Hydrolysis is carried out in a solution of concentrated sulfuric acid (minimum 75%) at 130–140 °C. Unlike the halogenation route, this method yields high-purity products. However, the large amount of HCl released has led to the increasing popularity of the halogenated route. Approximately 420,000 tons are produced globally each year.
Most reactions take advantage of the high reactivity of the C-Cl bond.
Among its greatest applications, chloroacetic acid is used in the preparation of thickeners carboxymethylcellulose and carboxymethylstarch.
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). It is a precursor to the herbicides glyphosate and dimethoate. Chloroacetic acid is converted to chloroacetyl chloride, which is the precursor of epinephrine (epinephrine). Displacement of chloride by sulfide yields thioglycolic acid, which is used as a stabilizer for PVC and as an ingredient in some cosmetics. [2]
Illustrative of its use in organic chemistry is the O-alkylation of salicylaldehyde with chloroacetic acid followed by decarboxylation of the resulting ether to yield benzofurans.
Like other chloroacetic acids and related halocarbons, chloroacetic acid is a dangerous alkylating agent. The LD50 in rats is 76 mg/kg. [2]
It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the United States Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and it is produced, stored, or used in large quantities.