174501-65-6Relevant articles and documents
Volumetric properties of 1-butyl-3-methylimidazolium tetrafluoroborate- glucose-water systems
Jin, Hui X.,Chen, Han Y.
, p. 1134 - 1138 (2012)
Densities for 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF 4)-glucose-water solutions were determined at 298.15 K. The measured densities were used to calculate the apparent molar volumes of glucose (V Φ,S) and [Bmim]BFsu
Crystallographic Insights into the Behavior of Highly Acidic Metal Cations in Ionic Liquids from Reactions of Titanium Tetrachloride with [1-Butyl-3-Methylimidazolium][X] Ionic Liquids (X = Chloride, Bromide, Tetrafluoroborate)
Mishra, Manish Kumar,Kelley, Steven P.,Dilip, Meghna,Vaid, Thomas P.,Cordes, David B.,Griffin, Scott T.,Rogers, Robin D.
, p. 1764 - 1773 (2019)
Highly charged metal ions are difficult to investigate in weakly coordinating ionic liquids (ILs) because of the insolubility of their solid forms, but the molecular liquid TiCl4 offers a way to react tetravalent metal ions in an IL. Reactions of TiCl4 with 1-butyl-3-methylimidazolium ([C4mim]+)-based ILs containing chloride or bromide lead to mixtures of highly metastable amorphous solids and small amounts of crystalline chlorotitanate salts including [C4mim]2[TiCl6] and two polymorphs of [C4mim]2[Ti2Cl10] in a manner not well correlated with stoichiometry or anion identity. The reaction of TiCl4 with [C4mim][BF4] yields crystals of the mixed fluoro-chloro complex [C4mim]2[Ti4F6Cl12], indicating spontaneous reaction of the IL ions to generate HF in situ. These unusual behaviors are explained in terms of the exceptionally high acidity of Ti4+ and the unusual behavior of TiCl4 among metal halides as a nonpolar molecular compound.
Interaction between the ionic liquids 1-alkyl-3-methylimidazolium tetrafluoroborate and Pluronic P103 in aqueous solution: A DLS, SANS and NMR study
Parmar, A.,Bahadur, P.,Aswal, V. K.
, p. 137 - 143,7 (2012)
The effect of three ionic liquids (ILs) 1-alkyl 3-methyl imidazlolium tetraflouroborates (Cnmim BF4 n = 4, 6, 8) on micellar solutions of an ethylene oxide-propylene oxide block copolymer (PEO-PPO-PEO), Pluronic P103 was examined from scattering and NMR techniques. The ILs alter the cloud point and micelle size dependant on their alkyl chain length and the results are discussed in terms of their behavior as cosolvent/cosurfactant. Cloud point data support the hydrogen bonding between the imidazolium cation and P103 while dynamic light scattering (DLS) and small angle neutron scattering (SANS) reveal that presence of ionic liquid is not conducive to the micelle formation of P103. The selective nuclear Overhauser effect (NOESY) indicates that the PPO block of the P103 interacts with the alkyl group of the C nmim+ cation by hydrophobic interaction. Through this kind of interactions, Cnmim BF4 and P103 can form mixed micelles. This result indicates that the presence of ILs hinders the micelle formation of P103 in solution and promotes P103 to orient at air/water interface.
Thermodynamics of cesium complexes formation with 18-crown-6 in ionic liquids
Vendilo,Roenkkoemaeki,Hannu-Kuure,Lajunen,Asikkala,Krasovsky,Chernikova,Oksman,Lajunen,Tuomi,Popov
, p. 223 - 230 (2010)
Thermodynamic data for cesium complexes formation with 18-crown-6 (18C6, L) [Cs(18C6)]+ in N-butyl-4-methyl-pyridinium tetrafluoroborate ([BMPy][BF4], I), in 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM][BF4], II) and in 1-butyl-3-methylimidazolium dicyanamide ([BMIM][N(CN)2], III) were measured with NMR 133Cs technique at 23-50 °C. The stability of cesium complex in RTILs is estimated to be in the range between water and DMFA. Stability constants for [Cs(18C6)]+ are found to decrease as temperature is increasing. The following values for lgK(Cs+L) and ΔH(Cs+L) at 23 °C are determined: 2.6 (0.3), -47(1) kJ/mol (RTIL I); 2.8(0.3), -80(3) kJ/mol (RTIL II) and 3.03 (0.08), -47(2) kJ/mol (RTIL III). It is demonstrated that enthalpy change promotes complex formation while the corresponding change of entropy is negative and provides decomposition of [Cs(18C6)]+.
