Acrylic Acid → Vinylphosphonate Acrylic Acid

HRID 502483Notes

Reaction equation

HRID 502483 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. customis held @ 80 deg. C
  3. filtrationthe beads filtered
  4. washwashed repeatedly by methanol and water in this order

Sources & evidence

ORD record
ord-cdc56b08ee934f91be7727f3744ae2c2
Source dataset
uspto-grants-2010_08
Patent number
US07776319B2

Reaction notes

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