Advanced Technology And Industrial Co., Ltd
Comprehensive application list of Ionic Liquids
Acros Organics latest additions
Reference
Product Name
Uses and Properties
35408
1-Bthyl-3-methylimidazolium chloride
Uses:
Ionic liquid synthesis and chlorination reactions. Preparation of [C
2
mim] [PtCl
4
] and [C
2
mim]2 [IrCl
6
]
1
stationary phase in GC
2
(1) Hasan, M.; Kozhevnikov, I. V.; Siddiqui, M. R. H.; Femoni, C.; Steiner, A.; Winterton, N.; Inorg. Chem.; 2001; 40; 795-800.
(2) Poole, C. F.; Butler, H. T.; Coddens, M. E.; Dhanesar, S. C.; Pacholec, F.; J. Chromat.; 1984; 289; 299-320.
35409
1-Butyl-3-methylimidazolium chloride
Uses:
Ionic liquid synthesis and chlorination reactions. Stationary phases
1
Cycloaddition of CO
2
to propylene oxide
2
Preparation of [C
4
mim]
2
[PtC
6
], [C
2
mim]
2
[PtCl
4
]
3
(1) Armstrong, D. W.; He, L.; Liu, Y.-S.; Anal. Chem.; 1999; 71; 3873-3876.
(2) Peng, J.; Deng, Y.; New J. Chem.; 2001; 25; 639-641.
(3) Hasan, M.; Kozhevnikov, I. V.; Siddiqui, M. R. H.; Femoni, C.; Steiner, A.; Winterton, N.; Inorg. Chem.; 2001; 40; 795-800.
35410
1-Hexyl-3-methylimidazolium chloride
Uses:
Ionic liquid synthesis and chlorination reactions.
35411
1-Ethyl-2,3-dimethylimidazolium chloride
Properties:
DSC
1
, TGA
1
.
Uses:
Ionic liquid synthesis and chlorination reactions. Particularly suitable for use in strongly basic conditions.
(1) Ngo, H. L.; LeCompte, K.; Hargens, L.; McEwen, A. B.; Thermochim. Act.; 2000; 357-358; 97-102.
35412
1-Butyl-2,3-dimethylimidazolium chloride
Uses:
Ionic liquid synthesis and chlorination reactions. Particularly suitable for use in strongly basic conditions.
35414
1-Ethylpyridinium chloride
Uses:
Ionic liquid synthesis and chlorination reactions.
35421
1-Butyl-3-methylimidazolium tetrafluoroborate
Properties:
Water-miscible ionic liquid at room-temperature, partially miscible at 5 ºC. Electrochemical window
5,6
. Diffusion coefficient
5
. Viscosity
4,6,7
. Density
4,6,7
. Decomposition
1
. Conductivity
1,4,7
. Polarity
8
. NMR
2
. Melting point
4,7
. DSC, TGA
2
. Solubilities
4,7
. IR
9
. ATR-IR study of CO
2
10
. Water content
4
. Influence of water on voltammetry
5
Uses:
Heck
11,12
. Reduction of aldehydes
13
. Sn-reagents
14
. Zn-reactions
15
. Wittig reaction
16
. Alkylation, allylation
17,18-20
. Alkoxycarbonylation
21
. Cycloaddition of CO
2
to propylene oxide
22
. Beckmann rearrangement
23
. Stille
24
. Ring opening of epoxides
25
. Hydrogenation
3,7,9,26-29
. Isomerisation
27
. Hydroformylation
27
. Diels-Alder
30,31
. Suzuki reaction
3
. Hydroesterification
32
. Cyclodimerisation
33
. Hydrodimerisation
4
. Dediazonisation
34
.
(1) Doyle, M.; Choi, S. K.; Proulx, G.; J. Electrochem. Soc.; 2000; 147; 34-37.
(2) Holbrey, J. D.; Seddon, K. R.; J. Chem. Soc., Dalton Trans.; 1999; 2133-2139.
(3) Dyson, P. J.; Ellis, D. J.; Lincoln, R.; Russel, K.; Smith, P. J.; Welton, T.; ; 2000; 161-168.
(4) Dullius, J. E. L.; Suarez, P. A. Z.; Einloft, S.; de Souza, R. F.; Organometal.; 1998; 17; 815-819.
(5) Schröder, U.; Wadhawan, J. D.; Compton, R. G.; Marken, F.; Suarez, P. A. Z.; Consorti, C.; De Souza, R. F.; Dupont, J.; New J. Chem.; 2000; 24; 1009-1015.
