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

HRID 1975813Notes

Reaction equation

HRID 1975813 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.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

4

Reactant 3

HCID 6623Bisphenol AHCID 7169Phenyl benzoateHCID 7597Diphenyl carbonate

Product 1

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

Conditions

Temperature
150 °C

Procedure

0.15 mol bisphenol A, 0.16 mol diphenyl carbonate 2×10-6 mol tetrabutyl ammonium bis-4-nitrophenolate, 3×10-3 mol phenyl benzoate were placed in a reactor which was blanketted with nitrogen. Temperature was raised from ambient to 150° C. during one hour while the reactor contents were maintained at atmospheric pressure. Then changing the temperature to 240° C. and pressure to 90 mm Hg in 11/2 hours, phenol removed from the reactor was nearly 75%. On subsequent increase in temperature to 260° C. and decrease in pressure to 20 mm Hg, phenol collected in 2 hours was 99%. In the end the reaction mixture was heated to 280° C. at 1 mm Hg for 1 hour. The colorfree polymer, bisphenol A polycarbonate in 99% yield obtained had a relative viscosity 1.24.

Workup

  1. temperaturewere maintained at atmospheric pressure
  2. customto 240° C.
  3. custompressure to 90 mm Hg in 11/2 hours, phenol removed from the reactor
  4. temperatureOn subsequent increase in temperature to 260° C.
  5. customcollected in 2 hours
  6. temperatureIn the end the reaction mixture was heated to 280° C. at 1 mm Hg for 1 hour

Sources & evidence

ORD record
ord-20ff391fdfc34749bad42d32aaccb9de
Source dataset
uspto-grants-1994_02
Patent number
US05288838

Reaction notes

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