ETHANAMIDE: STRUCTURE, PROPERTIES, USES AND EFFECTS - CHEMISTRY - 2025

The ethanamide is a chemical belonging to the group of organic nitrogen compounds. It is also called acetamide, according to the International Union of Pure and Applied Chemistry (IUPAC). It is commercially called acetic acid amide.

It is called an amide because the nitrogen is attached to a carbonyl group. It is primary, because it conserves the two hydrogen atoms attached to the nitrogen -NH ₂. It has been found in nature as a mineral only in dry weather; in the rainy or very humid season it dissolves in water.

It is a solid with a glassy (transparent) appearance. Its color ranges from colorless to gray, it forms small stalactites and sometimes granular aggregates. It can be produced by the reaction between acetic acid and ammonia, forming an intermediate salt: ammonium acetate. This is then dehydrated to produce the amide and form water:

Chemical structure

The internal chemical structure of the acetamide crystal is trigonal, but when it joins together to form agglomerates it acquires an octahedral form.

The structural formula of the compound consists of an acetyl group and an amino group:

These groups allow the different reactions that the compound can have to take place. The molecular formula of acetamide is C ₂ H ₅ NO.

Physical properties

Chemical properties

The chemical properties of a substance refer to its reactivity when in the presence of others that can cause transformation in its structure. Acetamide exhibits the following reactions:

Acid and basic hydrolysis

Reduction

Dehydration

In the industrial field the production of carboxylic acids is very advantageous due to the importance of their derivatives. However, obtaining ethanoic acid from acetamide has a very limited application, because the high temperatures at which the process occurs tend to decompose the acid.

In the laboratory, although ethanamide can be obtained from acetic acid, reconversion from an amide to the acid is highly unlikely, and this is generally true for all amides.

Applications

Acetamide has been produced commercially since 1920, although it is not certain that it is in commercial use to date. It was previously used for the synthesis of methylamines, thioacetamide, hypnotics, insecticides and for medicinal purposes.

Acetamide is a compound that, in the industrial field, is used as:

- Plasticizer, in leather, fabric films and coatings.

- Additive for paper, to give resistance and flexibility.

- Denaturation of alcohols. It is added to the alcohol under study to remove some of its purity and thus it can be used for other uses, such as as a solvent.

- Lacquer, to give shine to the surfaces and / or to protect the materials from the aggressions of the environment, especially from corrosion.

- Explosive.

- Flux, since when added to a substance it facilitates its fusion.

- In cryoscopy.

- As an intermediate in the preparation of drugs such as ampicillin and antibiotics derived from cephalosporins, such as: cefaclor, cephalexin, cephradine, enalapril maleate (treatment of hypertension) and sulfacetamide (antimicrobial eye drops), among others.

- Solvent, since it causes some substances to increase their solubility in water when acetamide is dissolved in it.

- As a solvent that fixes dyes in the textile industry.

- In the production of methylamines.

- As a biocide, in compounds that can be used as disinfectants, preservatives, pesticides, etc.

Health effects

In chemical industries where acetamide is used as a solvent and plasticizer, workers may experience skin irritation due to acute (short-term) exposure from the presence of these compounds.

There is no information on chronic (long-term) effects or the development of carcinogens in humans. According to the United States Environmental Protection Agency (EPA), acetamide is not classified as a carcinogen.

The International Agency for Research on Cancer has classified acetamide as a Group 2B, a possible human carcinogen.

The California Environmental Protection Agency has established an inhalation risk estimate of 2 × 10 ^-5 µg / m ³ (microgram per cubic meter), and a risk of oral cancer after ingestion of 7 × 10 ^-2 mg / kg / d (milligrams for every kilogram in a day) for a long time.

However, although the general population can be exposed by smoking cigarettes or by skin contact with products containing acetamide, it does not represent much risk due to the solubility and hygroscopic characteristics it has with water.

It can be easily moved through the soil by runoff, but is expected to be degraded by microorganisms and not accumulate in fish.

Acetamide is a mild skin and eye irritant, and no data is available to certify its toxic effects in humans.

In laboratory animals, toxicity was observed in the loss of body weight when subjected to a very high oral dose over time. However, no miscarriages or harmful effects were observed in the birth of the offspring of parents treated with acetamide.

References

1. Cosmos online, (since 1995), Technical and Commercial Information on Acetamide, retrieved on March 23, 2018, cosmos.com.mx
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3. Pine, S., Hammond, G., Cram, D., Hendrickson, J., (1982). Química Orgánica, (second edition), Mexico, McGraw-Hill de México, SA de CV
4. Guide of chemical products, (2013), Uses of acetamide, retrieved on March 24, 2018, guiadeproductosquimicos.blogspot.com.co
5. National Center for Biotechnology Information. PubChem Compound Database; CID = 178, Acetamide. Recovered pubchem.ncbi.nlm.nih.gov
6. Ronak Chemicals, (1995), Uses and Applications of Acetamide, Retrieved on March 25, 2018, ronakchemicals.com
7. , (2016), Acetamide,. Retrieved on March 26, 2018, epa.gov
8. National Library of Medicine Hazardous Substances Data Bank. (2016), Acetamide, Retrieved March 26, 2018, toxnet.nlm.nih.gov
9. IARC., (2016) Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Available from, Retrieved on March 26, 2018, monographs.iarc.fr