Description
Chloroacetamide is a preservative used in several
applications such as in cutting metalwork fluids, in
paints or in glues. It can induce contact dermatitis in
hairdressers, or in shoemakers when used as a leather
preservative.
Chemical Properties
white crystalline powder
Uses
preservative in cosmetic and pharmaceutical creams, shampoos, bath lotions, etc.; preservative in glues, cooling fluids.
Uses
2-Chloroacetamide is used as surface-active agent in home laundry, cleaning products & household formulated cleaners, other industrial uses, petroleum production, polymer processing.
Uses
A component of herbicidal mixtures of cellulose biosynthesis inhibitors with VLCFA inhibitors.
Flammability and Explosibility
Non flammable
Contact allergens
Chloroacetamide as a preservative is used in several
applications as in cutting metalworking fluids, in paints
or in glues. It can induce contact dermatitis in hairdressers
or in shoemakers, being used as a leather
preservative.
Safety Profile
Poison by ingestion,
intravenous, and intraperitoneal routes.
Mutation data reported. When heated to
decomposition it emits very toxic Cland
NOx. See also N-CHLOROACETAMIDE.
Synthesis
Chloroacetamide can be prepared from chloroacetyl chloride and dry ammonia gas and by treating ethyl chloroacetate or methyl chloroacetate with cold aqueous ammonia solutions in a 2-l. A round-bottomed flask fitted with a mechanical stirrer and surrounded by an ice-salt bath is placed 215 g. (1.75 moles) of ethyl chloroacetate. Vigorous stirring is started, and 200 cc. of chilled aqueous ammonia (sp. gr. 0.9) is added to the cold ester. The solution is stirred in the cold for about fifteen minutes, then another 200. A portion of aqueous ammonia is added, and the stirring is continued for about fifteen minutes. The mixture is then allowed to stand for thirty minutes, filtered with suction, and washed with two 25-cc. portions of cold water to remove ammonium chloride. The yield of air-dried material melting at 118–119℃ is 128–138 g. This product contains traces of ammonium chloride, which may be removed by crystallization from water. When 100 g. of crude product is recrystallized from 400 cc. of water, about 80 g. of product Chloroacetamide is obtained. The recrystallized product melts at 119–120°.
Purification Methods
Recrystallise the amide from acetone and dry it under vacuum over P2O5. [Beilstein 2 IV 490.]
