Carbon Dioxide → Ethanaminium, 2-hydroxy-N-(2-hydroxyethyl)-N,N-dimethyl-, hydroxide

HRID 1250805Notes

Reaction equation

HRID 1250805 reaction equation
C(=O)=[O:2].[CH3:4][N:5]([CH3:9])[CH2:6][CH2:7][OH:8].[CH2:10]1[O:12][CH2:11]1>O>[OH-:2].[OH:8][CH2:7][CH2:6][N+:5]([CH2:10][CH2:11][OH:12])([CH3:9])[CH3:4]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 6354Ethylene Oxide2×HCID 79022-(Dimethylamino)ethanol

Product 1

HCID 3017041Ethanaminium, 2-hydroxy-N-(2-hydroxyethyl)-N,N-dimethyl-, hydroxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A two-liter three-necked flask equipped with a thermometer, magnetic stirrer, dry ice condenser, cooling bath, and nitrogen inlet was charged with about 267 grams of dimethylethanolamine (DMEA) and 330 grams of de-ionized water. About 128 grams of ethylene oxide was fed slowly through a feeding tube into the reaction mixture using moderate agitation, and the reaction temperature was maintained below 20° C. After the ethylene oxide addition was completed, the reaction was allowed to digest for an additional hour. The reaction mixture was then purged with nitrogen for one hour. The product is a clear and colorless solution. However, after about four days of standing at room temperature, the product darkened somewhat.

Workup

  1. temperaturecooling bath, and nitrogen inlet
  2. temperaturethe reaction temperature was maintained below 20° C
  3. waitto digest for an additional hour
  4. customThe reaction mixture was then purged with nitrogen for one hour

Sources & evidence

ORD record
ord-9266f831d5554faa9307be2f077813e1
Source dataset
uspto-grants-2002_01
Patent number
US06340559B1

Reaction notes

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