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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. Many chlorinated solvents are produced in this way.
Benzyl chloride is prepared industrially by the gas-phase photochemical reaction of toluene with chlorine: [3] C 6 H 5 CH 3 + Cl 2 → C 6 H 5 CH 2 Cl + HCl. In this way, approximately 100,000 tonnes are produced annually. The reaction proceeds by the free radical process, involving the intermediacy of free chlorine atoms. [4]
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 ...
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.
Aluminium chloride is manufactured on a large scale by the exothermic reaction of aluminium metal with chlorine or hydrogen chloride at temperatures between 650 and 750 °C (1,202 and 1,382 °F). [12] 2 Al + 3 Cl 2 → 2 AlCl 3 2 Al + 6 HCl → 2 AlCl 3 + 3 H 2
Aromatic halogenation with bromine, chlorine, or iodine gives the corresponding aryl halides. This reaction is typically catalyzed by the corresponding iron or aluminum trihalide. The Friedel–Crafts reaction can be performed either as an acylation or as an alkylation. Often, aluminium trichloride is used, but almost any strong Lewis acid can ...
Toluene is also found in cigarette smoke and car exhaust. If not in contact with air, toluene can remain unchanged in soil or water for a long time. [39] Toluene is a common solvent, e.g. for paints, paint thinners, silicone sealants, [40] many chemical reactants, rubber, printing ink, adhesives (glues), lacquers, leather tanners, and ...
4-Toluenesulfonyl chloride (p-toluenesulfonyl chloride, toluene-p-sulfonyl chloride) is an organic compound with the formula CH 3 C 6 H 4 SO 2 Cl. This white, malodorous solid is a reagent widely used in organic synthesis. [2] Abbreviated TsCl or TosCl, it is a derivative of toluene and contains a sulfonyl chloride (−SO 2 Cl) functional group.