Acetic Acid → 1,1,1,2-Tetrafluoro-2-(trifluoromethyl)butane

Participants

Reaction Conditions

Reaction Steps

A mixture of perfluoroisopropyl iodide (5.6 g, 0.19 mole), ethylene (5 L, 0.2 mole) and benzoyl peroxide (3.2 g) was heated in a 100 mL steel autoclave at 100° C. for 6 hours with stirring. The reaction product contained perfluoroisopropyl,iodide and (CF3)2CFCH2CH2I in a 1:1 ratio. Distillation of the reaction mixture gave (CF3)2CFCH2CH2I (b.p. 118 to 124° C.) in 33% yield. (CF3)2CFCH2CH2I (10 g) was added dropwise to a mixture of zinc dust (5 g) and acetic acid (30 mL). After the exothermic reaction was completed, the reaction mixture was stirred for 2.5 hours at 60° C., diluted with water and distilled to collect a fraction with a b.p. less than 100° C. The distillate was separated from water, dried over calcium chloride, and redistilled to give (CF3)2CFCH2CH3 (b.p. 39 to 42° C., 56% yield). The 1H and 19F NMR were in accord with the assigned structure.

Provenance & Evidence