Zhen-Zhen,Lu, Zhang-Hui,Yang, Zhen,Chen, Xiang-Shu
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- New strategies for the synthesis of lactones using peroxymonosulphate salts, ionic liquids and microwave or ultrasound irradiation
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A new method for the rapid synthesis of lactones via the one-pot oxidation of alcohols with potassium peroxymonosulphate in an ionic liquid was developed. The use of microwave or ultrasonic irradiation increased the reaction rates significantly. Additionally, new peroxymonosulphate ionic liquids were synthesised and used as effective oxidants in the synthesis of lactones. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014.
- Matuszek, Karolina,Zawadzki, Przemyslaw,Czardybon, Wojciech,Chrobok, Anna
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p. 237 - 241
(2014/01/06)
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- An efficient one pot method for synthesis of carboxylic acids from nitriles using recyclable ionic liquid [bmim]HSO4 Dedicated to my mentor Professor (Mrs.) Krishna Misra on her 76th birthday
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Environmentally benign ionic liquid [bmim]HSO4 was found suitable for conversion of nitriles into carboxylic acids under mild conditions with excellent purity.
- Kumar, Satyanand,Dixit, Sandeep Kumar,Awasthi, Satish Kumar
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supporting information
p. 3802 - 3804
(2014/07/07)
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- Water effect on physicochemical properties of 1-butyl-3-methylimidazolium based ionic liquids with inorganic anions
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Room temperature ionic liquids of 1-butyl-3-methylimidazolium tetrafluoroborate, [bmim][BF4], nitrate, [NO3] -, phosphate, [PO4]3 -, and hydrogen sulfate, [HSO4]-, have been synthesized and characterized by 1H-NMR, 13C-NMR, mass spectrometry and IR spectroscopy methods. The effect of nature of inorganic anion on hygroscopic property has been studied. Physicochemical properties such as density, viscosity, melting point, freezing point, glass transition, thermal decomposition temperature and specific electrical conductivity have been determined. The influence of temperature and water concentration on density, viscosity and specific electrical conductivity values has been investigated. The dependence of physicochemical properties against anion nature and water content has been explained according to cation-anion interactions. The anomalous behaviors of density or conductivity values for equimolecular aqueous solutions of 1-butyl-3-methylimidazolium hydrogen sulfate or tetrafluoroborate ionic liquids have been found and associated with significant restructuring. The formation of crystalline hydrates of the composition of [bmim][BF4]x0.5H 2O was observed.
- Grishina,Ramenskaya,Gruzdev,Kraeva
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p. 267 - 272
(2013/03/13)
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- Acidic-functionalized ionic liquid as an efficient, green, and metal-free catalyst for benzylation of sulfur, nitrogen, and carbon nucleophiles to benzylic alcohols
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A series of HSO4- functionalized ILs was synthesized and used as efficient, green, and metal-free catalysts for benzylation. Notably, the catalytic system has wide substrate scopes and the ionic liquid catalysts were applied to investigate three different types of nucleophiles to give the desired benzylation products with moderate to excellent yields.
- Chu, Xue-Qiang,Jiang, Ran,Fang, Yi,Gu, Zheng-Yang,Meng, Hua,Wang, Shun-Yi,Ji, Shun-Jun
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p. 1166 - 1174
(2013/02/25)
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- An environmental friendly approach for the synthesis of spiro[indoline-3',2-quinazoline]2',4(3H)-dione using 1-methylimidazolium hydrogen sulfate, as reusable catalyst
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A facile and environmentally benign procedure for the synthesis of 3-aryl-1H-spiro[indoline-3',2-quinazoline] 2',4(3H)-dione from isatoic anhydride, aromatic amines and isatin derivatives in Bronsted acidic ionic liquid, 1-methylimidazoliumhydrogen sulfate, was reported. The ability to reuse the ionic liquid, the high yield, short reaction time and ease of purification are the important features of this process.
