Acrylic Acid → Prop-2-enoic acid--6-methylheptyl prop-2-enoate (1/1)

HRID 2396663Notes

Reaction equation

HRID 2396663 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]([OH:18])(=[O:17])[CH:15]=[CH2:16].N(C(C)(CC(C)C)C#N)=NC(C)(CC(C)C)C#N.C(OCC)(=O)C>C(O)(C)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]([OH:18])(=[O:17])[CH:15]=[CH2:16]

Participants

6

Reactant 4

HCID 6581Acrylic AcidHCID 8857Ethyl AcetateHCID 915372,2'-Azobis(2,4-dimethylvaleronitrile)HCID 165746Isooctyl acrylate

Product 1

HCID 165745Prop-2-enoic acid--6-methylheptyl prop-2-enoate (1/1)

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Isooctyl acrylate (21.6 g), acrylic acid (2.4 g), 2,2'-azobis (2,4-dimethylpentanenitrile) (0.05 g, VAZO™ 52, DuPont), ethyl acetate (34.2 g) and isopropanol (1.8 g) were placed in a 4 ounce (120 mL) bottle. The mixture was deoxygenated by purging with nitrogen (1 L/min) for 2 minutes. The bottle was sealed and placed in a 45° C. rotating water bath for 24 hours. The bottle was opened and 0.05 g of 2,2'-azobis(2,4-dimethylpentanenitrile) was added. The solution was deoxygenated as above, sealed and placed into the water bath for another 24 hours at 45° C. The inherent viscosity in ethyl acetate was 0.651 deciliter/gram.

Workup

  1. customThe mixture was deoxygenated
  2. customby purging with nitrogen (1 L/min) for 2 minutes
  3. customThe bottle was sealed
  4. customplaced in a 45° C.
  5. customfor 24 hours
  6. addition0.05 g of 2,2'-azobis(2,4-dimethylpentanenitrile) was added
  7. customThe solution was deoxygenated as above,
  8. customsealed

Sources & evidence

ORD record
ord-7d0b9eab756e4f37ab30491fc2839cb8
Source dataset
uspto-grants-1996_02
Patent number
US05494680

Reaction notes

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