Methanol → Isooctylacrylate Acrylamide

HRID 977039

Reaction equation

HRID 977039 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].CO.CC(N=NC(C#N)(C)C)(C#N)C>C(OCC)(=O)C.C(OCC)(=O)C.CO>[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]

Participants

7

Reactant 4

HCID 887MethanolHCID 6547Azobisisobutyronitrile2×HCID 6579AcrylamideHCID 165746Isooctyl acrylate

Product 1

HCID 6452299Isooctylacrylate Acrylamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent3×HCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
45 °C

Procedure

A reactor was charged with isooctyl acrylate (3500 g), acrylamide (263 g), methanol (614 g) and ethyl acetate (5,526 g). The mixture was deoxygenated and heated to 113° F. (45° C.). A solution of VAZO 52 (1.9 g) in ethyl acetate (150 g) was added when the temperature had stabilized at 113° F. (45° C.). Five and a half hours after the start of the reaction, a solution of VAZO 52 (1.9 g) in ethyl acetate (150 g) was added. Nine hours after the start of the reaction, a solution of VAZO 52(3.8 g) in ethyl acetate (150 g) was added. The reaction was continued at 113° F. (45° C.) until 98% minimum conversion was reached. The final polymer was diluted to 26-30% solids with ethyl acetate/methanol (90/10).

Workup

  1. customThe mixture was deoxygenated
  2. additionA solution of VAZO 52 (1.9 g) in ethyl acetate (150 g) was added when the temperature
  3. customhad stabilized at 113° F.
  4. custom(45° C.)
  5. customFive and a half hours after the start of the reaction
  6. customNine hours after the start of the reaction
  7. customwas continued at 113° F.
  8. custom(45° C.)

Sources & evidence

ORD record
ord-d6c9dfb0628d4a0595688d0489654ff2
Source dataset
uspto-grants-1997_03
Patent number
US05614210

Linked notes

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