Oxygen → Acryloyloxyethyltrimethyl ammonium chloride

HRID 257237

Reaction equation

HRID 257237 reaction equation
C[Cl:2].C(OCCN(C)C)(=O)C=C.COC1C=CC(O)=CC=1.C([O-])(=O)C=C.O.C([O-])(=O)C=C.O=O.[C:35]([O:39][CH2:40][CH2:41][N+:42]([CH3:45])([CH3:44])[CH3:43])(=[O:38])[CH:36]=[CH2:37]>O>[Cl-:2].[C:35]([O:39][CH2:40][CH2:41][N+:42]([CH3:44])([CH3:43])[CH3:45])(=[O:38])[CH:36]=[CH2:37]

Participants

9

Reactant 7

HCID 977OxygenHCID 6327Methyl ChlorideHCID 90154-MethoxyphenolHCID 171112-(Dimethylamino)ethyl acrylate2×HCID 25188Acrylate2×HCID 83146AcryloylcholineHCID 19805102Water acrylate

Product 1

HCID 162071Acryloyloxyethyltrimethyl ammonium chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
47 °C

Procedure

78 g of liquid methyl chloride are charged with stirring into a jacketed reactor. The temperature is raised to 47° C. and the pressure of the system equilibrates at 9.6 bars absolute. In the first stage 33 g of dimethylaminoethyl acrylate stabilized with the aid of 700 ppm of hydroquinone methyl ether are injected into the reactor over a period of 20 minutes (that is 16% of the total quantity of acrylate necessary for reaction) In a second stage the complement of the acrylate and the water are injected simultaneously and continuously in a water/acrylate weight ratio of the order of 0.4 over a period of 2 hours. Throughout the reaction the temperature is kept at 47° C. and the pressure in the reactor drops to 3.2 bars absolute at the end of the injection of reactants. 0.5 Nl/h of air is then injected continuously into the reactor and over a period of 1 hour the reactor pressure is returned progressively to atmospheric pressure while a blow-off exit flow rate lower than 1.5 Nl/h is maintained (whence a ratio of the blow-off volumetric flow rates to the oxygen introduced lower than 15). 71 g of water and 205 g of dimethylaminoethyl acrylate have been employed in this operation and 343 g of acryloyloxyethyltrimethylammonium at a concentration of. 80% in water are recovered. The final product is then subjected to an injection of air at a flow rate of 7 Nl/h for 1/2 hour hot and then for 1/2 hour at room temperature. The final product obtained has the following characteristics: water: 20.3% acrylic acid: 0.23% dimethylaminoethyl acrylate: 0.15% methyl chloride: 10 ppm polymer: nil storage stability: longer than 1 year.

Workup

  1. customThroughout the reaction the temperature
  2. customis kept at 47° C.
  3. wait0.5 Nl/h of air is then injected continuously into the reactor and over a period of 1 hour
  4. additionintroduced lower than 15)
  5. custom80% in water are recovered
  6. waitThe final product is then subjected to an injection of air at a flow rate of 7 Nl/h for 1/2 hour
  7. waithot and then for 1/2 hour at room temperature

Sources & evidence

ORD record
ord-96a3e85272e849f99582845cb67b2dea
Source dataset
uspto-grants-1993_11
Patent number
US05260480

Linked notes

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