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

HRID 1975812Notes

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

Reactant 3

HCID 6623Bisphenol A

HCID 7169Phenyl benzoate

HCID 7597Diphenyl carbonate

Product 1

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

Conditions

Temperature: 140 °C

Procedure

0.25 mol bisphenol A, 0.27 mol diphenyl carbonate 3.5×10-6 mol tetrabutyl ammonium bis-4-nitrobenzoate, 6×10-3 mol phenyl benzoate were added to the glass reactor flushed with nitrogen at room temperature. The temperature was increased to 140° C. in 11/2 hour duration. Later the pressure was reduced from atmosphere to 110 mm Hg and temperature increased to 240° C., and on maintenance of these conditions for 1 hour, about 85% phenol was collected. Subsequently, the temperature was increased to 270° C. and pressure reduced to 10 mm and under these conditions most of the phenol was collected in 2 hours. Finally, the reaction mixture was kept at 285° C. and 1 mm for 1 hour to remove traces of phenol. The polymer, bisphenol A polycarbonate obtained in 99% yield was white in color and its relative viscosity was 1.32.

Workup

customflushed with nitrogen at room temperature
temperatureincreased to 240° C.
customabout 85% phenol was collected
temperatureSubsequently, the temperature was increased to 270° C.
customwas collected in 2 hours
customwas kept at 285° C.
custom1 mm for 1 hour to remove traces of phenol

Sources & evidence

ORD record: ord-96d2ef8b257b4fae94d74c0db406c031
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05288838

Reaction notes

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