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Encyclopedia > Trichloroacetic acid

In organic chemistry, the chloroethanoic acids (trivial name chloroacetic acids) are three related chlorocarbon carboxylic acids:

  • chloroethanoic acid (chloroacetic acid), CH2ClCOOH
  • dichloroethanoic acid (dichloroacetic acid), CHCl2COOH
  • trichloroethanoic acid (trichloroacetic acid), CCl3COOH

As the number of chlorine atoms increases, the electronegativity of that end of the molecule increases, and the molecule adopts a progressively more ionic character: it's density, boiling point and acidity all increase.

Acid Melting point Boiling point Density pKa
Ethanoic acid 16.5°C 118.1°C 1.05 4.76
Chloroethanoic 61-63°C 189°C 1.58 2.87
Dichloroethanoic 9.7°C 194°C 1.57 1.25
Trichloroethanoic 57°C 196°C 1.63 0.77

Production

CCl2=CHCl + 2H2O → CH2ClCOOH + 2HCl
  • Dichloroethanoic acid is manufactured in small quantities by reducing trichloroethanoic acid.
  • Trichloroethanoic acid is made by the direct action of chlorine on ethanoic acid in the presence of a suitable catalyst.

Uses

Safety

All of these acids are unusually strong for organic acids, and should generally be treated with similar care as for strong mineral acids like hydrochloric acid. Even neutral salts however, tend to be significantly toxic, because the ions interfere in biological processes (such as the Krebs cycle) that normally process plain acetate ions. Interestingly, the chloroethanoate ion is the most toxic, with a rat, oral LD50 of about 0.5 g/kg.


  Results from FactBites:
 
TRICHLOROACETIC ACID (620 words)
The half-life of trichloroacetic acid, given orally or formed as a metabolite of trichloroethylene or trichloroethanol, is longer in humans than in rodents.
In male mice, trichloroacetic acid modified neither the incidence of mutations in exon 2 of H-ras in carcinomas, nor the mutational spectrum observed in tumours that bore a mutation in exon 2.
Trichloroacetic acid induced abnormal sperm in mice in vivo in one study and chromosomal aberrations in mouse and chicken bone marrow in vivo.
Glossary: Trichloroacetic acid (195 words)
Inhalation of trichloroacetic acid vapour may lead to a sore throat and cause fluid to fill the lungs (pulmonary oedema).
Trichloroacetic acid is used as a laboratory reagent but its main use is in the production of its sodium salt, which is used in many industries, for example, as a herbicide, etching agent and antiseptic.
In the environment, very small quantities of trichloroacetic acid are found in chlorinated drinking water as a disinfection by product as a consequence of the reaction of chlorine with natural organic matter and bromide ions in the raw water supply (from lake, reservoirs, rivers, etc.).
  More results at FactBites »


 

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