Methanol → p-Tert-butoxystyrene p-methylstyrene

HRID 430907

Reaction equation

HRID 430907 reaction equation
N(C(C)(CC)C([O-])=O)=NC(C)(CC)C([O-])=O.[C:17]([O:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[CH2:27])=[CH:24][CH:23]=1)([CH3:20])([CH3:19])[CH3:18].[CH3:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=[CH2:36])=[CH:33][CH:32]=1.CO>O1CCOCC1>[C:17]([O:21][C:22]1[CH:23]=[CH:24][C:25]([CH:26]=[CH2:27])=[CH:28][CH:29]=1)([CH3:20])([CH3:18])[CH3:19].[CH3:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=[CH2:36])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 121611-Ethenyl-4-methylbenzeneHCID 5775311-(Tert-butoxy)-4-ethenylbenzeneHCID 219175032,2'-Azobis(methyl 2-methylpropanate)

Product 1

HCID 67612459p-Tert-butoxystyrene p-methylstyrene

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,2′-Azobis(methyl 2-methylpropionate) was added to a mixture of 100 g (0.567 mole) of p-tert-butoxystyrene and 3.54 g (0.03 mole) of p-methylstyrene in 1,4-dioxane, followed by conducting a polymerization reaction at 80° C. for 6 hours under nitrogen gas streams. After cooling, the reaction solution was poured into 5000 ml of aqueous methanol solution to precipitate out. The precipitated polymer was filtered, washed with methanol and dried under reduced pressure to give 92.3 g of poly(p-tert-butoxystyrene/p-methylstyrene) as white powders. A ratio of p-tert-butoxystyrene unit and p-methylstyrene unit was about 95:5 by 1HNMR. Mw was about 20000 and Mw/Mn was 1.90 by GPC measurement using polystyrene as standard.

Workup

  1. customa polymerization reaction at 80° C. for 6 hours under nitrogen gas streams
  2. temperatureAfter cooling
  3. customto precipitate out
  4. filtrationThe precipitated polymer was filtered
  5. washwashed with methanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-ecdc3ce1f081466aaa85836965880355
Source dataset
uspto-grants-2003_12
Patent number
US06656660B1

Linked notes

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