Skip to main content Accessibility help
×
Hostname: page-component-78c5997874-mlc7c Total loading time: 0 Render date: 2024-11-06T01:22:38.074Z Has data issue: false hasContentIssue false

8 - Ionic Liquid Solvents and Intensification

Published online by Cambridge University Press:  12 May 2020

Laurence R. Weatherley
Affiliation:
University of Kansas
Get access

Summary

Ionic liquids are organic salts with potential for intensification of liquid–liquid processes. The structures of a range of significant ionic liquids are presented. The focus is on intensification of classical organic reactions and separations using ionic liquids in liquid–liquid systems. Their role as reaction media is briefly reviewed. Phase equilibrium properties of several liquid–liquid systems involving ionic liquids are described, demonstrating their potential for azeotrope breakage in vapor–liquid and liquid–liquid systems. Application of ionic liquid technology to phase-transfer catalysis is discussed, with inclusion of the classic example of the dimerization of butene to iso-octenes. The potential role of ionic liquids for the exploitation of biocatalytic processes is highlighted, with discussion of the potentially toxic effects on living biomass and on the activity of enzymes. The significance of the toxicity of some ionic liquids is summarized, together with a short discussion of potentially wider environmental impacts. The degradability of ionic liquids is an important part of environmental assessment that is also considered.

Type
Chapter
Information
Publisher: Cambridge University Press
Print publication year: 2020

