Synthesis and Characterization of Novel Fluorine Containing Alkylsulfonyls and Sulfonates : Fluorinated Sulfonyl Methanes and Derivatives

A series of salts of the strong fluorocarbon acid bis(trifluoromethylsulfonyl)methane were made: (CF3S02 ) 2CHK, (CF3S02 ) 2CHLi, [ (CF3S02 ) 2CH] 2Ca, [ (CF3S02 ) 2CH] 2Hg, (CF3S02 ) 2CHAg, [ (CF3S02 ) 2CH] 3La. Their reactivity and use as organic intermediates were investigated. The salts were made from their corresponding carbonates, oxides, or hydrides. The reaction times for the salts is generally short, however the purification process was laborious, involving recrystallization from organic solvents and drying under vacuum. The lithium salt is being evaluated as a solid state battery electrolyte. Derivatives of bis(trifluoromethylsulfonyl)methane were made by using the salts as nucleophiles in organic reactions. Reactions with Br2 , CH2=CH2CH2Br, CH3CH2CH2I, and OCH2CHCH2Br were carried out to make: bis(trifluormethylsulfonyl)bromomethane, 4,4-bis(trifluormethylsulfonyl)butene-1, 1,1-bis(trifluormethylsulfonyl)butane, and 4,4-bis(trifluormethylsulfonyl)-1,3-epoxybutane In addition, work was carried out on the synthesis of the polymer -(-O-CH2-C(CH20CF2CF2S02F)H-)n- and the corresponding lithium salt. The polymer was treated with aqueous lithium hydroxide in order to convert the S02F group to a S03-Li+ group. This salt is being investigated as a solid state ion conducting polymer. All products were characterized by infrared spectroscopy, mass spectroscopy, 1H and 19F nuclear magnetic resonance spectroscopy, elemental analysis, and melting points