Synthesis of hybrid anionic surfactants containing fluorocarbon and hydrocarbon chains

Six new hybrid anionic surfactants containing a fluorocarbon chain and a hydrocarbon chain in a molecule, CnF2n+1C6H4COCH(SO3Na)CmH2m+1 (n = 4 and 6, m = 2,4, and 6, and C6H4 = p-phenylene), were prepared. The compounds 1-(4-iodophenyl)-1-alkanones were prepared from the reaction of iodobenzene with corresponding alkanoyl chlorides in the presence of aluminum chloride in carbon disulfide. The compounds 1-[4-(perfluoroalkyl)phenyl]-1-alkanones were synthesized from 1-(4-iodophenyl)-1-alkanones with corresponding perfluoroalkyl iodies in the presence of copper bronze powder in dimethyl sulfoxide. Hybrid anionic surfactants were obtained from the reaction of 1-[4-(perfluoroalkyl)phenyl]-1-alkanones with a sulfur trioxide/1,4-dioxane complex in 1,2-dichloroethane, followed by neutralization with aqueous sodium hydroxide. These new hybrid surfactants have the ability to lower surface tension, and they can emulsify a ternary-component system of hydrocarbon/water/perfluoropolyether oil.