1-Butyl-3-methylimidazolium hexafluorophosphate
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477199310
| ImageFile = ILfromOS.svg
| ImageSize = 220
| ImageFile1 = BMIM-PF6-3D-balls.png
| ImageSize1 = 220
| ImageAlt1 = BMIM cation and PF6 anion
| IUPACName=1-butyl-3-methylimidazol-3-ium hexafluorophosphate
| OtherNames= BMIM-PF6
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2015930
| 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
| SMILES1 = CCCCn1cc[n+](c1)C.F[P-](F)(F)(F)(F)F
| InChIKey = IXQYBUDWDLYNMA-UHFFFAOYAH
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IXQYBUDWDLYNMA-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo= 174501-64-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ZGE3N4O8Q9
| PubChem=2734174
| SMILES= CCCCN1C=C[N+](=C1)C.F[P-](F)(F)(F)(F)F
}}
|Section2={{Chembox Properties
| C=8 | H=15 | F=6 | N=2 | P=1
| Appearance= Light yellow liquid
| Density= 1.38 g/mL (20 °C)
| MeltingPtC= -8
| Solubility=insoluble
}}
}}
1-Butyl-3-methylimidazolium hexafluorophosphate, also known as BMIM-PF6, is a viscous, colourless, hydrophobic and non-water-soluble ionic liquid with a melting point{{cite book|url=https://books.google.com/books?id=y8d9F7NG60cC&pg=PR27|page=xxvii|title=Ionic Liquids in Chemical Analysis|author=Mihkel Koel|publisher=CRC Press|year=2008|isbn=978-1-4200-4646-5}} of −8 °C. Together with 1-butyl-3-methylimidazolium tetrafluoroborate, BMIM-BF4, it is one of the most widely studied ionic liquids. It is known to very slowly decompose in the presence of water.{{cite journal |author1=R.P. Swatloski |author2=J.D. Holbrey |author3=R.D. Rogers|name-list-style=amp | title = Ionic liquids are not always green: hydrolysis of 1-butyl-3-methylimidazolium hexafluorophosphate | journal = Green Chem.| year = 2003 | volume = 5 | pages = 361–363 | doi = 10.1039/b304400a | issue = 4}}
Preparation and uses
BMIM-PF6 is commercially available. It may be obtained in two steps: BMIM-Cl is synthesized by alkylating 1-methylimidazole with 1-chlorobutane. A metathesis reaction with potassium hexafluorophosphate gives the desired compound; the tetrafluoroborate may be prepared by analogously using potassium tetrafluoroborate.{{OrgSynth | vauthors = Dupont J, Consorti C, Suarez P, de Souza R | title = Preparation of 1-Butyl-3-methyl imidazolium-based Room Temperature Ionic Liquids | collvol = 10 | collvolpages = 184 | year = 2004 | prep = v79p0236}}
BMIM-PF6 has been investigated in electrochemistry where it serves both as solvent and electrolyte,{{Citation |author=Álvaro Pérez-Salado Kamps, Dirk Tuma, Jianzhong Xia, Gerd Maurer |title=Solubility of CO2 in the Ionic Liquid [bmim] [PF6] |journal=Journal of Chemical & Engineering Data |volume=48 |number=3 |date=2003 |doi=10.1021/je034023f |pages=746–749}} and in electrochemical CO2 reduction.{{Citation |author=Yeonji Oh, Xile Hu |title=Ionic liquids enhance the electrochemical CO2 reduction catalyzed by MoO2 |journal=Chemical Communications |volume=51 |number=71 |date=2015 |doi=10.1039/C5CC05263G |pages=13698–13701|pmid=26229995 |url=https://infoscience.epfl.ch/handle/20.500.14299/119055 }}
See also
References
{{reflist}}
Further reading
- {{cite journal |author1=S. Carda-Broch |author2=A. Berthod |author3=D.W. Armstrong | title = Solvent properties of the 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid | journal = Analytical and Bioanalytical Chemistry | volume = 375 | issue = 2 | pages = 191–199 | doi = 10.1007/s00216-002-1684-1 | pmid = 12560962 | year = 2003|s2cid=32506513 }}
{{Hexafluorophosphates}}
{{DEFAULTSORT:Butyl-3-methylimidazolium hexafluorophosphate, 1-}}