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Encyclopedia Britannica



MALONIC ACID, C3H404

This article appears in Volume V17, Page 496 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: MAL-MAR
MALONIC ACID, C3H404 or CH2(000H)2, occurs in the form of its
calcium
 
salt
  in the
sugar
  beet. It was first prepared in 1858 by V. Dessaignes, who obtained it by oxidizing malic acid (Ann., 1858, 107, p. 251). It may also be obtained by oxidizing allylene and propylene with cold potassium permanganate solution, by the
hydrolysis
  of barbituric acid (malonyl urea) with alkalis (A. Baeyer, Ann., 1864, 130, p. 143) ; by the
hydrolysis
  of cyanacetic acid (H.
Kolbe
 , Ann., 1864, 131, p. 349; H. Muller, Ann., 1864, 131, p. 352), and by the action of silver
oxide
  on 13-di-chloracrylic ester at 125 C. (O. Wallach, Ann., 1878, 193, p. 25)
The half nitrile of malonic acid is cyanacetic acid, CNCH2 COOH, which, in the form of its ester, may be obtained by the action of a solution of potassium
cyanide
  on monochloracetic acid. The solution obtained is neutralized, concentrated on the water-bath, acidified by sulphuric acid and extracted with ether. It is then converted into the lead
salt
 , which is decomposed by sulphuretted hydrogen and the solution is carefully concentrated (Th. Nieves, Ann., 1867, 143, p. 201). It melts at 70 C.and at higher temperatures decomposes, with
evolution
  of carbon dioxide and formation of aceto-nitrile, CH3.CN. The true nitrile of malonic acid is methylene
cyanide
 , CH2 (CN)2, which is obtained by distilling a mixture of cyanacetamide and phosphorus pentoxide. It is a crystalline solid, which melts at 2930' C. and boils at 218-219 C., and is readily soluble in alcohol and ether.


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