Ionic Liquids

Ionic liquids are salts composed of cations such as imidazolium ions, pyridinium ions and anions such as BF4, PF6 and are liquid at relatively low temperatures. Their characteristic properties include; (1) essentially no vapor pressure, (2) non-flammability, (3) high thermal stability, (4) relatively low viscosity, (5) liquid state over extended temperature ranges, (6) high ionic conductivity. Applications of ionic liquids with these features are being vigorously explored in various fields. When an ionic liquid is used as a reaction solvent, the solute is solvated by ions only. Thus, the reaction proceeds in an environment totally different from that when water or ordinary organic solvents are used and therefore, high selectivity is possible. To date application in the Friedel-Crafts reaction, Diels-Alder reaction, metal-catalyzed asymmetric synthesis and so forth, have been reported.1) Furthermore, some ionic liquids have low solubility in water and low polar organic solvents. By using this property, ionic liquids can be recovered and reused after reaction product is extracted with organic solvents. Recently, methods are being studied which reduce the load on the environment from the viewpoint of green chemistry.
Ionic liquids are receiving much attention as a superb solvent from the point of safety, separation/purification procedures, and recyclability.2) Ionic liquids are used not only as a reaction solvent but also electrochemically, for example, as electrolytes of rechargeable batteries.3) Watanabe and co-workers have developed a novel solid electrolyte in which an ionic liquid is confined in a network polymer called "ion gel".4) This ion gel is expected to contribute to solidification of various electrochemical systems and safety improvement as it exhibits exceedingly high ion-conductivity compared with conventional solid polymer electrolytes.
Recently, Hamaguchi and co-workers reported that 1-butyl-3-methylimidazolium tetrachloroferrate is magnetic ionic liquid. The new magnetic ionic liquid overcomes various problems of traditional magnetic fluids, and is expected to be applied to many fields including the use as a sealing agent for the motor axis.5)

Below shows the major ionic liquids. The melting points are shown as the reference value. These are not specification value. The salts that form liquid state at room temperature are given the description "liquid".

Imidazolium Salts

Pyrrolidinium Salts

Pyridinium Salts

Ammonium, Phosphonium, Sulfonium Salts

Imidazolium Salts

D3341 D3341 D3240 D3240 B2473 B2473
B2474 B2474 B3028 B3028 B2475 B2475
B2193 B2193 B2194 B2194 B2320 B2320
B2708 B2708 B2672 B2672 B2195 B2195
B2337 B2337 E0683 E0683 E0543 E0543
E0490 E0490 E0680 E0680 E0650 E0650
E0493 E0493 E0754 E0754 E0556 E0556
E0755 E0755 E0651 E0651 E0706 E0706
E0496 E0496 E0494 E0494 H1227 H1227
H1097 H1097 H1098 H1098 H1099 H1099
M1904 M1904 M1440 M1440
D3341 1,3-Dimethylimidazolium Chloride
D3240 1,3-Dimethylimidazolium Dimethyl Phosphate
B2473 1-Butyl-2,3-dimethylimidazolium Chloride
B2474 1-Butyl-2,3-dimethylimidazolium Hexafluorophosphate
B3028 1-Butyl-2,3-dimethylimidazolium Polyethylene Glycol Hexadecyl Ether Sulfate coated Lipase
B2475 1-Butyl-2,3-dimethylimidazolium Tetrafluoroborate
B2193 1-Butyl-3-methylimidazolium Bromide
B2194 1-Butyl-3-methylimidazolium Chloride
B2320 1-Butyl-3-methylimidazolium Hexafluorophosphate
B2708 1-Butyl-3-methylimidazolium Iodide
B2672 1-Butyl-3-methylimidazolium Tetrachloroferrate
B2195 1-Butyl-3-methylimidazolium Tetrafluoroborate
B2337 1-Butyl-3-methylimidazolium Trifluoromethanesulfonate
E0683 1-Ethyl-3-methylimidazolium 2-(2-Methoxyethoxy)ethyl Sulfate
E0543 1-Ethyl-3-methylimidazolium Bromide
E0490 1-Ethyl-3-methylimidazolium Chloride [for Molten Salt]
E0680 1-Ethyl-3-methylimidazolium Dicyanamide
E0650 1-Ethyl-3-methylimidazolium Ethyl Sulfate
E0493 1-Ethyl-3-methylimidazolium Hexafluorophosphate [for Molten Salt]
E0754 1-Ethyl-3-methylimidazolium Hydrogen Sulfate
E0556 1-Ethyl-3-methylimidazolium Iodide
E0755 1-Ethyl-3-methylimidazolium Methanesulfonate
E0651 1-Ethyl-3-methylimidazolium p-Toluenesulfonate
E0706 1-Ethyl-3-methylimidazolium Tetrachloroferrate
E0496 1-Ethyl-3-methylimidazolium Tetrafluoroborate [for Molten Salt]
E0494 1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate
H1227 1-Hexyl-3-methylimidazolium Bromide
H1097 1-Hexyl-3-methylimidazolium Chloride
H1098 1-Hexyl-3-methylimidazolium Hexafluorophosphate
H1099 1-Hexyl-3-methylimidazolium Tetrafluoroborate
M1904 1-Methyl-3-n-octylimidazolium Bromide
M1440 1-Methyl-3-propylimidazolium Iodide

