Azobisisobutyronitrile → HCID 168686, compound

HRID 2254024Notes

Reaction equation

HRID 2254024 reaction equation
[CH2:1]([O:5][C:6](=[O:9])[CH:7]=[CH2:8])[CH2:2][CH2:3][CH3:4].[CH2:10]([O:12][C:13](=[O:16])[CH:14]=[CH2:15])[CH3:11].[C:17]([OH:21])(=[O:20])[CH:18]=[CH2:19].N(C(C)(C)C#N)=NC(C)(C)C#N>>[CH2:1]([O:5][C:6](=[O:9])[CH:7]=[CH2:8])[CH2:2][CH2:3][CH3:4].[CH2:10]([O:12][C:13](=[O:16])[CH:14]=[CH2:15])[CH3:11].[C:17]([OH:21])(=[O:20])[CH:18]=[CH2:19]

Participants

5

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 6581Acrylic AcidHCID 8821Ethyl AcrylateHCID 8846Butyl Acrylate

Product 1

HCID 168686HCID 168686, compound

Conditions

Temperature
10 °C

Procedure

To 1713 g of a monomer mixture consisting of 54.3% of butylacrylate, 42.3% of ethylacrylate and 3.4% of acrylic acid was added 40 g (2.5%) of azo-bis-isobutyronitrile and 6.8 g (0.4%) of lauryl mercaptane at 22° C. The solution was cooled to 10° C. and added dropwise to a stirred and heated reaction vessel with a wall temperature of approximately 70° C. The reaction started immediately. The addition was continued and the reaction vessel cooled at such a rate that the internal temperature remained between 105° and 135° C. Near the end of the addition, the stirring of the polymer becomes very difficult with a single-blade stirrer because of a strong Weissenberg effect. The addition was complete after 3 hours. The polymer was then heated for another 3 hours at 80°-100° C. The resulting polymer was a highly viscous material with comonomer proportions of 54:3:42:3:3.4.

Workup

  1. additionadded dropwise to
  2. temperatureheated
  3. customreaction vessel with a wall temperature of approximately 70° C
  4. additionThe addition
  5. temperaturethe reaction vessel cooled at such a rate that the internal temperature
  6. customremained between 105° and 135° C
  7. additionNear the end of the addition
  8. stirringthe stirring of the polymer
  9. custombecomes very difficult with a single-blade stirrer because of a strong Weissenberg effect
  10. additionThe addition
  11. temperatureThe polymer was then heated for another 3 hours at 80°-100° C

Sources & evidence

ORD record
ord-264d2bcbc176494d9ae539c4fb8c24d1
Source dataset
uspto-grants-1993_08
Patent number
US05234730

Reaction notes

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