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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.
These compounds are diazotized followed by treatment with cuprous chloride. [1] Industrially, the diazonium method is reserved for 3-chlorotoluene. The industrial route to 2- and 4-chlorotoluene entails direct reaction of toluene with chlorine. The more valuable 4-chlorotoluene is separated from 2-chlorotoluene by distillation.
The photochlorination of toluene is selective for the methyl group. Mono- to trichlorinated products are obtained. The most important of which is the mono-substituted benzyl chloride, which is hydrolyzed to benzyl alcohol. Benzyl chloride can also be converted via benzyl cyanide with subsequent hydrolysis into phenylacetic acid.
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 ...
This page contains tables of azeotrope data for various binary and ternary mixtures of solvents. The data include the composition of a mixture by weight (in binary azeotropes, when only one fraction is given, it is the fraction of the second component), the boiling point (b.p.) of a component, the boiling point of a mixture, and the specific gravity of the mixture.
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):
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Benzyl alcohol is produced industrially from toluene via benzyl chloride, which is hydrolyzed: . C 6 H 5 CH 2 Cl + H 2 O → C 6 H 5 CH 2 OH + HCl. Another route entails hydrogenation of benzaldehyde, a by-product of the oxidation of toluene to benzoic acid.