Azobisisobutyronitrile → HCID 86746602, compound

HRID 2225356Notes

Reaction equation

HRID 2225356 reaction equation
[CH:1]([P:9]([OH:12])(=[O:11])[OH:10])=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC(N=NC(C#N)(C)C)(C#N)C>O>[CH:1]([P:9]([OH:12])(=[O:10])[OH:11])=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:1]([P:9](=[O:10])([OH:12])[OH:11])=[CH2:2]

Participants

4

Reactant 2

HCID 6547AzobisisobutyronitrileHCID 74355Styrylphosphonic acid

Product 1

HCID 86746602HCID 86746602, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10.68 g. (0.058M) of beta-styrenephosphonic acid, 6.0 ml. (8.4 g., 0.058M) of vinylphosphonyl dichloride, and 0.5 g. of AIBN is heated, with stirring, under an anhydrous nitrogen atmosphere intermittently for a few hours, then overnight at 80°-90° C. The material is transferred to a beaker with 60-70 ml. of water. A crystalline precipitate forms as the warm solution cools. The mixture is filtered, the aqueous filtrate is diluted to 125 ml. with water, and the resulting solution is dialyzed vs. water at 3500 Dalton cutoff. The retentate solution is evaporated in vacuo to give 0.600 g. purified acid form of the copolymer. Proton nmr (D>O) shows two broad regions at 1.0-2.8 (alkyl, 11H) and 6.9-7.5 ppm. (aryl, 5H). These data indicate a ratio of beta-styrenephosphonic acid to vinylphosphonic acid of 1:3 in the copolymer. Phosphorus nmr (D>O) shows two main phosphorus signals centered at about 23.4 and 29.2 ppm. respectively.

Workup

  1. additionA mixture of 10.68 g
  2. customovernight
  3. customat 80°-90° C
  4. filtrationThe mixture is filtered
  5. additionthe aqueous filtrate is diluted to 125 ml
  6. customwith water, and the resulting solution is dialyzed vs
  7. customThe retentate solution is evaporated in vacuo
  8. customto give 0.600 g
  9. custompurified acid form of the copolymer

Sources & evidence

ORD record
ord-b5214023d364491598c4ab76e5c61196
Source dataset
uspto-grants-1994_09
Patent number
US05344641

Reaction notes

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