t-Butylacrylamide → t-butylacrylamide 4-styrenesulfonic Acid Sodium Salt

HRID 411790Notes

Reaction equation

HRID 411790 reaction equation
O.[Na+:2].[CH2:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([O-:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1.[C:15]([C:19](=[CH2:23])[C:20]([NH2:22])=[O:21])([CH3:18])([CH3:17])[CH3:16]>O>[C:15]([C:19](=[CH2:23])[C:20]([NH2:22])=[O:21])([CH3:18])([CH3:17])[CH3:16].[Na+:2].[CH2:3]=[CH:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([O-:14])(=[O:13])=[O:12])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 18539458t-ButylacrylamideHCID 23681144Sodium 4-ethenylbenzene-1-sulfonate--water (1/1/1)

Product 1

HCID 131723881t-butylacrylamide 4-styrenesulfonic Acid Sodium Salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

In a 250 mL Morton flask (fitted with mechanical stirrer, thermometer, and oil bath heating) under argon atmosphere were combined 4-styrenesulfonic acid sodium salt hydrate (0.10 g), t-butylacrylamide (Aldrich, 9.9 g), α-olefin sulfonate surfactant (Rhodia, Rhodacal A-246/L, 12.5 g of a ca. 40% aqueous solution), and water (175 g). The mixture was stirred and heated in a 90° C. oil bath until an internal temperature of ca. 75° C. was obtained, and then solid initiator (K2S2O8, Aldrich, 0.20 g) was added all at once. The appearance of the aqueous monomer slurry changed quickly over a period of 1-4 minutes, with the solid dissolving to form a nearly transparent, bluish scattering emulsion. The mixture was stirred and heated in a 100° C. oil bath for an additional 2 h (internal temperature of 93° C.) to decompose the excess initiator. The mixture was cooled with stirring, and filtered to remove any suspended solid. Yield 196.2 g of emulsion, pH ca. 3 to pH paper, 8.07% solids, particle size=9.3 nm Rh, by DLS, (2nd cumulant analysis PDI=0.10).

Workup

  1. customIn a 250 mL Morton flask (fitted with mechanical stirrer
  2. temperaturethermometer, and oil bath heating) under argon atmosphere
  3. customwas obtained
  4. additionsolid initiator (K2S2O8, Aldrich, 0.20 g) was added all at once
  5. dissolutiondissolving
  6. customto form a nearly transparent,
  7. stirringThe mixture was stirred
  8. temperatureheated in a 100° C. oil bath for an additional 2 h (internal temperature of 93° C.)
  9. temperatureThe mixture was cooled
  10. stirringwith stirring
  11. filtrationfiltered
  12. customto remove any suspended solid

Sources & evidence

ORD record
ord-0b16e048396b4a70b4066d0539157142
Source dataset
uspto-grants-2003_05
Patent number
US06559255B2

Reaction notes

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