bisphenol AF → 4-[1,1,1,3,3,3-Hexafluoro-2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol

HRID 2232661Notes

Reaction equation

[F:1][C:2]([F:23])([F:22])[C:3]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:4]([F:7])([F:6])[F:5].[H][H]>[C].[Ru].C(O)(C)C>[F:1][C:2]([F:22])([F:23])[C:3]([CH:15]1[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]1)([CH:8]1[CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][CH2:13]1)[C:4]([F:5])([F:7])[F:6]

Participants

Conditions

Temperature: 130 °C

Procedure

Into a stainless steel autoclave were placed 500 g of 4,4'-(perfluoroisopropylidene)diphenol, 100 ml of isopropanol and 2 g of 5% ruthenium-carbon. The mixture was maintained at a temperature of 130° C. and a hydrogen pressure of 50 kg/cm2G for 40 minutes and then at 160° to 170° C. and a hydrogen pressure of 60 to 70 kg/cm2G for 40 minutes. After cooled to room temperature, the catalyst is filtered off and isopropanol was removed at a reduced pressure. The residue was recrystallized from toluene to obtain 290 g of 4,4'-(perfluoroisopropylidene)dicyclohexanol in the form of white solid.

Workup

temperatureAfter cooled to room temperature
filtrationthe catalyst is filtered off
customisopropanol was removed at a reduced pressure
customThe residue was recrystallized from toluene

Sources & evidence

ORD record: ord-41540affc4e949d2b1bfef045f4874a3
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04788327

Reaction notes

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