Succinic Acid → Butanedioic acid;butane-1,4-diol

HRID 1939764Notes

Reaction equation

HRID 1939764 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH2:9]([OH:14])[CH2:10][CH2:11][CH2:12][OH:13]>O>[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH2:9]([OH:14])[CH2:10][CH2:11][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 1110Succinic AcidHCID 80641,4-Butanediol

Product 1

HCID 33167Butanedioic acid;butane-1,4-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 590.5 g (5 mol) of succinic acid in 504.7 g (5.6 mol) of 1,4-butanediol was placed in the first reactor of the same reactor cascade as in Example 1, the solution was heated with stirring to a reaction temperature of 130°-140° C., and the water of reaction which formed was distilled off under atmospheric pressure. After a residence time of 2 hours, the reaction mixture was run into the adjacent second reactor, where a further portion of the water of reaction was distilled off under atmospheric pressure at a reaction temperature of 140°-160° C. Finally, after a residence time of 1 hour, the reaction mixture was run into the third reactor and the remainder of the water of reaction was removed under a pressure of 800 mbar and at a reaction temperature of 160° C. After a reaction time of 2 hours more (5 hours in all), the desired degree of esterification had been reached. The oligomeric butane-1,4-diol succinate obtained (1,005 g) had an average degree of oligoesterification of n=5 (molecular mass distribution measured by gel permeability chromatography) and an acid number of 46 mg of KOH/g of reaction mixture. Following the partial or complete emptying of the first and/or second reactor, it was possible to continue the esterification process continuously by adding new quantifies of reaction mixture.

Workup

  1. temperaturethe solution was heated
  2. customformed
  3. distillationwas distilled off under atmospheric pressure
  4. customAfter a residence time of 2 hours
  5. customa further portion of the water of reaction
  6. distillationwas distilled off under atmospheric pressure at a reaction temperature of 140°-160° C
  7. customafter a residence time of 1 hour
  8. customthe remainder of the water of reaction
  9. customwas removed under a pressure of 800 mbar and at a reaction temperature of 160° C
  10. customAfter a reaction time of 2 hours
  11. custom5 hours

Sources & evidence

ORD record
ord-827cfee195834c01b6173b97c143a363
Source dataset
uspto-grants-1997_12
Patent number
US05696303

Reaction notes

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