L-butyl-3-methyl imidazolium hexafluorophosphate

According to the nature of their counter anion, ionic liquids (ILs) can dissolve a large amount of carbohydrates. In 2003, Moreau and co-workers reported the acid-catalyzed dehydration of fructose in a microbatch reactor at 80°C using l-butyl-3-methyl imidazolium tetrafluoroborate (BM1M BF4 ) (hydrophilic), and l-butyl-3-methyl imidazolium hexafluorophosphate (BMIM Fe (hydrophobic) (Scheme 10) [95]. 

Figure 9.5 Sammon map representing similarity of extraction ability of solvents (with respect to extraction of neutral organic compounds). The closer the points are on the map, the more similar are the corresponding solvents. Conventional solvents are designated by numbers, some representative numbers are m-xylene—35, butyl acetate—9, 1-octanol—40. The point marked BMImPF, represents l-butyl-3-methyl-imidazolium hexafluorophosphate ([C4CiIm][PF5]).

Triolo, A., Mandanici, A., Russina, O., Rodriguez-Mora, V., Cutroni, M., Hardacre, C., Nieuwenhuyzen, M., Bleif, H.-J., Keller, L., and Ramos, M. A., Thermodynamics, structure, and dynamics in room temperature ionic liquids The case of l-butyl-3-methyl Imidazolium hexafluorophosphate ([bmim][PFJ),7. Phys. Chem. B, 110,21357-21364, 2006. 

Antony, J. H., Mertens, D., Dolle, A., Wasserscheid, R, and Carper, W. R., Molecular reorientational dynamics of the neat ionic liquid l-butyl-3-methyl-imidazolium hexafluorophosphate by measurement of C nuclear magnetic relaxation data., Chem. Phys. Chem., 4, 588-594, 2003. 

The reaction does not occur obviously in three commonly used ILs l-butyl-3-methyl-imidazolium chloride ([BMIm]Cl), 1-butyl-3-methyl-imidazolium tetra-fluoroborate ([BMIm]BF4), l-butyl-3-methyl-imidazolium hexafluorophosphate ([BMIm]PF6). Only 3 % yield can be obtained in water, indicating PEG is the best solvent for the oxidation of secondary alcohols when using Co(II)/ZnO as catalyst. This is because PEG can form Co(II) complex (Co(II)L), which can activate 02 molecule and thereby promote the oxidation of organic compounds (Scheme 3.3) [26]. 

Figure 4.8 Cyclic voltammogram at the HRP/CNTs/l-butyl-3-methyl-imidazolium hexafluorophosphate-modified glassy carbon electrode in 0.1 M phosphate buffer solution (pH = 7.00] under nitrogen. The scan rate is 0.1 V/s. Reprinted with permission from Ref. [49]. Copyright 2004 American Chemical Society.

Green Electrochemistry, Fig. 4 l-Butyl-3-methyl imidazolium hexafluorophosphate, [bmimJlPFg]. m. p. = 10 °C... 

Seth, D., Chakraborty, A., Setua, P., and Sarkar, N. 2007. Interaction of ionic liquid with water with variation of water content in l-butyl-3-methyl-imidazolium hexafluorophosphate ([bmim][PFg])/TX-100/water ternary microemulsions monitored by solvent and rotational relaxation of Coumarin 153 and Coumarin 490. J. Chem. Phys. 126, 224512/1-224512/12. 

Ethyl (R)-3-hydroxybutyrate was prepared from the bioreducrion of ethyl acetoacetate using Acetobacter sp. (CCTCC M209061) cells in l-butyl-3-methyl-imidazolium hexafluorophosphate (C4mim PF6), an ionic liquid with good biocompatibility. The reaction was performed with a 1 1 ratio of buffer to C4mim PF6 and a substrate concentration of 55 mmol/L in buffer at pH 5.5. The reaction provided 90.8% conversion and more than 99% ee and was scaled to a 450 mL reaction volume. Also demonstrated in the paper was the successful recycle of the catalyst up to 10 times as an immobilized alginate [60]. 

Anthony, J. L., Maginn, E. J., and Brennecke, J. F, Solubilities and thermodynamic properties of gases in the ionic liquid l-n-butyl-3-methyl imidazolium hexafluorophosphate, /. Phys. Chem. B, 106, 7315, 2002. 

Phenothiazines contain positively charged amine groups in a mobile phase at low pH. Therefore, they are retained in the presence of ionic liquids through the combination of electrostatic interactions and hydrophobic effects. The effects of the concentration and the type of ionic liquid on the retention of the analyfes, peak symmetry, and efficiency were examined. The following trends increase the retention factor of the analytes and improve system efficiency 1-but-yl-3-methylimidazolium hexafluorophosphate > l-ethyl-3-methyl-imidazolium hexafluorophosphate > l-butyl-3-methylimidazolium chloride. 

Fig. 4.6 Behaviour of 7-(N,N-diethylamino)-4 -hydroxyflavylium tetrafluoroborate in biphasic systems constituted by aqueous solution (upper phase) and l-n-butyl-3-methyl-imidazolium hexafluorophosphate, [bmim] [PFe] (lower phase), upon pH jumps in the aqueous phase, a) pH=1.0 in the aqueous phase, AH+ species, before shaking b) after shaking, AH+ completely transfers to the ionic liquid c) upon addition of base and shaking for two minutes d) upon 10 minutes (shaking) e) upon addition of acid and shaking.

Bmim-PFg (l-butyl-3-methyl-lH-imidazolium hexafluorophosphate) was used as solvent and hydemim-PF (l-(2-hydroxyethyl)-3-methyl-l H-imidazolium hexafluorophosphate) was used as functionalized ionic liquid (so-called task-specific ionic liquid) (Scheme 16.5) [94],... 

Schroder, U., Wadhawan, J. D., Compton, R. G., Marken, F., Suarez, P. A. Z., Consorti, C. S., de Souza, R. F., and Dupont, J. [2000]. Water-induced accelerated ion diffusion voltammetric studies in l-methyl-3-[2,6-[S]-dimethylocten-2-yl]imidazolium tetrafluoroborate, l-butyl-3-methylimidazolium tetrafluoroborate and hexafluorophosphate ionic liquids. New J. Chem., 24, pp. 1009-1015. 

Interestingly, AfNashef et al. [10] reported the first evidence of the electrochemical generation of stable superoxide ions in the ionic liquid, l-n-butyl-3-methylimi-dazolium hexafluorophosphate ([C4mim][PF6]) (Scheme 18.2). However, the attachment of a methyl group to the carbon in the 2-position ([CqdmimjPFs]) led to an irreversible reduction process (Fig. 18.1) which in this work was attributed to the presence of impurities in the IL. The activity of the superoxide anions towards imidazolium-based ILs will be addressed below. 

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