Styrene → Butyl prop-2-enoate;styrene

HRID 1504362Notes

Reaction equation

HRID 1504362 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:12])[CH:10]=[CH2:11].C(S)CCCCCCCCCCC.C(OCCCCCCCCCCOC(=O)C=C)(=O)C=C>O>[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:12])[CH:10]=[CH2:11]

Participants

6

Reactant 4

HCID 7501StyreneHCID 81951-DodecanethiolHCID 8846Butyl AcrylateHCID 830792-Propenoic acid, 1,1'-(1,10-decanediyl) ester

Product 1

HCID 168422Butyl prop-2-enoate;styrene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Separately, the monomer emulsion was prepared in the following manner. 217 g of styrene, 52.0 g of butyl acrylate, 2.84 modified indigo, 8.1 g of β-CEA, 1.8 g of 1-dodecanethiol, 0.95 g of 1,10-decanediol diacrylate (ADOD), 4.6 g of Dowfax 2A1 (anionic surfactant), and 128.3 g of deionized water were mixed to form an emulsion. 1% of the above emulsion was then slowly fed into the reactor containing the aqueous surfactant phase at 80° C. to form the “seeds” while being purged with nitrogen. The initiator solution was then slowly charged into the reactor and after 10 minutes the rest of the emulsion was continuously fed in using a metering pump at a rate of 0.5%/min. Once all the monomer emulsion was charged into the main reactor, the temperature was held at 80° C. for an additional 2 hours to complete the reaction. Full cooling was then applied and the reactor temperature was reduced to 25° C. The product was collected into a holding tank and sieved with a 25 μm screen.

Workup

  1. customSeparately, the monomer emulsion was prepared in the following manner
  2. customto form an emulsion
  3. additioncontaining the aqueous surfactant phase at 80° C.
  4. customto form the “seeds”
  5. customwhile being purged with nitrogen
  6. additionThe initiator solution was then slowly charged into the reactor and after 10 minutes the rest of the emulsion
  7. additionOnce all the monomer emulsion was charged into the main reactor
  8. customthe reaction
  9. temperatureFull cooling
  10. customwas reduced to 25° C
  11. customThe product was collected into a holding tank
  12. filtrationsieved with a 25 μm screen

Sources & evidence

ORD record
ord-4634db5e5dba45a5a01dfac52b76ae85
Source dataset
uspto-grants-2015_12
Patent number
US09213248B2

Reaction notes

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