Online Encyclopedia

C3H404 MALONIC ACID

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Originally appearing in Volume V17, Page 496 of the 1911 Encyclopedia Britannica.
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C3H404 MALONIC ACID 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, CN•CH•2 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 29°—30' C. and boils at 218°-219° C., and is readily soluble in alcohol and ether.
End of Article: C3H404 MALONIC ACID
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