(6) Rooney, D. W.; Seddon, K. R.; Handbook of solvents; Wypych, G., Ed.; William Andrew; Toronto; 2000.
(7) Dupont, J.; Consorti, C. S.; Spencer, J.; J. Braz. Chem. Soc.; 2000; 11; 337-344.
(8) Carmichael, A. J.; Seddon, K. R.; J. Phys. Org. Chem.; 2000; 13; 591-595.
(9) Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; de Souza, R. F.; Dupont, J.; Polyhedron; 1996; 15; 1217-1219.
(10) Kazarian, S. G.; Briscoe, B. J.; Welton, T.; Chem. Commun.; 2000; 20; 2047-2048.
(11) Xu, L.; Chen, W.; Ross, J.; Xiao, J.; Org. Letts.; 2000; 3; 295-297.
(12) Xu, L.; Chen. W.; Xiao, J.; Organometal.; 2000; 19; 1123-1127.
(13) Kabalka, G. W.; Malladi, R. R.; Chem. Commun.; 2000; 22; 2191-2191.
(14) McCluskey, A.; Garner, J.; Young, D. J.; Caballero, S.; Tetrahedr. Letts.; 2000; 8147-8151.
(15) Kitazume, T.; Kasai, K.; Green Chem.; 2001; 3; 30-32.
(16) Le Boulaire, V.; Gree, R.; Chem. Commun.; 2000; 22; 2195-2196.
(17) Earle, M. J.; Seddon, K. R.; Pure Appl. Chem.; 2000; 72; xxxx-xxxx.
(18) Gordon, C. M.; McCluskey, A.; Chem. Commun.; 1999; 1431-1432.
(19) Chen, W.; Xu, L.; Chatterton, C.; Xiao, J.; Chem. Commun.; 1999; 1247-1248.
(20) Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H.; Chem. Commun.; 2000; 1695-1696.
(21) Mizushima, E.; Hayashi, T.; Tanaka, M.; Green Chem.; 2001; 3; 76-79.
(22) Peng, J.; Deng, Y.; New J. Chem.; 2001; 25; 639-641.
(23) Peng, J.; Deng, Y.; Tetrahedr. Letts.; 2001; 42; 403-405.
(24) Handy, S. T.; Zhang, X.; Org. Letts.; 2001; 3; 233-236.
(25) Song, C. E.; Oh, C. R.; Roh, E. J.; Choo, D. J.; Chem. Commun; 2000; 18; 1743-1744.
(26) Monteiro, A. L.; Zinn, F. K.; de Souza, R. F.; Dupont, J.; Tetrahedr. Asym.; 1997; 8; 177-179.
(27) Chauvin, Y.; Mussmann, L.; H., O.; Angew. Chem. Int. Ed. Engl.; 1995; 34; 2698.
(28) Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; de Souza, R. F.; Dupont, J.; Inorg. Chim. Acta; 1997; 255; 207-209.
(29) Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T.; Chem. Commun.; 1999; 25-26.
(30) Fischer, T.; Sethi, A.; Welton, T.; Woolf, J.; Tetrahedr. Lett.; 1999; 40; 793-795.
(31) Earle, M. J.; McCormac, P. B.; Seddon, K. R.; Green Chem.; 1999; 1; 23-25.
(32) Zim, D.; de Souza, R. F.; Dupont, J.; Monteiro, A. L.; Tetrahedr. Letts.; 1998; 39; 7071-7074.
(33) Ligabue, R. A.; Dupont, J.; de Souza, R. F.; J. Mol. Catal. A: Chem.; 2001; 169; 11-17.
(34) Laali, K. K.; Gettwert, V. J.; J. Fluor. Chem.; 2001; 107; 31-34.
