Butyl Acrylate → Styrene 4-styrenesulfonic Acid Sodium Salt

HRID 411792Notes

Reaction equation

HRID 411792 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(OCCCC)(=O)C=C>O>[CH2:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[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 8846Butyl AcrylateHCID 23681144Sodium 4-ethenylbenzene-1-sulfonate--water (1/1/1)

Product 1

HCID 87337954Styrene 4-styrenesulfonic Acid Sodium Salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

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 (0.20 g), butyl acrylate (Aldrich, 20.0 g), a-olefin sulfonate surfactant (Rhodia, Rhodacal A-246/L, 25.0 g of a ca. 40% aqueous solution), and water (145 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 a solution of initiator (K2S2O8, Aldrich, 0.40 g, dissolved in 10 mL H2O) was added all at once via a syringe. The appearance of the nearly opaque aqueous monomer emulsion changed quickly over less than 5 minutes to form a translucent, bluish scattering emulsion. The mixture was stirred and heated for an additional 6 h in the 95° C. oil bath (internal temperature ca. 92° C.) to decompose the excess initiator. The mixture was cooled with stirring, and filtered to remove a small amount of suspended solid. Yield 198.9 g of emulsion, pH ca. 4 to pH paper, 15.65% solids, particle size=12.3 nm Rh, by DLS, (2nd cumulant analysis PDI=0.07).

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. additionwas added all at once via a syringe
  5. waitThe appearance of the nearly opaque aqueous monomer emulsion changed quickly over less than 5 minutes
  6. customto form a translucent, bluish scattering emulsion
  7. stirringThe mixture was stirred
  8. temperatureheated for an additional 6 h in the 95° C. oil bath (internal temperature ca. 92° C.)
  9. temperatureThe mixture was cooled
  10. stirringwith stirring
  11. filtrationfiltered
  12. customto remove a small amount of suspended solid

Sources & evidence

ORD record
ord-b5c56ae776324bb8b7114a1b991f4871
Source dataset
uspto-grants-2003_05
Patent number
US06559255B2

Reaction notes

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