Pyrrolidinium Salts

B2851 B2851
B2851 1-Butyl-1-methylpyrrolidinium Bis(trifluoromethanesulfonyl)imide

Pyridinium Salts

B3104 B3104 B2700 B2700 B2701 B2701
B1743 B1743 B1329 B1329 B2196 B2196
E0682 E0682 E0681 E0681 E0171 E0171
E0544 E0544
B3104 1-Butyl-3-methylpyridinium Bromide
B2700 1-Butyl-4-methylpyridinium Bromide
B2701 1-Butyl-4-methylpyridinium Hexafluorophosphate
B1743 1-Butylpyridinium Bromide
B1329 1-Butylpyridinium Chloride
B2196 1-Butylpyridinium Hexafluorophosphate
E0682 1-Ethyl-3-(hydroxymethyl)pyridinium Ethyl Sulfate
E0681 1-Ethyl-3-methylpyridinium Ethyl Sulfate
E0171 1-Ethylpyridinium Bromide
E0544 1-Ethylpyridinium Chloride

Ammonium, Phosphonium, Sulfonium Salts

C1966 C1966 M1660 M1660 T0054 T0054
T0055 T0055 T1124 T1124 T2564 T2564
T2314 T2314
C1966 Cyclohexyltrimethylammonium Bis(trifluoromethanesulfonyl)imide
M1660 Methyltri-n-octylammonium Bis(trifluoromethanesulfonyl)imide
T0054 Tetrabutylammonium Bromide
T0055 Tetrabutylammonium Chloride
T1124 Tetrabutylphosphonium Bromide
T2564 Tributyl(2-methoxyethyl)phosphonium Bis(trifluoromethanesulfonyl)imide
T2314 Triethylsulfonium Bis(trifluoromethanesulfonyl)imide

Pyridinium Compounds


Quaternary Ammonium Compounds


Phosphonium Compounds

Literature

1)T. Welton, Chem. Rev., 1999, 99, 2071;
J. D. Holbrey, K. R. Seddon, Clean Prod. Proc., 1999, 1, 223; P. Wasserscheid, et al., Angew. Chem. Int. Ed., 2000, 39, 3772; T. Kitazume, Fain Kemikaru (Fine Chemical), 2001, 30(17), 5; idem, ibid., 2001, 30(18), 15; R. Sheldon, Chem. Commun., 2001, 2399; D. Zhao, M. Wu, Y. Kou, E. Min, Catal. Today, 2002, 74, 157.
2)M. Freemantle, Chem. & Eng. News, May 15, 2000, 78(20) 37.
3)R. T. Carlin, et al., J. Electrochem. Soc., 1994, 141, L73; A. B. McEwen, et al., J. Electrochem. Soc., 1997, 144, L84.
4)M. Watanabe, et al., Kagaku to Kogyo, 2001, 54, 281; A. Noda, et al., Electrochim. Acta, 2000, 45, 1265.
5)S. Hayashi, H. Hamaguchi, Chem. Lett., 2004, 33, 1590.


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