1- ethyl-3-methylimidazolium tetrafluoroborate

As reported by Griengl and coworkers, benzaldehyde, decanal, undecanal, and dodecanal were reacted with HCN in a two-phase solvent system aqueous buffer and ionic liquids 1 -ethyl-3-methylimidazolium tetrafluoroborate, 1 -methyl-3-propylimidazolium tetrafluoroborate, and l-butyl-3-methyl-imidazolium tetrafluoroborate in the presence of the HNLs from Prunus amygdalus and Hevea brasiliensis. When compared with the use of organic solvents as the nonaqueous phase, the reaction rate was significantly increased and the enantioselectivity remained good [51]. 

LI4TISO12/EMIBF4-LIBF4/UC0O2 [19]. EMIBF4 1-ethyl-3-methylimidazolium tetrafluoroborate... 

Palm, R., H. Kurig, K. Tonurist, A. Janes, and E. Lust. 2012. Is the mixture of 1-ethyl-3-methylimidazolium tetrafluoroborate and 1-butyl-3-methylimidazoliumtetrafluorob-orate applicable as electrolyte in electrical double layer capacitors Electrochemistry Communications 22 203-206. 

Kanzaki R, Mitsugi T, Fukuda S, Fujii K, Takeuchi M, Soejima Y, Takamuku T, Yamaguchi T, Umebayashi Y, Ishiguro S (2009) Ion-ion interaction in room temperature ionic liquid 1-ethyl-3-methylimidazolium tetrafluoroborate studied by large-angle X-ray scattering experiment and molecular dynamics simulations. J Mol Liq 147 77... 

Fukaya, Y. Hayashi, K Wada, M. Ohno, H. (2008). Cellulose dissolution with polar ionic liquids under mild conditions required factors for anions. Green Chem., 10,44-46 Fukumoto, K. Yoshizawa, M. Ohno, H. (2005). Room temperatiue ionic liquids from 20 natural amino acids. /. Am. Chem. Soc., 127, 2398-2399 Fuller, J. Carlin, R. T. Osteryoimg, R. A. (1997). The room temperature ionic liquid 1-ethyl-3-methylimidazolium tetrafluoroborate electrochemical couples and physical properties. /, Electrochem. Soc., 144,3881-3886... 

Lipases from C. antarctica and P. cepacia showed higher enantioselectivity in the two ionic liquids l-ethyl-3-methylimidazolium tetrafluoroborate and l-butyl-3-methylimidazolium hexafluoroborate than in THE and toluene, in the kinetic resolution of several secondary alcohols [49]. Similarly, with lipases from Pseudomonas species and Alcaligenes species, increased enantioselectivity was observed in the resolution of 1 -phenylethanol in several ionic liquids as compared to methyl tert-butyl ether [50]. Another study has demonstrated that lipase from Candida rugosa is at least 100% more selective in l-butyl-3-methylimidazolium hexafluoroborate and l-octyl-3-nonylimidazolium hexafluorophosphate than in n-hexane, in the resolution of racemic 2-chloro-propanoic acid [51]. 

Recently, there has been considerable interest in developing molten salts that are less air and moisture sensitive. Melts such as l-methyl-3-butylimidazolium hexa-fluorophosphate [211], l-ethyl-3-methylimidazolium trifluoromethanesulfonate [212], and l-ethyl-3-methylimidazolium tetrafluoroborate [213] are reported to be hydro-phobic and stable under environmental conditions. In some cases, metal deposition from these electrolytes has been explored [214]. They possess a wide potential window and sufficient ionic conductivity to be considered for many electrochemical applications. Of course if one wishes to take advantage of their potential air stability, one loses the opportunity to work with the alkali and reactive metals. Further, since these ionic liquids are neutral and lack the adjustable Lewis acidity common to the chloroaluminates, the solubility of transition metal salts into these electrolytes may be limited. On a positive note, these electrolytes are significantly different from the chloroaluminates in that the supporting electrolyte is not intended to be electroactive. 

Zhang, S. et al.. Determination of physical properties for the binary systems of l-ethyl-3-methylimidazolium tetrafluoroborate + H2O, /. Chem. Eng. Data, 49, 760,2004. 

The imidazolium ions present in the CE BGE coat the capillary walls, generating an anodic EOF at low pH values (see Figure 6.5). The direction and magnitude of EOF essentially depend on pH of BGE. The change of direction of EOF fakes place befween pH 7.5 and 8 in fhe case of l-ethyl-3-methylimidazolium tetrafluoroborate ([C2Cjlm][BFJ) [44]. 

