Isobutylene → 2,5-Di-tert-butyl-4-hydroxyanisole

HRID 1395085Notes

Reaction equation

HRID 1395085 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH2:10]=[C:11]([CH3:13])[CH3:12]>>[C:11]([C:4]1[CH:3]=[C:2]([OH:1])[C:7]([C:11]([CH3:13])([CH3:12])[CH3:10])=[CH:6][C:5]=1[O:8][CH3:9])([CH3:13])([CH3:12])[CH3:10]

Participants

3

Reactant 2

HCID 8255Isobutylene2×HCID 90154-Methoxyphenol2×

Product 1

HCID 748122,5-Di-tert-butyl-4-hydroxyanisoleYield 6%

Procedure

A suspension of 124 parts of 4-hydroxyanisole and 3 parts of exchanger resin is prepared in a stirred reactor by stirring at 500 revolutions per minute at 100° C. under 1 bar, and 28 parts of isobutene are passed in. The exchanger resin is a sulfonated styrene-divinylbenzene copolymer resin which has been dehydrated for 20 hours at 100° C. under reduced pressure before being used; it has a gel structure and a particle size for from 20 to 150 micrometers. The suspension in the reactor is now stirred steadily at 500 revolutions per minute. After one hour, 80 parts of 4-hydroxyanisole and 20 parts of isobutene are fed in hourly, and correspondingly 100 parts of suspension are filtered through a suction take-off line fitted with a metal filter (pore diameter 10 micrometers) and are fed to a fractional distillation. After 100 hours' operation, 5,486 parts (85% of theory, based on starting material II) of a mixture of 2-tert.butyl-4-hydroxyanisole and 3-tert.-butyl-4-hydroxyanisole of boiling point 140°-145° C./14 millibars are obtained in addition to 490 parts (6% of theory, based on starting material II) of 2,5-di-tert.-butyl-4-hydroxyanisole. The conversion is 51 percent, based on 4-hydroxyanisole employed. The isobutene is consumed quantitatively.

Workup

  1. customis prepared in a stirred reactor
  2. waitAfter one hour
  3. filtrationare filtered through a suction take-off line
  4. customfitted with a metal
  5. filtrationfilter (pore diameter 10 micrometers)
  6. distillationare fed to a fractional distillation
  7. additionAfter 100 hours' operation, 5,486 parts (85% of theory, based on starting material II) of a mixture of 2-tert.butyl-4-hydroxyanisole and 3-tert.-butyl-4-hydroxyanisole of boiling point 140°-145° C./14 millibars

Sources & evidence

ORD record
ord-f4184372c9ad40d88003e7daf013347d
Source dataset
uspto-grants-1980_05
Patent number
US04202199

Reaction notes

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