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Liquid-Liquid Equilibria of Binary and Ternary Systems Containing Ionic Liquids

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Encyclopedia of Ionic Liquids

Introduction

The unit operation “extraction” is mainly applied in the downstream process of the chemical industry when other unit operations are not suitable. This is especially the case if temperature-sensitive compounds are involved, if the product and solvent boiling temperatures are similar preventing distillation or if azeotropic behavior occurs [28]. Additionally, extraction can save energy consumption if large process streams are involved. The design of extraction columns highly depends on the knowledge of the underlying liquid-liquid equilibria (LLE). An ideal extraction agent has possibly lowest solubility in the solvent while fully solubilizing the solute resulting in a large miscibility gap between solvent and solute. Conventional extraction agents are volatile organic compounds (VOCs). VOCs exhibit high vapor pressure, have high flammability, and are often environmentally harmful and toxic. In contrast, ionic liquids (ILs) may be eligible extraction agents to their unique...

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References

  1. Abbott AP, Cullis PM, Gibson MJ et al (2007) Extraction of glycerol from biodiesel into a eutectic based ionic liquid. Green Chem 9(8):868

    Article  CAS  Google Scholar 

  2. Anderson JL, Armstrong DW, Wei G-T (2006) Ionic liquids in analytical chemistry. Anal Chem 78(9):2892–2902

    Article  PubMed  Google Scholar 

  3. Arce A, Earle MJ, Rodríguez H et al (2007) Separation of aromatic hydrocarbons from alkanes using the ionic liquid 1-ethyl-3-methylimidazoliumbis{(trifluoromethyl) sulfonyl}amide. Green Chem 9(1):70–74

    Article  CAS  Google Scholar 

  4. Bösmann A, Datsevich L, Jess A et al (2001) Deep desulfurization of diesel fuel by extraction with ionic liquids. Chem Commun:2494–2495

    Google Scholar 

  5. Bülow M, Ji X, Held C (2019) Incorporating a concentration-dependent dielectric constant into ePC-SAFT. An application to binary mixtures containing ionic liquids. Fluid Phase Equilib 492:26–33

    Article  Google Scholar 

  6. Chapeaux A, Simoni LD, Stadtherr MA et al (2007) Liquid phase behavior of ionic liquids with water and 1-octanol and modeling of 1-octanol/water partition coefficients. J Chem Eng Data 52(6):2462–2467

    Article  CAS  Google Scholar 

  7. Chapeaux A, Simoni LD, Ronan TS et al (2008) Extraction of alcohols from water with 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide. Green Chem 10(12):1301–1306

    Article  CAS  Google Scholar 

  8. Chapman WG, Gubbins KE, Jackson G et al (1989) SAFT: equation-of-state solution model for associating fluids. Fluid Phase Equilib 52:31–38

    Article  CAS  Google Scholar 

  9. Cull SG, Holbrey JD, Vargas-Mora V et al (2000) Room-temperature ionic liquids as replacements for organic solvents in multiphase bioprocess operations. Biotechnol Bioeng 69(2):227–233

    Article  CAS  PubMed  Google Scholar 

  10. Debye P, Hückel E (1923) Zur Theorie der Elektrolyte. I Gefrierpunktserniedrigung und verwandte Erscheinungen. Z Phys 1923(24):185–206

    Google Scholar 

  11. Du Z, Yu Y-L, Wang J-H (2007) Extraction of proteins from biological fluids by use of an ionic liquid/aqueous two-phase system. Chemistry 13(7):2130–2137

    Article  CAS  PubMed  Google Scholar 

  12. Freire MG, Neves CMSS, Carvalho PJ et al (2007) Mutual solubilities of water and hydrophobic ionic liquids. J Phys Chem B 111(45):13082–13089

    Article  CAS  PubMed  Google Scholar 

  13. Freire MG, Carvalho PJ, Gardas RL et al (2008) Mutual solubilities of water and the C(n)mimTf(2)N hydrophobic ionic liquids. J Phys Chem B 112(6):1604–1610

    Article  CAS  PubMed  Google Scholar 

  14. Gross J, Sadowski G (2001) Perturbed-chain SAFT: an equation of state based on a perturbation theory for chain molecules. Ind Eng Chem Res 40(4):1244–1260

    Article  CAS  Google Scholar 

  15. Ha SH, Mai NL, Koo Y-M (2010) Butanol recovery from aqueous solution into ionic liquids by liquid–liquid extraction. Process Biochem 45(12):1899–1903

    Article  CAS  Google Scholar 

  16. Huang C, Chen B, Zhang J et al (2004) Desulfurization of gasoline by extraction with new ionic liquids. Energy Fuel 18(6):1862–1864

    Article  CAS  Google Scholar 

  17. Huddleston JG, Willauer HD, Swatloski RP et al (1998) Room temperature ionic liquids as novel media for ‘clean’ liquid–liquid extraction. Chem Commun:1765–1766

    Google Scholar 

  18. Ji X, Held C, Sadowski G (2012) Modeling imidazolium-based ionic liquids with ePC-SAFT. Fluid Phase Equilib 335:64–73

    Article  CAS  Google Scholar 

  19. Kontogeorgis GM, Voutsas EC, Yakoumis IV et al (1996) An equation of state for associating fluids. Ind Eng Chem Res 35(11):4310–4318

    Article  CAS  Google Scholar 

  20. Lee SH, Doherty TV, Linhardt RJ et al (2009) Ionic liquid-mediated selective extraction of lignin from wood leading to enhanced enzymatic cellulose hydrolysis. Biotechnol Bioeng 102(5):1368–1376

