A sixteen year collaboration between the DuPont Company and the Fluorine Group at The University of Alabama has produced a number of improvements in either fluorochemical processes or products. An initial project was aimed at utilizing alkali metal polyhydrogen fluorides as a solvent and halogen exchange media for preparing CFC alternatives. A viable process was developed in which a chlorocarbon precursor and hydrogen fluoride could be fed to a reactor system and the desired fluorocarbon and hydrogen chloride could be removed.1 In a related project, a series of novel perfluoroalkyl sulfonates were prepared as were methods that employed these compounds as catalysts for increasing the fluorine content of halogenated hydrocarbons and as promoters for the hydrocyanation of olefins.2 More recently, synthetic methods for the preparation of perfluoropolyether primary bromides and iodides such as F[CF(CF3)-CF2-O-]n-1CF2X, where X = Br or I, were developed; these compounds are useful synthons for a variety of perfluoropolyether derivatives.3 In addition, the thermal stability of perfluoropolyethers have been increased via the incorporation of C3 or larger end groups, thereby extending the applicability and lifetime of this important class of lubricants, which often find application under harsh environmental conditions.4 These and related case histories from the aforementioned collaboration will be presented.
1. Fernandez, R. E.; Thrasher, J. S. Inorganic Fluorine Chemistry: Toward the 21st Century; Thrasher, J. S.; Strauss, S. H., Eds.; ACS Symposium Series 555; American Chemical Society: Washington, DC, 1994; pp 237-250. 2. Cicha, W. V.; Kornath, A. J.; McKinney, R. J.; Rao, V. N. M.; Thrasher, J. S.; Waterfeld, A. U.S. Patent 5,773,637, 1998. 3. Howell, J. L.; Perez, E. W.; Waterfeld, A.; Friesen, C. M.; Thrasher, J. S.; Nowak, I. U.S. Patent 6,653,511, 2003. 4. Howell, J. L.; Perez, E. W.; Waterfeld, A.; Friesen, C. M.; Thrasher, J. S. U.S. Patent 6,753,301, 2004.
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