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The net reaction is: Methane chlorination overall reaction. The steady-state approximation implies that this process has rate law k[CH 4][Cl 2] 1 ⁄ 2. [1] As a radical reaction, the process is halted or severely slowed by radical traps, such as oxygen.
The reaction typically involves free radical pathways. The regiochemistry of the halogenation of alkanes is largely determined by the relative weakness of the C–H bonds. This trend is reflected by the faster reaction at tertiary and secondary positions. Free radical chlorination is used for the industrial production of some solvents: [2]
A free-radical reaction is any chemical reaction involving free radicals.This reaction type is abundant in organic reactions.Two pioneering studies into free radical reactions have been the discovery of the triphenylmethyl radical by Moses Gomberg (1900) and the lead-mirror experiment [1] described by Friedrich Paneth in 1927.
Photochlorination is a chlorination reaction that is initiated by light. Usually a C-H bond is converted to a C-Cl bond. Photochlorination is carried out on an industrial scale. The process is exothermic and proceeds as a chain reaction initiated by the homolytic cleavage of molecular chlorine into chlorine radicals by ultraviolet radiation ...
A classic example of perceived RSP found in older organic chemistry textbooks concerns the free radical halogenation of simple alkanes. Whereas the relatively unreactive bromine reacts with 2-methylbutane predominantly to 2-bromo-2-methylbutane, the reaction with much more reactive chlorine results in a mixture of all four regioisomers.
This regenerates the chlorine radical and the cycle continues. This reaction occurs because while the radical methyl species are more stable than the radical chlorines, the overall stability of the newly formed chloromethane species more than makes up the energy difference. CH 3 • + Cl−Cl → CH 3 Cl + Cl• CH 2 Cl• + Cl−Cl → CH 2 Cl ...
Benzal chloride is produced by the free radical chlorination of toluene, being preceded in the process by benzyl chloride (C 6 H 5 CH 2 Cl) and followed by benzotrichloride (C 6 H 5 CCl 3):
This reaction is typically initiated by application of thermal or UV energy utilizing various approaches. In the process, chlorine gas is decomposed into free radical chlorine which is then reacted with PVC in a post-production step, essentially replacing a portion of the hydrogen in the PVC with chlorine.