Adipic Acid → Hexane-1,6-diol adipate

HRID 1637052Notes

Reaction equation

HRID 1637052 reaction equation
[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[CH2:11]([OH:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17]>>[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[CH2:11]([OH:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17]

Participants

3

Reactant 2

HCID 196Adipic AcidHCID 123741,6-Hexanediol

Product 1

HCID 168322Hexane-1,6-diol adipateYield 95.7%

Conditions

Temperature
155 °C

Procedure

A solution of 730.7 g (5 moles) adipic acid in 620 g (5.25 moles) 1,6-hexanediol 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 140 to 170° 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 170 to 190° C. The desired degree of esterification was achieved after a further residence time of 2.0 hours (3.5 hours in total). The oligomeric 1,6-hexanediol adipate (1265 g) which was obtained had an average degree of oligoesterification (=number of molecules of adipic acid in the oligoester) of n=4 (as measured by gel permeation chromatography) and an acid number of 50 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 170 to 190° C
  10. customafter a further residence time of 2.0 hours (3.5 hours in total)

Sources & evidence

ORD record
ord-dae5817f56ce46889abcc33c1d196cef
Source dataset
uspto-grants-2000_03
Patent number
US06037504

Reaction notes

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