A facile and efficient route to hydrophilic ionic liquids through metathesis reaction performed in saturated aqueous solution
Chen, Zhengjian,Li, Zuopeng,Ma, Xiaoyun,Long, Panfeng,Zhou, Yun,Xu, Lin,Zhang, Shiguo
, p. 1303 - 1307 (2017)
The preparation of ionic liquids most often involves the use of organic solvents or hazardous chemicals, especially for hydrophilic ionic liquids prepared from metathesis reaction. In this study, the salting-out effect was proposed to promote the metathesis reaction to afford water-miscible ionic liquids. The reaction proceeds in aqueous solution saturated with an inorganic precursor salt. After reaction for only 10 min, the hydrophilic product can be easily obtained by spontaneous liquid-liquid phase-separation caused by the salting-out effect, followed by concentration and filtration. In this process, no organic solvents or hazardous chemicals are required, and the saturated solution and inorganic by-product can be easily reused and recycled respectively.
Preparation of 1-butyl-3-methylimidazolium salts and study of their phase behavior and intramolecular intractions
Gruzdev,Ramenskaya,Chervonova,Kumeev
, p. 1720 - 1727 (2009)
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.
Water effect on physicochemical properties of 1-butyl-3-methylimidazolium based ionic liquids with inorganic anions
Grishina,Ramenskaya,Gruzdev,Kraeva
, p. 267 - 272 (2013)
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.
Microwave assisted Suzuki reaction in N-butylpyridinium salts/water systems
Dos Santos Castro, Kelly L.,De Lima, Paulo G.,E Miranda, Leandro S.M.,De Souza, Rodrigo O.M.A.
, p. 4168 - 4171 (2011)
A solvent mixture containing the ionic liquid derived from 4-picoline (C4MPyBF4) and water was tested for the Suzuki-Miyaura reaction under microwave irradiation. This solvent system led to very high conversions and clean reactions. When compared with the other more common ionic liquid, such as C4MImBF4, C4MPyBF4 proved to be superior.
Effects of methylation at the 2 position of the cation ring on phase behaviors and conformational structures of imidazolium-based ionic liquids
Endo, Takatsugu,Kato, Tatsuya,Nishikawa, Keiko
, p. 9201 - 9208 (2010)
The proton at the 2 position of the cation ring in imidazolium-based ionic liquids (ILs) strongly interacts with anions; therefore, the methylation at this position (C(2) methylation) causes significant changes in the physicochemical properties of these liquids. We investigated the C(2) methylation effects on the phase behaviors and cation conformations of ILs by calorimetric and Raman spectroscopic measurements, focusing on the pairs of 1-butyl-3-methylimidazolium salt ([C4mim]X) and 1-butyl-2,3-dimethylimidazolium salt ([C 4C1mim]X), where X- is Cl-, Br -, I-, BF4-, and PF6 -. The melting and freezing points of all pairs increased after the C(2) methylation, as reported previously, and the reason for the increase was the overcompensation of the ??Strans decrease for the ??Htrans decrease. The C(2) methylation also affected the phase behaviors of the ILs. With Raman spectroscopic measurements, all cation conformations in crystalline phases were assigned to trans-trans (TT), gauche-trans (GT), or gauchea?2-trans (Ga?2T) conformers of the butyl group. Except in [C4C1mim]BF4, all crystal-crystal phase transitions of the present samples occurred accompanied by conformational changes among TT, GT, and Ga?2T. For the gas states of [C4mim]+ and [C4C1mim]+, DFT calculations showed that there were hardly any differences in the structures of the butyl group for each set of paired conformers or in the energetic orders among the conformers. On the other hand, the conformer adopted in the crystalline phase differed between [C4mim]X and [C4C 1mim]X. In addition, the population of the conformers in the liquid state also differed in each pair. The data from higher frequency Raman spectra suggested that the difference in cation conformation in each pair, for the crystalline and liquid states, was due to the shift in the position of the anion relative to that of the cation. By C(2) methylation, the relative distance between the anion and cation decreased for Cl-, Br-, and I- salts, but it increased for BF4- and PF 6- salts. ? 2010 American Chemical Society.
An improved preparation of 1,3-dialkylimidazolium tetrafluoroborate ionic liquids using microwaves
Namboodiri, Vasudevan V,Varma, Rajender S
, p. 5381 - 5383 (2002)
An efficient microwave protocol is described for the preparation of room temperature ionic liquids consisting of alkyl imidazolium cations bearing tetrafluoroborate as anions.
