Acrylamide → N-Octylacrylamide Acrylamide Vinyl Sulfonate

HRID 2372870Notes

Reaction equation

HRID 2372870 reaction equation
[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].[CH:6]([S:8]([O-:11])(=[O:10])=[O:9])=[CH2:7].[Na+].[CH2:13]([NH:21][C:22](=[O:25])[CH:23]=[CH2:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].S([O-])(OCCCCCCCCCCCC)(=O)=O.[Na+].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+]>O.CO>[CH2:13]([NH:21][C:22](=[O:25])[CH:23]=[CH2:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].[CH:6]([S:8]([O-:11])(=[O:10])=[O:9])=[CH2:7]

Participants

8

Reactant 5

HCID 6579AcrylamideHCID 24412Potassium PersulfateHCID 823702-Propenamide, N-octyl-HCID 3270262Sodium vinylsulfonateHCID 3423265Sodium Lauryl Sulfate

Product 1

HCID 86742029N-Octylacrylamide Acrylamide Vinyl Sulfonate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent3×

Procedure

A one liter Morton style resin kettle, fitted with a chilled water condenser, thermometer, nitrogen sparger and mechanical stirrer was charged with 500 ml of purified water. The water was refluxed for 1 hour with a nitrogen purge and then cooled to room temperature. Acrylamide, 9.886 g (0.14 mole), 4.81 g (0.37 mole) of sodium vinyl sulfonate as a 25% solution in water, 0.33 g (0.002 mole) of N-octylacrylamide and 15 g of sodium dodecyl sulfate (SDS) were charged into the flask. The reaction solution was heated to 50° C. and 0.01 g potassium persulfate was added. After 17 hours at 50° C. and 300 rpm stirring the viscous solution was slowly poured into 3 L of methanol and the precipitated polymer was isolated by filtration. The polymer was then masticated in a Waring blender with 2 L of methanol for 30 seconds, filtered and dried under vacuum at room temperature. The yield of the polymer was 10.9 g.

Workup

  1. customA one liter Morton style resin kettle, fitted with a chilled water condenser
  2. custompurge
  3. temperatureThe reaction solution was heated to 50° C.
  4. customthe precipitated polymer was isolated by filtration
  5. filtrationfiltered
  6. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-126ead6f76854228a9fe5534ba185bb2
Source dataset
uspto-grants-1992_03
Patent number
US05100953

Reaction notes

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