Phthalic Anhydride → Phthalimide

HRID 979640Notes

Reaction equation

HRID 979640 reaction equation
[NH2:1]C1C=CC(CC2C=C(CC3C=CC(N)=CC=3)C=CC=2N)=CC=1.[C:24]1(=O)[O:29][C:27](=[O:28])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12>O>[C:24]1(=[O:29])[NH:1][C:27](=[O:28])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12

Participants

4

Reactant 2

HCID 6811Phthalic Anhydride2×HCID 331822,4-Bis(4-aminobenzyl)aniline

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A phthalimide-amine was prepared by mixing in a 2 liter glass resin kettle equipped with a mechanical stirrer, a heating mantle, a thermocouple connected to a temperature recorder, and an overhead water trap with a vertical condenser, 2.0 moles (600 grams) of BABA (a product of the E. I. duPont de Nemours & Company containing primarily 2,4-Bis(p-aminobenzyl)aniline) and 3.0 moles (444 grams) of phthalic anhydride. Heat was applied, and at about 100° C., the BABA melted and phthalic anhydride started slowly to react. The temperature was slowly allowed to rise to 150° C., at which time water began to condense overhead. Heating continued until 3.0 moles (54 grams) of water were collected. Since 2.0 moles of BABA contain 6 primary amines and three of them reacted with phthalic anhydride to form phthalimide linkages, 3 primary amine groups remained per 2 moles of BABA phthalimide. Since the molecular weight of this BABA phthalimide is 300+222-27=495, and contains 3 aminic hydrogens, its amine equivalent is 495/3=165, which corresponds to one epoxide equivalent or 180 grams of EPON-828 or 826 (the diglycidel ether of bisphenol-A such as is produced by the Shell Corporation). In other words, 47 grams of the aromatic amine of this example correspond to 51.3 grams of EPON-828.

Workup

  1. customequipped with a mechanical stirrer
  2. customa heating mantle, a thermocouple connected to a temperature recorder, and an overhead water trap with a vertical condenser
  3. temperatureHeat
  4. customat about 100° C.
  5. customto react
  6. custombegan to condense overhead
  7. temperatureHeating
  8. customwere collected
  9. customreacted with phthalic anhydride

Sources & evidence

ORD record
ord-655c494e88f845d38183f282549db063
Source dataset
uspto-grants-1987_05
Patent number
US04668757

Reaction notes

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