Abstract
A virtually unprecedented exponential burst of activity resulted following the publication, in 1998, of an article by Michael Freeman (Freemantle, M. Chemical & Engineering News, 1998, March 30, 32), which speculated on the role and contribution that ionic liquids (ILs) might make in the future on the development of clean technology. Up until that time only a handful of researchers were routinely engaged in the study of ILs but frenzied activity followed that continues until the present day. Scientists from all disciplines related to Chemistry have now embarked on studies, including theoreticians who are immersed in the aim of improving the “designer role” so that they can tailor ILs to deliver specified properties. This article, whilst not in any sense attempting to be exhaustive, highlights the main features which characterise ILs, presenting these in a form readily assimilated by newcomers to this area of research. An extensive glossary is featured in this article as well as a chronological list which charts the major areas of development. What follows consists of a number of sections briefly describing the role of ILs as solvents, hypergolic fuels, their use in some electrochemical devices such as solar cells and lithium batteries and their use in polymerisation reactions, followed by a concise summary of some of the other roles that they are capable of playing. The role of empirical, volume-based thermodynamics procedures, as well as large scale computational studies on ILs is also highlighted. These developments which are described are remarkable in that they have been achieved in less than a decade and a half, although knowledge of these materials has existed for much longer.
Keywords
ionic liquidsroom temperature ionic liquidsnon-aqueous ionic liquidsambient temperature ionic liquidsionic liquid solventsionic liquid hypergolic fuelsvolume-based thermodynamicslarge scale computations on ionic liquidsionic liquids in electrochemical devicesionic liquids in polymerisation reactions
References
1.
Wasserscheid P.
, and
Keim W.
(2000 ) Angew. Chem. , 112 , 3926 –3945 .
2.
Rebelo L.P.N.
,
Lopes J.N.C.J.
,
Esperanza M.S.S.
, and
Filipe E.
(2005 ) J. Phys. Chem , 109 , 6040 .
3.
Holbrey J.D.
, and
Rogers R.D.
(2008 ) In:
Wasserscheid P.
, and
Welton T.
(eds), ILs in Synthesis , Vol. 1 , p. 57 . Wiley VCH , Weinheim .
4.
Freemantle M.
(2010 ) An introduction to ILs. Royal Society of Chemistry , London .
5.
Bloom H.
(1962 ) Discuss. Faraday Soc. , 32 , 7 .
6.
Yoke J.T.
III
,
Weiss J.F.
, and
Tollin G.
(1963 ) Inorg. Chem. , 2 , 1210 .
7.
Bockris J.O.M.
, and
Reddy A.K.N.
(1970 ) Modern electrochemistry. Plenum Publishing , New York .
8.
Koch V.R.
,
Miller L.L.
, and
Oysteryoung R.A.
(1976 ) J. Am. Chem. Soc. , 98 , 5277 .
9.
Gale R.J.
,
Gilbert B.
, and
Oysteryoung R.A.
(1978 ) Inorg. Chem. , 17 , 2728 .
10.
Wilkes J.S.
,
Levisky J.A.
,
Wilson R.A.
, and
Hussey C.L.
(1982 ) Inorg. Chem. , 21 , 1263 .
11.
Wilkes J.S.
, and
Zaworotko M.J.
(1992 ) J. Chem. Soc. Chem. Commun. , 965 .
12.
Bonhöte P.
,
Dias A.-P.
,
Papageorgiou N.
,
Kalyanasundaram K.
, and
Grätzel M.
(1996 ) Inorg. Chem. , 35 , 1168 .
13.
Gordon J.E.
(1964 ) J. Am. Chem. Soc. , 86 , 4492 .
14.
Parshall G.W.
(1972 ) J. Am. Chem. Soc. , 94 , 8716 .
15.
Knifton J.F.
(1981 ) J. Am. Chem. Soc. , 103 , 3959 .
16.
Pacholec F.
,
Butler H.T.
, and
Poole C.F.
, (1982 ) Anal. Chem. , 54 , 1938 .
17.
Magnuson D.K.
,
Bodley J.W.
, and
Evans D.F.
