Ammonium → Isopropenyl Phosphonic Acid Hydroxypropylacrylate Methyl Acrylate

HRID 543459

Reaction equation

HRID 543459 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]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19].[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:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19]

Participants

6

Reactant 4

HCID 223AmmoniumHCID 7294Methyl AcrylateHCID 331012-Propenoic acid, 3-hydroxypropyl esterHCID 557541Isopropenylphosphonic acid

Product 1

HCID 86739388Isopropenyl Phosphonic Acid Hydroxypropylacrylate Methyl Acrylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aqueous isopropenyl phosphonic acid (71 g, 54%, 0.3 mole), hydroxypropylacrylate (13 g, 0.1 mole) and methyl acrylate (5 g, 0.06 mole) were mixed with 121.6 g water containing 6 g of ammonium pursulfate. After sparging with nitrogen for 1/2 hour, the mixture was heated to reflux for 11/2 hours. An additional 6 g of initiator was added followed by an equivalent period of reflux. The final product had a pH of 0.65. The 31PMR showed significant polymeric absorptions at -32.4 and -24.3 ppm.

Workup

  1. customAfter sparging with nitrogen for 1/2 hour
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 11/2 hours
  4. additionAn additional 6 g of initiator was added
  5. waitfollowed by an equivalent period
  6. temperatureof reflux

Sources & evidence

ORD record
ord-7fa10ca3bcd24269b6131511e212eec6
Source dataset
uspto-grants-1984_05
Patent number
US04446028

Linked notes

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