Chemical Properties
Acetamide occurs as hexagonal, colorless deliquescent crystals with a musty odor. It is
incompatible with strong acids, strong oxidizing agents, strong bases, and tribolumi-
nescent. Acetamide is used primarily as a solvent, as a plasticizer, and a wetting and
penetrating agent. Workplace exposures to acetamide are associated with the plastics
and chemical industries.
General Description
Colorless crystals with a mousy odor (NTP, 1999). Low toxicity.
Reactivity Profile
ACETAMIDE(60-35-5) may react with azo and diazo compounds to generate toxic gases. May form flammable gases with strong reducing agents. Reacts as a weak bases (weaker than water). Mixing with dehydrating agents such as P2O5 or SOCl2 generates acetonitrile Burns to give toxic mixed oxides of nitrogen (NOx).
Air & Water Reactions
Deliquescent. Very soluble in water.
Health Hazard
After oral exposures to acetamide, animals developed liver tumors. However, no informa-
tion is available on the carcinogenic effects of acetamide in humans. The US EPA has not
classifi
ed acetamide for carcinogenicity. The IARC has classifi
ed acetamide as a Group 2B,
meaning a possible human carcinogen.
Potential Exposure
Used as a stabilizer, plasticizer, wetting agent; solvent in plastics, lacquers, explosive; soldering flux ingredient; and chemical manufacturing
Fire Hazard
The flash point of this chemical has not been determined, but ACETAMIDE is probably combustible.
First aid
If this chemical gets into the eyes, remove any contact lenses at once, and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. If this chemical has been inhaled, remove from exposure and transfer promptly to a medical facility.
Shipping
UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
Incompatibilities
Reacts with strong acids, such as hydrochloric, sulfuric, and nitric, strong oxidizers; strong bases; strong reducing agents such as hydrides; ammoniaisocyanates, phenols, cresols. Contact with water causes slow hydrolyzation to ammonia and acetate salts.
Waste Disposal
Add to alcohol or benzene as a flammable solvent and incinerate; oxides of nitrogen produced may be scrubbed out with alkaline solution. All federal, state, and local environmental regulations must be observed.
Uses
- Acetamide is often used as plasticizer and as industrial solvent.
- molten acetamide is an excellent solvent for many organic and inorganic compounds.
- Solubilizer.
- renders sparingly soluble substances more soluble in water by mere addition or by fusion.
- stabilizer.
- manufacture of methylamine, denaturing alcohol.
- In organic syntheses.
- Acetamide is used as a co-monomer in the production of polymeric materials such as polyvinyl acetamide, a polymeric product used as an absorbent.
- It can be used for the transamidation of carbxamides in 1,4-dioxane in the absence of a catalyst.
Uses
As a dipolar solvent, acetamide finds many uses as a solvent for
both inorganic and organic compounds. The solvency has led
to widespread uses in industry including applications in
cryoscopy, soldering, and the textile industry. The neutral and
amphoteric characteristics allow its use as an antacid in the
lacquer, explosives, and cosmetics industries. Its hygroscopic
properties make it useful as a plasticizer in coatings, fixtures,
cloth, and leather, and as a humectant for paper. It is also a raw
material in organic synthesis of methylamine and thioacetamide
and as an intermediate in preparation of medicines,
insecticides, and plastics.
Uses
Cryoscopy; organic synthesis; general
solvent; lacquers; explosives, soldering flux;
wetting agent; plasticizer
Definition
ChEBI: Acetamide is a member of the class of acetamides that results from the formal condensation of acetic acid with ammonia. It is a monocarboxylic acid amide, a N-acylammonia and a member of acetamides. It is a tautomer of an acetimidic acid.
target
Histone Methyltransferase
Carcinogenicity
The IARC has determined that there is
sufficient evidence of carcinogenicity for
acetamide in experimental animals and that it
is possibly carcinogenic to humans.
Environmental Fate
The mechanism of toxicity of acetamide is not known; the
response profile is quite different from the better studied
dimethyl derivative. Acetamide appears to be in a class of
chemicals which, although producing liver cancer in rodents, is
less sensitive to inactive in genetic tests looking at formation of
micronuclei. The carcinogenic response in rodents appears
related to the formation of hydroxylamine from the primary
metabolite acetohydroxamic acid.
Purification Methods
Acetamide is crystallised by dissolving in hot MeOH (0.8mL/g), diluting with Et2O and allowing to stand [Wagner J Chem Edu 7 1135 1930]. Alternate crystallisation solvents are acetone, *benzene, chloroform, dioxane, methyl acetate or *benzene/ethyl acetate mixtures (3:1 and 1:1). It has also been recrystallised from hot water after treating with HCl-washed activated charcoal (which had been repeatedly washed with water until free from chloride ions), then crystallised again from hot 50% aqueous EtOH and finally twice from hot 95% EtOH [Christoffers & Kegeles J Am Chem Soc 85 2562 1963]. Finally it is dried in a vacuum desiccator over P2O5. Acetamide is also purified by distillation (b 221-223o) or by sublimation in vacuo. It has also been purified by two recrystallisations from cyclohexane containing 5% (v/v) of *benzene. Needle-like crystals separate and are filtered, washed with a small volume of distilled H2O and dried with a flow of dry N2. [Slebocka-Tilk et al. J Am Chem Soc 109 4620 1987, Beilstein 2 H 175, 2 I 80, 2 II 177, 2 III 384, 2 IV 399.]
Toxicity evaluation
Acetamide will exist as a vapor in the ambient atmosphere.
Atmospheric degradation occurs by reaction with photochemically
produced hydroxyl radicals. The half-life for this
reaction in air is estimated to be 7.6 days. If released to soil,
acetamide is expected to have very high mobility and is not
expected to adsorb to suspended solids and sediment. Experiments
suggest that this chemical may break down in the
environment through biodegradation and not through hydrolysis.
Volatilization from water surfaces is not expected to be an
important fate process based on this compound’s estimated
Henry’s law constant.
