tert-Butylacrylamide → vinyl acetate N-t-butyl acrylamide

HRID 614439

Reaction equation

HRID 614439 reaction equation
[C:1]([O:4][CH:5]=[CH2:6])(=[O:3])[CH3:2].[C:7]([NH:11][C:12](=[O:15])[CH:13]=[CH2:14])([CH3:10])([CH3:9])[CH3:8].C(OOC(C)(C)C)(=O)C(C)(C)C.C(NC(=O)C=C)CCC>CO.O>[C:1]([O:4][CH:5]=[CH2:6])(=[O:3])[CH3:2].[C:7]([NH:11][C:12](=[O:15])[CH:13]=[CH2:14])([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 7877tert-Butylacrylamide2×HCID 7904Vinyl Acetate2×HCID 61238tert-BUTYL PEROXYPIVALATE3×HCID 642908n-Butyl-2-propenamide

Product 1

HCID 86736402vinyl acetate N-t-butyl acrylamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A 2-liter separable flask equipped with a stirring device, a condenser, a thermometer and three metering pumps was used as a polymerization reactor, and charged with 200 ml of methanol, 25.8 g (0.3 mole) of vinyl acetate, and 10.7 g (0.08 mole) of N-t-butyl acrylamide in an atmosphere of nitrogen. With stirring, the temperature of the reaction system was raised to 50° C. When the temperature of the reaction system reached 50° C., 3.48 g (0.02 mole) of t-butyl peroxypivalate was added, and the copolymerization was started. The copolymerization was continued while continuously feeding 172.2 g (2.0 moles) of vinyl acetate from a first metering pump for 2 hours at a rate of 1 mole/hr, a solution of 366.3 g (2.88 moles) of N-t-butyl acrylamide in 800 ml of methanol from a second metering pump for 2 hours and 20 minutes so that the rate of N-butyl acrylamide fed was 1 mole/hr, and a solution of 6.97 g (0.04 mole) of t-butyl peroxypivalate in 200 ml of methanol from a third metering pump for 2.5 hours so that the feed rate of the t-butyl peroxypivalate became 0.01 mole/hr. The copolymerization proceeded while maintaining a homogeneous system. After the copolymerization for 2.5 hours, the polymerization reaction mixture was poured into a large amount of water. The resulting copolymer precipitated and came afloat on the surface of the water. The copolymer was collected, washed thoroughly with water, pulverized by a mixer into a powder, collected by filtration, and dried at 40° C. in vacuo. The amount of the vinyl acetate/N-t-butyl acrylamide copolymer so obtained was 465 g. NMR spectroscopy in deuterochloroform showed that the N-t-butyl acrylamide unit content of the copolymer was 51 mole%.

Workup

  1. customA 2-liter separable flask equipped with a stirring device, a condenser
  2. customa thermometer and three metering pumps was used as a polymerization reactor
  3. customreached 50° C.
  4. customfor 2 hours
  5. custom20 minutes
  6. temperaturewhile maintaining a homogeneous system
  7. customAfter the copolymerization for 2.5 hours
  8. customthe polymerization reaction mixture
  9. customThe resulting copolymer precipitated
  10. customThe copolymer was collected
  11. washwashed thoroughly with water
  12. filtrationcollected by filtration
  13. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-c0fb47afb50a453895c2c55e6915411f
Source dataset
uspto-grants-1979_03
Patent number
US04144388

Linked notes

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