O-Xylene → 2,5-Furandione, polymer with 1-octadecene

HRID 1588003Notes

Reaction equation

HRID 1588003 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[C:8]1([CH3:15])[C:9]([CH3:14])=[CH:10][CH:11]=[CH:12][CH:13]=1>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:10][CH2:9][CH2:8][CH2:13][CH2:12][CH2:11][CH2:14][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:8][CH3:15].[C:4]1(=[O:5])[O:6][C:1](=[O:7])[CH:2]=[CH:3]1

Participants

3

Reactant 2

HCID 7237O-XyleneHCID 7923Maleic Anhydride

Product 1

HCID 1683442,5-Furandione, polymer with 1-octadecene

Procedure

5.6 g PA-18 (0.02 equivalents as maleic anhydride, hereinafter "anhydride equivalents") and 100 ml xylene were mixed in a 250 ml flask equipped with a nitrogen atmosphere and a Dean Stark trap. This mixture was refluxed for 30 minutes to dry the polymer. The mixture was cooled slightly and Flame Retardant A (of Example 1) (5.1 g, 0.01 mole) was added. The mixture was refluxed for 2 hours with azeotropic removal of water as it formed. The solvent was stripped using aspirator and high vacuum systems to yield 10.4 g of yellow crystals. The infrared spectrum of this compound showed the N-(acylamino)imide carbonyl bands merged at 1710 cm-1 and a small residual anhydride carbonyl band at 1770 cm-1. The hydrazide carbonyl for the starting material was not observed in the product spectrum.

Workup

  1. customequipped with a nitrogen atmosphere
  2. temperatureThis mixture was refluxed for 30 minutes
  3. customto dry the polymer
  4. temperatureThe mixture was cooled slightly
  5. temperatureFlame Retardant A (of Example 1) (5.1 g, 0.01 mole)
  6. additionwas added
  7. temperatureThe mixture was refluxed for 2 hours with azeotropic removal of water as it
  8. customformed

Sources & evidence

ORD record
ord-6463208b345043acbeb70bd9f7fce84f
Source dataset
uspto-grants-1993_06
Patent number
US05220015

Reaction notes

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