Water → alpha-Methylene-gamma-Butyrolactone Acrylic Acid

HRID 83938

Reaction equation

HRID 83938 reaction equation
O.S([O-])(OCCCCCCCCCCCC)(=O)=O.[Na+].[CH2:20]=[C:21]1[CH2:26][CH2:25][O:24][C:22]1=[O:23].[C:27]([OH:31])(=[O:30])[CH:28]=[CH2:29].S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>>[CH2:20]=[C:21]1[CH2:26][CH2:25][O:24][C:22]1=[O:23].[C:27]([OH:31])(=[O:30])[CH:28]=[CH2:29]

Participants

7

Reactant 6

HCID 962Water2×HCID 6581Acrylic AcidHCID 14798Sodium HydroxideHCID 62655Sodium PersulfateHCID 68352alpha-Methylene butyrolactoneHCID 3423265Sodium Lauryl Sulfate2×

Product 1

HCID 86664973alpha-Methylene-gamma-Butyrolactone Acrylic Acid

Conditions

Temperature
75 °C

Procedure

To a 250 mL round bottom flask equipped with a magnetic stir bar was added 44.080 g (2.45 mol) water and 0.523 g (1.81×10−3 mol) sodium dodecyl sulfate (20% aqueous solution). The mixture was heated under flowing nitrogen to 75° C., at which time a monomer mixture consisting of 20.81 g (2.12×10−1 mol) α-methylene-γ-butyrolactone that had been previously filtered over basic alumina and 1.100 g (1.83×10−2 mol) acrylic acid was added dropwise over 110 minutes. After 10 minutes of monomer mixture addition, an aqueous mixture consisting of 83.48 g (4.63 mol) water, 1.32 g (4.58×10−3 mol) sodium dodecyl sulfate (20% aqueous solution), 0.065 g (2.73×10−4 mol) sodium persulfate, and 0.18 g of a 20% aqueous sodium hydroxide solution was added dropwise over 110 minutes. After both the monomer and aqueous mixtures were added completely, the emulsion was allowed to stir for an additional 60 minutes, after which the reaction was cooled to room temperature and dried under vacuum at 90° C. overnight. Size exclusion chromatography yielded a weight average molecular weight of 191 kDa and a polydispersity of 1.62, relative to polystyrene standards.

Workup

  1. customTo a 250 mL round bottom flask equipped with a magnetic stir bar
  2. additionwas added dropwise over 110 minutes
  3. additionAfter 10 minutes of monomer mixture addition
  4. additionwas added dropwise over 110 minutes
  5. additionAfter both the monomer and aqueous mixtures were added completely
  6. temperatureafter which the reaction was cooled to room temperature
  7. customdried under vacuum at 90° C. overnight
  8. customSize exclusion chromatography yielded a weight average molecular weight of 191 kDa

Sources & evidence

ORD record
ord-278e110c933c4c8497f4c9e5c8932920
Source dataset
uspto-grants-2014_09
Patent number
US08846817B2

Linked notes

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