(1984 ) J. Solution Chem. , 13 , 583 .
18.
Chauvin Y.
,
Gilbert B.
, and
Guibard I.
(1990 ) J. Chem. Soc., Chem. Commun. , 1715 .
19.
Chauvin Y.
,
Mussmann L.
, and
Oliver H.
(1995 ) Angew. Chem. Int. Ed. , 34 , 2698 .
20.
Seddon K.
(1997 ) J. Chem. Technol. Biotechnol. , 68 , 351 –356 .
21.
Freemantle M.
(1998 ) Chem. Eng. News , March 30, 32 .
22.
Christe K.O.
,
Wilson W.W.
,
Sheeby J.A.
, and
Boatz J.A.
(1999 ) Angew. Chem. Int. Ed. , 38 , 2004 –2009 .
23.
Vij A.
,
Wilson W.W.
,
Vij V.
,
Tham F.S.
,
Sheehy J.A.
, and
Christe K.O.
(2001 ) J. Am. Chem. Soc. , 123 , 6308 –6313 .
24.
Fau S.
,
Wilson K.J.
, and
Bartlett R.J.
(2002 ) J. Phys. Chem. A , 106 , 4639 –4644 .
25.
Dixon D.A.
,
Feller D.
,
Christe K.O.
,
Wilson W.W.
,
Vij A.
,
Vij V.
,
Jenkins H.D.B.
,
Olson R.M.
, and
Gordon M.S.
(2004 ) J. Am. Chem. Soc. , 126 , 834 –843 .
26.
Gutowski K.E.
,
Holbrey J.D.
,
Rogers R.D.
, and
Dixon D.A.
(2005 ) J. Phys. Chem. B , 109 , 23196 –23208 .
27.
Krossing I.
,
Slattery J.M.
,
Daguenet C.
,
Dyson P.
,
Oleinikova A.
,
Weingärtner H.
(2006 ) J. Am. Chem. Soc. , 128 , 13427 –13434 .
28.
Gutowski K.E.
,
Rogers R.D.
, and
Dixon D.A.
(2007 ) J. Phys. Chem. B , 111 , 4788 –4800 .
29.
Verevkin S.P.
,
Emel'yanenko V.N.
,
Zaitsau D.H.
,
Heintz A.
,
Muzny C.D.
, and
Frenkel M.
(2010 ) Phys. Chem. Chem. Phys. , 12 , 14994 –15000 .
30.
Emel'yanenko V.E.
,
Zaitsau D.H.
,
Verevkin S.P.
, and
Heintz A.
(2011 ) Thermochim. Acta , 518 , 107 –110 .
31.
Emel'yanenko V.N.
,
Verevkin S.P.
,
Heintz A.
,
Voss K.
, and
Schultz A.
(2009 ) J. Phys. Chem. B , 113 , 9871 –9876 .
32.
Emel'yanenko V.N.
,
Verevkin S.P.
,
Heintz A.
, and
Schick C
(2008 ) J. Phys. Chem. B , 112 , 8095 –8098 .
33.
Emel'yanenko V.E.
,
Verevkin S.P.
, and
Heintz A.
(2007 ) J. Am. Chem. Soc. , 129 , 3930 –3937 .
34.
Zaitsau D.H.
,
Kabo G.J.
,
Strechan A.A.
,
Paulechka Y.U.
,
Tschersich A.
,
Verevkin S.P.
, and
Heintz A.
(2006 ) J. Phys. Chem. A , 110 , 7303 –7308 .
35.
Emel'yanenko V.N.
,
Verevkin S.P.
,
Koutek B.
, and
Doubsky J.
(2005 ) J. Chem. Thermod. , 37 , 73 –81 .
36.
Roganov G.N.
,
Pisarev P.N.
, and
Emel'yanenko V.N.
(2005 ) J. Chem. Eng. Data , 50 , 1114 –1124 .
37.
Jenkins H.D.B.
(2011 ) Sci. Prog. , 94 , 184 –211 .
38.
Chambreau S.D.
,
Schneider S.
,
Rosander M.
,
Hawkins T.
,
Gallegos C.J.
,
Pastewait M.F.
, and
Vaghjiani G.L.
(2008 ) J. Phys. Chem. A , 112 , 7816 –7824 .
39.
Schneider S.
,
Hawkins T.
,
Rosander M.
,
Vaghjiani G.L.
,
Chambreau S.D.
, and
Drake G.
(2008 ) Energy Fuels , 22 , 2871 –2872 .
40.
Zhang Y.
,
Gao H.
,
Joo Y.-H.
, and
Shreeve J.M.
(2010 ) Angew. Chem. Int, Ed. , PMID:21077083.
41.
Jenkins H.D.B.
(2009 ) Sci. Prog. , 92 , 91 –112 .
42.
Glasser L.
, and
Jenkins H.D.B.
(2010 ) J. Chem. Eng. Data , 56 , 874 –880 .
43.
Jenkins H.D.B.
,
Roobottom H.K.
,
Passmore J.
, and
Glasser L.
(1999 ) Inorg. Chem. , 38 , 3609 –3620 .
44.
Klapötke T.M.
,
Stierstorfer J.
,
Jenkins H.D.B.
,
van Eldik R.
, and
Schmeisser M.
(2011 ) Z. Anorg. Allg. Chem. , in press.
45.
Rhodes C.J.
(2011 ) Sci. Prog. , 94 , 211 –220 .
46.
Borra E.F.
(2007 ) Nature , 447 , 979 .
47.
Hilgers C.
, and
Wasserscheid P.
(2002 ) In:
Wasserscheid P.
, and
Welton T.
(eds), ILs in synthesis , pp. 21 –33 . Wiley-VCH , Weinheim .
48.Solvent Innovation. www.solvent-innovation.com.
49.
Wasserscheid P.
,
van Hal R.
, and
Bössman A.
(2002 ) Green Chem. , 4 , 400 –404 .
50.
Pernak J.
,
Czepukowicz A.
, and
Pozniak R.
(2001 ) Ind. Eng. Chem. Res. , 40 , 2379 –2383 .
51.
Wassercheid P.
,
Bösmann A.
, and
van Hal R.
(2002 ) Application of new halogen-free ILs. 224th National Meeting ACS, Boston, MA.
52.
Swatloski R.P.
,
Spear S.K.
,
John D.J.
,
Holbrey D.
, and
Rogers R.D.
(2002 ) J. Am. Chem. Soc. , 124 , 4974 –4975 .
53.
Zhang H.
,
Wu J.
,
Zhang J.
, and
He J.S.
(2005 ) Macromolecules , 38 , 8272 –8277 .
54.
Fukaya Y.
,
Sugimoto A.
, and
Ohno H.
(2006 ) Biomacromolecules , 7 , 3295 –3297 .
55.
Cao Y.
,
Wu J.
,
Zhang J.
,
Li H.Q.
,
Zhang Y.
, and
He J.S.
(2009 ) Chem. Eng. J. , 147 , 13 –21 .
56.
Xu A.R.
,
Wang J.J.
, and
Wang H.Y.
(2010 ) Green Chem. , 12 , 268 –275 .
57.
Patell Y.
,
Seddon K.R.
,
Dutta L.
, and
Fleet A.
(2002 ) In:
Rodgers R.D.
,
Seddon K.R.
, and
Volkov S.
(eds), Green industrial applications of ILs , p. 499 . NATO Science Series, Kluwer Academic Publishers , Dordecht .
58.
Freemantle M.
(2000 ) Chem. Eng. News , 78 , 37 –50 .
59.
Freemantle M.
(2003 ) Chem. Eng. News , 81 , 9 .
60.
Jork C.
,
Seiler M.
,
Beste Y.-A.
, and
Arlt W.
(2004 ) J. Chem. Eng. Data , 49 , 852 –857 .
61.
Blanchard L.A.
,
Gu Z.
,
Brennecke J.F.
, and
Beckman E.J.
(2002 ) In:
Rodgers R.D.
,
Seddon K.R.
, and
Volkov S.
(eds), Green industrial applications of ILs , p. 403 . NATO Science Series, Kluwer , Dordrecht .
