Azobisisobutyronitrile → p-Tert-butoxystyrene cyclohexyl acrylate

HRID 330720

Reaction equation

HRID 330720 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].[C:14]([O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)(=[O:17])[CH:15]=[CH2:16].N(C(C)(C)C#N)=NC(C)(C)C#N>C(O)(C)C.CO>[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].[C:14]([O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)(=[O:17])[CH:15]=[CH2:16]

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 18298Cyclohexyl acrylateHCID 5775311-(Tert-butoxy)-4-ethenylbenzene

Product 1

HCID 86587325p-Tert-butoxystyrene cyclohexyl acrylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

p-tert-Butoxystyrene (176.3 g (1.0 mol)) and 16.2 g (0.105 mol) of cyclohexyl acrylate were dissolved in 250 ml of isopropanol, and in a nitrogen stream, 2,2′-azobisisobutyronitrile was added. The mixture was allowed to undergo a polymerization reaction at 75° C. for 6 hours. The reaction solution was cooled and then poured in 5,000 ml of methanol for crystallization. The precipitated crystal was collected by filtration, washed with methanol and dried under reduced pressure to obtain 172.5 g of poly(p-tert-butoxystyrene/cyclohexyl acrylate) as white powder crystal. The component ratio between p-tert-butoxystyrene unit and cyclohexyl acrylate unit in the obtained resin was found to be about 90:10 from 1HNMR and 13CNMR measurements. Also, the results of GPC measurement using polystyrene as a standard were Mw of about 20,600 and Mw/Mn of 1.55.

Workup

  1. customa polymerization reaction at 75° C. for 6 hours
  2. temperatureThe reaction solution was cooled
  3. filtrationThe precipitated crystal was collected by filtration
  4. washwashed with methanol
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-fc827500438e447a9fbd537c7d9446a6
Source dataset
uspto-grants-2014_11
Patent number
US08877423B2

Linked notes

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