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Concept
Halomethane
Summary
Halomethane compounds are derivatives of methane () with one or more of the hydrogen atoms replaced with halogen atoms (F, Cl, Br, or I). Halomethanes are both naturally occurring, especially in marine environments, and human-made, most notably as refrigerants, solvents, propellants, and fumigants. Many, including the chlorofluorocarbons, have attracted wide attention because they become active when exposed to ultraviolet light found at high altitudes and destroy the Earth's protective ozone layer.
Like methane itself, halomethanes are tetrahedral molecules. The halogen atoms differ greatly in size and charge from hydrogen and from each other. Consequently, most halomethanes deviate from the perfect tetrahedral symmetry of methane.
The physical properties of halomethanes depend on the number and identity of the halogen atoms in the compound. In general, halomethanes are volatile but less so than methane because of the polarizability of the halides. The polarizability of the halides and the polarity of the molecules makes them useful as solvents. The halomethanes are far less flammable than methane. Broadly speaking, reactivity of the compounds is greatest for the iodides and lowest for the fluorides.
The halomethanes are produced on an industrial scale from abundant precursors such as natural gas or methanol, and from halogens or halides. They are usually prepared by one of three methods.
Free radical chlorination of methane (under ultraviolet light):
This method is useful for the production of (n = 1, 2, 3, or 4). The main problems with this method are that it cogenerates HCl and it produces mixtures of different products. Using in large excess generates primarily and using in large excess generates primarily , but mixtures of other products will still be present.
Halogenation of methanol. This method is used for the production of the mono-chloride, -bromide, and -iodide.
Halogen exchange. The method is mainly used to produce fluorinated derivatives from the chlorides.
Reaction of methane with hypochlorous acid, producing water.
Official source
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