- Kefayati, Hassan,Vazifeh, Masoumeh,Kazemi-Rad, Reyhaneh
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p. 1197 - 1201
(2014/04/03)
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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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- Extraction and oxidative desulfurization of diesel fuel catalyzed by a Bronsted acidic ionic liquid at room temperature
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The Bronsted acidic ionic liquids 1-butyl-3-methylimidazolium hydrogen sulfate ([BMIM][HSO4]) and N-butylpyridinium hydrogen sulfate ([C4Py][HSO4]) were used as extractant and catalyst for desulfurization of diesel. The results show that [BMIM][HSO 4] is better as extractant and catalyst than [C4Py] [HSO4] during the desulfurization process. The sulfur removal of dibenzothiophene (DBT) in n-octane was 99.6% in 90 min under the conditions of Vmodel oil/VIL = 2:1 and H2O2/DBT molar ratio at 5 (O/S = 5), at room temperature. The sulfur removal of four sulfur compounds by extraction and catalytic oxidation process followed the order of DBT > benzothiophene (BT) > thiophene (TS) > 4,6-dimethyldibenzothiophene (4,6-DMDBT). Moreover, the [BMIM][HSO4] can be recycled for at least 6 times with a little decrease in the desulfurization activity. The sulfur removal of diesel fuel containing sulfur content of 97 ppm is 85.5%, which was much better than desulfurization performance by simple extraction with IL (11.0%). In this extraction and oxidative desulfurization process, DBT was oxidized to corresponding sulfone by H2O2 with Bronsted acidic IL [BMIM][HSO 4] which served as not only extractant but also catalyst. The Royal Society of Chemistry 2010.
- Gao, Hongshuai,Guo, Chen,Xing, Jianmin,Zhao, Junmei,Liu, Huizhou
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experimental part
p. 1220 - 1224
(2010/10/20)
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- ALKYLATION CATALYZED BY BINARY MIXTURES OF ACID AND IONIC LIQUID
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An alkylation catalyst can include: a Br?nsted acid ionic liquid; and a strong Br?nsted acid that is not considered an ionic liquid. The Br?nsted acid ionic liquid can be selected from the group consisting of [BMIm]HSO4, [MBSIm]HSO4, [MBSIm]OTf, [MPSIm]OTf, and [OMIm]HSO4 or the like. In one aspect, the strong Br?nsted acid is selected from the group consisting of sulfuric acid, hydrochloric acid (HCl), hydrobromic acid (HBr), HF, hydrogen iodide (HI), phosphoric acid, trifluoromethanesulfonic (triflic) acid. In one aspect, the strong Br?nsted acid is present at more than about 50 wt % of the composition; however, the Br?nsted acid can vary from about 10 wt % to about 99 wt %, more preferably about 20 wt % to about 90 wt %, and most preferably about 40 wt % to about 80 wt %.
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Page/Page column 7
(2011/01/11)
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- 1-Butyl-3-methylimidazolium hydrogen sulfate [bmim]HSO4: An efficient reusable acidic ionic liquid for the synthesis of 1,8-Dioxo- octahydroxanthenes
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1-Butyl-3-methylimidazolium hydrogen sulfate [bmim]HSO4 as an acidic ionic liquid was prepared and used as a catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes in excellent yields and short reaction times at 80 °C. The ionic liquid was easily separated fromthe reactionmixture by water extraction and was recycled four times without any loss in activity.
- Niknam, Khodabakhsh,Damya, Maryam
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scheme or table
p. 659 - 665
(2010/06/16)
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- Preparation of 1-butyl-3-methylimidazolium salts and study of their phase behavior and intramolecular intractions
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Seven organic salts of 1-butyl-3-methylimidazolium with anions Br -, BF4-, NO3-, SO 42-, HSO4-, SCN-, PO 43- were prepared. Structure of these compounds is elucidated and purity is confirmed. The products are characterized by melting point, thin layer chromatography, data of elemental analysis, cromatomass-, NMR and IR spectroscopy. All these compounds are ionic liquids, five are low temperature ones. Principal thermal characteristics are found that allow accounting for the phase behavior of the prepared compounds at their application. Existence of intramolecular and intermolecular interactions between the heterocyclic anion and inorganic cation in by means of the formation of hydrogen bond is established.
- Gruzdev,Ramenskaya,Chervonova,Kumeev
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experimental part
p. 1720 - 1727
(2011/05/14)
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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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- 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 27-28
(2008/06/13)
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