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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. The reaction proceeds by the free radical process, involving the intermediacy of free chlorine atoms. [4]
Structure of the chloromethyl group. In organic chemistry, the chloromethyl group is a functional group that has the chemical formula −CH 2 −Cl. The naming of this group is derived from the methyl group (which has the formula −CH 3), by replacing one hydrogen atom by a chlorine atom. Compounds with this group are a subclass of the ...
Chlorobenzene once was used in the manufacture of pesticides, most notably DDT, by reaction with chloral (trichloroacetaldehyde), but this application has declined with the diminished use of DDT. At one time, chlorobenzene was the main precursor for the manufacture of phenol : [ 10 ]
Typically these reactions would be conducted in the presence of a base which serves to absorb the HCl. Alkyl chloroformate esters degrate to give the alkyl chloride, with retention of configuration: ROC(O)Cl ' → RCl + CO 2. The reaction is proposed to proceed via a substitution nucleophilic internal mechanism. [3]
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): C 6 H 5 CH 3 + Cl 2 → C 6 H 5 CH 2 Cl + HCl C 6 H 5 CH 2 Cl + Cl 2 → C 6 H 5 CHCl 2 + HCl C 6 H 5 CHCl 2 + Cl 2 → C 6 H 5 CCl 3 + HCl
For example, the industrial production of chloroethane proceeds by the reaction of ethylene with HCl: H 2 C=CH 2 + HCl → CH 3 CH 2 Cl. In oxychlorination, hydrogen chloride instead of the more expensive chlorine is used for the same purpose: CH 2 =CH 2 + 2 HCl + 1 ⁄ 2 O 2 → ClCH 2 CH 2 Cl + H 2 O.
The structure of xylylene dichloride is characterized by an benzene ring with two chloromethyl groups and four hydrogen atoms bound to it. [4] The chloromethyl groups can be located on different sites on the ring, leading to a few different possible forms. These forms are: [3] o-xylylene dichloride: 1,2-bis(chloromethyl)benzene
In the process developed by Dow Chemical, glycerol undergoes two substitution reactions when treated with hydrogen chloride in the presence of a carboxylic acid catalyst. This is the same intermediate formed in the allyl chloride/hypochlorous acid process, and is likewise then treated with base to form epichlorohydrin.