Adipic Acid → Hexane-1,6-diol adipate

HRID 1939763Notes

Reaction equation

HRID 1939763 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]>O>[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

4

Reactant 2

HCID 196Adipic AcidHCID 123741,6-Hexanediol

Product 1

HCID 168322Hexane-1,6-diol adipate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 730.7 g (5 mol) of adipic acid in 620.5 g (5.25 mol) of, hexane-1,6-diol 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 from 140° to 150° C., and the water of reaction which formed was distilled off under atmospheric pressure. After a residence time of 1 hour, 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 from 140° to 180° 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 350 mbar and at a reaction temperature of 180° C. After a reaction time of 2 hours more (4 hours in all), the desired degree of esterification had been reached. The oligomeric hexane-1,6-diol adipate obtained (1,256 g) had an average degree of oligoesterification of n=5 (molecular mass distribution measured by gel permeability chromatography) and an acid number of 32 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 in a quasi-continuous manner by adding new quantities of reaction mixture.

Workup

  1. temperaturethe solution was heated
  2. customformed
  3. distillationwas distilled off under atmospheric pressure
  4. customAfter a residence time of 1 hour
  5. customa further portion of the water of reaction
  6. distillationwas distilled off under atmospheric pressure at a reaction temperature of from 140° to 180° C
  7. customafter a residence time of 1 hour
  8. customthe remainder of the water of reaction
  9. customwas removed under a pressure of 350 mbar and at a reaction temperature of 180° C
  10. customAfter a reaction time of 2 hours
  11. custom4 hours

Sources & evidence

ORD record
ord-ace5f2205a76477cb840a58b783ddb2f
Source dataset
uspto-grants-1997_12
Patent number
US05696303

Reaction notes

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