Adipic Acid → 1,6-Bis(2-(hexyloxy)ethyl) hexanedioate

HRID 1689605Notes

Reaction equation

HRID 1689605 reaction equation
[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[CH2:11]([O:17][CH2:18][CH2:19]O)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH2:21].[C:22]1([CH3:32])[CH:27]=[CH:26][C:25](S(O)(=O)=O)=[CH:24]C=1.[OH-].[Na+].[C:35]1([CH3:45])C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([O:10][CH2:19][CH2:18][O:17][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:45][CH2:35][O:21][CH2:24][CH2:25][CH2:26][CH2:27][CH2:22][CH3:32])=[O:7]

Participants

7

Reactant 5

HCID 196Adipic AcidHCID 6101p-Toluenesulfonic acidHCID 81702-HexyloxyethanolHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 80451,6-Bis(2-(hexyloxy)ethyl) hexanedioate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

In a reactor consisting of a 300-cc four-necked flask, a stirrer, a thermometer, a nitrogen inlet tube, a nitrogen line, a Dean-Stark tube, a condenser, a three-way cock, and a vacuum apparatus were placed 36.54 g (0.25 mole) of adipic acid, 87.74 g (0.60 mole) of ethylene glycol mono-n-hexyl ether, 2.38 g (0.0125 mole) of para-toluenesulfonic acid monohydrate, and 86 g of toluene and the mixture was allowed to react with stirring at 85° C. for 30 hours in a nitrogen atmosphere. An aqueous solution of sodium hydroxide was added to the reaction mixture to neutralize the para-toluenesulfonic acid and the oily layer was separated from the aqueous layer. The oily layer was washed with alkali and then with water and the oily layer was separated and dried over anhydrous sodium sulfate. The oil was stripped of water, ethylbenzene, and the unchanged ethylene glycol mono-n-hexyl ether by distillation to yield di(hexyloxyethyl) adipate.

Workup

  1. customIn a reactor consisting of a 300-cc four-necked flask, a stirrer
  2. customto react
  3. customthe oily layer was separated from the aqueous layer
  4. washThe oily layer was washed with alkali
  5. customwith water and the oily layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe unchanged ethylene glycol mono-n-hexyl ether by distillation

Sources & evidence

ORD record
ord-aa13b0342e834e53aa58627c133c6696
Source dataset
uspto-grants-2012_04
Patent number
US08153569B2

Reaction notes

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