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The reaction mechanism for chlorination of benzene is the same as bromination of benzene. Iron(III) bromide and iron(III) chloride become inactivated if they react with water, including moisture in the air. Therefore, they are generated by adding iron filings to bromine or chlorine. Here is the mechanism of this reaction:
Addition of Cl 2 destroys the aromaticity of the benzene ring, and the addition of two more Cl 2 molecules is rapid compared to the first. Hence, only thrice-dichlorinated product can be isolated from this reaction. Radical addition: C 6 H 6 + 3Cl 2 → C 6 H 6 Cl 6. Hexachlorocyclohexane isomers with more than one chlorine atom per carbon are:
A single-step chlorination from 2,3-dicyanohydroquinone was reported in 1965. ... benzene, alkanes), which facilitates workup. ... DDQ reacts with water to release ...
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 ...
The relative rates at which different halogens react vary considerably: [citation needed] fluorine (108) > chlorine (1) > bromine (7 × 10 −11) > iodine (2 × 10 −22).. Radical fluorination with the pure element is difficult to control and highly exothermic; care must be taken to prevent an explosion or a runaway reaction.
In commercial applications, the alkylating agents are generally alkenes, some of the largest scale reactions practiced in industry.Such alkylations are of major industrial importance, e.g. for the production of ethylbenzene, the precursor to polystyrene, from benzene and ethylene and for the production of cumene from benzene and propene in cumene process:
NCS is produced from succinimide by treatment with Cl + sources, such as sodium hypochlorite (bleach), and t-butylhypochlorite, and even chlorine. [2] Electron-rich arenes are readily monochlorinated by NCS. Aniline and mesitylene are converted to the respective chlorinated derivatives. [2]
Production capacity of benzotrichloride was estimated at 80,000 tonnes for the year 2000. It is produced by the free radical chlorination of toluene, catalysed by light or radical initiators such as dibenzoyl peroxide. Mono- and di-chlorinated intermediates are observed as benzyl chloride and benzal chloride: [2] C 6 H 5 CH 3 + Cl 2 → C 6 H 5 ...