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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence