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Licensed Unlicensed Requires Authentication Published by De Gruyter February 24, 2018

Industrial uses and applications of ionic liquids

  • Keith E. Gutowski EMAIL logo
From the journal Physical Sciences Reviews

Abstract

Ionic liquids are salts that melt at low temperatures (usually defined as less than 100 °C) and have a number of interesting properties that make them useful for industrial applications. Typical ionic liquid properties include high thermal stabilities, negligible vapor pressures, wide liquidus ranges, broad electrochemical windows, and unique solvation properties. Furthermore, the potential combinations of cations and anions provide nearly unlimited chemical tunability. This article will describe the diverse industrial uses of ionic liquids and how their unique properties are leveraged, with examples ranging from chemical processing to consumer packaged goods.

References

[1] Gabriel S, Weiner J. Ber Dtsch Chem Ges. 1888;21:2669–79.10.1002/cber.18880210288Search in Google Scholar

[2] Walden P. Bull Russian Acad Sci. 1914;8:405–22.Search in Google Scholar

[3] Haynes WM, ed. CRC handbook of chemistry and physics. 94th ed. Boca Raton: FL: CRC Press LLC; 2013-2014:4–89.Search in Google Scholar

[4] Abbott Andrew P., Capper Glen, Davies David L., Rasheed Raymond K., Tambyrajah Vasuki. Novel solvent properties of choline chloride/urea mixturesElectronic supplementary information (ESI) available: spectroscopic data. See http://www.rsc.org/suppdata/cc/b2/b210714g/. Chemical Communications. 2002 11 26;(1):70–71. DOI: 10.1039/B210714GSearch in Google Scholar

[5] Welton T. Chem Rev. 1999;99:2071–83.10.1021/cr980032tSearch in Google Scholar PubMed

[6] Wilkes John S., Zaworotko Michael J.. Air and water stable 1-ethyl-3-methylimidazolium based ionic liquids. Journal of the Chemical Society, Chemical Communications. 1992;(13):965–965. DOI: 10.1039/C39920000965Search in Google Scholar

[7] Gale R. J., Osteryoung R. A.. Potentiometric investigation of dialuminum heptachloride formation in aluminum chloride-1-butylpyridinium chloride mixtures. Inorganic Chemistry. 1979 6;18(6):1603–1605. DOI: 10.1021/ic50196a044Search in Google Scholar

[8] Wassersheid P, Welton T, eds. Ionic liquids in synthesis, 2nd ed., vol. 1. Wiley-VCH, 2008.10.1002/9783527621194Search in Google Scholar

[9] Earle MJ, Seddon KR. Pure Appl Chem. 2000;72:1391–98.10.1351/pac200072071391Search in Google Scholar

[10] Maase M, Massone K, Halbritter K, Noe R, Bartsch M, Siegel W, et al. U.S. Patent 7,351,339 B2, 2003.Search in Google Scholar

[11] Maase M. Industrial applications of Ionic liquids. In: Ionic liquids in synthesis, 2nd ed., vol. 1. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2008:663–87.Search in Google Scholar

[12] Hell K, Weyershausen B, Hesses U U.S. Patent Application US 20040014925 A1, 2003.Search in Google Scholar

[13] Gelbach TJ, Zhao D, Castillo NC, Laurenczy G, Weyerhausen B, Dyson PJ. J Am Chem Soc. 2006;128:9773–80.10.1021/ja0612293Search in Google Scholar PubMed

[14] Franke R, Fridag D, Hamers B, Zanthoff H-W, Blug M, Strautmann J, et al. U.S. Patent Application US 20130178657 A1, 2011.Search in Google Scholar

[15] Haumann M, Riisager A. Chem Rev. 2008;108:1474–97.10.1021/cr078374zSearch in Google Scholar PubMed

[16] Schönweiz A, Franke R. Supported ionic liquid phase (SILP) materials in hydroformylation catalysis. In: Fehrmann R, Riisager A, Haumann M, eds. Supported ionic liquids: fundamentals and applications. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA; 2014.10.1002/9783527654789.ch15Search in Google Scholar

[17] Evonik demonstrates for the first time that SILP catalyst systems can be used commercially. Evonik Industries Press Release, June 10, 2015, Essen, Germany,Search in Google Scholar

[18] Klemm D, Heublein B, Fink H-P, Bohn A. Angew Chem Int Ed. 2005;44:3358–93.10.1002/anie.200460587Search in Google Scholar

[19] Edgar KJ, Buchanan CM, Debenham JS, Rundquist PA, Seiler BD, Shelton MC, et al. Prog Polym Sci. 2001;26:1605–88.10.1016/S0079-6700(01)00027-2Search in Google Scholar

