- Density, thermal expansion and viscosity of cholinium-derived ionic liquids
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Density and viscosity data of the N-alkyl-N,N-dimethyl-N-(2-hydroxyethyl) ammonium bis(trifluoromethylsulfonyl)imide ionic liquids homologous series [N1 1 n 2(OH)][Ntf2] with n=1, 2, 3, 4 and 5 have been measured at atmospheric pressure in the 2832 group on the alkyl chain of the cation of about 17.2 cm 3mol-1, except for [N1 1 1 2(OH)]+, which exhibits an outlier behaviour. Molecular dynamics simulation results are used to explain the volumetric behaviour along the homologous series from a molecular perspective. The predictive power of group contribution methods for density and viscosity is also tested.
- Costa, Anabela J.L.,Soromenho, Mario R.C.,Shimizu, Karina,Marrucho, Isabel M.,Esperanca, Jose M.S.S.,Lopes, Jose N. Canongia,Rebelo, Luis Paulo N.
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Read Online
- Proton transport properties in an ionic liquid having a hydroxyl group
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An ionic liquid having a hydroxyl group, choline bis(trifluoromethylsulfonyl)amide ([N111(2OH)][N(Tf)2]), was synthesized to investigate the effect of hydroxyl groups on the proton transport. 1,1,1-Trifluoro-N-(trifluoromethylsulfonyl)methanesulfoneamide (HN(Tf)2) as a proton source was mixed with the choline derivative at various molar ratios. Their thermal properties, viscosities, and ionic conductivities were investigated. [N111(2OH)][N(Tf)2] showed a melting point at 27 °C, and its thermal stability was higher than 400 °C. The viscosity of [N111(2OH)][N(Tf)2]/HN(Tf) 2 mixtures increased as the acid molar fraction increased. The ionic conductivity of [N111(2OH)][N(Tf)2] was 2.1 × 10-3 S cm-1 at 25 °C; the ionic conductivity monotonously decreased as the acid molar fraction increased. There was a clear correlation between the ionic conductivity and the viscosity for the mixtures of the choline derivative and the acid. PFG-NMR measurements were carried out to investigate the diffusion behavior of protons. Although the acid and the hydroxyl group were indistinguishable by 1H NMR, the self-diffusion coefficient of the 1H of the hydroxyl group and the acid was larger than those of other 1H nuclei. This difference suggests that a fast intermolecular proton transfer exists between the hydroxyl group and the acid. the Owner Societies 2011.
- Yoshizawa-Fujita, Masahiro,Kousa, Yuri,Kidena, Koh,Ohira, Akihiro,Takeoka, Yuko,Rikukawa, Masahiro
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- Structural Engineering and Optimization of Zwitterionic Salts for Expeditious Discovery of Thermoresponsive Materials
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This work reported the discovery of N-triflimide (NTf)-based zwitter-ionic liquids (ZILs) that exhibit UCST-type phase transitions in water, and their further structural optimization in finetuning polarity to ultimately afford newfangled thermosensitive materials carrying attractive and biocompatible Tc values that clearly demonstrated the true value of the tunability of ZIL structure. This research established that with non-aromatic, acyclic ZILs as small-molecule thermoresponsive materials, their mixing and de-mixing with water triggered by temperatures are entirely reversible.
- Chen, Chien-Yuan,Chen, Jin-Syuan,Chu, Yen-Ho
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- Expanding the structural diversity of hydrophobic ionic liquids: physicochemical properties and toxicity of Gemini ionic liquids
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Ionic liquids (ILs) have been labeled as a promising green alternative to traditional materials; however, many ILs have been discovered to be toxic, especially hydrophobic ILs (HILs). HILs are limited in their structural diversity as most are composed of heteroaromatic cations with long alkyl chains and paired with [BF4], [PF6], or [NTf2] anions. This study aims to diversify HILs by synthesizing two sets of HILs with unique cations and anions. The first set of HILs contain cholinium- and dicholinium-based cations paired with the [NTf2] anion. The [DC-ether] cation is identified as a promising cation and is paired with an array of asymmetric bis(sulfonyl)amide anions to form the second set of HILs. In total, twenty HILs are synthesized. Each HIL is characterized using traditional physicochemical techniques and is evaluted for toxicity usingin vitroandin vivomethods.
