Maleic Anhydride → p-Butoxystyrene maleic anhydride

HRID 962375

Reaction equation

HRID 962375 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].[C:14]1(=[O:20])[O:19][C:17](=[O:18])[CH:16]=[CH:15]1.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].[C:17]1(=[O:18])[O:19][C:14](=[O:20])[CH:15]=[CH:16]1

Participants

5

Reactant 3

HCID 7923Maleic AnhydrideHCID 11715272p-ButoxystyreneHCID 22065482t-Butylperoxy(2-ethylhexanoate)

Product 1

HCID 86752682p-Butoxystyrene maleic anhydrideYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
90 °C

Procedure

In an autoclave equipped with a 1.5-liter glass polymerization vessel and purged with nitrogen, polymerization reaction was carried out by dissolving 125.0 grams (0.71 mol) of p-butoxystyrene and 125.0 grams (1.28 mol) of maleic anhydride in 500 grams of acetone, adding 7.5 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, 5.0 grams after 21/2 hours and 2.5 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 9,600, a dispersity (Mw/Mn) of 1.58, and a copolymerization ratio of 6:7. The yield was 70.0%.

Workup

  1. custompurged with nitrogen, polymerization reaction
  2. additionThereafter, the catalyst was added in incremental amounts
  3. custom5.0 grams after 21/2 hours and 2.5 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-1f83f2d28cdb454cb4075c13574d9f7f
Source dataset
uspto-grants-1998_06
Patent number
US05759739

Linked notes

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