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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] C 6 H 5 Cl + NaOH → C 6 H 5 OH + NaCl
When 1-[14 C]-1-chlorobenzene was subjected to aqueous NaOH at 395 °C, ipso substitution product 1-[14 C]-phenol was formed in 54% yield, while cine substitution product 2-[14 C]-phenol was formed in 43% yield, indicating that an elimination-addition (benzyne) mechanism is predominant, with perhaps a small amount of product from addition ...
Dow process (phenol), a method of phenol production through the hydrolysis of chlorobenzene Topics referred to by the same term This disambiguation page lists articles associated with the title Dow process .
Chlorobenzene can be hydrolyzed to phenol using base (Dow process) or steam (Raschig–Hooker process): [24] [25] [29] C 6 H 5 Cl + NaOH → C 6 H 5 OH + NaCl C 6 H 5 Cl + H 2 O → C 6 H 5 OH + HCl. These methods suffer from the cost of the chlorobenzene and the need to dispose of the chloride byproduct.
The Raschig–Hooker process suffers from selectivity issues in both steps. In the first step, the reaction is only run to 10% to 15% conversion to prevent the second addition of a chlorine atom to the desired chlorobenzene. Despite this, the overall selectivity of the reaction is 70% to 85%.
2,4-Dinitrochlorobenzene (DNCB) is an organic compound with the chemical formula (O 2 N) 2 C 6 H 3 Cl. It is a yellow solid that is soluble in organic solvents.It is an important intermediate for the industrial production of other compounds.
4-Nitrochlorobenzene is prepared industrially by nitration of chlorobenzene: ClC 6 H 5 + HNO 3 → ClC 6 H 4 NO 2 + H 2 O. This reaction affords both the 2- and the 4-nitro derivatives, in about a 1:2 ratio. These isomers are separated by a combination of crystallization and distillation.
The reaction usually requires a catalyst, such as concentrated sulfuric acid: R − OH + R ′ − CO 2 H R ′ − CO 2 R + H 2 O {\displaystyle {\ce {R-OH + R'-CO2H -> R'-CO2R + H2O}}} Other types of ester are prepared in a similar manner−for example, tosyl (tosylate) esters are made by reaction of the alcohol with 4-toluenesulfonyl ...