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Final report of research done utilizing a fluorination technique for the synthesis of perfluorinated and polyfluorinated organic compounds. (Author).
The fluorine atom, by virtue of its electronegativity, size and bond strength with carbon, can be used to create compounds with remarkable properties. Small molecules containing fluorine have many positive impacts on everyday life of which blood substitutes, pharmaceuticals and surface modifiers are only a few examples. Fluoropolymers, too, while traditionally associated with extreme high-performance applications have found their way into our homes, our clothing and even our language. Much progress has been made in understanding the sometimes confounding properties of fluoropolymers. Computer simulation is now contributing to this with new fluorine force fields and other parameters, bringing realistic prediction within reach of the practicing physical chemist. Fluoropolymers 1: Synthesis and Fluoropolymers 2: Properties attempt to bring together in one place the chemistry, physics and engineering properties of fluoropolymers. The collection was intended to provide balance between breadth and depth, with contributions ranging from the introduction of fluoropolymer structure-property relationships, to reviews of subfields, to more focused topical reports.
"In this book fundamental features and industrial applications of the direct fluorination of polymers are reviewed. Direct fluorination of polymers (i.e. treatment of a polymer surface with gaseous fluorine and its mixtures) proceeds at room temperature spontaneously and can be considered as a surface modification process."--BOOK JACKET.
The synthesis of several perflourinated ethers of pentaerythritol, dipentaerythritol, and tripentaerythritol by direct fluorination in solution is described. These ethers were perfluorinated using elemental fluorine in a two step process. In the first step, up to 95 percent of the hydrogens were replaced by fluorine while the ether was dissolved in a chlorofluorocarbon slolvent. The remaining hydrogens were replaced by exposing the partially fluorinated product to pure fluorine at elevated temperature. The hydrocarbon ethers used as starting material were prepared by applying the use of phase transfer catalysis to the Williamson ether synthesis. Six of the perfluorinated ethers prepared have been previously synthesized by other methods: perfluoro-5, 5-bis (ethoxymethyl)-3, 7-dioxanonane, perfluoro-6, 6-bis(propyloxymethyl)-4, 8-dioxaundecane, perfluoro-7, 7-bis(butyloxymethyl)-5, 9-dioxatridecane, perfluoro-8, 9-bis(pentyloxymethyl)-6, 10-dioxapentadecane, perfluoro-7, 7-bis(2-methoxyethoxymethyl)-2, 5, 9, 12-tetraoxatridecane, and perfluoro-4, 4, 8, 8-tetrakis (methoxymethyl)-2, 6, 10-trioxaundecane. In addition, the following compounds were isolated and characterized: Perfluoro-2, 12-dimethyl-7, 7-bis (2-methylbutyloxymethyl)-5, 9-dioxatridecane, perfluoro-9, 9-bis (hexyloxymethyl)-7, 11-dioxaheptadecane, perfluoro-10, 10-bis (heptyloxymethyl)-8, 12-dioxanonadecane, perfluoro-11, 11-bis(octyloxymethyl)-9, 13-dioxaheneicosane, perfluoro-5, 5, 9, 9-tetrakis (ethoxymethyl)-3, 7, 11-trioxatridecane, perfluoro-6, 6, 10, 10,-tetrakis (propyloxymethyl)-4, 8, 12-trioxapentadecane, perfluoro-7, 7, 11, 11-tetrakis (butyloxymethyl) -5, 9, 13-trioxaheptadecane, perfluoro-7, 7, 11, 11-tetrakis (2-methoxyethoxymethyl)-2, 5, 9, 13, 16-pentaoxaheptadecane, perfluoro-4, 4, 8, 8, 12, 12-hexakis (methoxymethyl)-2, 6, 10, 14-tetraoxapentadecane and perfluoro-5, 5, 9, 9, 13, 13-hexakis (ethoxymethyl)-3, 7, 11, 15-tetraoxaheptadecane.