- Berdusco, Nicole,Bertz, Colin,Mecozzi, Sandro,Padilla, Marshall S.
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supporting information
p. 4375 - 4385
(2021/06/28)
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- NH3absorption in Br?nsted acidic imidazolium- And ammonium-based ionic liquids
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This paper reports the NH3 solubilities and absorption mechanisms in the imidazolium- and ammonium-based ionic liquids. The cations were 1-methyl-3-(4-sulfobutyl)-imidazolium, 1-(2-hydroxyethyl)-3-methylimidazolium, 1-ethyl-3-methyl-imidazolium, N-carboxymethyl-N,N,N-trimethylammonium, N-(2-hydroxyethyl)-N,N,N-trimethylammonium, and N-butyl-N,N,N-trimethylammonium, whereas the anions were bis(trifluoromethanelsulfonyl)amide, tris(pentafluoroethyl)trifluorophosphate, trifluoromethylsulfonate, and hydrogensulfate. The Br?nsted acidic ionic liquids, consisting of sulfo and carboxy groups and hydrogensulfate anion, absorbed larger amounts of NH3, followed by the hydroxy-functionalized and nonfunctionalized ionic liquids. The NMR and Raman spectra indicated that the Br?nsted acidic ionic liquids absorbed NH3 as both the molecular ammonia (physical absorption) and the ammonium cation (chemical absorption). Although the hydroxy group strongly interacted with NH3, the hydroxy-functionalized ionic liquids dissolved NH3 only physically, similar to the nonfunctionalized ionic liquids. In conclusion, the chemical absorption brought about the higher NH3 solubilities in the Br?nsted acidic imidazolium- and ammonium-based ionic liquids. This journal is
- Makino, Takashi,Kanakubo, Mitsuhiro
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p. 20665 - 20675
(2020/12/28)
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- Cleaner enzymatic production of biodiesel with easy separation procedures triggered by a biocompatible hydrophilic ionic liquid
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The great challenges of modern industry and the environment make it important to develop sustainable energy resources with low cost. In this work, a cleaner enzymatic procedure for biodiesel production was developed through the utilization of a biocompatible and hydrophilic ionic liquid [Choline][H2PO4]. This ionic liquid can be synthesized from cheap raw materials through simple neutralization procedures, and it has been proved to be well biocompatible. The utilization of this ionic liquid in Novozym 435 catalyzed biodiesel production makes the reaction and work-up procedures very simple, because its hydrophilicity can lead to the implementation of a pseudo homogeneous reaction and then heterogeneous separation. Various oil resources such as triolein, sunflower oil and castor oil can all be converted to biodiesels with high yields. After the completion of reaction, both the ionic liquid and Novozym 435 can be recycled and reutilized for at least five cycles without a significant activity decrease. In addition, this reaction system can be conveniently scaled up to the multi-gram level with high efficiency and feasible separation. Overall, the above mentioned benefits make this ionic liquid based enzymatic system cleaner for the production of biodiesel and promising for further industrial applications.
