Reaction #451334

ord-57f95205742e47b6b0325573bd6e0ab4

Reaction equation

C=CCCC12C=CC(C1)C1C(=O)OC(=O)C12
allylmethylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride
NCCCCCCN
hexamethylene diamine
→
C=CCCC12C=CC(C1)C1C(=O)N(CCCCCCN3C(=O)C4C5C=CC(CCC=C)(C5)C4C3=O)C(=O)C12
N,N'-Hexamethylene-bis-(allylmethylbicyclo[2.2.1]hept-5-ene-2,3-dicarboximide)

Reactants

C=CCCC12C=CC(C1)C1C(=O)OC(=O)C12
allylmethylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride
NCCCCCCN
hexamethylene diamine

Reagents

None

Conditions

Temperature
130°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherWater is removed by distillation
  2. 2
    Temperaturethe temperature is raised to 180° C.
  3. 3
    Temperature180° C. and 53 Pa are maintained for 15 minutes
  4. 4
    Otherat 80° C.

Procedure

300 g of allylmethylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride are taken and heated to 130° C., and 79.9 g of melted hexamethylene diamine are added dropwise, with stirring. Water is removed by distillation, the temperature is raised to 180° C. and the pressure is reduced to 53 Pa. 180° C. and 53 Pa are maintained for 15 minutes. This gives 345 g (97% of theory) of a brown, viscous resin having a viscosity of 1.356 Pa.s at 80° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04604437uspto-grants-1986_08