Methanol → NaMAU AMPS

HRID 405652

Reaction equation

HRID 405652 reaction equation
CO.[C:3]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O-:21])=[O:20])(=[O:7])[C:4]([CH3:6])=[CH2:5].[Na+:22].[C:23]([NH:27][C:28]([CH3:35])([CH3:34])[CH2:29][S:30]([OH:33])(=[O:32])=[O:31])(=[O:26])[CH:24]=[CH2:25].[OH-].[Na+]>N(C(C)(C)C#N)=NC(C)(C)C#N.CCOCC.O>[C:3]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O-:21])=[O:20])(=[O:7])[C:4]([CH3:6])=[CH2:5].[Na+:22].[C:23]([NH:27][C:28]([CH3:35])([CH3:34])[CH2:29][S:30]([OH:33])(=[O:31])=[O:32])(=[O:26])[CH:24]=[CH2:25]

Participants

8

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 653602-Acrylamido-2-methyl-1-propanesulfonic acidHCID 87229187Sodium 11-methacrylamidoundecanoate

Product 1

HCID 131731611NaMAU AMPSYield 619.5%

Reagents, catalysts & solvents 3

HCID 6547AzobisisobutyronitrileCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

Into a mixed solvent of 32.4 mL of methanol and 3.6 mL water (methanol/water=9/1) were dissolved 4.9823 g (17.1 mmol) of sodium 11-methacrylamidoundecanoate (NaMAU), 186.5 mg (0.9 mmol) of 2-acrylamido-2-methylpropanesulfonic acid (AMPS), 39.6 mg (0.99 mmol) of sodium hydroxide, and 7.4 mg (0.045 mmol) of azobisisobutyronitrile. The solution was deaerated by bubbling argon for 30 minutes, the container was covered with a septum, and the polymerization was conducted by heating the solution at 60° C. for 12 hours. After the completion of the polymerization reaction, the reaction solution was dropwise added into a large excess of ether, and the resulting precipitate was collected by filtration under suction. This precipitate was dissolved in water, dialyzed against pure water for 1 week, and 2.78 g of random NaMAU/AMPS copolymer (95/5) was obtained by freeze-drying (yield: 53.71%).

Workup

  1. customby bubbling argon for 30 minutes
  2. customAfter the completion of the polymerization reaction
  3. filtrationthe resulting precipitate was collected by filtration under suction
  4. dissolutionThis precipitate was dissolved in water
  5. customdialyzed against pure water for 1 week

Sources & evidence

ORD record
ord-e74563a5dfd343de944fdb3e46ef7ccc
Source dataset
uspto-grants-2014_06
Patent number
US08753686B2

Linked notes

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