Synthesis and characterization of a new class of polyfluorinated alkanes: tetrakis(perfluoroalkyl)alkane

Abstract The synthesis and physico-chemical characterization of 1,1,2,2-tetrakis(perfluoroalkyl-methylene)ethane {[F(CF 2 ) n CH 2 ] 2 CH} 2 ( n =6, TK6 ; n =8, TK8 ) are reported. The synthesis consists of four steps: (1) addition of allyl alcohol to a perfluoroalkyl iodide, F(CF 2 ) n I ( n =6,8) to give the corresponding iodo-adduct; (2) dehalogenation of the adduct by treatment with zinc in aqueous acetic acid, yielding 3-perfluoro- n -alkyl-1-propene; (3) addition of 3-perfluoro- n -alkyl-l-propene to perfluoroalkyl iodide, F(CF 2 ) n I ( n =6,8) to give 1,3-perfluoro- n -alkyl-2-iodo-propane; (4) coupling of 1,3-perfluoro- n -alkyl-2-iodo-propane by zinc in acetic anhydride giving the final products. TK6 and TK8 are characterized by very low surface tension values and exhibit very good properties as potential ski-waxes.