Abstract
AbstractThe most important of the halogenated derivatives of acetic acid is chloroacetic acid, which has wide applications as an industrial chemical intermediate in the manufacture of cellulose ethers, herbicides, and thioglycolic acid. Most chloroacetic acid is produced by the chlorination of acetic acid. Chloroacetic acid is extremely corrosive and will cause serious chemical burns. It is readily absorbed through the skin; contamination of 5–10% of the skin is usually fatal. Sodium chloroacetate, C2H2ClO2Na, is produced by reaction of chloroacetic acid with sodium hydroxide or sodium carbonate. Dichloroacetic acid, C2H2Cl2O2, is a reactive intermediate in organic synthesis. It has been manufactured by the chlorination of acetic and chloroacetic acids and by other means. Trichloroacetic acid, C2HCl3O2, forms white deliquescent crystals. Sodium trichloroacetate, C2Cl3O2Na, is used as a herbicide. Chloroacetyl chloride (ClCH2COCl) is the corresponding acid chloride of chloroacetic acid, and is manufactured by reaction of chloroacetic acid with chlorinating agents. Much of the chloroacetyl chloride produced is used captively as a reactive intermediate. It is useful in many acylation reactions and in the production of adrenalin, diazepam, and chloroacetic anhydride. Two chloroacetate esters of industrial importance are methyl chloroacetate, C3H5ClO2, and ethyl chloroacetate, C4H7ClO2. Both are used as agricultural and pharmaceutical intermediates. Other derivatives are bromoacetic acid, dibromoacetic acid, tribromoacetic acid, iodoacetic acid, diiodoacetic acid, and triiodoacetic acid.
Published Version
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