1-Eicosene → Undecylenyl Iodide Eicosene

Participants

Reaction Steps

To a glass screw top jar were added undecylenyl iodide (6.3 grams), toluene solvent (63.1 grams), and eicosene (18.73 grams). Under argon atmosphere were added 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). The sealed jar was stirred for 2 hours. Methanol was added dropwise until the mixture turned green. The reaction mixture was then added to methanol/hydrochloric acid in a Waring blender to precipitate the solid polymer. In the blender, the polymer was washed successively with methanol, water and then methanol. After filtration, the isolated polymer was dried in vacuo to yield 21.04 grams of the semicrystalline polymer product, poly(undecylenyl iodide-eicosene) copolymer, the DSC of this product indicated two semicrystalline endotherms at 30° and 55° C. Solid state 13C NMR analysis measured 17 weight percent of CH2 --I groups present.

Provenance & Evidence