Phenol → Adipic Acid

HRID 1578475Notes

Reaction equation

HRID 1578475 reaction equation
C1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]2C([O:12][C:13](=[O:14])[C:3]=2C=1)=O.C1(O)C=CC=CC=1>>[C:13]([OH:14])(=[O:12])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

3

Reactant 2

HCID 996PhenolHCID 11089Trimellitic anhydride

Product 1

HCID 196Adipic AcidYield 59.2%

Procedure

A solution is formed by mixing 60.0 grams of trimellitic acid anhydride and 130.0 grams of p,p' diphenyl methane diisocyanate and 110.0 grams of Bis 2-ethoxy ethylether and 4.8 grams of phenol by heating the mixture. At approximately 135°C. a clear, homogeneous solution is obtained. Once clarity is obtained 27.0 grams of adipic acid is added slowly. The temperature of the mixture is raised to approximately 190°C. and slow reflux is maintained. After approximately 45 minutes, a brownish viscous resin is obtained and 346.2 grams of phenol are added to quench and stop the reaction. The solution is maintained at 130°C. until all the resin is dissolved. The resultant solution is cooled to room temperature and filtered. The viscosity of the product at 25°C. was measured at about 210 cps, utilizing a Brookfield viscometer, and a resin solution of approximately 30% weight resin.

Workup

  1. customA solution is formed
  2. temperatureby heating the mixture
  3. customAt approximately 135°C. a clear, homogeneous solution is obtained

Sources & evidence

ORD record
ord-3d92eaf1c9bd48e485dfd969161f4524
Source dataset
uspto-grants-1976_02
Patent number
US03937673

Reaction notes

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