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Final report of research done utilizing a fluorination technique for the synthesis of perfluorinated and polyfluorinated organic compounds. (Author).
Modern Synthesis Processes and Reactivity of Fluorinated Compounds focuses on the exceptional character of fluorine and fluorinated compounds. This comprehensive work explores examples taken from all classes of fluorine chemistry and illustrates the extreme reactivity of fluorinating media and the peculiar synthesis routes to fluorinated materials. The book provides advanced and updated information on the latest synthesis routes to fluorocompounds and the involved reaction mechanisms. Special attention is given to the unique reactivity of fluorine and fluorinated media, along with the correlation of those properties to valuable applications of fluorinated compounds. Contains quality content edited, and contributed, by leading scholars in the field Presents applied guidance on the preparation of original fluorinated compounds, potentially transferable from the lab scale to industrial applications Provides practical synthesis information for a wide audience interested in fluorine compounds in many branches of chemistry, materials science, and physics
During the past fifteen years commercial interest in compounds containing carbon fluorine bonds has burgeoned beyond all expectations, mainly owing to business opportunities arising from work on biologically active fluoroorganics-particularly agrochemicals, the relentless search for new markets for fluoropolymers and fluoro carbon fluids, developments in the field of medical diagnostics, and the drive to find replacements for ozone-depleting CFCs and Halon fire-extinguishing agents. Judging the situation to warrant the publication of a comprehensive collection of up-to-date reviews dealing with commercial organofluorine compounds within a single volume of manageable size (and hence reasonable cost), we were delighted to be invited by Plenum Publishing Corporation to produce a suitable book. In order to provide an authentic and wide-ranging account of current commercial applications of fluoroorganic materials, it clearly was necessary to assemble a sizeable team of knowledgeable contributing authors selected almost entirely from industry. Through their efforts we have been able to produce an almost complete coverage of the modem organofluorochemicals business in a manner designed to attract a reader ship ranging from experts in the field, through chemists and technologists currently unaware of the extent of industrial involvement with fluoroorganics, to students of applied chemistry. Promised chapters dedicated to perfluoroolefin oxides and 18F labeling of radiopharmaceuticals failed to materialize. This is somewhat unfortunate in view of our aim to achieve comprehensive coverage of the subject.
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.
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 hi- performance applications have found their way into our homes, our clothing, and even our language. A recent American president was often likened to the tribology of PTFE. Since the serendipitous discovery of Teflon at the Dupont Jackson Laboratory in 1938, fluoropolymers have grown steadily in technological and marketplace importance. New synthetic fluorine chemistry, new processes, and new apprec- tion of the mechanisms by which fluorine imparts exceptional properties all contribute to accelerating growth in fluoropolymers. There are many stories of harrowing close calls in the fluorine chemistry lab, especially from the early years, and synthetic challenges at times remain daunting. But, fortunately, modern techniques and facilities have enabled significant strides toward taming both the hazards and synthetic uncertainties. In contrast to past environmental problems associated with fluorocarbon refrigerants, the exceptional properties of fluorine in polymers have great environmental value. Some fluoropolymers are enabling green technologies such as hydrogen fuel cells for automobiles and oxygen-selective membranes for cleaner diesel combustion.