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SUCCINIC ACID, CZH4(CO2H)2

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Originally appearing in Volume V26, Page 7 of the 1911 Encyclopedia Britannica.
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SUCCINIC See also:

ACID, CZH4(See also:CO2H)2 . Two acids corresponding to this empirical See also:formula are known—namely See also:ethylene suecinic acid, HO2C•See also:CH2-CH2-CO2II and ethylidene succinic acid CH2.CH(CO2H)2. Ethylene succinic acid occurs in See also:amber, in various resins and lignites, in fossilized See also:wood, in many members of the natural orders of Papaveraceae and See also:Compositae, in unripe grapes, urine and See also:blood. It is also found in the thymus gland of calves and in the See also:spleen of See also:cattle. It may be prepared by the oxidation of fats and of fatty acids by nitric acid, and is also a product of the See also:fermentation of malic and tartaric acids. It is usually obtained by the See also:distillation of amber, or by the fermentation of See also:calcium malate or ammonium tartrate. Synthetically it may be obtained by reducing malic or tartaric acids with hydriodic acid (R. Schmitt, See also:Ann., 186o, 114, p. ro6; V. Dessaignes; ibid., 186o, 115, p. 12o; by reducing fumaric and maleic acids with See also:sodium See also:amalgam; by See also:heating bromacetic acid with See also:silver to 13o° C.; in small quantity by the oxidation of acetic acid with See also:potassium persulphate (C. See also:Moritz and R. Wolffenstein, Ber., 1899, 32, p.

2534); by the See also:

hydrolysis of succinonitrile (from ethylene dibromide) C2H4--->C2H4Br2-.sC2H4(CN)2---C2H4(CO2H)2; by the hydrolysis of 0-cyanpropionic ester; and by the condensation of sodiomalonic ester with monochloracetic ester and hydrolysis of the resulting ethane tricarboxylic ester (See also:R02C)2CH. CH2• CO2R; this method is applicable to the preparation of substituted succinic acids. It is also produced by the See also:electrolysis of a concentrated See also:solution of potassium See also:ethyl malonate. It crystallizes in prisms or plates which melt at 185° C. and See also:boil at 235° C. with partial See also:conversion into the anhydride. It is readily soluble in See also:water. Aqueous solutions of the acid are decomposed in sunlight by See also:uranium salts, with See also:evolution of See also:carbon dioxide and the formation of propionic acid. Potassium permanganate, in acid solution, oxidizes it to carbon dioxide and water. The sodium See also:salt on distillation with See also:phosphorus trisulphide gives thiophene. The See also:esters of the acid condense readily with aromatic See also:aldehydes and See also:ketones to See also:form 7-disubstituted itaconic acids and y-alkylen pyrotartaric acids (H. Stobbe, Ann., 1899, 308, p. 71). ry-Oxyacids are formed when aldehydes are heated with sodium succinate and sodium acetate. Numerous salts of the acid are known, the basic ferric salt being occasionally used in quantitative See also:analysis for the separation of See also:iron from See also:aluminium.

Succinyl chloride, obtained by the See also:

action of phosphorus pentachloride on succinic acid, is a colourless liquid which boils at 19o° C. In many respects it behaves as though it were dichlorbutyro-lactone, CiH` 0; e.g. on reduction it yields butyro-lactone, and when condensed with See also:benzene in the presence of aluminium chloride it yields chiefly y-diphenylbutyro-lactone. succinic anhydride, C2H4(CO)2O, is obtained by heating the acid or its sodium salt with acetic anhydride; by the action of acetyl chloride on the See also:barium salt; by distilling a mixture of succinic acid and succinyl chloride, or by heating succinyl chloride with anhydrous oxalic acid. It crystallizes in plates which melt at 12o° C., and distils without decomposition. It is slowly dissolved by water with the formation of the acid. It combines readily with the See also:meta-aminophenols to form rhodamines, which are valuable dyestuffs. Heated in a current of See also:ammonia it gives succinimide, which is also obtained on heating acid ammonium succinate. It crystallizes in colourless octahedra which melt at 125–126° C., and is easily soluble in water. When warmed with baryta water it yields succinamic acid, HO2C•CH2•CH2•CONH2; and with alcoholic ammonia at 10o° C. it gives succinamide. The imino See also:hydrogen See also:atom is easily replaced by metals. Distillation with See also:zinc dust gives See also:pyrrol (q.v.). By the action of See also:bromine in alkaline solution it is converted into /-aminopropionic acid. Succinamide, C2H4(CONH2)2, best obtained by the action of ammonia on diethyl succinate, crystallizes in needles which melt at 242–243° C., and is soluble in hot water.

Succinonitrile, C2H4(CN)2, is obtained by the action of potassium See also:

cyanide on ethylene dibromide or by the electrolysis of a solution of potassium cyan-acetate. It is an amorphous solid which melts at 54–550 C. On reduction with sodium in alcoholic solution it yields tetraethylene diamine (putrescein) and pyroilidine. Methyl succinic acid (pyrotartaric acid), H02C•CH2•CH(CH2).0O2H, is formed by the dry distillation of tartaric acid; by heating pyruvic acid with concentrated hydrochloric acid to 18o° C.; by the reduction of eitraconic and mesaconic acids with sodium amalgam; and by the hydrolysis of 0-cyanbutyric acid. It crystallizes in small prisms which melt at 112° C. and are soluble in water. It forms an anhydride when heated. The sodium salt on heating with phosphorus trisulphide yields methylthiophen. Ethylidene succinic acid or isosuccinic acid, See also:CH3.CH(CO2H)2, is produced by the hydrolysis of a-cyanpropionic acid and by the action of methyl iodide on sodio-malonic ester. It crystallizes in prisms which melt at 12o° C. (T. Salzer, Journ. prak. Chem., 1898 12], 57, p.

497), and dissolve in water. It does not yield an anhydride, but when heated loses carbon dioxide and leaves a See also:

residue of propionic acid. It may be distinguished from the isomeric ethylene succinic acid by the fact that its sodium salt does not give a precipitate with ferric chloride.

End of Article: SUCCINIC ACID, CZH4(CO2H)2

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