Azobisisobutyronitrile → HCID 131731622, compound

HRID 405662Notes

Reaction equation

HRID 405662 reaction equation
[C:1]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:20]([O:25][CH2:26][CH2:27][O:28][P:29](=[O:32])([OH:31])[OH:30])(=[O:24])[C:21]([CH3:23])=[CH2:22].[OH-].[Na+].N(C(C)(C)C#N)=NC(C)(C)C#N>CO.O>[C:1]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:20]([O:25][CH2:26][CH2:27][O:28][P:29](=[O:30])([OH:31])[OH:32])(=[O:24])[C:21]([CH3:23])=[CH2:22]

Participants

7

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 14798Sodium HydroxideHCID 905512-(Methacryloyloxy)ethyl dihydrogen phosphateHCID 276418511-(Methacryloylamino)undecanoic acid

Product 1

HCID 131731622HCID 131731622, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

In a mixed solvent of 75 g of methanol and 25 g of ion-exchanged water were dissolved 18.40 g (68.32 mmol) of 11-methacrylamidoundecanoic acid (MAU), 1.60 g (7.59 mmol) of 2-methacryloxyethyl phosphoric acid (Phosmer-M: Uni-Chemical Co.), 0.30 g (7.59 mmol) of sodium hydroxide, and 0.31 g (1.89 mmol) of azobisisobutyronitrile (Nacalai Tesque, Inc.). The solution was deaerated by bubbling nitrogen for 60 minutes. The container was covered with a septum, and the polymerization was conducted by heating at 60° C. for 20 hours. After the completion of the polymerization reaction, a gelatinous product was obtained. This product was dried under reduced pressure, and 6.0 g of the dried material was added to 200 g of methanol. After sufficient stirring, insoluble material was removed by filtration. The obtained solution was dropwise added into a large excess of ethyl acetate, and the resulting precipitate was collected by filtration under suction. After drying under reduced pressure, 2.01 g of random MAU/2-methacryloxyethyl phosphoric acid copolymer (90/10) was obtained. The weight average molecular weight was 190000.

Workup

  1. customby bubbling nitrogen for 60 minutes
  2. customAfter the completion of the polymerization reaction
  3. customa gelatinous product was obtained
  4. dry with materialThis product was dried under reduced pressure, and 6.0 g of the dried material
  5. additionwas added to 200 g of methanol
  6. customAfter sufficient stirring, insoluble material was removed by filtration
  7. additionThe obtained solution was dropwise added into a large excess of ethyl acetate
  8. filtrationthe resulting precipitate was collected by filtration under suction
  9. customAfter drying under reduced pressure

Sources & evidence

ORD record
ord-939768e41d7c4e51b0574b06167fca0b
Source dataset
uspto-grants-2014_06
Patent number
US08753686B2

Reaction notes

Loading…