Acrylic Acid → alpha-Methylene-gamma-butyrolactone acrylic acid pentaerythritol allyl ether

HRID 83936

Reaction equation

HRID 83936 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4].[C:8]([OH:12])(=[O:11])[CH:9]=[CH2:10].[CH2:13]([O:16][CH2:17][C:18]([CH2:23][OH:24])([CH2:21][OH:22])[CH2:19][OH:20])[CH:14]=[CH2:15].S([O-])(OCCCCCCCCCCCC)(=O)=O.[Na+].S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>O>[CH2:1]=[C:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4].[C:8]([OH:12])(=[O:11])[CH:9]=[CH2:10].[CH2:13]([O:16][CH2:17][C:18]([CH2:21][OH:22])([CH2:23][OH:24])[CH2:19][OH:20])[CH:14]=[CH2:15]

Participants

8

Reactant 6

HCID 6581Acrylic Acid2×HCID 14798Sodium HydroxideHCID 62655Sodium PersulfateHCID 68352alpha-Methylene butyrolactone2×HCID 3086330Allyl pentaerythritol2×HCID 3423265Sodium Lauryl Sulfate2×

Product 1

HCID 131731900alpha-Methylene-gamma-butyrolactone acrylic acid pentaerythritol allyl ether

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

The crosslinked polymer poly(α-methylene-γ-butyrolactone-acrylic acid-pentaerythritol allyl ether) was prepared by emulsion polymerization of α-methylene-γ-butyrolactone and acrylic acid with the crosslinking monomer pentaerythritol allyl ether. To a four neck round bottom glass flask, equipped with a mechanical stirrer and a thermocouple with a nitrogen inlet at the side of the inlet-tube and two dropping funnels was added the initial charge of 44.03 g of water and 0.51 g of a 20% solution of sodium dodecyl sulfate surfactant. Into the monomer dropping funnel a mixture of 20.8 g of α-methylene-γ-butyrolactone, 1.1 g of acrylic acid and 0.16 g of pentaerythritol allyl ether were added. Into the second dropping funnel the aqueous mixture consisting of 83.43 g water, 1.32 g 20% sodium dodecylsulfate, 0.14 g sodium persulfate and 0.17 g 20% sodium hydroxide solution were added. The initial charge was heated to 75° C. dropwise addition of the monomer was started. Dropwise addition of the aqueous mixture started 5 minutes later. The monomer feed ended 120 minutes after the start of monomer addition, and the aqueous stream ended 5 minutes after the monomer stream ended. After a cook-down time of one hour, the reaction mixture was cooled to room temperature.

Workup

  1. customTo a four neck round bottom glass flask, equipped with a mechanical stirrer
  2. additiona thermocouple with a nitrogen inlet at the side of the inlet-tube and two dropping funnels was added the
  3. additionwere added
  4. additionwere added
  5. additionThe initial charge
  6. additiondropwise addition of the monomer
  7. additionDropwise addition of the aqueous mixture
  8. waitThe monomer feed ended 120 minutes
  9. additionafter the start of monomer addition
  10. waitthe aqueous stream ended 5 minutes
  11. temperatureAfter a cook-down time of one hour, the reaction mixture was cooled to room temperature

Sources & evidence

ORD record
ord-40aa735a4fc642b2855ba315df9fa102
Source dataset
uspto-grants-2014_09
Patent number
US08846817B2

Linked notes

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