Azobisisobutyronitrile → Vinylphosphonic Acid Acrylamide

HRID 1499665Notes

Reaction equation

HRID 1499665 reaction equation
[CH:1]([P:3](=[O:6])([OH:5])[OH:4])=[CH2:2].[C:7]([NH2:11])(=[O:10])[CH:8]=[CH2:9].CC(N=NC(C#N)(C)C)(C#N)C>C(O)C>[CH:1]([P:3](=[O:4])([OH:6])[OH:5])=[CH2:2].[C:7]([NH2:11])(=[O:10])[CH:8]=[CH2:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 6579AcrylamideHCID 168725Poly(vinylphosphonic acid)

Product 1

HCID 18401329Vinylphosphonic Acid Acrylamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

In a 10 liter flask equipped with a stirrer, a capacitor, and a dropping device, 3,500 g of ethanol was charged and then heated to 70° C. After dissolving 231.1 g (2.14 mol) of a vinylphosphonic acid monomer, 1368.9 g (19.26 mol) of acrylamide, and 52 g of AIBN in 1,000 g of ethanol, this solution was added dropwise in a reactor over 4 hours. During dropwise addition of the monomer solution, a white precipitate was formed. While maintaining at 70° C., the monomer solution was heated and stirred for 2 hours, followed by stopping of heating and further cooling to room temperature. The precipitated white powder was separated by filtration, washed with 1,000 g of ethanol and then dried.

Workup

  1. customIn a 10 liter flask equipped with a stirrer
  2. additionthis solution was added dropwise in a reactor over 4 hours
  3. additionDuring dropwise addition of the monomer solution
  4. customa white precipitate was formed
  5. temperatureWhile maintaining at 70° C.
  6. temperaturethe monomer solution was heated
  7. temperatureof heating
  8. temperaturefurther cooling to room temperature
  9. customThe precipitated white powder was separated by filtration
  10. washwashed with 1,000 g of ethanol
  11. customdried

Sources & evidence

ORD record
ord-e9b9ea6229fc49e894525b6a11bc3ea7
Source dataset
uspto-grants-2015_12
Patent number
US09201307B2

Reaction notes

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