- Chen, Qianhan,Cheng, Shuang,Fan, Dongshuang,Feng, Wanlu,Guo, Yuanyang,Li, Lingjun,Li, Zhiyong,Wang, Jianji,Zhu, Anlian
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p. 1944 - 1951
(2020/04/09)
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- ONIUM SALT HAVING ISOCYANATE GROUP AND IONIC POLYMER CONTAINING THE ONIUM SALT, AND ANTISTATIC AGENT CONTAINING THE SAME
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PROBLEM TO BE SOLVED: To provide a new onium salt which can impart antistatic properties to a resin and an ionic polymer having a structure of the onium salt as a partial skeleton, and an antistatic agent containing the ionic polymer, and to provide an antistatic agent which shows less lowering of antistatic properties even by water immersion treatment and a resin composition. SOLUTION: There are provided onium salt represented by formula (1); an ionic polymer obtained by reaction of an acrylic polymer having a hydroxyl group and the onium salt represented by formula (1); and an antistatic agent containing the ionic polymer. In formula (1), L represents an alkylene group which may have a substituent or an arylene group which may have a substituent; A- represents anion which has a fluorine atom; B+ represents ammonium cation, pyridinium cation, imidazolium cation or phosphonium cation; and D represents O, NH or S. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0131
(2018/10/19)
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- Functionalized choline chloride ionic liquid, preparation method thereof and use in electrochemical energy storage device
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The present invention discloses a process for preparing a functionalized choline chloride ionic liquid as defined in formula (I), and thereof use in an electrochemical energy storage device, as an electrolyte solution or an additive for a lithium ion battery and a supercapacitor. The ionic liquid electrolyte material has better biocompatibility, flame retardance, high ionic conductivity, low viscosity, and wide electrochemical window. wherein R1 is selected from the group consisting of: (CH2═CH—(CH2)n)—, CN(CH2)n—, or R23Si—; R2 is selected from CH3—(CH2)m—, n is an integer selected from 1 to 3, m is an integer selected from 0 to 2; or one of R2 is (CH3)3Si—O—. Anion A in Formula I is selected from the group consisting of: Cl?, Br?, I?, BF4?, NO3?, SO42?, CF3COO?, CF3SO3?, (CF3SO2)2N?, PF6?, BF2C2O4?, or B(C2O4)2?.
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(2017/09/02)
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- With three alkoxy silyl alkyl onium salt
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An onium salt represented by formula (1) (In the formula: A- represents an anion; and the remainder of the formula represents a quaternary onium cation (therein, Q+ represents a nitrogen cation or a phosphorous cation; R1-R3 represent C1-6 alkyl groups, and the terminals of R1 and R2 may bond to form a pyrrolidine ring, a piperidine ring, a pyridine ring, a phosphorane ring, a phosphorinane ring or a phosphorin ring; if a pyridine ring or a phosphorin ring is formed then R3 will not be present; R4 represents a C1-4 alkyl group; D represents CH2, CH(CH3) or CH(CH3)CH2; E represents NH or a sulfur atom; m is an integer in the range of 0-3, and n is an integer in the range of 1-4).
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Paragraph 0071
(2017/01/12)
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- Onium salt, acrylic acid copolymer containing onium salt, and antistatic agent containing the same
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The present invention provides an onium salt, an acrylic acid copolymer containing the onium salt, and an antistatic agent containing the same capable of imparting excellent antistatic properties to a resin. The solution is an onium salt of formula (1), a
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Paragraph 0098
(2017/02/24)
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- IONIC COMPOUNDS HAVING A SILYLOXY GROUP
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There is provided an ionic compound having attached thereto a silyloxy group. There is also provided methods of making this ionic compound as well as electrolytes, electrochemical cells and capacitors comprising this ionic compound.
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Paragraph 0239; 0240; 0241; 0242
(2015/04/15)
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- Selective Single-Step Separation of a Mixture of Three Metal Ions by a Triphasic Ionic-Liquid-Water-Ionic-Liquid Solvent Extraction System
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In a conventional solvent extraction system, metal ions are distributed between two immiscible phases, typically an aqueous and an organic phase. In this paper, the proof-of-principle is given for the distribution of metal ions between three immiscible phases, two ionic liquid phases with an aqueous phase in between them. Three-liquid-phase solvent extraction allows separation of a mixture of three metal ions in a single step, whereas at least two steps are required to separate three metals in the case of two-liquid-phase solvent extraction. In the triphasic system, the lower organic phase is comprised of the ionic liquid betainium- or choline bis(trifluoromethylsulfonyl)imide, whereas the upper organic phase is comprised of the ionic liquid trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide. The triphasic system was used for the separation of a mixture of tin(II), yttrium(III), and scandium(III) ions. Triple crown: A novel triphasic extraction system for the separation of metals consisting of two ionic liquids and an aqueous phase is presented. The triphasic system allows the separation of three metals in one single step, whereas at least two steps are necessary to separate three metals in conventional biphasic extraction systems.
