Water → Trimethylolpropane Dilinoleate

Participants

Reaction Conditions

Reaction Steps

308.02 grams (2.30 moles) of trimethylol propane (MW-134 g/mole) were dissolved in benzene and dried by refluxing and draining the azeotrope. The dry solution was added to 3 liters of diglyme dried with sodium ribbon. The solution was warmed with stirring in a 12 liter flask to 180° F. 682 grams (2.30 moles) of linolenoyl chloride (MW-296.45 g) was added dropwise over a period of three hours. The mixture was stirred overnight at 180° F. An additional 682 grams (2.30 moles) of linolenoyl chloride was added over a period of three hours and again heated at 180° F. overnight. After cooling, an excess of sodium carbonate in a water slurry was added to the reaction mixture to remove the hydrogen chloride. The mixture was then filtered. Approximately 250 ml of hexane were added to approximately 500 ml batches of the product, placed in a separatory funnel of appropriate size and washed three times with 200 ml of deionized water to remove any unreacted TMP and acid along with the diglyme and sodium carbonate. The hexane was removed by rotary evaporation, and the product was stored over molecular sieves.

Provenance & Evidence