Adipic Acid → HCID 131715119, compound

HRID 543337Notes

Reaction equation

HRID 543337 reaction equation
C[CH:2]([CH3:19])[CH2:3][CH2:4][C:5]([CH2:15][CH2:16][CH2:17]O)([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:6]([OH:8])=[O:7].[CH2:20](OC(=O)CCCCC([O:32][CH2:33][CH2:34][CH:35]([CH3:37])[OH:36])=O)CCC.C(O)(=O)CCCCC(O)=O.C(O)CC(O)C>C(O)CCC>[CH2:15]([C:5]([CH2:4][CH2:3][CH2:2][CH3:19])([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:6]([OH:8])=[O:7])[CH2:16][CH2:17][CH3:20].[CH2:33]([OH:32])[CH2:34][CH:35]([OH:36])[CH3:37]

Participants

5

Reactant 3

HCID 196Adipic AcidHCID 78961,3-ButanediolHCID 86741464HCID 86741464, compound

Product 1

HCID 131715119HCID 131715119, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
160 °C

Procedure

The ester-alcohol can be obtained in the method of the present invention by not carrying out the alcohol removing ester-interchange reaction, or as an unreacted fraction in the ester-interchange reaction which distills between the bis compound and the starting diester. On the other hand, it can be obtained as an intermediate of direct alcohol removing ester-interchange reaction between the diester and the diol. Adipic acid 3-methyl-3-hydroxypropyl butyl ester (3-methyl-3-hydroxypropyl butyl adipate), an ester alcohol prepared from adipic acid, 1,3-butanediol, and butanol may be purified after dehydrating esterification as in Example 1, and catalyst removing treatment and then distillation. The boiling point is 155° to 160° C./0.2 mmHg. Using a mixture of 82.8 g of this product and 405 g of dibutyl adipate (mol ratio is 1:5.2) to which 0.5 g of butyl titanate was added, reaction was carried out under a reduced pressure of 20 mmHg and heating at 160° C. for 12 hours with stirring while removing 21.5 g (97%) of resulting butanol, and after completion of the reaction, catalyst removing alkali washing and water washing as well as distillation was carried out to obtain 342 g of DBA and 5.2 g of unreacted ester-alcohol and 94.9 g (75.8%) of 1,3-butanediol bis-butyl adipate having a boiling point of 235° to 245° C./0.8 mmHg and 7.6 g (8.4%) of a residual material which was considered to be an oligomer of n=2.

Workup

  1. customremoving
  2. customester-interchange reaction between the diester
  3. custommay be purified
  4. customremoving treatment
  5. distillationdistillation
  6. additiona mixture of 82.8 g of this product and 405 g of dibutyl adipate (mol ratio is 1:5.2) to which 0.5 g of butyl titanate
  7. additionwas added
  8. customreaction
  9. customwhile removing 21.5 g (97%) of resulting butanol
  10. customafter completion of the reaction, catalyst
  11. customremoving alkali
  12. washwashing
  13. distillationwater washing as well as distillation

Sources & evidence

ORD record
ord-f5b1f5768a6e42ee8aa613140e723508
Source dataset
uspto-grants-1987_04
Patent number
US04661622

Reaction notes

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