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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 ...
For this purpose, chloral is treated with chlorobenzene in the presence of a catalytic amount of sulfuric acid: Cl 3 CCHO + 2 C 6 H 5 Cl → Cl 3 CCH(C 6 H 4 Cl) 2 + H 2 O. This reaction was described by Othmar Zeidler in 1874. [5] The related herbicide methoxychlor is also produced from chloral.
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.
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 .
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[6] [7] Due to the two step nature, the Raschig–Hooker process can be used to produce either chlorobenzene or phenol. Reaction scheme of the Raschig-Hooker process. The Raschig–Hooker process's ability to make phenol makes it comparable to other methods, such as the Dow and Bayer process, which also converts benzene into phenol. In fact ...
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