[20] De Wyss G. Ind Eng Chem. 1925;17:1043–45.10.1021/ie50190a018Search in Google Scholar

[21] Dawson T. Coloration Technol. 2011;128:1–8.10.1111/j.1478-4408.2011.00346.xSearch in Google Scholar

[22] Graenacher C U.S. Patent 1,943,176, 1931.10.1136/bmj.1.3673.943Search in Google Scholar

[23] Swatloski RP, Spear SK, Holbrey JD, Rogers RD. J Am Chem Soc. 2002;124:4974–75.10.1021/ja025790mSearch in Google Scholar PubMed

[24] Swatloski RP, Holbrey JD, Rogers RD U.S. Patent 6,824,599 B2, 2002.Search in Google Scholar

[25] Wang H, Gurau G, Rogers RD. Chem Soc Rev. 2012;41:1519–37.10.1039/c2cs15311dSearch in Google Scholar PubMed

[26] Remsing Richard C., Swatloski Richard P., Rogers Robin D., Moyna Guillermo. Mechanism of cellulose dissolution in the ionic liquid 1-n-butyl-3-methylimidazolium chloride: a 13C and 35/37Cl NMR relaxation study on model systems. Chemical Communications. 2006;(12):1271–1271. DOI: 10.1039/b600586cSearch in Google Scholar PubMed

[27] BASF, UA formalize ionic liquids partnership. UA News Press Release, March 8, 2006, Tuscaloosa, AL.Search in Google Scholar

[28] Fort DA, Remsing RC, Swatloski RP, Moyna P, Moyna G, Rogers RD. Green Chem. 2007;9:63–69.10.1039/B607614ASearch in Google Scholar

[29] Hurley FH U.S. Patent 2,446,331, 1944.10.1136/bmj.2.4369.446-aSearch in Google Scholar

[30] Ziegler K, Lehmkuhl H. Chemie. 1956;283:414–25.10.1002/zaac.19562830142Search in Google Scholar

[31] O’Meara M, Alemany A, Maase M, Vagt U, Malkowsky I. Deposition of aluminum using ionic liquids. Materials Today, 10 August 2009. http://www.materialstoday.com/metal-finishing/features/deposition-of-aluminum-using-ionic-liquids/10.1016/S0026-0576(09)80204-3Search in Google Scholar

[32] Sun X, Luo H, Dai S. Chem Rev. 2012;112:2100–28.10.1021/cr200193xSearch in Google Scholar PubMed

[33] http://www.euronuclear.org/info/encyclopedia/r/reprocessing-plants-ww.htm. Accessed February 13, 2018.Search in Google Scholar

[34] Lumetta GJ, Nash KL, Clark SB, Friese JI. Separations for the nuclear fuel cycle in the 21st century. Washington, DC: American Chemical Society; 2006.10.1021/bk-2006-0933Search in Google Scholar

[35] Allen D, Baston G, Bradley AE, Gorman T, Haile A, Hamblett I, et al. Green Chem. 2002;4:152–158.10.1039/b111042jSearch in Google Scholar

[36] Bates ED, Mayton RD, Ntai I, Davis J. H. Jr. J Am Chem Soc. 2002;124:926–27.10.1021/ja017593dSearch in Google Scholar PubMed

[37] Visser Ann E., Swatloski Richard P., Reichert W. Matthew, Davis Jr. James H., Rogers Robin D., Mayton Rebecca, Sheff Sean, Wierzbicki Andrzej, et al. Task-specific ionic liquids for the extraction of metal ions from aqueous solutions. Chemical Communications. 2001;(1):135–136. DOI: 10.1039/B008041LSearch in Google Scholar

[38] Huddleston Jonathan G., Willauer Heather D., Swatloski Richard P., Visser Ann E., Rogers Robin D.. Room temperature ionic liquids as novel media for ‘clean’ liquid–liquid extraction. Chem. Commun.. 1998;(16):1765–1766. DOI: 10.1039/A803999BSearch in Google Scholar

[39] Swatloski RP, Holbrey JD, Rogers RD. Green Chem. 2005;5:361–363.10.1039/b304400aSearch in Google Scholar

[40] Gutowski KE, Broker GA, Willauer HD, Huddleston JG, Swatloski RP, Holbrey JD, et al. J Am Chem Soc. 2003;125:6632–33.10.1021/ja0351802Search in Google Scholar PubMed

[41] Dai S, Ju YH, Barnes CE. Dalton Trans. 1999;8:1201–02.10.1039/a809672dSearch in Google Scholar

[42] Visser AE, Rogers RD. J Solid State Chem. 2003;171:109–13.10.1016/S0022-4596(02)00193-7Search in Google Scholar

[43] Sun X, Bell JR, Luo H, Dai S. Dalton Trans. 2011;40:8019–23.10.1039/c1dt10873eSearch in Google Scholar PubMed