62.
Kulkarni S.G.
(1980 ) J. Armament Stud. , 16 , 23 –27 .
63.
Arnold S.L.
(1999 ) Chemical Propulsion Information Agency Publication No 687 (JANAF 28th Propellant and Characterisation and 17th Safety and Environmental Protection Subcommittee Joint Meeting, Vol. 1) p. 301 and references therein.
64.
Thompson D.M.
(2000 ) U.S. Patent 6,013,143., Jan. 11th. (2001) U.S. Patent 6,210,504, Apr. 3rd. (2001) U.S. Patent 6,299,654., Oct. 9th.
65.
Jain S.R.
(2003 ) J. Sci. Ind. Res. , 62 , 293 –310 .
66.
McQuaid D.
(2005 ) U.S. Patent 6,962,633., Nov. 8th.
67.
Hallit R.E.A.
, and
Bauerle G.
(2005 ) U.S. Patent 6,949,152, Sep. 27th.
68.
Katritzky A.R.
,
Rogers R.M.
,
Witek A.V.
,
Vakulenko A.V.
,
Mohapatra P.P.
,
Steel P.J.
, and
Damavarapu R.
(2007 ) J. Energ. Mater. , 25 , 79 –109 .
69.
Sengupta D.
(2008 ) U.S. Patent Appl. 2008/0202655, Aug. 28th.
70.
Williams F.A.
(2009 ) J. Prop. Power , 25 , 1354 –1356 .
71.
Kulkarni S.G.
,
Bagalkote V.S.
,
Patil S.
,
Kumar U.P.
, and
Kumar V. A.
(2009 ) Propell. Explos. Pyrot. , 34 , 520 –525 .
72.
Wang S.
,
Thynell S.T.
, and
Chowdhury A.
(2010 ) Energy Fuels , 24 , 5320 –5330 .
73.
Kulkarni S.G.
, and
Bagalkote V.S.
(2010 ) J. Energ. Mater. , 28 , 173 –188 .
74.
Desai S.C.
,
Willitsford A.H.
,
Sumanasekera G.U.
,
Yu M.
,
Tian W.Q.
,
Jayanthi C.S.
, and
Wu S.Y.
(2010 ) J. Appl. Phys. , 107 , 114509/1–114509/7.
75.
Yokel S.
, and
Schatz G.C.
(2010 ) J. Phys. Chem. B , 114 , 14241 –14248 .
76.
ESTEC Tender Invitation AO6817 (2011 ) Technologies and Product Division , Spacecraft Bus/Propulsion, ARTES 5.1., 11.1TT.68.
77.
Christe K.O.
, and
Drake G.W.
(2010 ) U.S. 7771549B1. U.S. Department of the Air Force.
78.
Kappenstein C.
, and
Joulin J. P.
(2006 ) Adv. Sci. Tech. , 45 , 2143 –2152 .
79.
Zhang Y.
,
Joo Y.-H.
, and
Shreeve J.M.
(2010 ) Prep. Symp. Am. Chem. Soc., Div. Fuel Chem. , 55 , 159 .
80.
Izgorodina E.I.
(2011 ) Phys. Chem. Chem. Phys. , in press, doi: 10.1039/c0cp02315a.
81.
Sun J.
,
Forsyth M.
, and
MacFarlane D.R.
(1998 ) J. Phys. Chem. B , 102 , 8858 –8864 .
82.
Weingärtner H.
, (2008 ) Angew. Chem. Int. Ed. , 47 , 654 –670 .
83.
Krossing I.
, and
Slattery J.M.
(2006 ) Z. Phys. Chem. , 220 , 1343 –1359 .
84.
Slattery J.M.
,
Dagunet C.
,
Dyson P.J.
,
Schubert T.J.S.
, and
Krossing I.
(2007 ) Angew. Chem. Int. Edit. , 46 , 5384 –5388 .
85.
Ludwig R.
, and
Paschek D.
(2009 ) Chem. Phys. Phys. Chem. , 10 , 516 –519 .
86.
Bonhote P.
,
Dias A.-P.
,
Papageorgiou N.
,
Kalyanasundaram K.
