Bisphenol A → Carbonic acid;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol

HRID 1975811Notes

Reaction equation

HRID 1975811 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[C:18](=[O:33])([O:26]C1C=CC=CC=1)[O:19]C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.C1C=CC(C(O)=O)=CC=1.C1C=CC(C([O-])=O)=CC=1.C(OC1C=CC=CC=1)(=O)C1C=CC=CC=1>>[CH3:10][C:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)([C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[CH3:9].[C:18]([OH:33])([OH:26])=[O:19]

Participants

5

Reactant 4

HCID 6623Bisphenol AHCID 7169Phenyl benzoateHCID 7597Diphenyl carbonateHCID 11081419Bioxyanion

Product 1

HCID 159987Carbonic acid;4-[2-(4-hydroxyphenyl)propan-2-yl]phenolYield 99%

Conditions

Temperature
160 °C

Procedure

0.20 mol bisphenol A, 0.21 mol diphenyl carbonate, 3×10-6 mol tetrabutyl ammonium bibenzoate and 4×10-3 mol phenyl benzoate are taken in a 250 ml glass reactor equipped with stirrer, nitrogen inlet and distillation assembly. Under the blanket of nitrogen the contents in the reactor were heated by means of thermostatically controlled furnace to 160° C. for 11/2 hr. Subsequently, the temperature was increased to 230° C. and pressure reduced from atmospheric to 100 mm Hg, and on keeping constant the temperature and pressure for one hour, about 80% phenol was collected. Maintaining the temperature at 230° C., the pressure was decreased sequentially in a following way: 80 mm, 1/2 hour; 60 mm, 1/2 hour; 40 mm, 1/2 hour; 20 mm, 1/2 hour; 10 mm, 1/2 hour and 1 mm, 1/2 hour. It was then observed that phenol removal was almost quantitative. Finally reaction mixture was heated to 280° C. at 1 mm for one hour to remove any residual phenol. The polymer, bisphenol A polycarbonate obtained in 99% yield was colorfree and its relative viscosity measured in chloroform at 25° C. in an ubbelohde viscometer was 1.26.

Workup

  1. customequipped with stirrer, nitrogen inlet
  2. distillationdistillation assembly
  3. temperatureSubsequently, the temperature was increased to 230° C.
  4. customfor one hour
  5. customabout 80% phenol was collected
  6. temperatureMaintaining the temperature at 230° C.
  7. custom80 mm, 1/2 hour
  8. custom60 mm, 1/2 hour
  9. custom40 mm, 1/2 hour
  10. custom20 mm, 1/2 hour
  11. custom10 mm, 1/2 hour and 1 mm, 1/2 hour
  12. customIt was then observed that phenol removal
  13. customFinally reaction mixture
  14. temperaturewas heated to 280° C. at 1 mm for one hour
  15. customto remove any residual phenol

Sources & evidence

ORD record
ord-6cdaa9d93b854f038e1ad895bd887e79
Source dataset
uspto-grants-1994_02
Patent number
US05288838

Reaction notes

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