p-Toluenesulfonic acid → 3-(3-Butenyl)oxolane-2,5-dione

HRID 1395341Notes

Reaction equation

HRID 1395341 reaction equation
[C:1]1(C)[CH:6]=CC(S(O)(=O)=O)=[CH:3][CH:2]=1.[C:12]1(=[O:18])[O:17][C:15](=[O:16])[CH:14]=[CH:13]1>C(OC(=O)C)(=O)C.C1(=O)OC(=O)C=C1>[CH2:6]=[CH:1][CH2:2][CH2:3][CH:14]1[C:15](=[O:16])[O:17][C:12](=[O:18])[CH2:13]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 7923Maleic Anhydride3×

Product 1

HCID 118159603-(3-Butenyl)oxolane-2,5-dione

Reagents, catalysts & solvents 2

HCID 7923Maleic AnhydrideCatalystHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
215 °C

Procedure

Into a 5 liter/3 neck Pyrex flask equipped with a condenser, addition funnel, thermometer, gas inlet tube, mechanical stirrer, and heating mantle was weighed 2200 grams of polybutene having a molecular weight of about 432 and an unsaturation content of 99.6. Into the addition funnel was placed 3.3 grams of paratoluene sulfonic acid dissolved in 6.6 grams of acetic anhydride and 450.5 grams of maleic anhydride (4.24 moles) which was melted and kept in a liquid state with heat lamps. The polymer in the flask is stirred and heated to a temperature of about 215° C. under a nitrogen atmosphere. The melted maleic anhydride catalyst mixture was added dropwise to the stirred polymer at a rate such that the reaction mixture temperature could be maintained between 210° to 215° C. without flooding the condenser. The addition under these conditions required 4 hours. During the addition, two drops of anti-foam fluid was added to reduce foaming. After the addition of the maleic anhydride the reaction mixture was maintained at 215° C. for 21 hours. The reaction mixture at the end of this period was increased to 235° C. The condenser was replaced with a distillation head and air cooled condenser. The nitrogen flow through the gas inlet tube was increased to 4 SCFH and the unreacted maleic anhydride was thus stripped from the reaction mixture for 2 hours. The mixture was cooled and filtered. The product polybutenyl succinic anhydride obtained had an activity of 67%, the balance of the material being unreacted polybutene with a viscosity of 336 SUS at 100° C. The infrared spectrum displayed carbonyl absorptions at 1870 (medium), 1790 (strong), and 1710 (weak).

Workup

  1. customInto a 5 liter/3 neck Pyrex flask equipped with a condenser, addition funnel
  2. temperaturethermometer, gas inlet tube, mechanical stirrer, and heating mantle
  3. temperaturecould be maintained between 210° to 215° C.
  4. additionThe addition under these conditions required 4 hours
  5. additionDuring the addition, two drops of anti-foam fluid
  6. additionwas added
  7. temperaturewas maintained at 215° C. for 21 hours
  8. temperatureThe reaction mixture at the end of this period was increased to 235° C
  9. temperaturecooled condenser
  10. temperatureThe nitrogen flow through the gas inlet tube was increased to 4 SCFH
  11. temperatureThe mixture was cooled
  12. filtrationfiltered

Sources & evidence

ORD record
ord-a7b8a8b71bc34f62a49529bf557e0667
Source dataset
uspto-grants-1980_05
Patent number
US04203730

Reaction notes

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