Reaction #323570

Reaction equation

tetrachlorophthalic anhydride

p-phenylenediamine

→

ivory-yellow material

Yield 53.0%

N,N'-(p-phenylene)-bis[3,4,5,6-tetrachlorophthalimide]

Yield 53.0%

Solvents

N-methyl-2-pyrrolidone

Conditions

Workup

1. 1
   OtherIn a 5 liter round-bottom flask equipped with a heating mantle, a stirrer
2. 2
   Othera thermometer, a condenser and a nitrogen purge
3. 3
   Temperaturewas heated
4. 4
   OtherAt 170° C., precipitation
5. 5
   Temperaturewas maintained for 90 minutes
6. 6
   Temperatureto cool overnight
7. 7
   FiltrationThe cooled mixture was filtered
8. 8
   Otherthe yellow precipitate was recovered
9. 9
   WashThe precipitate was washed with NMP
10. 10
    workup.STIRRINGthoroughly stirred in acetone
11. 11
    Filtrationfiltered
12. 12
    Washwashed with more acetone
13. 13
    OtherThe product was dried under vacuum at 150° C. for 16 hours

Procedure

In a 5 liter round-bottom flask equipped with a heating mantle, a stirrer, a thermometer, a condenser and a nitrogen purge, there were reacted 457.5 gms (1.6 mole) of tetrachlorophthalic anhydride and 86.5 gms (0.8 mole) of p-phenylenediamine in 2000 ml. of N-methyl-2-pyrrolidone (NMP), the reactants going into solution as the mixture was heated with stirring. At 170° C., precipitation began and continued as the temperature was raised to 200° C. where it was maintained for 90 minutes. The reaction mixture was then allowed to cool overnight. The cooled mixture was filtered and the yellow precipitate was recovered. The precipitate was washed with NMP, thoroughly stirred in acetone, filtered and washed with more acetone. The product was dried under vacuum at 150° C. for 16 hours. 272.7 gms (yield=53%) of an ivory-yellow material was obtained, having a melting point in excess of 500° C., with one sublimation at about 425° C. The IR spectrum had the characteristics of an imide with the absorption bands at 1710s and 1770w cm-1. The product was insoluble in water.

Source