Trimethylamine → (6-Bromohexyl)trimethylammonium Bromide

HRID 2213704Notes

Reaction equation

HRID 2213704 reaction equation
C(OCC)(=O)C.[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]Br.[CH3:15][N:16]([CH3:18])[CH3:17]>>[Br-:7].[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N+:16]([CH3:18])([CH3:17])[CH3:15]

Participants

4

Reactant 3

HCID 1146TrimethylamineHCID 8857Ethyl AcetateHCID 123681,6-Dibromohexane

Product 1

HCID 9857584(6-Bromohexyl)trimethylammonium Bromide

Conditions

Temperature
60 °C

Procedure

494 kg (5606 mol) of ethyl acetate and 244 kg (1000 mol) of 1,6-dibromohexane were charged into a reactor with stirring and simultaneous heating to 60° C. 64 kg (1080 mol) of trimethylamine were metered in at 1 bar in the course of 3 hours. After an after-reaction time of a further 3 h, the reaction mixture was cooled and filtered through a suction filter and the crystallizate obtained was washed with ethyl acetate. After drying had taken place, 288 kg (95.1%) of (6-bromohexyl)trimethylammonium bromide of 99.8% purity were obtained.

Workup

  1. customwere metered in at 1 bar in the course of 3 hours
  2. temperatureAfter an after-reaction time of a further 3 h, the reaction mixture was cooled
  3. filtrationfiltered through a suction
  4. filtrationfilter
  5. customthe crystallizate obtained
  6. washwas washed with ethyl acetate
  7. customAfter drying
  8. customwere obtained

Sources & evidence

ORD record
ord-012b3e774e684dac8cd3c6e3fad2549f
Source dataset
uspto-grants-2006_09
Patent number
US07105631B2

Reaction notes

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