Azobisisobutyronitrile → Acrylic Acid

HRID 64665Notes

Reaction equation

HRID 64665 reaction equation
[C:1]([CH2:3][CH2:4][O:5][C:6](=[O:9])[CH:7]=[CH2:8])#[N:2].[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12].N(C(C)(C)C#N)=NC(C)(C)C#N>C1(=O)CCCCC1>[C:1]([CH2:3][CH2:4][O:5][C:6](=[O:9])[CH:7]=[CH2:8])#[N:2].[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12].[C:1]([CH2:3][CH2:4][O:5][C:6](=[O:9])[CH:7]=[CH2:8])#[N:2].[C:6]([OH:9])(=[O:5])[CH:7]=[CH2:8]

Participants

7

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 6581Acrylic Acid2×HCID 78252-Cyanoethyl acrylate2×

Product 3

HCID 6581Acrylic AcidHCID 78252-Cyanoethyl acrylateHCID 86740974Cyanoethylacrylate acrylic acid

Reagents, catalysts & solvents 1

HCID 7967CyclohexanoneSolvent

Procedure

A cyanoethylacrylate/acrylic acid copolymer is prepared by mixing cyanoethylacrylate and acrylic acid in a molar ratio of 0.5 at a total solids concentration of 25 percent in cyclohexanone. The reaction solution also contains 0.04 percent 2,2'-azobis(isobutyronitrile) which acts as a free radical chain reaction initiator. As the reaction solution is heated, the 2,2'-azobis(isobutyronitrile) decomposes, with the evolution of nitrogen, forming two free radicals which initiate the polymerization of the cyanoethylacrylate and acrylic acid. The reaction solution is held at a temperature of 90° to 100° C. for 24 hours to form an oligomer of cyanoethylacrylate and acrylic acid having the following structure ##STR3## wherein x is such that the molecular weight is sufficiently low so that the oligomer remains soluble in cyclohexanone.

Workup

  1. temperatureAs the reaction solution is heated
  2. customforming two free radicals which

Sources & evidence

ORD record
ord-bafccd99970f48ca971298c00fe3f68a
Source dataset
uspto-grants-1986_09
Patent number
US04609703

Reaction notes

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