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Concept
Carbon tetrafluoride
Summary
Tetrafluoromethane, also known as carbon tetrafluoride or R-14, is the simplest perfluorocarbon (CF4). As its IUPAC name indicates, tetrafluoromethane is the perfluorinated counterpart to the hydrocarbon methane. It can also be classified as a haloalkane or halomethane. Tetrafluoromethane is a useful refrigerant but also a potent greenhouse gas. It has a very high bond strength due to the nature of the carbon–fluorine bond.
Because of the multiple carbon–fluorine bonds, and the high electronegativity of fluorine, the carbon in tetrafluoromethane has a significant positive partial charge which strengthens and shortens the four carbon–fluorine bonds by providing additional ionic character. Carbon–fluorine bonds are the strongest single bonds in organic chemistry. Additionally, they strengthen as more carbon–fluorine bonds are added to the same carbon. In the one carbon organofluorine compounds represented by molecules of fluoromethane, difluoromethane, trifluoromethane, and tetrafluoromethane, the carbon–fluorine bonds are strongest in tetrafluoromethane. This effect is due to the increased coulombic attractions between the fluorine atoms and the carbon because the carbon has a positive partial charge of 0.76.
Tetrafluoromethane is the product when any carbon compound, including carbon itself, is burned in an atmosphere of fluorine. With hydrocarbons, hydrogen fluoride is a coproduct. It was first reported in 1926. It can also be prepared by the fluorination of carbon dioxide, carbon monoxide or phosgene with sulfur tetrafluoride. Commercially it is manufactured by the reaction of hydrogen fluoride with dichlorodifluoromethane or chlorotrifluoromethane; it is also produced during the electrolysis of metal fluorides MF, MF2 using a carbon electrode.
Although it can be made from a myriad of precursors and fluorine, elemental fluorine is expensive and difficult to handle. Consequently, CF4 is prepared on an industrial scale using hydrogen fluoride:
CCl2F2 + 2 HF → CF4 + 2 HCl
Tetrafluoromethane and silicon tetrafluoride can be prepared in the laboratory by the reaction of silicon carbide with fluorine.
Official source
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