Phenol → 2,3-Bis(1-phenylethyl)phenol

HRID 2049815

Reaction equation

HRID 2049815 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:10]1([CH:9]([C:3]2[C:2]([CH:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH3:8])=[C:1]([OH:7])[CH:6]=[CH:5][CH:4]=2)[CH3:8])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:10]1([CH:9]([C:2]2[CH:3]=[C:4]([CH:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH3:8])[CH:5]=[C:6]([CH:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH3:8])[C:1]=2[OH:7])[CH3:8])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 996Phenol2×HCID 7501Styrene2×

Product 2

HCID 866882,4,6-Tris(1-phenylethyl)phenolYield 27%HCID 190103942,3-Bis(1-phenylethyl)phenolYield 56%

Procedure

A suspension of 94 parts of phenol, 208 parts of styrene and 5 parts of ion exchange resin is prepared in a stirred reactor at 80° C. and 1 bar pressure, the mixture being stirred at 700 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 700 rpm. After 10 hours, 4.7 parts of phenol and 10.4 parts of styrene are introduced per hour at 80° C. and 1 bar pressure and correspondingly 15.1 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, 248 parts of 4-mono-(α-phenylethyl)-phenol (13% of theory, based on starting material II) of boiling point 182°-189° C./13 millibars, 845 parts (56% of theory, based on starting material II) of 2,4-di-(α-phenylethyl)-phenol of boiling point 231°-235° C./6 millibars and 366 parts (27% of theory, based on starting material II) of 2,4,6-tri-(α-phenylethyl)-phenol of boiling point 260°-268° C./6 millibars are obtained. The conversion is 98%, based on phenol, or 97%, based on starting material II.

Workup

  1. customis prepared in a stirred reactor at 80° C.
  2. stirringThe suspension is then stirred constantly in the reactor at 700 rpm
  3. waitAfter 10 hours
  4. filtration1 bar pressure and correspondingly 15.1 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-0d14234d4e5847d2ae3c5a49b278ca53
Source dataset
uspto-grants-1980_04
Patent number
US04198531

Linked notes

Loading…