- Vander Hoogerstraete, Tom,Blockx, Jonas,Decoster, Hendrik,Binnemans, Koen
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p. 11757 - 11766
(2015/08/11)
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- Silylated quaternary ammonium salts-ionic liquids with hydrophobic cations
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Another class of ionic liquids was obtained by a combination of bis(perfluoroalkylsulfonyl)amide anions and O-silylated choline like cations. The protection of the hydrophilic hydroxyl group of hydroxyalkyl substituted quaternary ammonium salts with a trialkylsilyl group changes cations' properties from hydrophilic to hydrophobic; both constituents (cations and anions) of resulting ionic liquids have a hydrophobic character. Their essential physical and chemical properties were investigated. Moderate viscosity and conductivity of ionic liquids follow the Vogel-Tammann-Fulcher model of their dependency on the temperature. All ionic liquids show similar electrochemical stability as anticipated from CV measurements. The cathodic stability for most compounds is below 0 V vs. Li/Li+, and anodic decomposition starts typically over more than 5 V vs. Li/Li+. These properties suggest that these ionic liquids have potential for the preparation of electrolytes for high voltage lithium batteries. This journal is
- Ko?elj, Matja?,Guerfi, Abdelbast,Zaghib, Karim
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supporting information
p. 15964 - 15971
(2014/12/11)
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- Homogeneous liquid-liquid extraction of neodymium(iii) by choline hexafluoroacetylacetonate in the ionic liquid choline bis(trifluoromethylsulfonyl)imide
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The ionic liquid choline bis(trifluoromethylsulfonyl)imide, [Chol][Tf 2N], was used for the extraction of neodymium(iii), in combination with choline hexafluoroacetylacetonate, [Chol][hfac], as the extractant. The binary mixture of [Chol][Tf2N] and water shows temperature-dependent phase behavior, with an upper critical solution temperature of 72 °C. A novel extraction technique, homogeneous liquid-liquid extraction (HLLE), was applied to this solvent system. HLLE is based on the use of thermomorphic solvent mixtures and has the advantage of forming a homogeneous phase during mixing. Extraction is not kinetically hindered by an interface and the extraction equilibrium is reached faster than in the case of heterogeneous mixing in conventional solvent extraction. Several extraction parameters were studied for the extraction of neodymium(iii) with [Chol][hfac]: temperature, pH, extractant concentration and loading of the ionic liquid phase. A speciation study was performed to determine the stoichiometry of the extracted neodymium(iii) complex and a plausible extraction mechanism is proposed. Neodymium is extracted as a tetrakis hexafluoroacetylacetonate complex with one choline cation as counter ion. The crystal structure of the extracted complex showed the presence of a coordination bond between the choline counter ion and the neodymium(iii) center, resulting in a coordination number of nine. The stripping of the loaded neodymium and the influence of acid and extractant concentrations on the phase behavior of the [Chol][Tf2N]-H 2O system were investigated. This journal is the Partner Organisations 2014.
- Onghena, Bieke,Jacobs, Jeroen,Van Meervelt, Luc,Binnemans, Koen
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p. 11566 - 11578
(2014/07/22)
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- METHOD FOR PREPARING DIALKYL CARBONATE
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The present invention provides a method for preparing dialkyl carbonate from urea or alkyl carbamate and alkyl alcohol using an ionic liquid comprising a cation, which produces a hydrogen ion, and a hydrophobic anion containing fluorine with high temperature stability in the presence of catalyst containing a metal oxide or hydrotalcite. Since the present invention can prepare dialkyl carbonate at a pressure lower than those of existing methods, it does not require an expensive pressure control device and peripheral devices for maintaining high pressure including the installation cost. It is also the method for preparing a dialkyl carbonate with high yield, thus improving economical efficiency. Moreover, the method of the present invention hardly produces any waste during the process and is thus an eco-friendly method.
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Page/Page column 10-11
(2011/02/24)
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- Use of functionalized onium salts as a soluble support for organic synthesis
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The invention relates to the use of a onium salt functionalized by at least one organic function, as a soluble support, in the presence of at least one organic solvent, for organic synthesis of a molecule, in a homogenous phase, by at least one transformation of said organic function. The onium salt enables the synthesized molecule to be released. The onium salt is present in liquid or solid form at room temperature and corresponds to formula A1+, X1?, wherein A1+ represents a cation and X1? represents an anion.
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Page/Page column 46
(2010/11/25)
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