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2-Phenylvinyl acetate → Hydroxystyrene

HRID 496978
Notes
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Reaction equation

HRID 496978 reaction equation
C([O:4][CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=O)C.[CH2:13]([O:18][CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:14][CH2:15][CH2:16][CH3:17]>>[OH:4][CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:13]([O:18][CH:19]=[CH:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:14][CH2:15][CH2:16][CH3:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 1145762-Phenylvinyl acetateHCID 54173547Amyloxystyrene

Product 2

HCID 138202HydroxystyreneHCID 54173547Amyloxystyrene

Procedure

In one typical embodiment, the polymer can be synthesized by dissolving an acetoxystyrene monomer, a (meth)acrylic acid tertiary ester monomer and an amyloxystyrene monomer in an organic solvent, adding a radical initiator thereto, heat polymerizing the monomers, and subjecting the resulting polymer to alkaline hydrolysis in an organic solvent for deblocking the acetoxy group, thereby forming a ternary copolymer of hydroxystyrene, (meth)acrylic acid tertiary ester and amyloxystyrene. Examples of the organic solvent used in polymerization include toluene, benzene, tetrahydrofuran, diethyl ether, and dioxane. Representative of the polymerization initiator are 2,2′-azobisisobutyronitrile, 2,2′-azobis(2,4-dimethyl-valeronitrile), dimethyl-2,2-azobis(2-methylpropionate), benzoyl peroxide and lauroyl peroxide. Polymerization may be effected by heating at about 50 to 80° C. The reaction time is usually about 2 to 100 hours, preferably about 5 to 20 hours. The base used in the alkaline hydrolysis is selected from aqueous ammonia and triethylamine, to name a few. The reaction temperature is about −20° C. to 100° C., preferably about 0 to 60° C. The reaction time is usually about 0.2 to 100 hours, preferably about 0.5 to 20 hours.

Workup

  1. customIn one typical embodiment, the polymer can be synthesized
  2. temperatureheat
  3. custompolymerizing the monomers
  4. customhydrolysis in an organic solvent

Sources & evidence

ORD record
ord-7c9e780ecfc842609fca553328ebefb1
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06949323B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes