4,4'-Methylenebis(N,N-diglycidylaniline) synthesis

Yield:28768-32-3 91%

Reaction Conditions:

Stage #1:4,4'-diamino diphenyl methane;epichlorohydrin with lanthanum nitrate in toluene at 60 - 85; under 150.015 - 300.03 Torr;
Stage #2: with benzyltrimethylammonium chloride;sodium hydroxide in water;toluene at 60 - 70; under 150.015 - 375.038 Torr;Pressure;Reagent/catalyst;

Steps:

1 Example 1:
Bis(4-aminophenyl) methane, toluene and 50 % lanthanum nitrate in 2- butoxyethanol are stirred and heated to 60 to 70°C under a reduced pressure (200- 400mbar) followed by addition of epichlorohydrin over a period of 2 to 5 hours. After completion of epichlorohydrin addition, the mixture is maintained at 60 to 70 °C and then vacuum is released. A further portion of catalyst solution is added and the temperature is raised to 75 to 85 °C under reduced pressure. The mixture is then maintained under this condition for about 3 to 5 hours under constant stirring. The temperature is reduced to 60 to 70 °C and 50% aqueous benzyltrimethylammonium chloride is then added and the apparatus is set up for vacuum azeotrope. 50% aqueous sodium hydroxide is then added over a period of 1 to 3 hours, water being azeotroped out under vacuum (200-500 mbar). At the end of addition, azeotrope is continued for a further of 2 to 3 hours. Toluene and water are then added with stirring and aqueous and organic layer are separated by known method. The aqueous layer is discarded and organic layer is washed with 10 % aqueous sodium dihydrogen phosphate. An organic mass so obtained is filtered through high flow. Toluene is evaporated under vacuum at reduced pressure. The aromatic N-glycidylamine has an epoxide content 8.82 g/eq (91 % of theory) and viscosity of 4560cPs.

References:

GRASIM INDUSTRIES LIMITED;SINGH, Ashok Kumar;SAMANT, Prashant;LALANI, Alif;KATHALEWAR, Mukesh;MORE, Vishnu WO2017/134609, 2017, A1 Location in patent:Page/Page column 6-7

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