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

HRID 1637053Notes

Reaction equation

HRID 1637053 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]>>[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

3

Reactant 2

HCID 1110Succinic AcidHCID 80641,4-Butanediol

Product 1

HCID 33167Butanedioic acid;butane-1,4-diolYield 105.2%

Conditions

Temperature
125 °C

Procedure

A solution of 590.5 g (5 moles) succinic acid in 602 g (5.1 moles) 1,4-butanediol was introduced at 100° C. into a reaction apparatus made of acid-resistant material with a volume of 5 liters, which was fitted with a high-speed stirrer system of the usual type (turbine agitator; speed of rotation 800 to 1200 rpm) and a distillation column (10 theoretical plates). The mixture was rapidly heated, with stirring, to a reaction temperature of 120 to 130° C. and the water of reaction formed was distilled off at normal pressure. The remainder of the water of reaction was finally removed after a residence time of 1.5 hours at a pressure of 400 mbar and at a reaction temperature of 130 to 160° C. The desired degree of esterification was achieved after a further residence time of 2.0 hours (3.5 hours in total). The oligomeric 1,4-butanediol succinate (1095 g) which was obtained had an average degree of oligoesterification (=number of molecules of succinic acid in the oligoester) of n=4 (as measured by gel permeation chromatography) and an acid number of 58 mg KOH/g reaction mixture.

Workup

  1. customwas fitted with a high-speed stirrer system of the usual type (turbine agitator; speed of rotation 800 to 1200 rpm)
  2. distillationa distillation column (10 theoretical plates)
  3. temperatureThe mixture was rapidly heated
  4. customthe water of reaction
  5. customformed
  6. distillationwas distilled off at normal pressure
  7. customThe remainder of the water of reaction
  8. customwas finally removed after a residence time of 1.5 hours at a pressure of 400 mbar
  9. customat a reaction temperature of 130 to 160° C
  10. customafter a further residence time of 2.0 hours (3.5 hours in total)

Sources & evidence

ORD record
ord-e5a79e0436ce409fabd191859f1b9329
Source dataset
uspto-grants-2000_03
Patent number
US06037504

Reaction notes

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