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Protic ionic liquid

April 11, 2024

A protic ionic liquid is an ionic liquid that is formed via proton transfer from a Brønsted acid to a Brønsted base.[1] Unlike many other types of ionic liquids, which are formed through a series of synthesis steps,[2] protic ionic liquids are easier to create because the acid and base must simply be mixed together.[1]

Monoethanolamine oleate is a typical protic ionic liquid.

Properties edit

Because the proton transfer reaction is reversible, the equilibrium between reactants and ionic products can shift depending on the conditions. This equilibration significantly impact the properties of protic ionic liquids since some neutral acid and base species are generally present in the solution.

Many protic ionic liquids have non-negligible vapor pressure,[1] even though traditional ionic liquids are often touted for their low vapor pressures.[3][4] Some protic ionic liquids are distillable.[1][5][6] Additionally, during distillation protic ionic liquids exhibit what appears to be a reactive azeotrope.[7][8][6] In other words, initially only the acid or base is vaporized, but at a specific composition both the acid and base start to vaporize and the composition of the vapor and liquid is the same. This composition depends on the anion and cation and contains more acid than base.[7] However, when mixed with water the vaporization behavior is different and an azeotrope no longer occurs at that same composition.[9]

The density of a protic ionic liquid mixture also appears to be higher for the composition at which the azeotrope forms. That is, if some excess of the acid is present in the mixture the density increases.[10]

References edit

  1. ^ a b c d Greaves, Tamar L.; Drummond, Calum J. (2008-01-01). "Protic Ionic Liquids: Properties and Applications". Chemical Reviews. 108 (1): 206–237. doi:10.1021/cr068040u. ISSN 0009-2665. PMID 18095716.
  2. ^ Ratti, Rajni (2014-10-29). "Ionic Liquids: Synthesis and Applications in Catalysis". Advances in Chemistry. 2014: 1–16. doi:10.1155/2014/729842.
  3. ^ Rogers, Robin D.; Seddon, Kenneth R. (2003-10-31). "Ionic Liquids--Solvents of the Future?". Science. 302 (5646): 792–793. doi:10.1126/science.1090313. ISSN 0036-8075. PMID 14593156. S2CID 94376105.
  4. ^ Earle, Martyn J.; Esperança, José M. S. S.; Gilea, Manuela A.; Canongia Lopes, José N.; Rebelo, Luís P. N.; Magee, Joseph W.; Seddon, Kenneth R.; Widegren, Jason A. (February 2006). "The distillation and volatility of ionic liquids". Nature. 439 (7078): 831–834. Bibcode:2006Natur.439..831E. doi:10.1038/nature04451. ISSN 1476-4687. PMID 16482154. S2CID 4357175.
  5. ^ Parviainen, Arno; King, Alistair W. T.; Mutikainen, Ilpo; Hummel, Michael; Selg, Christoph; Hauru, Lauri K. J.; Sixta, Herbert; Kilpeläinen, Ilkka (2013-11-01). "Predicting Cellulose Solvating Capabilities of Acid–Base Conjugate Ionic Liquids". ChemSusChem. 6 (11): 2161–2169. doi:10.1002/cssc.201300143. ISSN 1864-5631. PMID 24106149.
  6. ^ a b Ahmad, Waqar; Ostonen, Alexandr; Jakobsson, Kaj; Uusi-Kyyny, Petri; Alopaeus, Ville; Hyväkkö, Uula; King, Alistair W. T. (2016-10-01). "Feasibility of thermal separation in recycling of the distillable ionic liquid [DBNH][OAc] in cellulose fiber production". Chemical Engineering Research and Design. 114: 287–298. doi:10.1016/j.cherd.2016.08.032. ISSN 0263-8762.
  7. ^ a b Ribeiro, Filipe M. S.; Lima, Carlos F. R. A. C.; Silva, Artur M. S.; Santos, Luís M. N. B. F. (2018-09-18). "Experimental Evidence for Azeotrope Formation from Protic Ionic Liquids". ChemPhysChem. 19 (18): 2364–2369. doi:10.1002/cphc.201800335. ISSN 1439-4235. PMID 29799151. S2CID 44127885.
  8. ^ Lopes, José N. Canongia; Rebelo, Luís Paulo N. (2010-02-09). "Ionic liquids and reactive azeotropes: the continuity of the aprotic and protic classes". Physical Chemistry Chemical Physics. 12 (8): 1948–1952. Bibcode:2010PCCP...12.1948L. doi:10.1039/B922524M. ISSN 1463-9084. PMID 20145863.
  9. ^ Baird, Zachariah Steven; Uusi-Kyyny, Petri; Witos, Joanna; Rantamäki, Antti H.; Sixta, Herbert; Wiedmer, Susanne K.; Alopaeus, Ville (2020-05-14). "Vapor–Liquid Equilibrium of Ionic Liquid 7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-enium Acetate and Its Mixtures with Water". Journal of Chemical & Engineering Data. 65 (5): 2405–2421. doi:10.1021/acs.jced.9b01039. ISSN 0021-9568.
  10. ^ Baird, Zachariah Steven; Uusi-Kyyny, Petri; Dahlberg, Artur; Cederkrantz, Daniel; Alopaeus, Ville (2020-10-01). "Densities, Viscosities, and Thermal Conductivities of the Ionic Liquid 7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-enium Acetate and Its Mixtures with Water". International Journal of Thermophysics. 41 (12): 160. Bibcode:2020IJT....41..160B. doi:10.1007/s10765-020-02742-4. ISSN 1572-9567.

