Itaconic acid → HCID 86664978, compound

HRID 83951Notes

Reaction equation

HRID 83951 reaction equation
O.[C:2]([OH:10])(=[O:9])[C:3]([CH2:5][C:6]([OH:8])=[O:7])=[CH2:4].[CH2:11]=[C:12]1CC[O:15][C:13]1=[O:14].C(O)(=O)C=C.S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>>[CH2:4]=[C:3]1[CH2:5][CH2:6][O:10][C:2]1=[O:9].[C:2]([OH:10])(=[O:9])[C:3]([CH2:5][C:6]([OH:8])=[O:7])=[CH2:4].[C:13]([OH:15])(=[O:14])[CH:12]=[CH2:11]

Participants

7

Reactant 6

HCID 811Itaconic acidHCID 962Water2×HCID 6581Acrylic AcidHCID 14798Sodium HydroxideHCID 62655Sodium PersulfateHCID 68352alpha-Methylene butyrolactone

Product 1

HCID 86664978HCID 86664978, compound

Conditions

Temperature
75 °C

Procedure

To a 100 mL round bottom flask with a magnetic stir bar and reflux condenser is added 25 g (1.389 mol) water and 22.75 g (1.75×10−1 mol) itaconic acid. The mixture is heated under flowing nitrogen to 75° C., at which time a monomer mixture consisting of 17.20 g (1.75×10−1 mol) α-methylene-γ-butyrolactone and 2.00 g (3.33×10−2 mol) acrylic acid is added via syringe pump over 300 minutes at reflux. After 10 minutes of monomer mixture addition, an aqueous mixture consisting of 18.015 g (1.00 mol) water, 1.42 g (5.97×10−3 mol) sodium persulfate, and 1.32 g (3.33×10−2 mol) sodium hydroxide is added via syringe pump over 300 minutes at reflux. After both the monomer and aqueous mixtures are added completely, the emulsion is allowed to stir for an additional 60 minutes before cooling to room temperature and drying under vacuum at elevated temperature for isolation.

Workup

  1. temperatureTo a 100 mL round bottom flask with a magnetic stir bar and reflux condenser
  2. additionis added via syringe pump over 300 minutes
  3. temperatureat reflux
  4. additionAfter 10 minutes of monomer mixture addition
  5. additionis added via syringe pump over 300 minutes
  6. temperatureat reflux
  7. additionAfter both the monomer and aqueous mixtures are added completely
  8. temperaturebefore cooling to room temperature
  9. customdrying under vacuum at elevated temperature for isolation

Sources & evidence

ORD record
ord-486cfa2c2a014d9497da304df501f565
Source dataset
uspto-grants-2014_09
Patent number
US08846817B2

Reaction notes

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