Succinic anhydride

Description

Succinic anhydride, also called di hydro - 2,5- furandione , is an organic compound with the molecular formula C₄H₄O₃.This colorless solid is the acid anhydride of succinic acid.

Chemical properties

fine white crystalline solid

Chemical properties

Succinic anhydride is an odourless, colourless needle-like or white crystalline solid natural product. Molecular formula C4H4O3, molecular weight 100.07 g/mol, relative density 1.503, melting point 237 °F. 239 °F at 5 mmHg, 239 °F at 198 °F and 1 mmHg. Soluble in chloroform, carbon tetrachloride, and ethanol; very slightly soluble in ether and water (insoluble in water). Moderately toxic and irritating, emits pungent and irritating fumes when heated to decomposition.

The Uses of Succinic anhydride

Succinic Anhydride is an acidulant that hydrolyzes very slowly to succinic acid in water. it has thermal stability and a low melting point of 118°c which permits it to be used in products at compara- tively low temperatures. it is used as a leavening acidulant for bak- ing powder.

The Uses of Succinic anhydride

It was used in the preparation of covalently cross-linked oxidized-alginate/N-succinyl-chitosan hydrogels, as injectable systems towards tissue engineering.It was also used in preparing functionalized oxide surfaces on a chip.

The Uses of Succinic anhydride

Succinic Anhydride is a useful compound in the paper manufacturing process.

What are the applications of Application

Succinic anhydride is an acid anhydride of succinic acid

What are the applications of Application

Alkyl succinic anhydride (ASA) is used as a sizing agent or wet strength additive in paper production.

Production Methods

The compound is produced from succinic anhydride and hydrogen peroxide . This material must be stabilized by using a dehydrating agent such as disodium sulfate or magnesium sulfate.

Preparation

A solution of succinic acid (500 mg, 42 mmol) and triethylamine (1.23 mL, 42 mmol) in anhydrous THF (120 mL) was allowed to react with triphosgene (42 mg, 7.0 mmol) at ice-water temperature for 10 min. The reaction mixture was subsequently stirred for a further 15 min at room temperature. The solution was then filtered, and the filtrate was concentrated to dryness. The residue was crystallized from ethyl acetate to afford the desired product as white crystals (370 mg, 85%).

Definition

ChEBI: Succinic anhydride is a cyclic dicarboxylic anhydride and a tetrahydrofurandione. It is functionally related to a succinic acid.

Synthesis Reference(s)

Synthetic Communications, 23, p. 419, 1993 DOI: 10.1080/00397919308009796

General Description

Colorless needles or white crystalline solid. Melting point 237°F. Sublimes at 239°F at 5 mm Hg pressure; and at 198°F and 1 mm Hg pressure. Moderately toxic and an irritant.

General Description

Succinic anhydride is a cyclic anhydride of succinic acid with a five-membered ring. It is widely used in the manufacture of polymeric materials, pharmaceuticals, agrochemicals, dyes, surface-active agents, and organic flame-retardant materials. It also finds application as a cross-linking agent in ion-exchange membranes and a curing agent for epoxy resins.

Air & Water Reactions

Reacts slowly with water. Insoluble in water.

Reactivity Profile

Succinic anhydride reacts exothermically with water. Reactions are usually slow, but might become violent if local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.

Fire Hazard

Flash point data for Succinic anhydride are not available, however, Succinic anhydride is probably combustible.

Flammability and Explosibility

Not classified

Materials Uses

Succinic anhydride can be used:
(1) In the preparation of covalently cross-linked oxidized-alginate/N-succinyl-chitosan hydrogels, as injectable systems towards tissue engineering.
(2) In preparing functionalized oxide surfaces on a chip.
(3) As a starting material to synthesize polyesters in presence of a metal triflate as a catalyst.
(4) As a cross-linking agent to enhance the mechanicalproperties and antimicrobial activities of zein films.

Safety Profile

Experimental teratogenic effects. Moderately toxic by ingestion. A severe eye irritant. Mutation data reported. Questionable carcinogen with experimental neoplastigenic data. When heated to decomposition it emits acrid smoke and irritating fumes. See also ANHYDRIDES.

Purification Methods

Crystallise the anhydride from redistilled acetic anhydride or CHCl3, then filter, wash with diethyl ether and dry it in a vacuum. [Beilstein 17 H 606, 17 V 6.]