April 11, 2024
protic, ionic, liquid, protic, ionic, liquid, ionic, liquid, that, formed, proton, transfer, from, brønsted, acid, brønsted, base, unlike, many, other, types, ionic, liquids, which, formed, through, series, synthesis, steps, protic, ionic, liquids, easier, cre. A protic ionic liquid is an ionic liquid that is formed via proton transfer from a Bronsted acid to a Bronsted base 1 Unlike many other types of ionic liquids which are formed through a series of synthesis steps 2 protic ionic liquids are easier to create because the acid and base must simply be mixed together 1 Monoethanolamine oleate is a typical protic ionic liquid Properties editBecause the proton transfer reaction is reversible the equilibrium between reactants and ionic products can shift depending on the conditions This equilibration significantly impact the properties of protic ionic liquids since some neutral acid and base species are generally present in the solution Many protic ionic liquids have non negligible vapor pressure 1 even though traditional ionic liquids are often touted for their low vapor pressures 3 4 Some protic ionic liquids are distillable 1 5 6 Additionally during distillation protic ionic liquids exhibit what appears to be a reactive azeotrope 7 8 6 In other words initially only the acid or base is vaporized but at a specific composition both the acid and base start to vaporize and the composition of the vapor and liquid is the same This composition depends on the anion and cation and contains more acid than base 7 However when mixed with water the vaporization behavior is different and an azeotrope no longer occurs at that same composition 9 The density of a protic ionic liquid mixture also appears to be higher for the composition at which the azeotrope forms That is if some excess of the acid is present in the mixture the density increases 10 References edit a b c d Greaves Tamar L Drummond Calum J 2008 01 01 Protic Ionic Liquids Properties and Applications Chemical Reviews 108 1 206 237 doi 10 1021 cr068040u ISSN 0009 2665 PMID 18095716 Ratti Rajni 2014 10 29 Ionic Liquids Synthesis and Applications in Catalysis Advances in Chemistry 2014 1 16 doi 10 1155 2014 729842 Rogers Robin D Seddon Kenneth R 2003 10 31 Ionic Liquids Solvents of the Future Science 302 5646 792 793 doi 10 1126 science 1090313 ISSN 0036 8075 PMID 14593156 S2CID 94376105 Earle Martyn J Esperanca Jose M S S Gilea Manuela A Canongia Lopes Jose N Rebelo Luis P N Magee Joseph W Seddon Kenneth R Widegren Jason A February 2006 The distillation and volatility of ionic liquids Nature 439 7078 831 834 Bibcode 2006Natur 439 831E doi 10 1038 nature04451 ISSN 1476 4687 PMID 16482154 S2CID 4357175 Parviainen Arno King Alistair W T Mutikainen Ilpo Hummel Michael Selg Christoph Hauru Lauri K J Sixta Herbert Kilpelainen Ilkka 2013 11 01 Predicting Cellulose Solvating Capabilities of Acid Base Conjugate Ionic Liquids ChemSusChem 6 11 2161 2169 doi 10 1002 cssc 201300143 ISSN 1864 5631 PMID 24106149 a b Ahmad Waqar Ostonen Alexandr Jakobsson Kaj Uusi Kyyny Petri Alopaeus Ville Hyvakko Uula King Alistair W T 2016 10 01 Feasibility of thermal separation in recycling of the distillable ionic liquid DBNH OAc in cellulose fiber production Chemical Engineering Research and Design 114 287 298 doi 10 1016 j cherd 2016 08 032 ISSN 0263 8762 a b Ribeiro Filipe M S Lima Carlos F R A C Silva Artur M S Santos Luis M N B F 2018 09 18 Experimental Evidence for Azeotrope Formation from Protic Ionic Liquids ChemPhysChem 19 18 2364 2369 doi 10 1002 cphc 201800335 ISSN 1439 4235 PMID 29799151 S2CID 44127885 Lopes Jose N Canongia Rebelo Luis Paulo N 2010 02 09 Ionic liquids and reactive azeotropes the continuity of the aprotic and protic classes Physical Chemistry Chemical Physics 12 8 1948 1952 Bibcode 2010PCCP 12 1948L doi 10 1039 B922524M ISSN 1463 9084 PMID 20145863 Baird Zachariah Steven Uusi Kyyny Petri Witos Joanna Rantamaki Antti H Sixta Herbert Wiedmer Susanne K Alopaeus Ville 2020 05 14 Vapor Liquid Equilibrium of Ionic Liquid 7 Methyl 1 5 7 triazabicyclo 4 4 0 dec 5 enium Acetate and Its Mixtures with Water Journal of Chemical amp Engineering Data 65 5 2405 2421 doi 10 1021 acs jced 9b01039 ISSN 0021 9568 Baird Zachariah Steven Uusi Kyyny Petri Dahlberg Artur Cederkrantz Daniel Alopaeus Ville 2020 10 01 Densities Viscosities and Thermal Conductivities of the Ionic Liquid 7 Methyl 1 5 7 triazabicyclo 4 4 0 dec 5 enium Acetate and Its Mixtures with Water International Journal of Thermophysics 41 12 160 Bibcode 2020IJT 41 160B doi 10 1007 s10765 020 02742 4 ISSN 1572 9567 Retrieved from https en wikipedia org w index php title Protic ionic liquid amp oldid 1183423823, wikipedia, wiki, book, books, library,

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