Phenol → 4-Tert-octylphenol

HRID 2049812Notes

Reaction equation

HRID 2049812 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH2:10]>>[C:9]([C:4]1[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=1)([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:8]

Participants

3

Reactant 2

HCID 996Phenol2×HCID 78682,4,4-Trimethyl-1-pentene2×

Product 1

HCID 88144-Tert-octylphenolYield 0.9%

Procedure

A suspension of 1,000 parts of phenol, 700 parts of diisobutylene and 40 parts of ion exchange resin is prepared in a stirred reactor at 100° C. and 1 bar pressure, the mixture being stirred at 500 rpm. The ion exchange resin is a sulfonated styrene/divinylbenzene copolymer resin, which has been dehydrated under reduced pressure for 20 hours at 100° C. before being used; it has a gel structure and its particle size is from 20 to 150 micrometers. The suspension is then stirred constantly in the reactor at 500 rpm. After 30 minutes, 1,000 parts of phenol and 700 parts of diisobutylene are introduced per hour at 100° C. and 1 bar pressure and correspondingly 1,700 parts per hour of suspension are filtered through a suction line equipped with a metal filter (pore diameter 10 micrometers) and are subjected to fractional distillation. After 100 hours' operation, 116,100 parts (86% of theory, based on starting material II) of 4-tert.-octylphenol of boiling point 160°-162° C./27 millibars are obtained, in addition to 3,400 parts (2.5% of theory, based on starting material II) of 2-tert.-octylphenol and 1,750 parts (0.9% of theory, based on starting material II) of tert.-butylphenol. The conversion is 54%, based on phenol employed, or 91%, based on starting material II.

Workup

  1. customis prepared in a stirred reactor at 100° C.
  2. stirringThe suspension is then stirred constantly in the reactor at 500 rpm
  3. waitAfter 30 minutes
  4. filtration1 bar pressure and correspondingly 1,700 parts per hour of suspension are filtered through a suction line
  5. customequipped with a metal
  6. filtrationfilter (pore diameter 10 micrometers)
  7. distillationare subjected to fractional distillation

Sources & evidence

ORD record
ord-e9f4a120fa3f42f09abe4d8a654e22e3
Source dataset
uspto-grants-1980_04
Patent number
US04198531

Reaction notes

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