Maleic Anhydride → Isopropenyl Phosphonic Acid Hydroxypropylacrylate Maleic Anhydride

HRID 543458

Reaction equation

HRID 543458 reaction equation
[C:1]([P:4](=[O:7])([OH:6])[OH:5])([CH3:3])=[CH2:2].[OH:8][CH2:9][CH2:10][CH2:11][O:12][C:13](=[O:16])[CH:14]=[CH2:15].[C:17]1(=[O:23])[O:22][C:20](=[O:21])[CH:19]=[CH:18]1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>O>[C:1]([P:4](=[O:5])([OH:7])[OH:6])([CH3:3])=[CH2:2].[OH:8][CH2:9][CH2:10][CH2:11][O:12][C:13](=[O:16])[CH:14]=[CH2:15].[C:20]1(=[O:21])[O:22][C:17](=[O:23])[CH:18]=[CH:19]1

Participants

6

Reactant 4

HCID 7923Maleic AnhydrideHCID 331012-Propenoic acid, 3-hydroxypropyl esterHCID 62648Ammonium PersulfateHCID 557541Isopropenylphosphonic acid

Product 1

HCID 86739387Isopropenyl Phosphonic Acid Hydroxypropylacrylate Maleic Anhydride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aqueous isopropenyl phosphonic acid (47 g, 54%, 0.2 mole), hydroxypropylacrylate (26 g, 0.2 mole) and maleic anhydride (5 g, 0.05 mole, neutralized to pH 5 in 50 ml water) were mixed with 82.6 g water in a resin kettle under nitrogen. Ammonium persulfate (6 g) was added followed by 11/2 hours of reflux. An equivalent amount of initiator was added and the reflux period repeated. The final product was yellow with a pH of 0.99. The 31PMR showed polymer absorptions centered at δ=-34, -32.3 and -28.8 ppm.

Workup

  1. custom2 hours
  2. temperatureof reflux
  3. additionAn equivalent amount of initiator was added

Sources & evidence

ORD record
ord-f012e04f3b2241b4ad4d63afbf922651
Source dataset
uspto-grants-1984_05
Patent number
US04446028

Linked notes

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