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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:
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 ...
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]
The water used is usually brackish water or brine (i.e. a solution with >0.5% salinity). In these cases, additional contaminant chemicals may be present in the water feed. The low voltage DC current still performs electrochlorination. The excess chemicals are left untouched and can be easily discarded. [2]
p-DCB is produced by chlorination of benzene using ferric chloride as a catalyst: . C 6 H 6 + 2 Cl 2 → C 6 H 4 Cl 2 + 2 HCl. The chief impurity is the 1,2 isomer.The compound can be purified by fractional crystallization, taking advantage of its relatively high melting point of 53.5 °C; the isomeric dichlorobenzenes and chlorobenzene melt well below room temperature.
Chlorination modifies the physical properties of hydrocarbons in several ways. These compounds are typically denser than water due to the higher atomic weight of chlorine versus hydrogen. They have higher boiling and melting points compared to related hydrocarbons. Flammability reduces with increased chlorine substitution in hydrocarbons.
Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C 6 H 5 Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals. [6]