Online Encyclopedia

Search over 40,000 articles from the original, classic Encyclopedia Britannica, 11th Edition.

CZH4 SUCCINIC ACID (CO2H)2

Online Encyclopedia
Originally appearing in Volume V26, Page 7 of the 1911 Encyclopedia Britannica.
Spread the word: del.icio.us del.icio.us it!

CZH4 SUCCINIC See also:

ACID (See also:CO2H)2  . Two acids corresponding to this empirical See also:formula are known—namely See also:ethylene suecinic See also:acid, HO2C•See also:CH2-CH2-CO2II and ethylidene succinic acid CH2.CH(See also: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: CZH4 SUCCINIC ACID (CO2H)2
[back]
SUCCESSION DUTY
[next]
ROSA SUCHER (1849– )

Additional information and Comments

There are no comments yet for this article.
» Add information or comments to this article.
Please link directly to this article:
Highlight the code below, right click and select "copy." Paste it into a website, email, or other HTML document.