Trimethylamine → Glycidyl trimethylammonium chloride

HRID 2308593Notes

Reaction equation

HRID 2308593 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 gas sparger, mechanical stirrer, thermometer and an aqueous acid trap was charged with epichlorohydrin (55.2 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-epoxypropyltrimethylammonium chloride.

Workup

  1. customA one-liter flask equipped with gas sparger, mechanical stirrer
  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-epoxypropyltrimethylammonium chloride

Sources & evidence

ORD record
ord-7d25f22219cb4295966d39c8635faa72
Source dataset
uspto-grants-1987_09
Patent number
US04690817

Reaction notes

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