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.5) 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.

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

B2473 B2473 B2474 B2474 B2475 B2475
B2193 B2193 B2194 B2194 B2320 B2320
B2708 B2708 B2672 B2672 B2195 B2195
B3596 B3596 B2337 B2337 B3542 B3542
D3341 D3341 D3240 D3240 D3903 D3903
E0543 E0543 E0490 E0490 E0680 E0680
E0650 E0650 E0493 E0493 E0754 E0754
E0556 E0556 E0755 E0755 E0706 E0706
E0496 E0496 E0494 E0494 E0836 E0836
H1227 H1227 H1097 H1097 H1098 H1098
H1099 H1099 M1904 M1904 M2062 M2062
M2063 M2063 M1440 M1440
B2473 1-Butyl-2,3-dimethylimidazolium Chloride
B2474 1-Butyl-2,3-dimethylimidazolium Hexafluorophosphate
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
B3596 1-Butyl-3-methylimidazolium Tribromide
B2337 1-Butyl-3-methylimidazolium Trifluoromethanesulfonate
B3542 1-Butyl-3-methylimidazolium Trifluoro(trifluoromethyl)borate
D3341 1,3-Dimethylimidazolium Chloride
D3240 1,3-Dimethylimidazolium Dimethyl Phosphate
D3903 1,2-Dimethyl-3-propylimidazolium Iodide
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
E0706 1-Ethyl-3-methylimidazolium Tetrachloroferrate
E0496 1-Ethyl-3-methylimidazolium Tetrafluoroborate [for Molten Salt]
E0494 1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate
E0836 1-Ethyl-3-methylimidazolium Trifluoro(trifluoromethyl)borate
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
M2062 1-Methyl-3-n-octylimidazolium Chloride
M2063 1-Methyl-3-n-octylimidazolium Hexafluorophosphate
M1440 1-Methyl-3-propylimidazolium Iodide

Pyrrolidinium Salts

B2851 B2851 B3427 B3427 B3358 B3358
M2098 M2098
B2851 1-Butyl-1-methylpyrrolidinium Bis(trifluoromethanesulfonyl)imide
B3427 1-Butyl-1-methylpyrrolidinium Bromide
B3358 1-Butyl-1-methylpyrrolidinium Chloride
M2098 1-Methyl-1-propylpyrrolidinium Bis(trifluoromethanesulfonyl)imide

Pyridinium Salts

B2700 B2700 B3104 B3104 B3425 B3425
B3426 B3426 B2701 B2701 B1743 B1743
B1329 B1329 B2196 B2196 B3232 B3232
E0682 E0682 E0681 E0681 E0171 E0171
E0544 E0544
B2700 1-Butyl-4-methylpyridinium Bromide
B3104 1-Butyl-3-methylpyridinium Bromide
B3425 1-Butyl-3-methylpyridinium Chloride
B3426 1-Butyl-4-methylpyridinium Chloride
B2701 1-Butyl-4-methylpyridinium Hexafluorophosphate
B1743 1-Butylpyridinium Bromide
B1329 1-Butylpyridinium Chloride
B2196 1-Butylpyridinium Hexafluorophosphate
B3232 1-Butylpyridinium Tetrafluoroborate
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

A2274 A2274 C1966 C1966 M1660 M1660
T0054 T0054 T0055 T0055 T1124 T1124
H1047 H1047 T2564 T2564 T2679 T2679
T2680 T2680 T2314 T2314 T2761 T2761
A2274 Amyltriethylammonium Bis(trifluoromethanesulfonyl)imide
C1966 Cyclohexyltrimethylammonium Bis(trifluoromethanesulfonyl)imide
M1660 Methyltri-n-octylammonium Bis(trifluoromethanesulfonyl)imide
T0054 Tetrabutylammonium Bromide
T0055 Tetrabutylammonium Chloride
T1124 Tetrabutylphosphonium Bromide
H1047 Tributylhexadecylphosphonium Bromide
T2564 Tributyl(2-methoxyethyl)phosphonium Bis(trifluoromethanesulfonyl)imide
T2679 Tributylmethylammonium Bis(trifluoromethanesulfonyl)imide
T2680 Tributylmethylphosphonium Bis(trifluoromethanesulfonyl)imide
T2314 Triethylsulfonium Bis(trifluoromethanesulfonyl)imide
T2761 Trimethylpropylammonium Bis(trifluoromethanesulfonyl)imide

Pyridinium Compounds


Quaternary Ammonium Compounds


Phosphonium Compounds

Literature

1) T. Welton, Chem. Rev., 1999, 99, 2071 [DOI]; J. D. Holbrey, K. R. Seddon, Clean Prod. Proc., 1999, 1, 223; P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed., 2000, 39, 3772 [DOI]; T. Kitazume, Fain Kemikaru, 2001, 30(17), 5; T. Kitazume, Fain Kemikaru, 2001, 30(18), 15; R. Sheldon, Chem. Commun., 2001, 2399 [DOI]; D. Zhao, M. Wu, Y. Kou, E. Min, Catal. Today, 2002, 74, 157 [DOI].
2) M. Freemantle, Chem. & Eng. News, May 15, 2000, 78(20), 37.
3) R. T. Carlin, H. C. De Long, J. Fuller, P. C. Trulove, J. Electrochem. Soc., 1994, 141, L73 [DOI];
A. B. McEwen, S. F. McDevitt, V. R. Koch, J. Electrochem. Soc., 1997, 144, L84[DOI].
4) M. Watanabe, A. Noda, T. Kaneko, R. Kawano, Kagaku to Kogyo (Tokyo), 2001, 54, 281; A. Noda, M. Watanabe, Electrochim. Acta, 2000, 45, 1265 [DOI].
5) S. Hayashi, H. Hamaguchi, Chem. Lett., 2004, 33, 1590 [DOI]; H. Hamaguchi. Mirai Zairyo, 2005, 5, 29.



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