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PROPIOLIC ACID

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Originally appearing in Volume V22, Page 449 of the 1911 Encyclopedia Britannica.
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PROPIOLIC See also:

ACID , CH:C•See also:CO2H, See also:acetylene mono-carboxylic acid, an unsaturated organic acid prepared by boiling acetylene dicarboxylic acid (obtained by the See also:action of alcoholic potash on dibromsuccinic acid) or its acid See also:potassium See also:salt with See also:water (E. v. Bandrowski, Ber., 188o, 13, p. 2340). It forms silky crystals which melt at 6° C., and See also: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 (See also:benzene-1.3.5-tricarboxylic acid). See also:Bromine converts it into dibromacrylic acid, and it gives with hydrochloric acid 0-chloracrylic acid. It forms a characteristic explosive See also:silver salt on the addition of ammoniacal silver nitrate to its aqueous See also:solution, and an amorphous precipitate which explodes on warming with ammoniacal cuprous chloride. Its See also:ethyl ester condenses with See also:hydrazine to See also:form pyrazolone (R: v. Rothenburg, Ber., 1893, 26, p. 1722). Phenylpropiolic acid, C6H5C:C•CO2H, formed by the action of alcoholic potash on cinnamic acid dibromide, C6H5CHBr•CHBr•CO2H, crystallizes in See also:long needles or prisms which melt at 136–1370 C.

When heated with water to I2o° C. it yields phenyl acetylene See also:

C6H5•C;CH. Chromic acid oxidizes it to benzoic acid; See also:zinc and acetic acid reduce it to cinnamic acid, C6H5•CH:CH•CO2H, whilst See also:sodium See also:amalgam reduces it to hydrocinnamic acid, C6H5•See also:CH2•CO2H. Ortho-nitrophenylpropiolic acid, NO2•See also:C6H4•C: C•CO2H, prepared by the action of alcoholic potash on ortho-nitrocinnamic acid dibromide (A. v. See also:Baeyer, Ber., 188o, 13, p. 2258), crystallizes in needles which decompose when heated to 155–156° C. It is readily converted into See also:indigo (q.v.).

End of Article: PROPIOLIC ACID

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