Phenol → 2,6-Di-tert-butylphenol

HRID 986619Notes

Reaction equation

HRID 986619 reaction equation
C1(O)C=CC=CC=1.[Al].[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])([CH3:12])([CH3:11])[CH3:10].[CH3:20][C:21](=[CH2:23])[CH3:22]>>[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:21]([CH3:23])([CH3:22])[CH3:20])[C:14]=1[OH:19])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 4

HCID 996Phenol2×HCID 69232-Tert-ButylphenolHCID 8255IsobutyleneHCID 5359268Aluminum

Product 1

HCID 314052,6-Di-tert-butylphenolYield 98.5%

Procedure

The heterogeneous catalyst of the invention provides a new route to ortho-alkylphenols, especially commercially valuable phenols such as 2,6-di-tert-butylphenol, ortho-sec-butylphenol, and the like. Furthermore, the heterogeneous catalyst process of the invention is well suited to a fixed bed embodiment for a continuous process when the bed is properly sized to provide the reactivity required by the reaction conditions, the phenol being alkylated, and the olefin being used. Use of the heterogeneous catalyst of the invention reduces pollution control problems by greatly reducing the amount of phenol-bearing aluminum waste encountered in homogeneous aluminum aryloxide catalyst systems thereby greatly reducing the operating costs for alkylating phenols. Use of the heterogeneous catalyst systems of the invention has resulted in very high yields suitable for commercial operation. For example, ortho-tert-butylphenol and isobutylene may be reacted to form 2,6-di-tert-butylphenol in a yield as high as 98.5%.

Workup

  1. customto provide the reactivity
  2. customrequired by the reaction conditions
  3. customUse of the heterogeneous catalyst systems of the invention has resulted
  4. customin very high yields suitable for commercial operation

Sources & evidence

ORD record
ord-487d9cffac59466099e410146ac8a516
Source dataset
uspto-grants-1987_12
Patent number
US04714691

Reaction notes

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