Azobisisobutyronitrile → p-Tert-butoxystyrene styrene

HRID 1592793Notes

Reaction equation

HRID 1592793 reaction equation
[C:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[CH2:11])=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N(C(C)(C)C#N)=NC(C)(C)C#N>COCC(O)C>[C:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH:10]=[CH2:11])=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3].[CH2:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 7501StyreneHCID 5775311-(Tert-butoxy)-4-ethenylbenzene

Product 1

HCID 69102216p-Tert-butoxystyrene styreneYield 188.5%

Reagents, catalysts & solvents 1

HCID 79001-Methoxy-2-propanolSolvent

Procedure

p-tert-Butoxystyrene (100 g), 19.7 g of styrene, 8.1 g of azobisisobutyronitrile and 2.5 g of tert-dodecylmercaptane were dissolved in 180 g of propylene glycol monomethyl ether, and the polymerization reaction was performed at 80° C. for 9 hours. The polymerization solution was purified by reprecipitation with methanol to obtain 100 g of a p-tert-butoxy styrene/styrene copolymer (Mw: 72,00, Mw/Mn: 1.80). Subsequently, this copolymer and 50 g of 10 mass % aqueous sulfuric acid were dissolved in 300 g of propylene glycol monomethyl ether, and the hydrolysis reaction was performed at 90° C. for 6 hours. The reaction solution was purified by reprecipitation with a large amount of water until the solution became neutral, whereby Resin (B-3) which is a p-hydroxystyrene/styrene (=75/25 mol %) copolymer was obtained. The weight average molecular weight of this resin was 5,200.

Workup

  1. customthe polymerization reaction
  2. customThe polymerization solution was purified by reprecipitation with methanol

Sources & evidence

ORD record
ord-e1c7dacc9ab84b9caa1a74f48f5d39f7
Source dataset
uspto-grants-2007_11
Patent number
US07294450B2

Reaction notes

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