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1-Butyl-3-methylimidazolium hexafluorophosphate

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[1] 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.[2]

1-Butyl-3-methylimidazolium hexafluorophosphate
Names
IUPAC name
1-butyl-3-methylimidazol-3-ium hexafluorophosphate
Other names
BMIM-PF6
Identifiers
  • 174501-64-5 Y
3D model (JSmol)
  • Interactive image
  • Interactive image
ChemSpider
  • 2015930 Y
ECHA InfoCard 100.203.179
  • 2734174
UNII
  • ZGE3N4O8Q9 Y
  • DTXSID4047911
  • 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 Y
    Key: IXQYBUDWDLYNMA-UHFFFAOYSA-N Y
  • 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).
N verify (what is YN ?)

Preparation edit

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.[3]

 

See also edit

References edit

  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.

Further reading edit

  • S. Carda-Broch; A. Berthod; D.W. Armstrong (2003). "Solvent properties of the 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid". Analytical and Bioanalytical Chemistry. 375 (2): 191–199. doi:10.1007/s00216-002-1684-1. PMID 12560962. S2CID 32506513.

butyl, methylimidazolium, hexafluorophosphate, also, known, bmim, viscous, colourless, hydrophobic, water, soluble, ionic, liquid, with, melting, point, together, with, butyl, methylimidazolium, tetrafluoroborate, bmim, most, widely, studied, ionic, liquids, k. 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 1 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 2 1 Butyl 3 methylimidazolium hexafluorophosphate Names IUPAC name 1 butyl 3 methylimidazol 3 ium hexafluorophosphate Other names BMIM PF6 Identifiers CAS Number 174501 64 5 Y 3D model JSmol Interactive imageInteractive image ChemSpider 2015930 Y ECHA InfoCard 100 203 179 PubChem CID 2734174 UNII ZGE3N4O8Q9 Y CompTox Dashboard EPA DTXSID4047911 InChI 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 YKey IXQYBUDWDLYNMA UHFFFAOYSA N YInChI 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 1Key IXQYBUDWDLYNMA UHFFFAOYAH SMILES CCCCN1C C N C1 C F P F F F F FCCCCn1cc n c1 C F P F F F F F Properties Chemical formula C 8H 15F 6N 2P 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 Solubility in water insoluble Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Preparation 2 See also 3 References 4 Further readingPreparation editBMIM 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 3 nbsp See also edit1 Butyl 3 methylimidazolium tetrachloroferrateReferences edit Mihkel Koel 2008 Ionic Liquids in Chemical Analysis CRC Press p xxvii ISBN 978 1 4200 4646 5 R P Swatloski J D Holbrey amp 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 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 Further reading editS Carda Broch A Berthod D W Armstrong 2003 Solvent properties of the 1 butyl 3 methylimidazolium hexafluorophosphate ionic liquid Analytical and Bioanalytical Chemistry 375 2 191 199 doi 10 1007 s00216 002 1684 1 PMID 12560962 S2CID 32506513 Retrieved from https en wikipedia org w index php title 1 Butyl 3 methylimidazolium hexafluorophosphate amp oldid 1067830925, wikipedia, wiki, book, books, library,

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