Water-Immiscible Ionic Liquids
Reference
Product Name
Uses and Properties
35417
1-Butyl-3-methylimidazolium hexafluorophosphate
Properties:
Electrochemical window
5,6
. Influence of water on voltammetry
5
. Diffusion Coefficieny
5
. Polarity
7
. Viscosity
6,8-10
. Density
6,9-11
. NMR
4,12
. Melting point
9,10,13
. Solubilities
8-10,14
. Conductivity
9,10
. IR
15
Structure:
16
Uses:
Living radical polymerisation
17
. Hydrodimerisation
10
. Cyclodimerisation
18
. Friedel-Crafts
19
. Allylic substitution
20
. Allylation
21,22
. Complete synthesis of pravadoline
22
. Alkylation
22
. Reactions of Zn-reagents
23
. Coupling reactions
24
. Diels-Alder
25
. Heck
26,27
. Membranes
28
. Hydrogenation
3,15,29-32
. Ring-opening of epoxides
33
. Oxidation of aldehydes
34
. Epoxidation
35
. Deazonisation
36
. Extraction technology
2,8,12,14,37-40
. Biotransformation
1,41
. Stationary phases
42
. Isomerisation
31
. Hydroformylation
4,31,43
. Alkoxycarbonylation
44
. Cycloaddition of CO
2
to propylene oxide
45
. Behaviour with CO
2
46,47
.
(1) Cull, S. G.; Holbrey, J. D.; Vargas-Mora, V.; Seddon, K. R.; Lye, G. J.; Biotech. Bioeng.; 2000; 69; 227-233.
(2) Visser, A. E.; Swatloski, R. P.; Rogers, R. D.; Green Chem.; 2000; 2; 1-4.
(3) Cho, T. H.; Fuller, J.; Carlin, R. T.; High Temp. Mat. Proc.; 1998; 2; 543-558.
(4) Keim, W.; Vogt, D.; Waffenschmidt, H.; Wasserscheid, P.; J. Catal.; 1999; 186; 481-484.
(5) Schröder, U.; Wadhawan, J. D.; Compton, R. G.; Marken, F.; Suarez, P. A. Z.; Consorti, C.; De Souza, R. F.; Dupont, J.; New J. Chem.; 2000; 24; 1009-1015.
(6) Rooney, D. W.; Seddon, K. R.; Handbook of solvents; Wypych, G., Ed.; William Andrew; Toronto; 2000.
(7) Carmichael, A. J.; Seddon, K. R.; J. Phys. Org. Chem.; 2000; 13; 591-595.
(8) Fadeev, A. G.; Maegher, M. M.; Chem. Commun.; 2001, 295-296.
(9) Dupont, J.; Consorti, C. S.; Spencer, J.; J. Braz. Chem. Soc.; 2000; 11; 337-344.
(10) Dullius, J. E. L.; Suarez, P. A. Z.; Einloft, S.; de Souza, R. F.; Organometal.; 1998; 17; 815-819.
(11) Hasan, M.; Kozhevnikov, I. V.; Siddiqui, M. R. H.; Femoni, C.; Steiner, A.; Winterton, N.; Inorg. Chem.; 2001; 40; 795-800.
(12) Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Griffin, S. T.; Rogers, R. D.; Ind. Eng. Chem. Res.; 2000; 39; 3596-3604.
(13) Holbrey, J. D.; Seddon, K. R.; Clean Prod. Proc.; 1999; 1; 223-236.
(14) Blanchard, L. A.; Brennecke, J. F.; Ind. Eng. Chem. Res.; 2001; 40; 287-292.
(15) Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; de Souza, R. F.; Dupont, J.; Polyhedron; 1996; 15; 1217-1219.
(16) Gannon, T. J.; Law, G.; Watson, P. R.; Carmichael, A. J.; Seddon, K. R.; Langmuir; 1999; 15; 8429-8434.
(17) Carmichael, A. J.; Haddleton, D. M.; Bon, S. A. F.; Seddon, K. R.; Chem. Comm.; 2000; 1237-1238.
(18) Ligabue, R. A.; Dupont, J.; de Souza, R. F.; J. Mol. Catal. A: Chem.; 2001; 169; 11-17.
(19) Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H.; Chem. Commun.; 2000; 1695-1696.
(20) Toma, S.; Gotov, B.; Kmentova, I.; Solcaniova, E.; Green Chem.; 2000; 2; 149-151.
(21) Gordon, C. M.; McCluskey, A.; Chem. Commun.; 1999; 1431-1432.
(22) Earle, M. J.; Seddon, K. R.; Pure Appl. Chem.; 2000; 72; xxxx-xxxx.
(23) Kitazume, T.; Kasai, K.; Green Chem.; 2001; 3; 30-32.
(24) Howarth, J.; James, P.; Dai, J.; Tetrahedr. Letts.; 2000; 41; 10319-10321.
(25) Earle, M. J.; McCormac, P. B.; Seddon, K. R.; Green Chem.; 1999; 1; 23-25.
(26) Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R.; Org.Lett.; 1999; 1; 997-1000.
