Maleic Anhydride → Butyl Acrylate Maleic Anhydride

HRID 441932Notes

Reaction equation

HRID 441932 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:4])[CH:2]=[CH2:3].[C:10]1(=[O:16])[O:15][C:13](=[O:14])[CH:12]=[CH:11]1>C1(C)C=CC=CC=1>[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:4])[CH:2]=[CH2:3].[C:13]1(=[O:14])[O:15][C:10](=[O:16])[CH:11]=[CH:12]1

Participants

4

Reactant 2

HCID 7923Maleic Anhydride2×HCID 8846Butyl Acrylate2×

Product 1

HCID 86735011Butyl Acrylate Maleic Anhydride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
144 °C

Procedure

To a three-liter, 4-necked, round-bottomed flask eqipped with a stirrer, thermometer, condenser and addition funnel is added 338.6 g. toluene, 142.5 g. of butyl acrylate 22.5 g. maleic anhydride and 0.5 g. of t-butyl peroctoate. The contents are heated to reflux (144° C.) and held for 15 minutes. A monomer mixture composed of 757.5 g. of butyl acrylate, 77.5 g. maleic anhydride and 2.5 g. of t-butyl peroctoate is fed at a uniform rate over the next 23/4 hours to the reaction contents held at 115° C. The mixture is then held at 115° C. for 15 minutes and then chased with 3.0 g. t-butyl peroctoate dissolved in 97 g. of toluene fed over 45 minutes. The reaction flask is equipped with a Dean-Stark apparatus and azeotroped to dryness -- 19.5 g. of water and toluene are removed. The product has 69.8% solids (99.3% monomer conversion) with a viscosity of 3640 cps. (91.7% of the maleic anhydride is converted to polymer and the polymer has a number average molecular weight of 10,000; therefore, an anhydride functionality of 10.)

Workup

  1. customTo a three-liter, 4-necked, round-bottomed flask eqipped with a stirrer
  2. additionthermometer, condenser and addition funnel
  3. additionis added 338.6 g
  4. temperatureThe contents are heated
  5. custom4 hours
  6. customto the reaction contents
  7. customheld at 115° C
  8. waitThe mixture is then held at 115° C. for 15 minutes
  9. dissolutiont-butyl peroctoate dissolved in 97 g
  10. customThe reaction flask is equipped with a Dean-Stark apparatus
  11. customazeotroped to dryness
  12. customof water and toluene are removed

Sources & evidence

ORD record
ord-bcf3f3112d23464d990709ab0f6d0691
Source dataset
uspto-grants-1977_08
Patent number
US04043956

Reaction notes

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