, and
Grätzel M.
(1996 ) Inorg. Chem. , 35 , 1168 –1178 .
87.
Huddleston J.G.
,
Visser A.E.
,
Reichert W.M.
,
Willauer H.D.
,
Broker G.A.
, and
Rogers R.D.
(2001 ) Green Chem. , 3 , 516 –519 .
88.
Bhargava B.L.
,
Balasubramanian S.
, and
Klein M.
(2008 ) Chem. Commun. , 3339 –3351 .
89.
Del Pópolo M.G.
,
Kohanoff J.
,
Lynden-Bell R.M.
, and
Pinilla
, (2007 ) Accounts Chem. Res. , 40 , 1156 –1164 .
90.
Car R.
, and
Parinello M.
(1985 ) Phys. Rev. Lett. , 55 , 2471 –2474 .
91.
Gordon M.S.
,
Mullin J.M.
,
Pruitt S.R.
,
Roskop L.B.
,
Slipchenko L.V.
, and
Boatz J.A.
(2009 ) J. Phys. Chem. B , 113 , 9646 –9663 .
92.
Wang P.
,
Zakeeruddin S.M.
,
Moser J.-E.
, and
Graetzel M.
(2003 ) J. Phys. Chem. B , 107 , 13280 .
93.
Kuang D.
,
Wang P.
,
Ito S.
,
Zakeeruddin S.M.
, and
Graetzel M.
(2006 ) J. Am. Chem. Soc. , 128 , 7732 –7733 .
94.
Oda T.
,
Tanaka S.
, and
Hayase S.
(2006 ) Sol. Energy Mater. Sol. Cells , 90 , 2696 –2709 .
95.
Wang P.
,
Zakeeruddin S.M.
,
Moser J.-E.
,
Humphry-Baker R.
, and
Graetzel M.
(2004 ) J. Am. Chem. Soc. , 126 , 7165 .
96.
Holzapfel M.
,
Jost C.
,
Prodi-Schwab A.
,
Krumeich F.
,
Würsig A.
,
Buqa H.
, and
Novák P.
(2005 ) Carbon , 43 , 1488 .
97.
Carmichael A.J.
,
Haddleton D.M.
,
Bon S.A.F.
, and
Seddon K.R.
(2000 ) Chem. Commun. , 1237 .
98.
Scott M.
,
Brazel C.S.
,
Benton M.G.
,
Mays J.W.
,
Holbrey J.D.
, and
Rogers R.D.
(2002 ) Chem. Commun. , 1370 .
99.
Majewski P.
,
Pernak A.
,
Grzymislawski M.
,
Iwanik K.
, and
Penak J.
(2003 ) Acta Histochem. , 105 , 135 .
100.
Kumar V.
, and
Malhorta S.V.
(2008 ) Bioorg. Med. Chem. Lett. , 18 , 5640 .
101.
Pernak J.
,
Sobaskiewicz K.
, and
Mirska I.
(2003 ) Green Chem. , 5 , 52 .
102.
Rodriquez H.
,
Williams M.
,
Wilkes J.S.
, and
Rogers R.D.
(2008 ) Green Chem. , 10 , 502 .
103.
Ye C.
,
Liu W.
,
Chen Y.
, and
Yu L.
(2001 ) Chem. Commun. , 2244 .
104.
Kömpf M.
(2006 ) Linde Technol. (January) 24 .
105.
Valette H.
,
Ferron L.
,
Coquerel G.
,
Gaumont A.-C.
, and
Plaquevent J.-C.
(2006 ) Tetrahedron Lett. , 45 , 1617 .
106.
Howarth J.
(2000 ) Tetrahedron Lett. , 41 , 6627 .
107.
Muzat J.
(2006 ) Adv. Synth. Catal. , 348 , 275 .
108.
Dai S.
,
Ju Y.H.
,
Gao H.J.
,
Lin J.S.
,
Pennycook S.J.
, and
Barnes C.E.
(2000 ) Chem. Commun. , 243 .
109.
Freemantle M.
(2010 ) An Introduction to ILs , Royal Society of Chemistry Publishing , London .