Methanol → Undecylenyl Triethyl Ammonium Iodide Eicosene

Participants

Reaction Steps

Triethyl ammonium undecylenyl iodide (7.5 grams), eicosene (22.5 grams) and toluene (60 grams) were added to a glass screw cap jar under an argon atmosphere. Diethyl aluminum chloride (25 milliliters of a 1.8 molar solution in toluene) and 1.25 teaspoons of TiCl3 --AA (available from Alfa, about 5 grams) were added. After 1.5 hours, the reaction was treated with methanol until the mixture turned green. The mixture was added to methanol in a Waring blender to precipitate the polymer which was washed successively with water and then methanol. The solid polymer was isolated by filtration and dried in vacuo to afford 19 grams of a white powder. Solid state 13C NMR analysis was consistent with the attachment of 5 weight percent of quaternary ammonium groups. The DSC of this product showed two semicrystalline melting endotherms at 45° and 81° C. and a melting peak at 117° C. attributed to the quaternary ammonium iodide group.

Provenance & Evidence