halogenation

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halogenation

[‚hal·ə·jə′nā·shən]
(organic chemistry)
A chemical process or reaction in which a halogen element is introduced into a substance, generally by the use of the element itself.

Halogenation

A chemical reaction or process which results in the formation of a chemical bond between a halogen atom and another atom. Reactions resulting in the formation of halogen-carbon bonds are especially important. The halogenated compounds produced are employed in many ways, for example, as solvents, intermediates for numerous chemicals, plastic and polymer intermediates, insecticides, fumigants, sterilants, refrigerants, additives for gasoline, and materials used in fire extinguishers.

Halogenation reactions can be subdivided in several ways, for example, according to the type of halogen (fluorine, chlorine, bromine, or iodine), type of material to be halogenated (paraffin, olefin, aromatic, hydrogen, and so on), and operating conditions and methods of catalyzing or initiating the reaction.

Halogenation reactions with elemental chlorine, bromine, and iodine are of considerable importance. Because of high exothermocities, fluorinations with elemental fluorine tend to have high levels of side reactions. Consequently, elemental fluorine is generally not suitable for direct fluorination. Two types of reactions are possible with these halogen elements, substitution and addition.

Substitution halogenation is characterized by the substitution of a halogen atom for another atom (often a hydrogen atom) or group of atoms (or functional group) on paraffinic, olefinic, aromatic, and other hydrocarbons. A chlorination reaction of importance that involves substitution is that between methane and chlorine.

Addition halogenation involves a halogen reacting with an unsaturated hydrocarbon. Chlorine, bromine, and iodine react readily with most olefins; the reaction between ethylene and chlorine to form 1,2-dichloroethane is of considerable commercial importance, since it is used in the manufacture of vinyl chloride.

Addition reactions with bromine or iodine are frequently used to measure quantitatively the number of —CH═CH— (or ethylenic-type) bonds in organic compounds. Bromine numbers or iodine values are measures of the degree of unsaturation of the hydrocarbons.

Substitution halogenation on the aromatic ring can be made to occur via ionic reactions. The chlorination reactions with elemental chlorine are similar to those used for addition chlorination of olefins.