Acrylic Acid → Vinylphosphonate Acrylic Acid

HRID 1684874Notes

Reaction equation

HRID 1684874 reaction equation
[CH:1]([P:3](=[O:6])([O-:5])[O-:4])=[CH2:2].[C:7]([OH:11])(=[O:10])[CH:8]=[CH2:9].[OH-].[Na+].C(C=CC(N)=O)C=CC(N)=O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>O.CCCCCC>[CH:1]([P:3](=[O:4])([O-:6])[O-:5])=[CH2:2].[C:7]([OH:11])(=[O:10])[CH:8]=[CH2:9]

Participants

8

Reactant 5

HCID 6581Acrylic AcidHCID 14798Sodium HydroxideHCID 62655Sodium Persulfate2×HCID 7204855VinylphosphonateHCID 53800990Methylene-bisacrylamide

Product 1

HCID 131728280Vinylphosphonate Acrylic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

Vinylphosphonate and acrylic acid are first 50 mol-% neutralized with NaOH to form a 50 wt-% aqueous solution; to this mixture methylene-bis-acrylamide is added in a 10 wt-% to monomers. 100 parts of that monomer mixture are then emulsified in 200 parts of hexane and 1 part of sesquioleate sorbital as a surfactant. 10 parts of a 5 wt-% aqueous solution of sodium persulfate is further added to the suspension. The reaction is held (80 deg. C. for 10 hrs, while 10 parts of sodium persulfate solution are added. The water is then stripped off by a Dean-stark apparatus, the beads filtered and washed repeatedly by methanol and water in this order.

Workup

  1. customto form a 50 wt-% aqueous solution
  2. custom80 deg. C
  3. filtrationthe beads filtered
  4. washwashed repeatedly by methanol and water in this order

Sources & evidence

ORD record
ord-99b3714e32de4184ae8c2218b8716510
Source dataset
uspto-grants-2012_04
Patent number
US08147873B2

Reaction notes

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