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Anastas, P. T. and Warner, J. C. (1998). Green Chemistry: Theory and Practice. Oxford: Oxford University Press.Google Scholar
Awad, W. H., Gilman, J. W., Nyden, M., et al. (2004). Thermal degradation studies of alkyl-imidazoliumsalts and their application in nanocomposites. Thermochimica. Acta, 409, 311.Google Scholar
Baranyai, K. J., Deacon, G. B., MacFarlane, D. R., Pringle, J. M., and Scott, J. L. (2004). Thermal degradation of ionic liquids at elevated temperatures. Australian Journal of Chemistry, 57, 145147.Google Scholar
Baumann, M. D., Daugulis, A. J., and Jessop, P. G. (2005). Phosphonium ionic liquids for degradation of phenol in a two-phase partitioning bioreactor. Applied Microbiology and Biotechnology, 67, 131137.Google Scholar
Behr, A., Bayrak, Z., Peitz, S., Stochniol, G., and Maschmeyer, D. (2015). Oligomerization of 1-butene with a homogeneous catalyst system based on allylic nickel complexes. RSC Advances, 5, 4137241376.CrossRefGoogle Scholar
Bernot, R. J., Brueske, M. A., Evans-White, M. A., and Lambert, G. A. (2005). Acute and chronic toxicity of imidazolium-based ionic liquids on Daphnia magna. Environmental Toxicology and Chemistry, 24, 8792.Google Scholar
Berthon, L., Nikitenko, S. I., Bisel, I., et al. (2006). Influence of gamma irradiation on hydrophobic room-temperature ionic liquids [BuMeIm]PF6 and [BuMeIm](CF3SO2)2N. DaltonTransactions, 2526–2534.Google Scholar
Brautigam, S., and Bringer-Meyerb, S. W.-B. D. (2007). Asymmetric whole cell biotransformations in biphasic ionic liquid/water-systems by use of recombinant Escherichia coli with intracellular cofactor regeneration. Tetrahedron: Asymmetry, 18, 18831887.CrossRefGoogle Scholar
Chauvin, Y. (2006). Olefin metathesis: the early days (Nobel Lecture). Angewandte Chemie International Edition, 45, 37403765.Google Scholar
Chauvin, Y., Gaillard, J. F., Quang, D. V., and Andrews, J. W. (1974) The IFP dimersol process for the dimerization of C3 and C4 olefinic cuts. Chemistry & Industry, 375–378.Google Scholar
Cho, C.-W., Pham, T. P. T., Jeon, Y.-C., et al. (2007). Toxicity of imidazolium salt with anion bromide to a phytoplankton Selenastrum capricornutum: effect of alkyl chain length. Chemosphere, 69, 10031007.Google Scholar
Cho, C.-W., Pham, T. P. T., Jeon, Y.-C., et al. (2008). Microalgal photosynthetic activity measurement system for rapid toxicity assessment. Ecotoxicology, 17, 455463.Google Scholar
Coleman, D., Spulak, M., Garcia, M. T., and Gathergood, N. (2012). Antimicrobial toxicity studies of ionic liquids leading to a ‘hit’ MRSA selective antibacterial imidazolium salt. Green Chemistry, 14, 13501356.Google Scholar
Cornmell, R. J., Winder, C. L., Gordon, J. T. G., Goodacre, R., and Stephens, G. (2008). Accumulation of ionic liquids in Escherichia coli cells. Green Chemistry, 10, 836841.Google Scholar
Cota, I., Gonzalez-Olmos, R., Iglesias, M., and Medina, F. (2007). New short aliphatic chain ionic liquids: synthesis, physical properties, and catalytic activity in aldol condensations. Journal of Physical Chemistry B, 111 , 1246812477.Google Scholar
Docherty, K. M. and Kulpa, C. F. (2005). Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids. Green Chemistry, 7, 185189.Google Scholar
Domańska, U. and Marciniak, A. (2008). Activity coefficients at infinite dilution measurements for organic solutes and water in the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate. Journal of Physical Chemistry B, 112, 1110011105.Google Scholar
Dupont, J., de Souza, R. F., and Suarez, P. A. Z. (2002). Ionic liquid (molten salt) phase organometallic catalysis. Chemical Reviews, 102, 36673692.CrossRefGoogle ScholarPubMed
Foco, G. M., Bottini, S. B., Quezada, N., de la Fuente, J. C., and Peters, C. J. (2006). Activity coefficients at infinite dilution in 1-alkyl-3-methylimidazolium tetrafluoroborate ionic liquids. Journal of Chemical Engineering Data, 51, 10881091.CrossRefGoogle Scholar
Gangu, S. A. (2013). Towards in situ extraction of fine chemicals and biorenewable fuels from fermentation broths using ionic liquids and the intensification of contacting by the application of electric fields. Ph.D. thesis, The University of Kansas.Google Scholar
Ganske, F. and Bornscheuer, U. T. (2006). Growth of Escherichia coli, Pichia pastoris and Bacillus cereus in the presence of the ionic liquids [BMIM] [BF4] and [BMIM] [PF6] and organic solvents. Biotechnology Letters, 28(7), 465469.Google Scholar
García, G., García, S., Torrecilla, J. S., and Rodríguez, F. (2011). N-Butylpyridinium bis-(trifluoromethylsulfonyl)imide ionic liquids as solvents for the liquid–liquid extraction of aromatics from their mixtures with alkanes: Isomeric effect of the cation. Fluid Phase Equilibria, 301, 6266.Google Scholar
García, S., Larriba, M., García, J., Torrecilla, J. S., and Rodríguez, F. (2012). Liquid–liquid extraction of toluene from n-heptane using binary mixtures of N-butylpyridinium tetrafluoroborate and N-butylpyridinium bis(trifluoromethylsulfonyl) imide ionic liquids. Chemical Engineering Journal, 180, 210215.Google Scholar