(27) Howarth, J.; Dallas, A.; Molecules; 2000; 5; 851-855.
(28) Carlin, R. T.; Fuller, J.; Chem. Commun.; 1997; 1345-1346.
(29) Brown, R. A.; Pollet, P.; McKoon, E.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G.; J. Am. Chem. Soc.; 2001; 123; 1254-1255.
(30) Liu, F.; Abrams, M. B.; Baker, R. T.; Tumas, W.; Chem. Comm.; 2001; 433-434.
(31) Chauvin, Y.; Mussmann, L.; H., O.; Angew. Chem. Int. Ed. Engl.; 1995; 34; 2698.
(32) Dupont, J.; Suarez, P. A. Z.; Umpierre, A. P.; de Souza, R. F.; J. Braz. Chem. Soc.; 2000; 11; 293-297.
(33) Song, C. E.; Oh, C. R.; Roh, E. J.; Choo, D. J.; Chem. Commun; 2000; 18; 1743-1744.
(34) Howarth, J.; Tetrahedr. Letts.; 2000; 41; 6627-6629.
(35) Song, C. E.; Roh, E. J.; Chem. Commun.; 2000; 837-838.
(36) Laali, K. K.; Gettwert, V. J.; J. Fluor. Chem.; 2001; 107; 31-34.
(37) Dai, S.; Ju, Y. H.; Barnes, C. E.; J. Chem. Soc., Dalton Trans.; 1999; 1201-1202.
(38) Huddelston, J. D.; Willauer, H. D.; Swaloski, R. P.; Visser, A. E.; Rogers, R. D.; Chem. Commun.; 1998; 1765-1766.
(39) Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Mayton, R.; Sheff, S.; Wierzbicki, A.; Davis, J. H.; Rogers, R. D.; Chem. Commun.; 2001; 135-136.
(40) Blanchard, L. A.; Hancu, D.; Beckman, E. J.; Brennecke, J. F.; Nature; 1999; 399; 28-29.
(41) Erbeldinger, M.; Mesiano, A.; Russell, A. J.; Biotechnol. Progr.; 2000; 16; 1129-1131.
(42) Armstrong, D. W.; He, L.; Liu, Y.-S.; Anal. Chem.; 1999; 71; 3873-3876.
(43) Brasse, C. C.; Englert, U.; Salzer, A.; Waffenschmidt, H.; Wasserscheid, P.; Organometal.; 2000; 19; 3818-3823.
(44) Mizushima, E.; Hayashi, T.; Tanaka, M.; Green Chem.; 2001; 3; 76-79.
(45) Peng, J.; Deng, Y.; New J. Chem.; 2001; 25; 639-641.
(46) Kazarian, S. G.; Briscoe, B. J.; Welton, T.; Chem. Commun.; 2000; 20; 2047-2048.
(47) Blanchard, L. A.; Gu, Z.; Brennecke, J. F.; J.Phys.Chem. B; 2001; 105; 2437-2444.
35418
1-Hexyl-3-methylimidazolium hexafluorophosphate
Properties:
Polarity
2
. Melting point
3
Uses:
Extraction technology
1,4
. Friedel-Crafts alkylation
5
(1) Visser, A. E.; Swatloski, R. P.; Rogers, R. D.; Green Chem.; 2000; 2; 1-4.
(2) Carmichael, A. J.; Seddon, K. R.; J. Phys. Org. Chem.; 2000; 13; 591-595.
(3) Holbrey, J. D.; Seddon, K. R.; Clean Prod. Proc.; 1999; 1; 223-236.
(4) Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Griffin, S. T.; Rogers, R. D.; Ind. Eng. Chem. Res.; 2000; 39; 3596-3604.
(5) Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H.; Chem. Commun.; 2000; 1695-1696.
35420
1-Hexylpyridinium hexafluorophosphate
Uses:
Heck
1
(1) Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R.; Org.Lett.; 1999; 1; 997-1000.
35422
1-Hexyl-3-methylimidazolium tetrafluoroborate
Properties:
Polarity
2
. NMR
1
. DSC
1
.
(1) Holbrey, J. D.; Seddon, K. R.; J. Chem. Soc., Dalton Trans.; 1999; 2133-2139.
(2) Carmichael, A. J.; Seddon, K. R.; J. Phys. Org. Chem.; 2000; 13; 591-595.
35424
1-Hexylpyridinium tetrafluoroborate
Uses:
Heck
1
(1) Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R.; Org.Lett.; 1999; 1; 997-1000.
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