Draft:C2mim
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Last edited by Bearcat (talk | contribs) 12 days ago. (Update) |
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C6H11N2+ | |
| Molar mass | 111.167 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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C2mim is the short form of 1-n-ethyl-3-methylimidazolium cation. C2 refers to the ethyl group. C2mim, abbreviated as EMIM, is the basis for a number of common ionic liquids whose properties can be tuned by combining them with a wide variety of anions.[1][2][3] The salt containing this imidazole cation is an ionic liquid, a common example being 1-ethyl-3-methylimidazolium chloride ([C2mim][Cl]).
C2mim was introduced as a component of chloroaluminate-based ionic liquids in the 1980s, during the early stages of ionic liquid development, by Wilkes et al.[4] C2mim was also preferred because it brings good physical properties, such as a liquid state at room temperature.[4] Furthermore, C2mim has become one of the most widely studied and used cations due to its ease of synthesis, relatively low viscosity (compared to cations with long-chain alkyl groups), and excellent performance in a variety of applications.[1][4][5][6]
Chemical structure of 1-n-ethyl-3-methylimidazolium chloride
Examples of salts
[edit]Anions commonly paired with C2mim include:
- Halides: Chloride (Cl−), Bromide (Br−). Often used as synthetic precursors, they may be solids at room temperature (e.g., Cl−).[7]
- Tetrafluoroborate (BF−
4): common, relatively low viscosity, stable to water (but anions may slowly hydrolyze). - Hexafluorophosphate (PF−
6): common, often hydrophobic, but prone to release hydrogen fluoride (HF) upon hydrolysis. - Bis(trifluoromethylsulfonyl)imide: hydrophobic, high thermal and electrochemical stability, with relatively low viscosity.
- Acetate (AcO−
or CH
3COO−
): hydrophilic, good biomass solvent, somewhat low thermal stability, possibly biodegradable. - Ethyl sulfate: hydrophilic, used in synthetic routes .
- Dicyanamide ((C
2N−
3): low viscosity, possible heat transfer medium. - Trifluoromethanesulfonate ((CF3SO−3): stable anion.
- Thiocyanates ([SCN]−)
- Hydrogen sulfates (HSO−4): may have protonic properties.
- Diethyl phosphate ([DEP]−): good solvent in certain applications.
- Bis(fluorosulfonyl)imide: low viscosity, good conductivity.
- bicarbonate (HCO−
3): used in synthesis.
References
[edit]- ^ a b Chemistry Stack Exchange. Why is 1-ethyl-3-methylimidazolium tetrafluoroborate (EMI-BF4) often considered a prototypical room temperature ionic liquid?. Retrieved 2025-04-23.
- ^ Alguacil, Francisco Jose; Robla, Jose Ignacio (2024-11-15). "Using Ionic Liquids to Improve CO2 Capture". Molecules. 29 (22): 5388. doi:10.3390/molecules29225388. PMC 11596754. PMID 39598774.
- ^ Friess, Karel; Izák, Pavel; Kárászová, Magda; Pasichnyk, Mariia; Lanč, Marek; Nikolaeva, Daria; Luis, Patricia; Jansen, Johannes Carolus (2021-01-30). "A Review on Ionic Liquid Gas Separation Membranes". Membranes. 11 (2): 79. doi:10.3390/membranes11020097. PMID 33573138.
- ^ a b c Welton, Tom (2018-04-26). "Ionic liquids: a brief history". Biophys Rev. 10 (3): 691–706. doi:10.1007/s12551-018-0419-2. PMC 5988633. PMID 29700779.
- ^ Dzulkipli, Mariah Zuliana; Karim, Jamilah; Ahmad, Azizan; Dzulkurnain, Nurul Akmaliah; Su’ait, Mohd Sukor; Yoshizawa-Fujita, Masahiro; Khoon, Lee Tian; Hassan, Nur Hasyareeda (2021-04-14). "The Influences of 1-Butyl-3-Methylimidazolium Tetrafluoroborate on Electrochemical, Thermal and Structural Studies as Ionic Liquid Gel Polymer Electrolyte". Polymers. 13 (8): 1277. doi:10.3390/polym13081277. PMC 8070978. PMID 33919960.
- ^ Ionic Liquids Today (PDF) (Report). Iolitec. 2010-05-04.
- ^ Babilas, Dorota; Kowalik-Klimczak, Anna; Dydo, Piotr (2021-12-01). "Study on the Effectiveness of Simultaneous Recovery and Concentration of 1-Ethyl-3-methylimidazolium Chloride Ionic Liquid by Electrodialysis with Heterogeneous Ion-Exchange Membranes". Int J Mol Sci. 22 (23): 13014. doi:10.3390/ijms222313014. PMC 8657828. PMID 34884819.