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.

Propiolic acid
Names
Preferred IUPAC name
Prop-2-ynoic acid[1]
Other names
Propiolic acid
Acetylene carboxylic acid
Propargylic acid
Acetylene mono-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.763
EC Number
  • 207-437-8
KEGG
MeSH C011537
UNII
Properties
C3H2O2
Molar mass 70.047 g·mol−1
Density 1.1325 g/cm3
Melting point 9 °C (48 °F; 282 K)
Boiling point 144 °C (291 °F; 417 K) (decomposes)
Acidity (pKa) pka = 1.89 [2]
Hazards
Safety data sheet External MSDS
T+
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

It is soluble in water and possesses an odor like that of acetic acid.[3][4]

Preparation

It is prepared commercially by oxidizing propargyl alcohol at a lead electrode.[5] 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).[4] It undergoes bromination to give dibromoacrylic acid. With hydrogen chloride it forms chloroacrylic acid. Its ethyl ester condenses with hydrazine to form pyrazolone.[4]

It forms a characteristic explosive solid upon treatment to its aqueous solution with ammoniacal silver nitrate.[4] 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.

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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. https://pubchem.ncbi.nlm.nih.gov/compound/propiolic_acid
  3. 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.
  4. Chisholm, Hugh, ed. (1911). "Propiolic Acid" . Encyclopædia Britannica. 22 (11th ed.). Cambridge University Press. p. 449.
  5. Wilhelm Riemenschneider (2002). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235. ISBN 3527306730.
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