[44] Binnemans K. Chem Rev. 2007;107:2592–614.10.1021/cr050979cSearch in Google Scholar PubMed

[45] Adler R, Pfandi M, Siebert G U.S. Patent 9,109,587 B2, 2011.Search in Google Scholar

[46] Linde company website. “Hydrogen Technologies: The Ionic Compressor 90 MPa – IC90” brochure.Search in Google Scholar

[47] Dyson Paul J., Laurenczy Gábor, André Ohlin C., Vallance James, Welton Thomas. Determination of hydrogen concentration in ionic liquids and the effect (or lack of) on rates of hydrogenation. Chem. Commun.. 2003;(19):2418–2419. DOI: 10.1039/B308309HSearch in Google Scholar PubMed

[48] Ramdin M, De Loos TW, Vlugt TJH. Ind End Chem Res. 2012;51:8149–77.10.1021/ie3003705Search in Google Scholar

[49] Blanchard LA, Hancu D, Beckman EJ, Brennecke JF. Nature. 1999;399:28–29.10.1038/19887Search in Google Scholar

[50] Kazarian Sergei G., Briscoe Brian J., Welton Thomas. Combining ionic liquids and supercritical fluids: in situ ATR-IR study of CO2 dissolved in two ionic liquids at high pressures. Chemical Communications. 2000;(20):2047–2048. DOI: 10.1039/B005514JSearch in Google Scholar

[51] Blanchard LA, Gu Z, Brennecke JF. J Phys Chem B. 2001;105:2437–44.10.1021/jp003309dSearch in Google Scholar

[52] Cadena C, Anthony JL, Shah JK, Morrow TI, Brennecke JF, Maginn EJ. J Am Chem Soc. 2004;126:5300–08.10.1021/ja039615xSearch in Google Scholar PubMed

[53] Shi W, Maginn EJ. J Phys Chem B. 2008;112:16710–1670.10.1021/jp8075782Search in Google Scholar PubMed

[54] Gutowski KE, Maginn EJ. J Am Chem Soc. 2008;130:14690–704.10.1021/ja804654bSearch in Google Scholar PubMed

[55] Gurkan BE, De La Fuente J, Mindrup EM, Ficke LE, Goodrich BF, Price EA, et al. J Am Chem Soc. 2010;132:2116–17.10.1021/ja909305tSearch in Google Scholar PubMed

[56] Freemantle M. Chapter 14: applications. In: An introduction to ionic liquids. RSC Publishing; 2010. ISBN 978-1-84755-161-0.Search in Google Scholar

[57] O’Regan B, Grätzel M. Nature. 1991;353:737–40.10.1038/353737a0Search in Google Scholar

[58] MacFarlane DR, Tachikawa N, Forsyth M, Pringle JM, Howlett PC, Elliott GD, et al. Energy Environ Sci. 2014;7:232–50.10.1039/C3EE42099JSearch in Google Scholar

[59] BASF and G24i develop solar cells. Chem Eng News. 2077;85:25.Search in Google Scholar

[60] 3M™ company website. Antistatic Additives for Electronics.Search in Google Scholar

[61] BASF company website. “Basionics: high performance antistatic additives” brochure. http://www.intermediates.basf.com/chemicals/ionic-liquids/. Accessed February 13, 2018.Search in Google Scholar

[62] Price K, Hartshorn R, Rohrbaugh R, Scheper W, Showell M, Baker K, et al. U.S. Patent Application 20040077519A1, 2003.Search in Google Scholar

[63] Hecht SE, Cron SL, Scheibel JJ, Miracle GS, Seddon KR, Earle M, et al. U.S. Patent 7,737,102, 2005.Search in Google Scholar

[64] Hecht SE, Miracle GS, Cron SL, Showell MS U.S. Patent 7,786,065, 2006.Search in Google Scholar

[65] Kenneally CJ, Hecht SE, Cron SL U. S. Patent 7,737,106 B2, 2006.Search in Google Scholar

[66] Price KN, Hecht SE, Jordan GT, IV, Kenneally CJ, Aouad YG, Showell MS, et al. U.S. Patent 7,939,485 B2, 2005.Search in Google Scholar

[67] Hecht SE, Price KN, Berger PS, Foley PR, Hutton HD, III, Showell MS, et al. U.S. Patent 7,928,053, 2009.Search in Google Scholar

[68] Plechkova NV, Seddon KR. Chem Soc Rev. 2008;37:123–50.10.1039/B006677JSearch in Google Scholar PubMed


Notes

The author would like to thank Dr. Martin Johannes Schneider for providing the SILP graphic in Figure 3.


Published Online: 2018-2-24

© 2018 Walter de Gruyter GmbH, Berlin/Boston

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