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Perfluoroalkanes are very stable because of the strength of the carbon–fluorine bond, one of the strongest in organic chemistry. [4] Its strength is a result of the electronegativity of fluorine imparting partial ionic character through partial charges on the carbon and fluorine atoms, which shorten and strengthen the bond (compared to carbon-hydrogen bonds) through favorable covalent ...
Certain firearm lubricants such as "Tetra Gun" contain fluorocarbons. Capitalizing on their nonflammability, fluorocarbons are used in fire fighting foam. Organofluorine compounds are components of liquid crystal displays. The polymeric analogue of triflic acid, nafion is a solid acid that is used as the membrane in most low temperature fuel cells.
Fluorocarbons are both lipophobic and hydrophobic, repelling both oil and water. Their lipophobicity results from the relative lack of London dispersion forces compared to hydrocarbons, a consequence of fluorine's large electronegativity and small bond length, which reduce the polarizability of the surfactants' fluorinated molecular surface.
Fluorocarbons with few C–F bonds behave similarly to the parent hydrocarbons, but their reactivity can be altered significantly.For example, both uracil and 5-fluorouracil are colourless, high-melting crystalline solids, but the latter is a potent anti-cancer drug.
As with fluorocarbons, chlorofluorocarbons and bromofluorocarbons are not flammable: they do not have carbon–hydrogen bonds to react and released halides quench flames. [121] Perfluorodecalin (the trans isomer is shown), a perfluorocarbon that is a liquid at room temperature. It boils at a lower temperature than its hydrocarbon analog, decalin.
Use of certain chloroalkanes as solvents for large scale application, such as dry cleaning, have been phased out, for example, by the IPPC directive on greenhouse gases in 1994 and by the volatile organic compounds (VOC) directive of the EU in 1997. Permitted chlorofluoroalkane uses are medicinal only.
Making organic fluorides is the main use for hydrofluoric acid, consuming over 40% of it (over 20% of all mined fluorite). Within organofluorides, refrigerant gases are still the dominant segment, consuming about 80% of HF. Even though chlorofluorocarbons are widely banned, the replacement refrigerants are often other fluorinated molecules.
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