The ILs interact with surfaces and electrodes [23-25], and many more studies have been done that what we can cite. As one example, in situ Fourier-transform infrared reflection absorption spectroscopy (FT-IRAS) has been utilized to study the molecular structure of the electrified interphase between a l-ethyl-3-methylimidazolium tetrafluoroborate [C2Qlm][BF4] liquid and gold substrates [26]. Similar results have been obtained by surface-enhanced Raman scattering (SERS) for [C4Cilm][PFg] adsorbed on silver [24,27] and quartz [28]. 

The electrodeposition of silver from chloroaluminate ionic liquids has been studied by several authors [45-47], Katayama et al. [48] reported that the room-temperature ionic liquid l-ethyl-3-methylimidazolium tetrafluoroborate ([EMIM]BF4) is applicable as an alternative electroplating bath for silver. The ionic liquid [EMIM]BF4 is superior to the chloroaluminate systems since the electrodeposition of silver can be performed without contamination of aluminum. Electrodeposition of silver in the ionic liquids 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM]BF4) and l-butyl-3-methylimidazoliumhexafluorophosphate was also reported [49], Recently we showed that isolated silver nanoparticles can be deposited on the surface of the ionic liquid Tbutyl-3-methylimidazolium trifluoromethylsulfonate ([BMIMJTfO) by electrochemical reduction with free electrons from low-temperature plasma [50] (see Chapter 10). This unusual reaction represents a novel electrochemical process, leading to the reproducible growth of nanoscale materials. In our experience silver is quite easy to deposit in many air- and water-stable ionic liquids. 

Naphthol (0.35 mmol) was dissolved in 2 ml l-ethyl-3-methylimidazolium tetrafluoroborate containing benzyl bromide (1.5 eq) and KOH (2eq). The mixture was reacted in a microwave apparatus at 200°C 2 minutes, the product extracted with diethyl ether, and isolated in quantitative yield. 

Fuller J, Carlin R T, Osteryoung R A. The room temperature ionic liquid l-ethyl-3-methylimidazolium tetrafluoroborate Electrochemical couples and physical properties. J. Electrochem. Soc. 1997. 144, 3881-3886. 

Butyl-i-methylimidazolium tetrafluoroborate [BMIMJBF as the eco-friendly reaction medium could also be applied to the 0-acylation reaction of dehydroabietic acid chloride with 2-hydroxyethyl acrylate to yield dehydroabietic acid (2-acryloloxy) ethyl ester. This new method showed the advantages of mild reaction conditions, short reaction times, good yields, and recyclable solvent [121]. 

The use of ion-supported [bis(acyloxy)iodo]arene in the ionic liquid [emim]+[BF4] (l-ethyl-3-methylimidazolium tetrafluoroborate) in the presence of bromide anion or ion-supported TEMPO for the oxidation of primary and secondary alcohols is discussed in Section 5.3.3 [52,53],... 

Pahn et al. [34] employed the CV method to investigate the effect of the concentration of the addition of l-butyl-3-methylimidazolium tetrafluoroborate ([BMIM] [BFJ) in l-ethyl-3-methylimidazolium tetrafluoroborate ([EMIM][BF4]) electrolyte on the electrochemical characteristics for electrical double-layer capacitors (EDLCs). They found the concentration of [BM1M][BF4] has little influence on the... 

FIGURE 4.33 Reaction schemes at (a) —2.4 V and (b) at E >2V. (Reprinted from Electrochimica Acta, 125, Romann, T. et al., Snrface chemistry of carbon electrodes in l-ethyl-3-methylimidazolium tetrafluoroborate ionic tiqnid— An in situ infrared stndy, 183-190, Copyright 2014, with permission from Elsevier.)... 

Figure 5 Separation of poly(phenols) using (A) 1-ethyl-3-methyl-imidazolium tetrafluoroborate, (B) 1-butyl-3-methylimidazolium tetrafluoroborate, and (C) 1-ethyl-3-methylimidazolium hexafluoro-phosphate. The electrolyte solution was a 150mmoll concentration of the ionic liquid in water. The fused-silica capillary column was 50cm x 50 m ID, operating voltage 16kV, and absorbance detection at the anode end at 240nm. (Reprinted with permission from Yanes EG, Gratz SR, Baldwin MJ, Robison SE, and Stalcup AM (2001) Capillary electrophoretic application of 1-alkyl-3-methyl-imidazolium-based ionic liquids. Analytical Chemistry 73 3838-3844 American Chemical Society.)...

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