Maleic Anhydride → HCID 21326706, compound

HRID 725280Notes

Reaction equation

HRID 725280 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8](O)[CH2:9][CH2:10][CH2:11][OH:12]>>[C:4]1(=[O:5])[O:12][CH2:11][CH2:10][CH2:9][CH2:8][O:6][C:1](=[O:7])[CH:2]=[CH:3]1

Participants

3

Reactant 2

HCID 7923Maleic AnhydrideHCID 80641,4-Butanediol

Product 1

HCID 21326706HCID 21326706, compound

Procedure

A solution of 768 g (7.83 mol) of maleic anhydride (MA) in 1059 g (11.75 mol) of 1,4-butanediol was placed in the first reactor of a reactor cascade made of acid-resistant material, which cascade comprised 3 reactors connected in series each having a volume of 5 l and each being provided with a high-speed stirring system of conventional construction (turbine stirrer, speed: 800-1200/min) and a distillation column (10 theoretical plates), the solution was quickly heated while stirring to a reaction temperature of 105°-100° C. and the water of reaction which formed was distilled off. After a reaction time of 6 hours, the reaction mixture was transferred into the connected second reactor; there a further part of the water of reaction was distilled off at a reaction temperature of 110°-115° C. while stirring. After a reaction time of 4 hours, the reaction mixture was finally transferred into the connected third reactor; there the remainder of the water of reaction was removed under a pressure of 400 mbar and at a reaction temperature which was gradually increased from 115° to 125° C. After a further 2 hours (total of 12 hours), the esterification was ended. The oligomeric 1,4-butanediyl maleate obtained (1682 g) had a mean degree of oligomerization of n=3 (measured by gel permeation chromatography) and an acid number of 21 mg KOH/g of reaction mixture.

Workup

  1. customeach being provided with a high-speed stirring system of conventional construction (turbine stirrer, speed: 800-1200/min)
  2. distillationa distillation column (10 theoretical plates)
  3. temperaturethe solution was quickly heated
  4. customthe water of reaction which
  5. customformed
  6. distillationwas distilled off
  7. customAfter a reaction time of 6 hours
  8. customthere a further part of the water of reaction
  9. distillationwas distilled off at a reaction temperature of 110°-115° C.
  10. stirringwhile stirring
  11. customAfter a reaction time of 4 hours
  12. customthere the remainder of the water of reaction
  13. customwas removed under a pressure of 400 mbar and at a reaction temperature which
  14. temperaturewas gradually increased from 115° to 125° C

Sources & evidence

ORD record
ord-32c0b2254665496c84dca49d8d29308c
Source dataset
uspto-grants-1998_01
Patent number
US05705715

Reaction notes

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