Reaction #2044993

ord-e08e86e018834cdcb9d1a110d47855ea

Reaction equation

C=CP(=O)([O-])[O-]
Vinylphosphonate
O=S(=O)([O-])OOS(=O)(=O)[O-].[Na+].[Na+]
sodium persulfate
[Na+].[OH-]
NaOH
NC(=O)C=CCC=CC(N)=O
methylene-bis-acrylamide
O=S(=O)([O-])OOS(=O)(=O)[O-].[Na+].[Na+]
sodium persulfate
C=CC(=O)O
acrylic acid
→
C=CC(=O)O.C=CP(=O)([O-])[O-]
Vinylphosphonate Acrylic Acid

Reactants

C=CP(=O)([O-])[O-]
Vinylphosphonate
O=S(=O)([O-])OOS(=O)(=O)[O-].[Na+].[Na+]
sodium persulfate
[Na+].[OH-]
NaOH
NC(=O)C=CCC=CC(N)=O
methylene-bis-acrylamide
O=S(=O)([O-])OOS(=O)(=O)[O-].[Na+].[Na+]
sodium persulfate
C=CC(=O)O
acrylic acid

Reagents

None

Solvents

O
water
CCCCCC
hexane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherto form a 50 wt-% aqueous solution
  2. 2
    Otheris held @ 80 deg
  3. 3
    Filtrationthe beads filtered
  4. 4
    Washwashed repeatedly by methanol and water in this order

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08409561B2uspto-grants-2013_04