Alpha-Methylstyrene → Dicumyl peroxide

HRID 1395578Notes

Reaction equation

HRID 1395578 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].[C:10](Cl)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:12])[CH3:11].[O-:20][OH:21].C1(C(C)C)C=CC=CC=1.[OH-].[Na+]>>[C:2]([O:20][O:21][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:12])[CH3:11])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 4

HCID 7407Alpha-MethylstyreneHCID 14798Sodium HydroxideHCID 70281(1-Chloro-1-methylethyl)benzeneHCID 53627471Cumen hydroperoxide

Product 1

HCID 6641Dicumyl peroxide

Procedure

Into a 100 ml. open-top, jacketed reactor was placed 19.2 g. (0.162 m.) of α-methylstyrene, 4.4 g. (0.0285 m.) of distilled cumyl chloride and 37 g. (0.20 m.) of 82% assay cumene hydroperoxide. The mixture was stirred at 40°±2° C. for 5 hours. The reaction mixture was cooled to 20° and then stirred for 15 minutes with 40 ml. of 20% sodium hydroxide solution. The aqueous layer was discarded. The washing with caustic was repeated twice and the organic layer washed with 50 ml. portions of 20% sodium chloride solution until neutral. The organic layer was added to 400 ml. of water and the mixture distilled at 80-90 mm. on a steam bath until no further oil came over with the water. The pot residue was stirred vigorously and cooled to 0° by adding ice.

Workup

  1. temperatureThe reaction mixture was cooled to 20°
  2. stirringstirred for 15 minutes with 40 ml
  3. washthe organic layer washed with 50 ml
  4. additionThe organic layer was added to 400 ml
  5. distillationof water and the mixture distilled at 80-90 mm
  6. customon a steam bath until no further oil came over with the water
  7. stirringThe pot residue was stirred vigorously
  8. temperaturecooled to 0°
  9. additionby adding ice

Sources & evidence

ORD record
ord-8826059533644b5dac12cff57da20cd7
Source dataset
uspto-grants-1980_05
Patent number
US04204075

Reaction notes

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