Activity coefficients at infinite dilution of organic compounds in 1-butyl-3-methylimidazolium tetrafluoroborate using inverse gas chromatography
Revelli, Anne-Laure,Mutetet, Fabrice,Turmine, Mireille,Solimando, Roland,Jaubert, Jean-Noel
, p. 90 - 101 (2009)
Activity coefficients at infinite dilution (γ∞) of organic compounds in the room-temperature ionic liquid 1-butyl-3- methylimidazolium tetrafluoroborate were determined using inverse gas chromatography from (303.35 to 332.55) K. Retention data
Synthesis of symmetrical and unsymmetrical 3,3-di(indolyl)indolin-2-ones under controlled catalysis of ionic liquids
Rad-Moghadam, Kurosh,Sharifi-Kiasaraie, Masoumeh,Taheri-Amlashi, Homayun
, p. 2316 - 2321 (2010)
Three ionic liquids, [BMIM][BF4] doped with 60 mol % of LiCl ([BMIM][BF4]-LiCl), N,N,N,N-tetramethylguanidinium trifluoroacetate (TMGT), and N,N,N,N-tetramethylguanidinium triflate (TMGTf) were found useful as catalyst solvents for controlled 3-indolylation of isatins. Our investigation revealed that the reaction between isatin and indoles in [BMIM][BF4]-LiCl or TMGTf media stops at the step of addition of the two components providing 3-indolyl-3-hydroxyindolin-2-ones while the ionic liquid TMGT runs the reaction further through accompanying Friedel-Crafts substitution to afford symmetrical 3,3-di(indol-3-yl)indolin-2-ones. To take advantage of the difference between the effects of these ionic liquids on?the reaction progress, we planned a two-step protocol for the efficient synthesis of unsymmetrical 3,3-di(indol-3-yl)indolin-2-ones.
Ionic liquid-assisted gelation of an organic solvent
Smith, Nicholas W.,Knowles, Joshua,Albright, John G.,Dzyuba, Sergei V.
, p. 83 - 87 (2010)
Tetrafluoroborate-containing ionic liquids allow for a room temperature gelation of dimethylsulfoxide, which contains an organogelator at below the minimum gelation concentration. The gel formation has no effect on the mobility of ions, as the conductivity values of ionic liquid-DMSO gels are virtually identical to those of ionic liquid-DMSO solutions.
Study of a novel gel electrolyte based on poly-(methoxy/hexadecyl- poly(ethylene glycol) methacrylate) co-polymer plasticized with 1-butyl-3-methylimidazolium tetrafluoroborate
Wang, Long,Zhu, Hua-Jun,Zhai, Wei,Cai, Feng,Liu, Xiao-Min,Yang, Hui
, p. 36357 - 36365 (2014)
Compared with traditional liquid electrolytes, solid polymer electrolytes possess higher reliability and safety but much lower ionic conductivity, which can be improved by incorporating plasticizers to form gel polymer electrolytes (GPEs). However, the commonly employed plasticizers are flammable organic solvents which may cause safety issues. Herein, ionic liquid 1-bultyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF4) is selected as the plasticizer to fabricate inflammable GPE due to its non-volatility and inflammability. The solid matrix is co-polymerized from methoxy-poly(ethylene glycol) methacrylate (MPEGM) and hexadecyl-poly(ethylene glycol) methacrylate (HPEGM). The effect of the electrolyte composition on its properties is systematically studied. The synthesized GPEs possess excellent thermal stability and exhibit relatively high ionic conductivity, among which the one named as PMH12-60, composed of 32 wt% MPEGM, 8 wt% HPEGM and 60 wt% [Bmim]BF4, presents an ionic conductivity comparable to liquid electrolytes, up to 1.13 × 10-3 S cm-1 at 30 °C. In addition, the GPE shows good compatibility with metallic lithium. Furthermore, the coin cell based on PMH12-60, with a LiFePO 4 cathode and a lithium anode shows a discharge capacity as high as 145 mA h g-1 and 158 mA h g-1 when cycled at 30 °C and 50 °C, respectively, under the cycling rate of 0.1 C. Moreover, no obvious capacity loss is observed after 30 cycles at both temperatures. This journal is the Partner Organisations 2014.
