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Concept
Chloroacetic acid
Summary
Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds are dichloroacetic acid and trichloroacetic acid.
Chloroacetic acid was first prepared (in impure form) by the French chemist Félix LeBlanc (1813–1886) in 1843 by chlorinating acetic acid in the presence of sunlight, and in 1857 (in pure form) by the German chemist Reinhold Hoffmann (1831–1919) by refluxing glacial acetic acid in the presence of chlorine and sunlight, and then by the French chemist Charles Adolphe Wurtz by hydrolysis of chloroacetyl chloride (ClCH2COCl), also in 1857.
Chloroacetic acid is prepared industrially by two routes. The predominant method involves chlorination of acetic acid, with acetic anhydride as a catalyst:
H3C−COOH + Cl2 → ClH2C−COOH + HCl
This route suffers from the production of dichloroacetic acid and trichloroacetic acid as impurities, which are difficult to separate by distillation:
H3C−COOH + 2 Cl2 → Cl2HC−COOH + 2 HCl
H3C−COOH + 3 Cl2 → Cl3C−COOH + 3 HCl
The second method entails hydrolysis of trichloroethylene:
2 H2O → ClH2C−COOH + 2 HCl
The hydrolysis is conducted at 130–140 °C in a concentrated (at least 75%) solution of sulfuric acid. This method produces a highly pure product, unlike the halogenation route. However, the significant quantities of HCl released have led to the increased popularity of the halogenation route. Approximately 420,000 tonnes are produced globally per year.
Most reactions take advantage of the high reactivity of the C–Cl bond.
In its largest-scale application, chloroacetic acid is used to prepare the thickening agent carboxymethyl cellulose and carboxymethyl starch.
Chloroacetic acid is also used in the production of phenoxy herbicides by etherification with chlorophenols. In this way 2-methyl-4-chlorophenoxyacetic acid (MCPA), 2,4-dichlorophenoxyacetic acid, and 2,4,5-trichlorophenoxyacetic acid (2,4,5-T) are produced.
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