1-Butyl-3-methylimidazolium hexafluorophosphate

1-Butyl-3-methylimidazolium hexafluorophosphate
BMIM cation and PF6 anion
Names
Systematic IUPAC name
1-Butyl-3-methyl-1H-imidazol-3-ium hexafluoro-λ5-phosphanuide
Other names
BMIM-PF6
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.203.179 Edit this at Wikidata
UNII
  • InChI=1S/C8H15N2.F6P/c1-3-4-5-10-7-6-9(2)8-10;1-7(2,3,4,5)6/h6-8H,3-5H2,1-2H3;/q+1;-1 checkY
    Key: IXQYBUDWDLYNMA-UHFFFAOYSA-N checkY
  • InChI=1/C8H15N2.F6P/c1-3-4-5-10-7-6-9(2)8-10;1-7(2,3,4,5)6/h6-8H,3-5H2,1-2H3;/q+1;-1
    Key: IXQYBUDWDLYNMA-UHFFFAOYAH
  • CCCCN1C=C[N+](=C1)C.F[P-](F)(F)(F)(F)F
  • CCCCn1cc[n+](c1)C.F[P-](F)(F)(F)(F)F
Properties
C8H15F6N2P
Molar mass 284.186 g·mol−1
Appearance Light yellow liquid
Density 1.38 g/mL (20 °C)
Melting point −8 °C (18 °F; 265 K)
insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1-Butyl-3-methylimidazolium hexafluorophosphate, also commonly known as BMIM-PF6, is a viscous, colourless, hydrophobic and non-water-soluble ionic liquid with a melting point of −8 °C. Together with BMIM-BF4, it is one of the most extensively studied ionic liquids. It is known to very slowly decompose in the presence of water.

Preparation and uses

BMIM-PF6 is commercially available. It may be obtained in two steps, as shown below.

  1. BMIM-Cl is synthesized by alkylating the compound 1-methylimidazole with 1-chlorobutane.
  2. A metathesis reaction with potassium hexafluorophosphate and the product from the previous reaction gives the desired compound. BMIM-BF4 may be prepared by analogously using potassium tetrafluoroborate in place of the hexafluorophosphate.

BMIM-PF6 has been investigated in electrochemistry where it ambiguously serves as both a solvent and an electrolyte, and it also has potential uses in electrochemical CO2 reduction.

See also

References

  1. ↑ Mihkel Koel (2008). Ionic Liquids in Chemical Analysis. CRC Press. p. xxvii. ISBN 978-1-4200-4646-5.
  2. ↑ R.P. Swatloski; J.D. Holbrey & R.D. Rogers (2003). "Ionic liquids are not always green: hydrolysis of 1-butyl-3-methylimidazolium hexafluorophosphate". Green Chem. 5 (4): 361–363. doi:10.1039/b304400a.
  3. ↑ Dupont J, Consorti C, Suarez P, de Souza R (2004). "Preparation of 1-Butyl-3-methyl imidazolium-based Room Temperature Ionic Liquids". Organic Syntheses; Collected Volumes, vol. 10, p. 184.
  4. ↑ Yeonji Oh, Xile Hu (2015), "Ionic liquids enhance the electrochemical CO2 reduction catalyzed by MoO2", Chemical Communications, 51 (71): 13698–13701, doi:10.1039/C5CC05263G, PMID 26229995
  5. ↑ Álvaro Pérez-Salado Kamps, Dirk Tuma, Jianzhong Xia, Gerd Maurer (2003), "Solubility of CO2 in the Ionic Liquid [bmim] [PF6]", Journal of Chemical & Engineering Data, 48 (3): 746–749, doi:10.1021/je034023f{{citation}}: CS1 maint: multiple names: authors list (link)

Further reading