Trimethylamine → 2-Buten-1-aminium, 4-chloro-N,N,N-trimethyl-, chloride (1:1)

HRID 1076936Notes

Reaction equation

HRID 1076936 reaction equation
[CH2:1]([Cl:6])/[CH:2]=[CH:3]/[CH2:4][Cl:5].[CH3:7][N:8]([CH3:10])[CH3:9].CC(=O)CCCC>O>[Cl-:5].[Cl:6][CH2:1][CH:2]=[CH:3][CH2:4][N+:8]([CH3:10])([CH3:9])[CH3:7]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 115832-HexanoneHCID 6421971,4-Dichloro-2-butene, (2E)-

Product 1

HCID 1075282-Buten-1-aminium, 4-chloro-N,N,N-trimethyl-, chloride (1:1)Yield 93.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

About 125 parts 1,4-dichlorobutene-2 and 60 parts trimethylamine are mixed with 700 parts 2-hexanone in a stainless steel pressure reactor. The mixture is allowed to react for 5 hours at a temperature of about 75°C. to about 80°C. Next, 60 parts of water are added to the cooled reaction mixture. This mixture yields about 93.5% 4-chloro-2-butenyltrimethylammonium chloride. The 2-hexanone is removed either by vacuum distillation or separated by decantation from the reaction mixture. About 95% of the 2-hexanone is recovered for reuse.

Workup

  1. customto react for 5 hours at a temperature of about 75°C. to about 80°C

Sources & evidence

ORD record
ord-b23a1d77f9594aad9a9f2012b5169ba6
Source dataset
uspto-grants-1976_05
Patent number
US03959169

Reaction notes

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