Glutaric acid

Description

Glutaric acid, a five-carbon dicarboxylic acid, is a by-product of adipic acid production. It possesses carboxylic acid functional groups at both ends of its molecular chain. The terminal carboxyl group can react with primary amines in the presence of an activating agent (such as EDC or HATU) to form a stable amide bond.

Chemical properties

white or off-white crystals, usually containing 1mol crystal water. Soluble in water, alcohol, ether and chloroform, slightly soluble in petroleum ether.

Occurrence

Glutaric acid occurs in washings from fleece and, together with malonic acid, in the juice of unripened sugar beet.

The Uses of Glutaric acid

Glutaric acid is used as the raw material for organic synthesis, pharmaceutical intermediate and synthetic resin. It serves as a precursor in the production of polyester polyols, polyamides, ester plasticizers and corrosion inhibitors. It is useful to decrease polymer elasticity and in the synthesis surfactants and metal finishing compounds. It acts as an intermediate during the catabolism of lysine in mammals.

Definition

ChEBI: glutaric acid is an alpha,omega-dicarboxylic acid that is a linear five-carbon dicarboxylic acid. It has a role as a human metabolite and a Daphnia magna metabolite. It is an alpha,omega-dicarboxylic acid and a dicarboxylic fatty acid. It is a conjugate acid of a glutarate(1-) and a glutarate.

Preparation

glutaric acid is produced as a by-product of the production process of adipic acid (about 2% of the output of an adipic acid plant is glutaric); Glutaric acid can be produced through various chemical routes, for example, from cyclopentane by oxidation with molecular oxygen and cobalt (III) catalysts or by ozonolysis; and from cyclopentanol–cyclopentanone by oxidation with oxygen and Co(CH3CO2)2, with potassium peroxide in benzene, or with N2O4 or nitric acid. Together with succinic acid, glutaric acid is formed as a by-product during oxidation of cyclohexanol–cyclohexanone in the adipic acid production process.

What are the applications of Application

The applications of glutaric acid, e.g., as an intermediate, are limited. Its use as a starting material in the manufacture of maleic acid has no commercial importance. it does not usually reach the market because it is converted into dibasic esters and sold as environmentally friendly solvents.

Synthesis

Glutaric acid is synthesised from α-ketoglutaric acid, with hydrogenation of the intermediate 1,3-dithiolane diamine serving as the key step. α-Ketoglutaric acid itself is produced from glucose via fermentation using Glutamic acid bacillus GKGA.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 2489, 1956 DOI: 10.1021/ja01592a042
Organic Syntheses, Coll. Vol. 1, p. 290, 1941
Synthetic Communications, 10, p. 205, 1980 DOI: 10.1080/00397918008064223

Fire Hazard

Flash point data for 1,5-Pentanedioic acid are not available; however, 1,5-Pentanedioic acid is probably combustible.

Flammability and Explosibility

Not classified

Purification Methods

Crystallise the acid from *benzene, CHCl3, distilled water or *benzene containing 10% (w/w) of diethyl ether. Dry it under vacuum. [Beilstein 2 IV 1934.]