Reaction #939014

ord-27d7c300e41e40c18111994c03482af2

Reaction equation

CCCC[n+]1ccn(C)c1.[Cl-]
1-n-butyl-3-methylimidazolium chloride
CCCCCCCCCCCCOS(=O)(=O)[O-].[Na+]
sodium lauryl sulfate
→
CCCCCCCCCCCCOS(=O)(=O)[O-].CCCC[n+]1ccn(C)c1
product
Yield 94.2%
CCCCCCCCCCCCOS(=O)(=O)[O-].CCCC[n+]1ccn(C)c1
1-n-Butyl-3-methylimidazolium Lauryl Sulfate
Yield 94.2%

Reactants

CCCC[n+]1ccn(C)c1.[Cl-]
1-n-butyl-3-methylimidazolium chloride
CCCCCCCCCCCCOS(=O)(=O)[O-].[Na+]
sodium lauryl sulfate

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe water is slowly removed under vacuum
  2. 2
    OtherThe solid formed
  3. 3
    Filtrationis filtered off
  4. 4
    workup.ADDITIONafter adding methylene chloride to the batch
  5. 5
    WashThe filtrate is washed with water until the aqueous phase
  6. 6
    DryingThe organic phase is dried over Na2SO4
  7. 7
    ConcentrationConcentrating
  8. 8
    Otherdrying under a high vacuum

Procedure

15.30 g (87.6 mmole) of 1-n-butyl-3-methylimidazolium chloride (BMIM Cl) and 26.60 g (minimum 87.6 mmole) of sodium lauryl sulfate (technical grade, content 95-99%) are dissolved in 50 ml of hot water. The water is slowly removed under vacuum. The solid formed is filtered off after adding methylene chloride to the batch. The filtrate is washed with water until the aqueous phase is colourless and free from chloride. The organic phase is dried over Na2SO4. Concentrating and drying under a high vacuum gives 33.40 g of product (82.5 mmole; 94% of the theoretical yield, based on BMIM Cl) which is obtained as a white beige waxy solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07252791B2uspto-grants-2007_08