Trimethylamine → Glycidyl trimethylammonium chloride

HRID 1196063Notes

Reaction equation

HRID 1196063 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)[Cl:2].[CH3:6][N:7]([CH3:9])[CH3:8]>>[Cl-:2].[O:5]1[CH2:4][CH:3]1[CH2:1][N+:7]([CH3:9])([CH3:8])[CH3:6]

Participants

3

Reactant 2

HCID 1146TrimethylamineHCID 7835Epichlorohydrin2×

Product 1

HCID 18205Glycidyl trimethylammonium chloride

Procedure

A one-liter flask equipped with was gas sparger, mechanical stirrer, thermometer and an aqueous acid trap was charged with epichlorohydrin (552 grams, 6.0 mol) and placed in an isothermal bath at 19° C. Trimethylamine gas (119.5 grams, 2.0 mol) was then sparged into the epichlorohydrin over a period of 3 hours. The temperature was maintained below 23° C. The solution was stirred for an additional 30 minutes and the precipitate collected by filtration. The crystalline product was washed with diethylether and vacuum dried to afford 262.2 grams of 2,3-epoxypropyltri-methylammonium chloride.

Workup

  1. customA one-liter flask equipped
  2. customplaced in an isothermal bath at 19° C
  3. temperatureThe temperature was maintained below 23° C
  4. filtrationthe precipitate collected by filtration
  5. washThe crystalline product was washed with diethylether and vacuum
  6. customdried
  7. customto afford 262.2 grams of 2,3-epoxypropyltri-methylammonium chloride

Sources & evidence

ORD record
ord-c679b4d4cb4c43d79dcab181e71323a7
Source dataset
uspto-grants-1992_05
Patent number
US05112886

Reaction notes

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