Reaktion #171123

ord-8b4a69f5fc8b419986adf0036e62e433

Reaktionsgleichung

O
water
C=C1CC(C)OC1=O
α-methylene-γ-valerolactone
C=CC(=O)O
acrylic acid
CCCCCCCCCCCCOS(=O)(=O)[O-].[Na+]
sodium dodecyl sulfate
O=S(=O)([O-])OOS(=O)(=O)[O-].[Na+].[Na+]
sodium persulfate
[Na+].[OH-]
sodium hydroxide
O
water
CCCCCCCCCCCCOS(=O)(=O)[O-].[Na+]
sodium dodecyl sulfate
→
C=C1CC(C)OC1=O.C=CC(=O)O
α-methylene-γ-valerolactone acrylic acid

Edukte

O
water
C=C1CC(C)OC1=O
α-methylene-γ-valerolactone
C=CC(=O)O
acrylic acid
CCCCCCCCCCCCOS(=O)(=O)[O-].[Na+]
sodium dodecyl sulfate
O=S(=O)([O-])OOS(=O)(=O)[O-].[Na+].[Na+]
sodium persulfate
—
polystyrene
[Na+].[OH-]
sodium hydroxide
O
water
CCCCCCCCCCCCOS(=O)(=O)[O-].[Na+]
sodium dodecyl sulfate

Reagenzien

Keine

Reaktionsbedingungen

Temperatur
73°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeTo a 50 mL round bottom flask equipped with a magnetic stir bar
  2. 2
    workup.DISTILLATIONhad been previously fractionally distilled
  3. 3
    workup.ADDITIONwere added via syringe pump over 120 minutes
  4. 4
    workup.ADDITIONAfter 10 minutes of monomer mixture addition
  5. 5
    workup.ADDITIONwas also added via syringe pump over 120 minutes
  6. 6
    workup.ADDITIONAfter both the monomer and aqueous mixtures were added completely
  7. 7
    Temperaturafter which the reaction was cooled to room temperature
  8. 8
    Sonstigedried under vacuum under vacuum at 90° C. overnight
  9. 9
    SonstigeSize exclusion chromatography yielded a weight average molecular weight of 647 kDa

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08846817B2uspto-grants-2014_09