Water → alpha-Methylene-gamma-Valerolactone Acrylic Acid

HRID 83941

Reaction equation

HRID 83941 reaction equation
O.S([O-])(OCCCCCCCCCCCC)(=O)=O.[Na+].[CH2:20]=[C:21]1[CH2:26][CH:25]([CH3:27])[O:24][C:22]1=[O:23].[C:28]([OH:32])(=[O:31])[CH:29]=[CH2:30].S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>>[CH2:20]=[C:21]1[CH2:26][CH:25]([CH3:27])[O:24][C:22]1=[O:23].[C:28]([OH:32])(=[O:31])[CH:29]=[CH2:30]

Participants

7

Reactant 6

HCID 962Water2×HCID 6581Acrylic AcidHCID 14798Sodium HydroxideHCID 62655Sodium PersulfateHCID 99939gamma-Methyl-alpha-methylene-gamma-butyrolactoneHCID 3423265Sodium Lauryl Sulfate2×

Product 1

HCID 86664974alpha-Methylene-gamma-Valerolactone Acrylic Acid

Conditions

Temperature
73 °C

Procedure

To a 50 mL round bottom flask equipped with a magnetic stir bar was added 6.172 g (0.343 mol) water and 0.078 g (2.70×10−4 mol) sodium dodecyl sulfate (20% aqueous solution). The mixture was heated under flowing nitrogen to 73° C., at which point a monomer mixture consisting of 2.913 g (2.58×10−2 mol) α-methylene-γ-valerolactone that had been previously fractionally distilled and filtered over basic alumina and 0.154 g (2.56×10−3 mol) acrylic acid were added via syringe pump over 120 minutes. After 10 minutes of monomer mixture addition, an aqueous mixture consisting of 11.677 g (0.649 mol) water, 0.198 g (6.87×10−4 mol) sodium dodecyl sulfate (20% aqueous solution), 0.004 g (1.68×10−5 mol) sodium persulfate, and 0.029 g of a 20% aqueous sodium hydroxide solution was also added via syringe pump over 120 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 under vacuum at 90° C. overnight. Size exclusion chromatography yielded a weight average molecular weight of 647 kDa and a polydispersity of 2.77, relative to polystyrene standards.

Workup

  1. customTo a 50 mL round bottom flask equipped with a magnetic stir bar
  2. distillationhad been previously fractionally distilled
  3. additionwere added via syringe pump over 120 minutes
  4. additionAfter 10 minutes of monomer mixture addition
  5. additionwas also added via syringe pump over 120 minutes
  6. additionAfter both the monomer and aqueous mixtures were added completely
  7. temperatureafter which the reaction was cooled to room temperature
  8. customdried under vacuum under vacuum at 90° C. overnight
  9. customSize exclusion chromatography yielded a weight average molecular weight of 647 kDa

Sources & evidence

ORD record
ord-8b4a69f5fc8b419986adf0036e62e433
Source dataset
uspto-grants-2014_09
Patent number
US08846817B2

Linked notes

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