4-Aminobenzoic Acid → Poly(p-phenylene terephthalamide)

HRID 2058099Notes

Reaction equation

HRID 2058099 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([NH2:8])[CH:2]=1.CN(C)P(N(C)C)(N(C)C)=[O:12].N[C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1.[C:30](Cl)(=[O:40])C1C=CC(C(Cl)=O)=CC=1>O>[CH:23]1[C:24]([C:25]([OH:27])=[O:26])=[CH:28][CH:29]=[C:21]([C:30]([OH:40])=[O:12])[CH:22]=1.[CH:5]1[C:6]([NH2:7])=[CH:1][CH:2]=[C:3]([NH2:8])[CH:4]=1

Participants

6

Reactant 4

HCID 9784-Aminobenzoic AcidHCID 7488Terephthaloyl chlorideHCID 7814P-PhenylenediamineHCID 12679Hexamethylphosphoramide

Product 1

HCID 62788Poly(p-phenylene terephthalamide)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of p-phenylenediamine (31.08 g., 0.287 mole) in a mixture of 360 ml. of hexamethylphosphoramide and 180 ml. of N-methylpyrrolidone-2 is added 3.36 g. of p-aminobenzoic acid, using water bath cooling. To this cooled solution is added terephthaloyl chloride (60.90 g., 0.300 mole.) The reaction mixture is stirred overnight, then combined with water in a blender to precipitate polymer. The product is washed with water and dried in a vacuum oven at 65° C. The product is then combined with acetone in a blender, the mixture filtered, and the product collected and dried at 65° C. in a vaccum oven. There is obtained a quantitative yield of poly(p-phenylene terephthalamide) (ηinh=1.32).

Workup

  1. temperaturecooling
  2. customto precipitate polymer
  3. washThe product is washed with water
  4. customdried in a vacuum oven at 65° C
  5. filtrationthe mixture filtered
  6. customthe product collected
  7. customdried at 65° C. in a vaccum oven

Sources & evidence

ORD record
ord-5f4f6324624b45a7be5e9ea19c9575c4
Source dataset
uspto-grants-1980_07
Patent number
USRE030352

Reaction notes

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