Gathergood, N. and Scammells, P. J. (2002). Design and preparation of room-temperature ionic liquids containing biodegradable side chains. Australian Journal of Chemistry, 55, 557560.Google Scholar
Gathergood, N., Garcia, M. T., and Scammells, P. J. (2004). Biodegradable ionic liquids: part I. Concept, preliminary targets and evaluation. Green Chemistry, 6, 166175.Google Scholar
Gathergood, N., Scammells, P. J., and Garcia, M. T. (2006). Biodegradable ionic liquids. Part II: the first readily biodegradable ionic liquids. Green Chemistry, 8, 156160.CrossRefGoogle Scholar
Holbrey, J. and Seddon, K. R. (1999). Ionic liquids. Clean Products and Processes, 1, 223236.Google Scholar
Holbrey, J. D., Reichert, W. M., Swatloski, R. P., et al. (2002). Efficient, halide free synthesis of new, low cost ionic liquids: 1,3-dialkylimidazolium salts containing methyl and ethyl-sulfate anions. Green Chemistry, 4, 407413.Google Scholar
Howarth, J., James, P., and Dai, J. (2001). Immobilized baker’s yeast reduction of ketones in an ionic liquid, [bmim]PF6 and water mix. Tetrahedron Letters, 42, 75177519.Google Scholar
Itakura, T., Hirata, K., Aoki, M., et al. (2009). Decomposition and removal of ionic liquid in aqueous solution by hydrothermal and photocatalytic treatment. Environmental Chemistry Letters, 7(4), 343345.Google Scholar
Jork, C., Seiler, M., Beste, Y., and Arlt, W. (2004). Influence of ionic liquids on the phase behavior of aqueous azeotropic systems. Journal of Chemical Engineering Data, 49, 852857.Google Scholar
Kaminski, K., Krawczyk, M., Augustyniak, J., Weatherley, L. R., and Petera, J. (2014). Electrically induced liquid–liquid extraction from organic mixtures with the use of ionic liquids. Chemical Engineering Journal, 235, 109123.Google Scholar
Krawczyk, M., Kamiński, K., and Petera, J. (2012). Experimental and numerical investigation of electrostatic spray liquid–liquid extraction with ionic liquids. Chemical Process Engineering, 33(1), 167183.Google Scholar
Landry, T. D., Brooks, K., Poche, D., and Woolhiser, M. (2005). Acute toxicity profile of 1-butyl-3-methylimidazolium chloride. Bulletin of Environmental Contamination and Toxicology, 74, 559565.CrossRefGoogle ScholarPubMed
Larriba, M., Navarro, P., Gonzalez-Miquel, M., et al. (2016). Dicyanamide-based ionic liquids in the liquid–liquid extraction of aromatics from alkanes: Experimental evaluation and computational predictions. Chemical Engineering Research and Design, 109, 561572.Google Scholar
Lee, S.-M., Chang, W.-J., Choi, A.-R., and Koo, Y.-M. (2005). Influence of ionic liquids on the growth of Escherichia coli. Korean Journal of Chemical Engineering, 22(5), 687690.Google Scholar
Li, X., Zhao, J., Li, Q., Wang, L., and Tsang, S.C. (2007). Ultrasonic chemical oxidative degradations of 1,3-dialkylimidazolium ionic liquids and their mechanistic elucidations. Dalton Transactions, 1875–1880.Google Scholar
Marsh, K. N. (2006). Room Temperature Ionic Liquids – A Review of Properties and Applications. Presented at Process Intensification and Innovation Process Conference, Christchurch, New Zealand, September 24–29, 2006.Google Scholar
Matsumoto, M., Mochiduki, K., and Kondo, K. (2004). Toxicity of ionic liquids and organic solvents to lactic acid-producing bacteria. Journal of Bioscience and Bioengineering, 98, 343347.Google Scholar
Meindersma, G. W., Hansmeier, A. R., and de Haan, A. B. (2010). Ionic liquids for aromatics extraction. Present status and future outlook. Industrial and Engineering. Chemistry Research, 49, 75307540.Google Scholar
Mokhtarania, B., Musavib, J., and Parvini, M. (2014). Extraction of toluene from alkane using [Bmim] [NO3] or [Omim] [NO3]ionic liquid at 298.15 K and atmospheric pressure. Fluid Phase Equilibria, 363, 4147.Google Scholar
Morawski, A. W., Janus, M., Goc-Maciejewska, I., Syguda, A., and Pernak, J. (2005). Decomposition of ionic liquids by photocatalysis. Polish Journal of Chemistry, 79, 19291935.Google Scholar
Oliveira, M. V. S., Vidal, B. T., Melo, C. M., et al. (2016). (Eco)toxicity and biodegradability of protic ionic liquids. Chemosphere, 147, 460466.Google Scholar
Olivier-Bourbigou, H. and Hugues, F. (2002). In Rogers, R. D., Seddon, K. R., and Volkov, S., eds., Green Industrial Applications of Ionic Liquids (NATO Science Series II: Mathematics, Physics and Chemistry). Dordrecht: Kluwer, Vol. 92, pp. 6784.Google Scholar
Pereiro, A. B. and Rodrıguez, A. (2008). Azeotrope-breaking using [BMIM] [MeSO4] ionicliquid in an extraction column. Separation and Purification Technology, 62, 733738.Google Scholar
Perica, B., Sierra, J., Martí, E., et al. (2013). (Eco)toxicity and biodegradability of selected protic and aprotic ionic liquids. Journal of Hazardous Materials, 261, 99105.Google Scholar
Pham, T. P. T., Chul-Woong Cho, C. W., and Yun, Y. S. (2010). Environmental fate and toxicity of ionic liquids: A review. Water Research, 44, 352372.Google Scholar
