tert-Butyl acrylate → p-Butoxystyrene p-hydroxystyrene t-butyl acrylate

HRID 962372

Reaction equation

HRID 962372 reaction equation
[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[CH2:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[OH:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[CH2:20])=[CH:17][CH:16]=1.[C:23]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:26])[CH:24]=[CH2:25].C(OOC(CC)(CCCC)C([O-])=O)(C)(C)C>CC(C)=O>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH:10]=[CH2:11])=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH3:4].[OH:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[CH2:20])=[CH:17][CH:16]=1.[C:23]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:26])[CH:24]=[CH2:25]

Participants

6

Reactant 4

HCID 15458tert-Butyl acrylateHCID 624534-VinylphenolHCID 11715272p-ButoxystyreneHCID 22065482t-Butylperoxy(2-ethylhexanoate)

Product 1

HCID 86752679p-Butoxystyrene p-hydroxystyrene t-butyl acrylateYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
90 °C

Procedure

In an autoclave equipped with a 1.0-liter glass polymerization vessel and purged with nitrogen, polymerization reaction was carried out by dissolving 19.4 grams (0.11 mol) of p-butoxystyrene, 13.2 grams (0.11 mol) of p-hydroxystyrene and 25.0 grams (0.20 mol) of t-butyl acrylate in 300 grams of acetone, adding 3.5 grams of t-butylperoxy(2-ethylhexanoate) as a polymerization catalyst, and heating the mixture at 90° C. Thereafter, the catalyst was added in incremental amounts, that is, 1.0 grams after 21/2 hours and 1.0 grams after 41/2 hours from the start of polymerization reaction. After 6 hours of polymerization, the reaction solution was cooled down and the acetone was distilled off. A 9/1 methanol/water mixture was added to the reaction solution, causing the copolymer to crystallize. The copolymer had a weight average molecular weight (Mw) of 6,900, a dispersity (Mw/Mn) of 1.72, and a copolymerization ratio (p-butoxystyrene/p-hydroxystyrene/t-butyl acrylate) of 1:1:2. The yield was 70.0%.

Workup

  1. custompurged with nitrogen, polymerization reaction
  2. additionThereafter, the catalyst was added in incremental amounts
  3. custom1.0 grams after 21/2 hours and 1.0 grams after 41/2 hours from the start of polymerization reaction
  4. customAfter 6 hours of polymerization
  5. temperaturethe reaction solution was cooled down
  6. distillationthe acetone was distilled off
  7. additionA 9/1 methanol/water mixture was added to the reaction solution
  8. customto crystallize

Sources & evidence

ORD record
ord-1e1bb40dab454e528bf24cf28e47fb48
Source dataset
uspto-grants-1998_06
Patent number
US05759739

Linked notes

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