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DCM is produced by treating either chloromethane or methane with chlorine gas at 400–500 °C. At these temperatures, both methane and chloromethane undergo a series of reactions producing progressively more chlorinated products. In this way, an estimated 400,000 tons were produced in the US, Europe, and Japan in 1993. [12] CH 4 + Cl 2 → CH ...
Two free radicals (chlorine and chlorine, chlorine and methyl, or methyl and methyl) combine: Methane chlorination: termination The last possibility generates in an impurity in the final mixture (notably, an organic molecule with a longer carbon chain than the reactants). The net reaction is: Methane chlorination overall reaction
Given appropriate conditions, methane reacts with halogen radicals as follows: •X + CH 4 → HX + •CH 3 •CH 3 + X 2 → CH 3 X + •X. where X is a halogen: fluorine (F), chlorine (Cl), bromine (Br), or iodine (I). This mechanism for this process is called free radical halogenation.
The reaction of methane and chlorine atoms acts as a primary sink of Cl atoms and is a primary source of hydrochloric acid (HCl) in the stratosphere. [71] CH 4 + Cl → CH 3 + HCl The HCl produced in this reaction leads to catalytic ozone destruction in the stratosphere. [66]
A smaller amount of chloromethane is produced by treating a mixture of methane with chlorine at elevated temperatures. This method, however, also produces more highly chlorinated compounds such as dichloromethane, chloroform, and carbon tetrachloride. For this reason, methane chlorination is usually only practiced when these other products are ...
Chloroform is produced by heating mixtures of methane or methyl chloride with chlorine. Dichloromethane is a coproduct. [4] Bromochlorofluoromethane is one of the simplest possible stable chiral compounds, and is used for studies.
Methane has a limited atmospheric lifetime, about 10 years, due to substantial methane sinks. The primary methane sink is atmospheric oxidation, from hydroxyl radicals (~90% of the total sink) and chlorine radicals (0-5% of the total sink). The rest is consumed by methanotrophs and other methane-oxidizing bacteria and archaea in soils (~5%). [5]
One or more of the hydrogen atoms can be replaced with other atoms, for example chlorine or another halogen: this is called a substitution reaction. An example is the conversion of methane to chloroform using a chlorination reaction. Halogenating a hydrocarbon produces something that is not a hydrocarbon. It is a very common and useful process.