Plechkova, N. V. and Seddon, K. R. (2008). Applications of ionic liquids in the chemical industry. Chemical Society Reviews, 37, 123150.Google Scholar
Prett, C., Chiappe, C., Pieraccini, D., et al. (2006). Acute toxicity of ionic liquids to the zebrafish (Danio rerio). Green Chemistry, 8, 238240.Google Scholar
Rebros, M., Gunaratne, H. Q. N., Ferguson, J., Seddon, K. R., and Stephens, G. A. (2009). High throughput screen to test the biocompatibility of water-miscible ionic liquids. Green Chemistry, 11, 402408.Google Scholar
Rogers, R. D. and Seddon, K. R. (2003). Ionic liquids –solvents of the future? Science, 302, 792793.Google Scholar
Siedlecka, E. M., Mrozik, W., Kaczyński, Z., and Stepnowski, P. (2008a). Degradation of 1-butyl-3-methylimidazolium chloride ionic liquid in a Fenton-like system. Journal of Hazardous Materials, 154, 893900.Google Scholar
Siedlecka, E. M., Golębiowski, M., Kumirska, J., and Stepnowski, P. (2008b). Identification of 1-butyl-3-methylimidazolium chloride degradation products formed in Fe(III)/H2O2 oxidation system. Chemia Analityczna (Warsaw), 53, 943951.Google Scholar
Siedlecka, E. M., Gołebiowski, M., Czupryniak, K. J., Ossowski, T., and Stepnowski, P. (2009). Degradation of ionic liquids by Fenton reaction; the effect of anions as counter and background ions. Applied Catalysis B: Environmental, 91, 573579.Google Scholar
Sipes, I. G., Knudsen, G. A., and Kuester, R. K. (2008). The effects of dose and route on the toxicokinetics and disposition of 1-butyl-3-methylimidazolium chloride in male F-344 rats and female B6C3F1 mice. Drug Metabolism and Disposition, 36(2), 284293.CrossRefGoogle ScholarPubMed
Stepnowski, P. and Zaleska, A. (2004). Comparison of different advanced oxidation processes for the degradation of room temperature ionic liquids. Journal of Photochemistry and Photobiology A: Chemistry, 170, 4550.Google Scholar
Stepnowski, P., Skladanowski, A., Ludwiczak, A., and Laczynska, E. (2004). Evaluating the cytotoxicity of ionic liquids using human cell line HeLa. Human and Experimental Toxicology, 23(11), 513517.CrossRefGoogle ScholarPubMed
Stock, F., Hoffmann, J., Ranke, J., et al. (2004). Effects of ionic liquids on the acetycholinesterase: A structure–activity relationship consideration. Green Chemistry, 6, 286290.Google Scholar
Swatloski, R. P., Holbrey, J. D., and Rogers, R. D. (2003). Ionic liquids are not always green: hydrolysis of 1-butyl-3methylimidazolium hexafluorophosphate. Chemistry Communication, 5, 361363.Google Scholar
Wang, W., Zong, M.-H., and Lou, W.-Y. (2009). Use of an ionic liquid to improve asymmetric reduction of 4-methoxyacetophenone catalyzed by immobilized Rhodotorula sp. AS2.2241 cells. Journal of Molecular Catalysis B: Enzymatic, 56, 7076.Google Scholar
Wang, X., Ohlin, C. A., Lu, Q., et al. (2007). Cytotoxicity of ionic liquids and precursor compounds towards human cell line HeLa. Green Chemistry, 9, 11911197.Google Scholar
Weissermel, K. and Arpe, H.J. (2003). Industrial Organic Chemistry, 4th ed. Weinheim: Wiley-VCH.Google Scholar
Wells, A. S. and Coombe, V. T. (2006). On the freshwater ecotoxicity and biodegradation properties of some common ionic liquids. Organic Process Research & Development, 10, 794798.Google Scholar
Welton, T. (1999). Room temperature ionic liquids: Solvents for synthesis and catalysis. Chemical Reviews, 99, 20712083.Google Scholar
Werpy, T. and Petersen, G. (2004). Top Value Added Chemicals From Biomass, Vol. 1. US Department of Energy.Google Scholar
Yang, Z.-H., Zeng, R., and Wang, Y., et al. (2009).Tolerance of immobilized yeast cells in imidazolium-based ionic liquids. Food Technology and Biotechnology, 47, 6266.Google Scholar

Save book to Kindle

To save this book to your Kindle, first ensure [email protected] is added to your Approved Personal Document E-mail List under your Personal Document Settings on the Manage Your Content and Devices page of your Amazon account. Then enter the ‘name’ part of your Kindle email address below. Find out more about saving to your Kindle.

Note you can select to save to either the @free.kindle.com or @kindle.com variations. ‘@free.kindle.com’ emails are free but can only be saved to your device when it is connected to wi-fi. ‘@kindle.com’ emails can be delivered even when you are not connected to wi-fi, but note that service fees apply.

Find out more about the Kindle Personal Document Service.

Available formats
×

Save book to Dropbox

To save content items to your account, please confirm that you agree to abide by our usage policies. If this is the first time you use this feature, you will be asked to authorise Cambridge Core to connect with your account. Find out more about saving content to Dropbox.

Available formats
×

Save book to Google Drive

To save content items to your account, please confirm that you agree to abide by our usage policies. If this is the first time you use this feature, you will be asked to authorise Cambridge Core to connect with your account. Find out more about saving content to Google Drive.

Available formats
×