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Propiolic acid

Propiolic acid is the organic compound with the formula HC2CO2H. It is the simplest acetylenic carboxylic acid. It is a colourless liquid that crystallises to give silky crystals. Near its boiling point, it decomposes.

It is soluble in water and possesses an odor like that of acetic acid.[4][5]

Preparation

It is prepared commercially by oxidizing propargyl alcohol at a lead electrode.[6] It can also be prepared by decarboxylation of acetylenedicarboxylic acid.

Reactions and applications

Exposure to sunlight converts it into trimesic acid (benzene-1,3,5-tricarboxylic acid).[5] It undergoes bromination to give dibromoacrylic acid. With hydrogen chloride it forms chloroacrylic acid. Its ethyl ester condenses with hydrazine to form pyrazolone.[5]

It forms a characteristic explosive solid upon treatment to its aqueous solution with ammoniacal silver nitrate.[5] An amorphous explosive precipitate forms with ammoniacal cuprous chloride.

Propiolates

Propiolates are esters or salts of propiolic acid. Common examples include methyl propiolate and ethyl propiolate.

See also

References

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 748. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ "Propiolic acid".
  3. ^ "Propiolic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 16 December 2021.
  4. ^ ed, Susan Budavari (1990). The Merck index an encyclopedia of chemicals, drugs, and biologicals (11. ed., 2. print. ed.). Rahway, NJ: Merck. pp. 7833, 1911. ISBN 9780911910285.
  5. ^ a b c d Chisholm, Hugh, ed. (1911). "Propiolic Acid" . Encyclopædia Britannica. Vol. 22 (11th ed.). Cambridge University Press. p. 449.
  6. ^ Wilhelm Riemenschneider (2002). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235. ISBN 3527306730.