Methanol → Isooctyl Acrylate Acrylamide Vinyl Acetate

HRID 2206943Notes

Reaction equation

HRID 2206943 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])(=[O:4])[CH:2]=[CH2:3].[C:14]([NH2:18])(=[O:17])[CH:15]=[CH2:16].[C:19]([O:22][CH:23]=[CH2:24])(=[O:21])[CH3:20].CO>C(OCC)(=O)C>[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])(=[O:4])[CH:2]=[CH2:3].[C:14]([NH2:18])(=[O:17])[CH:15]=[CH2:16].[C:19]([O:22][CH:23]=[CH2:24])(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 6579AcrylamideHCID 7904Vinyl AcetateHCID 165746Isooctyl acrylate

Product 1

HCID 86608178Isooctyl Acrylate Acrylamide Vinyl Acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
42 °C

Procedure

Isooctyl acrylate (IOA) (75 g), acrylamide (ACM) (5 g), vinyl acetate (VOAc) (20 g), ethyl acetate (136.5 g), and methanol (13.5 g) were added to a 1 quart vessel and the vessel was purged with nitrogen (2 minutes, 1.5 liters per minute nitrogen flow). 2,2′-azobis(2,4-dimethylvaleronitrile) (0.05 g) was added and the reaction was agitated at 42° C. for 6 hours. An additional portion of 2,2′-azobis(2,4-dimethylvaleronitrile) (0.05 g) was added and the vessel was again purged with nitrogen (2 minutes, 1.5 liters per minute nitrogen flow). The reaction was maintained at 42° C. for an additional 22 hours. The temperature was raised to 57° C. and the reaction was maintained an additional 6 hours. The resulting polymerization reaction product was diluted with ethyl acetate (30.6 g) and methanol (5 g). The percent solids of the resultant copolymer solution was 31 weight %. The measured inherent viscosity was 1.34 dL/g.

Workup

  1. customthe vessel was purged with nitrogen (2 minutes, 1.5 liters per minute nitrogen flow)
  2. addition2,2′-azobis(2,4-dimethylvaleronitrile) (0.05 g) was added
  3. additionAn additional portion of 2,2′-azobis(2,4-dimethylvaleronitrile) (0.05 g) was added
  4. customthe vessel was again purged with nitrogen (2 minutes, 1.5 liters per minute nitrogen flow)
  5. temperatureThe reaction was maintained at 42° C. for an additional 22 hours
  6. temperatureThe temperature was raised to 57° C.
  7. temperaturethe reaction was maintained an additional 6 hours
  8. customThe resulting polymerization reaction product

Sources & evidence

ORD record
ord-0ab6cf86400e4c5783036b043c4baada
Source dataset
uspto-grants-2016_06
Patent number
US09375510B2

Reaction notes

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