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Encyclopedia Britannica



PROPIOLIC ACID

This article appears in Volume V22, Page 449 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: PRE-PYR
PROPIOLIC ACID , CH:CCO2H, acetylene mono-carboxylic acid, an unsaturated organic acid prepared by boiling acetylene dicarboxylic acid (obtained by the action of alcoholic potash on dibromsuccinic acid) or its acid potassium
salt
  with water (E. v. Bandrowski, Ber., 188o, 13, p. 2340). It forms silky crystals which melt at 6 C., and
boil
  at about 144 C. with decomposition. It is soluble in water and possesses an odour resembling that of acetic acid. Exposure to sunlight converts it into trimesic acid (
benzene
 -1.3.5-tricarboxylic acid). Bromine converts it into dibromacrylic acid, and it gives with hydrochloric acid 0-chloracrylic acid. It forms a characteristic explosive silver
salt
  on the addition of ammoniacal silver nitrate to its aqueous solution, and an amorphous precipitate which explodes on warming with ammoniacal cuprous chloride. Its
ethyl
  ester condenses with hydrazine to form pyrazolone (R: v. Rothenburg, Ber., 1893, 26, p. 1722). Phenylpropiolic acid, C6H5C:CCO2H, formed by the action of alcoholic potash on cinnamic acid dibromide, C6H5CHBrCHBrCO2H, crystallizes in
long
  needles or prisms which melt at 1361370 C. When heated with water to I2o C. it yields phenyl acetylene C6H5C;CH. Chromic acid oxidizes it to benzoic acid;
zinc
  and acetic acid reduce it to cinnamic acid, C6H5CH:CHCO2H, whilst sodium
amalgam
  reduces it to hydrocinnamic acid, C6H5CH2CO2H. Ortho-nitrophenylpropiolic acid, NO2C6H4C: CCO2H, prepared by the action of alcoholic potash on ortho-nitrocinnamic acid dibromide (A. v. Baeyer, Ber., 188o, 13, p. 2258), crystallizes in needles which decompose when heated to 155156 C. It is readily converted into indigo (q.v.).


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