1-Butyl-3-methyl-imidazolium-bis (trifluoromethylsulfonyl) -imide

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Structural formula
Structural formula of BMIIm
General
Surname 1-Butyl-3-methyl-imidazolium-bis (trifluoromethylsulfonyl) -imide
other names
  • BMIIm
  • BMIM TFSI
  • [BMIM] [Tf 2 N]
Molecular formula C 10 H 15 F 6 N 3 O 4 S 2
Brief description

colorless, viscous liquid

External identifiers / databases
CAS number 174899-83-3
EC number 605-742-4
ECHA InfoCard 100.109.437
PubChem 11258643
ChemSpider 9433669
Wikidata Q161593
properties
Molar mass 419.36 g mol −1
Physical state

liquid

density

1.44 g cm −3

Melting point

2 ° C

safety instructions
GHS labeling of hazardous substances
05 - Corrosive 06 - Toxic or very toxic 08 - Dangerous to health 09 - Dangerous for the environment

danger

H and P phrases H: 301 + 311-314-373-411
P: 273-280-301 + 310-305 + 351 + 338-310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1-Butyl-3-methyl-imidazolium-bis (trifluoromethylsulfonyl) -imide is an ionic liquid (also: ionic liquid or liquid salt).

properties

1-Butyl-3-methyl-imidazolium-bis (trifluoromethylsulfonyl) -imide is an ionic liquid . It is a very temperature-stable, water-insoluble compound . It is neither flammable nor does it have a measurable vapor pressure at room temperature . The melting point is 2 ° C. It is very suitable as a solvent or coolant .

presentation

It is prepared by reacting 1-butyl-3-methylimidazolium chloride (C 8 H 15 ClN 2 ) and lithium bis (trifluoromethanesulphone) imide (C 2 F 6 LiNO 4 S 2 ) in water. Two phases are formed. The lower one is the ionic liquid.

use

1-Butyl-3-methyl-imidazolium-bis (trifluoromethylsulfonyl) -imide is used, like many other ionic liquids, in organic synthesis. Due to its ionic structure, it is a polar solvent. Like many other ionic liquids, it is not miscible with water or with many other organic solvents. Therefore, the reactants are extracted after a reaction and the ionic liquid can be used again.

Individual evidence

  1. ↑ Data sheet 1-Butyl-3-methyl-imidazolium-bis (trifluoromethylsulfonyl) -imide (PDF) from Merck , accessed on January 18, 2011.
  2. ↑ a b c S. Holopainen, M. Nousiainen, J. Puton, M. Sillanpää, U. Bardi, A. Tolstogouzov: Evaporation of ionic liquids at atmospheric pressure: Study by ion mobility spectrometry . In: Talanta . No. 3 . Elsevier BV, Amsterdam 2011, p. 907-915 , doi : 10.1016 / j.talanta.2010.10.062 .
  3. ↑ a b Data sheet 1-Butyl-3-methylimidazolium bis (trifluoromethylsulfonyl) imide from Sigma-Aldrich , accessed on October 23, 2016 ( PDF ).
  4. ↑ Michelle H. Dunn, Marcus L. Cole, Jason B. Harper: Effects of an ionic liquid solvent on the synthesis of γ-butyrolactones by conjugate addition using NHC organocatalysts. In: RSC Advances. 2, 2012, p. 10160, doi: 10.1039 / C2RA21889E .
  5. ↑ Jonathan G. Huddleston, Ann E. Visser, W. Matthew Reichert, Heather D. Willauer, Grant A. Broker, Robin D. Rogers: Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. In: Green Chemistry. 3, p. 156, doi: 10.1039 / b103275p .
  6. ↑ R. Hamidova, I. Kul, J. Safarov, A. Shahverdiyev, E. Hassel: THERMOPHYSICAL PROPERTIES OF 1-BUTYL-3-METHYLIMIDAZOLIUM BIS (TRIFLUOROMETHYLSULFONYL) IMIDE AT HIGH TEMPERATURES AND PRESSURES. In: Brazilian Journal of Chemical Engineering. 32, 2015, p. 303, doi: 10.1590 / 0104-6632.20150321s00003120 .