    Article  CAS  PubMed  Google Scholar 

  21. Liu J-f, Jiang G-b, Jönsson JÅ (2005) Application of ionic liquids in analytical chemistry. Trends Anal Chem 24(1):20–27

    Article  Google Scholar 

  22. Maia FM, Rodríguez O, Macedo EA (2010) LLE for (water+ionic liquid) binary systems using [Cxmim][BF4] (x=6, 8) ionic liquids. Fluid Phase Equilib 296(2):184–191

    Article  CAS  Google Scholar 

  23. Maribo-Mogensen B, Kontogeorgis GM, Thomsen K (2012) Comparison of the Debye–Hückel and the mean spherical approximation theories for electrolyte solutions. Ind Eng Chem Res 51(14):5353–5363

    Article  CAS  Google Scholar 

  24. Meindersma GW, Podt AJG, de Haan AB (2006) Ternary liquid–liquid equilibria for mixtures of toluene+n-heptane+an ionic liquid. Fluid Phase Equilib 247(1–2):158–168

    Article  CAS  Google Scholar 

  25. Nann A, Held C, Sadowski G (2013) Liquid–liquid equilibria of 1-butanol/water/IL systems. Ind Eng Chem Res 52(51):18472–18481

    Article  CAS  Google Scholar 

  26. Neves CMSS, Granjo JFO, Freire MG et al (2011) Separation of ethanol–water mixtures by liquid–liquid extraction using phosphonium-based ionic liquids. Green Chem 13(6):1517

    Article  CAS  Google Scholar 

  27. Pei Y, Wang J, Wu K et al (2009) Ionic liquid-based aqueous two-phase extraction of selected proteins. Sep Purif Technol 64(3):288–295

    Article  CAS  Google Scholar 

  28. Pereiro AB, Tojo E, Rodríguez A et al (2006) HMImPF6 ionic liquid that separates the azeotropic mixture ethanol + heptane. Green Chem 8(3):307

    Article  CAS  Google Scholar 

  29. Pereiro AB, Rodríguez A (2010) An ionic liquid proposed as solvent in aromatic hydrocarbon separation by liquid extraction. AIChE J 56(2):381–386

    CAS  Google Scholar 

  30. Pereiro AB, Rodríguez A (2007) Experimental liquid−liquid equilibria of 1-Alkyl-3-methylimidazolium Hexafluorophosphate with 1-alcohols. J Chem Eng Data 52(4):1408–1412

    Article  CAS  Google Scholar 

  31. Srncik M, Kogelnig D, Stojanovic A et al (2009) Uranium extraction from aqueous solutions by ionic liquids. Appl Radiat Isot 67(12):2146–2149

    Article  CAS  PubMed  Google Scholar 

  32. Strassner T, Ahrens S (2010) Salze mit aryl-alkyl-substituierten imidazolium- und triazoliumkationen als Ionische Flüssigkeiten(EP2254871A1)

    Google Scholar 

  33. Sun P, Armstrong DW (2010) Ionic liquids in analytical chemistry. Anal Chim Acta 661(1):1–16

    Article  CAS  PubMed  Google Scholar 

  34. Tokuda H, Hayamizu K, Ishii K et al (2004) Physicochemical properties and structures of room temperature ionic liquids. 1. Variation of anionic species. J Phys Chem B 108(42):16593–16600

    Article  CAS  Google Scholar 

  35. Tokuda H, Hayamizu K, Ishii K et al (2005) Physicochemical properties and structures of room temperature ionic liquids. 2. Variation of alkyl chain length in imidazolium cation. J Phys Chem B 109(13):6103–6110

    Article  CAS  PubMed  Google Scholar 

  36. Visser AE, Swatloski RP, Griffin ST et al (2001) Liquid/liquid extraction of metal ions in room temperature ionic liquids. Sep Sci Technol 36(5–6):785–804

    Article  CAS  Google Scholar 

  37. Visser AE, Swatloski RP, Reichert WM et al (2001) Task-specific ionic liquids for the extraction of metal ions from aqueous solutions. Chem Commun:135–136

    Google Scholar 

  38. Waisman E, Lebowitz JL (1970) Exact solution of an integral equation for the structure of a primitive model of electrolytes. J Chem Phys 52(8):4307–4309

    Article  CAS  Google Scholar 

  39. Wei G-T, Yang Z, Chen C-J (2003) Room temperature ionic liquid as a novel medium for liquid/liquid extraction of metal ions. Anal Chim Acta 488(2):183–192

    Article  CAS  Google Scholar 

  40. Wertheim MS (1984) Fluids with highly directional attractive forces. I. Statistical thermodynamics. J Stat Phys 35(1–2):19–34

    Article  Google Scholar 

  41. Wertheim MS (1984) Fluids with highly directional attractive forces. II. Thermodynamic perturbation theory and integral equations. J Stat Phys 35(1–2):35–47

    Article  Google Scholar 

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Correspondence to Christoph Held .

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Bülow, M., Danzer, A., Held, C. (2020). Liquid-Liquid Equilibria of Binary and Ternary Systems Containing Ionic Liquids. In: Zhang, S. (eds) Encyclopedia of Ionic Liquids. Springer, Singapore. https://doi.org/10.1007/978-981-10-6739-6_108-1

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  • DOI: https://doi.org/10.1007/978-981-10-6739-6_108-1

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  • Print ISBN: 978-981-10-6739-6

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