Ultrasound-assisted surfactant/ionic liquid aqueous two-phase system extraction prior to high performance liquid chromatography for the determination of tetracyclines in milk and honey samples
Antep, Hayriye Mine,Mumcu, Ta?k?n,Bostanci, Kamil,Seyhan Bozkurt, Serap,Merdivan, Melek
, p. 955 - 966 (2017)
In this work, an ultrasonic-assisted surfactant/ionic liquid aqueous two-phase system (ATPS) extraction method was developed to extract six tetracycline antibiotics from food samples before their chromatographic determination using high performance liquid chromatography. The ATPS was formed with 1-allyl-3-methyl-imidazolium bromide, Triton X-100, and dipotassium hydrogen phosphate. The parameters including type and amount of surfactant, ionic liquid and salt, pH of sample solution, and sonication time were optimized. Under the optimized conditions, linear calibration curves of the six tetracyclines were obtained in the range of 10–500 μg L?1 with > r2 = 0.990 (n = 9). The proposed green analytical extraction method was applied to the analysis of tetracycline antibiotics in milk and honey samples with recovery of 50%–110% and 68%–117%, respectively.
PET depolymerisation in supercritical ethanol catalysed by [Bmim][BF 4]
Nunes, Catia Santos,Vieira Da Silva, Michael Jackson,Cristina Da Silva, Danielle,Freitas, Adonilson Dos Reis,Rosa, Fernanda Andreia,Rubira, Adley Forti,Muniz, Edvani Curti
, p. 20308 - 20316 (2014)
Poly(ethylene terephthalate) (PET) was successfully depolymerised under supercritical ethanol. Robust conversion of 98 wt% from PET to diethylterephthalate (DET) was obtained by adding [Bmim][BF4], as catalyst, accompanied by reduction of depolymerization time from ca. 6 h to 45 min. DET formation in the depolymerization process was characterized by HPLC, 1H NMR, FTIR, TGA, DSC and SEM showing high purity and yield. The yields for different runs were determined by HPLC combined with interpolation from the standard/calibration curve. A 23 factorial design was employed to evaluate the effect of different inputs such as (i) reaction time after supercritical condition, (ii) volume of ionic liquid (VIL) and (iii) amount of PET in the yield of DET. By the analysis of variance (ANOVA), including F-test and P-values, it was found that reaction time and amount of PET inputs correspond, respectively, to 44% and 23% of the evaluated response. Another positive aspect showed by the factorial design is that the amount of catalyst was not significant in the process, and the depolymerization can be conducted successfully since a small amount (this study used VIL ranging 0.15 to 0.35 mL) is present in the reaction media. The method proposed in this paper is advantageous over others, reported in the literature, due to the lower reaction time required for PET depolymerization and the higher DET yield. This journal is the Partner Organisations 2014.
Quantum dots in which ionic liquids are ion-bonded and their preparation method
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Page/Page column 15, (2021/09/01)
A quantum dot particle in which an ionic liquid is ion-bonded is disclosed. The quantum dot particle includes a quantum dot having a core/shell nanostructure; and an ionic liquid compound represented by following Chemical Formula 1, bonded to the surface of the quantum dot, wherein the quantum dot and the ionic liquid compound form an ionic bond: wherein, R1 and R2 are each independently a branched or unbranched hydrocarbon group having 1 to 22 carbon atoms, and X? is a monovalent anion, wherein the hydrocarbon group includes a saturated or unsaturated group and may include one or more hetero atoms.
Validation of structural grounds for anomalous molecular mobility in ionic liquid glasses
Adonin, Nicolay Yu.,Bakulina, Olga D.,Fedin, Matvey V.,Ivanov, Mikhail Yu.,Kiryutin, Alexey S.,Prikhod’ko, Sergey A.
supporting information, (2021/10/01)
Ionic liquid (IL) glasses have recently drawn much interest as unusual media with unique physicochemical properties. In particular, anomalous suppression of molecular mobility in imi-dazolium IL glasses vs. increasing temperature was evidenced by pulse Electron Paramagnetic Resonance (EPR) spectroscopy. Although such behavior has been proven to originate from dynamics of alkyl chains of IL cations, the role of electron spin relaxation induced by surrounding protons still remains unclear. In this work we synthesized two deuterated imidazolium-based ILs to reduce electron–nuclear couplings between radical probe and alkyl chains of IL, and investigated molecular mobility in these glasses. The obtained trends were found closely similar for deuterated and proto-nated analogs, thus excluding the relaxation-induced artifacts and reliably demonstrating structural grounds of the observed anomalies in heterogeneous IL glasses.
