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Ethanamide: structure, properties, uses, effects

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.

Molecular structure of acetamide

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. Then it is dehydrated to produce the amide and form water:

Ethanamide

 

Chemical structure

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

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 of ethanamide

 

Appearance

They are crystals that range from colorless to gray.

Odor

Lavatory. When it has impurities it has an ammonia-urea smell.

Idea

It can be found in nature, in addition to mines, in the roots of sugar beets, in wine that has been over-oxidized, and in tobacco smoke.

Molar mass

59.07 g / mL

Water density

1,159 g / cm³

Melting point

Between a range of 79 ° C-81 ° C

Boiling point

221 ° C

Solubility in water, ethanol, pyridine, chloroform, glycerol and benzene

Very soluble

Vapor pressure

1.3×10-5 atm.

Chemical properties

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

Acid and basic hydrolysis

Ethanamide
Ethanamide

Reduction

Ethanamide

Dehydration

Ethanamide

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 acid is highly unlikely, and this is generally true for all amides.

Uses of acetamide

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 part of its purity and thus can be used for other uses, such as, for example, as a solvent.
  • Lacquer, to give shine to surfaces and / or to protect 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 manufacture 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 a risk estimate for inhalation 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 ground 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 abortions or harmful effects were observed in the birth of the offspring of parents treated with acetamide.

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