Preparation of Glutaric Acid

  • Glutaric acid can be synthesized from malonic ester synthesis, where diiodomethane reacts with the two-molar equivalent of diethyl malonate.

 

  • It can be prepared by the oxidative ring fission of cyclopentane with 50% of nitric acid in the presence of vanadium cyanide.
  • It is produced as a by-product in the production of adipic acid from cyclohexane by oxidation with air and nitric acid.
  • We can also prepare glutaric acid by reacting 1,3-dibromopropane with sodium or potassium cyanide to produce the dinitrile, followed by hydrolysis.

Glutaric Acid Formula

Glutaric acid, also termed pentanedioic acid or n-pyrotartaric acid, is an alpha, omega-dicarboxylic acid with the formula C3H6(COOH)2. The body naturally produces glutaric acid as a by-product during the metabolism of some amino acids, such as lysine and tryptophan. It is an organic compound that appears as colorless crystals or white solids. It decomposes slightly at a temperature of 302-304 °C. At room temperature, the solubility of the related “linear” dicarboxylic acids adipic and succinic acids in water is only a few percent, whereas glutaric acid has a water-solubility of approximately 50% (w/w). Its conjugate bases are glutarate (1-) and glutarate. It functions as both a human and a Daphnia Magna metabolite. Glutaric acid is used as a precursor in organic synthesis.

Similar Reads

Structure of Glutaric Acid

Glutaric acid is a linear five-carbon dicarboxylic acid that has a chemical formula of C5H8O4 or C3H6(COOH)2 or COOH(CH2)3COOH. It is composed of 5 carbon atoms, 8 hydrogen atoms, and 4 oxygen atoms. C(CC(=O)O)CC(=O)O is its canonical SMILES structure....

Preparation of Glutaric Acid

Glutaric acid can be synthesized from malonic ester synthesis, where diiodomethane reacts with the two-molar equivalent of diethyl malonate....

Properties of Glutaric Acid

Chemical formula  C5H8O4  IUPAC Name Pentanedioic acid  Molecular weight 132.12 g/mol  Appearance Colorless crystals or white solid Density 1.4 g/cm³ Melting point 95 to 98 °C  Boiling point    200 °C at 20 mmHg Solubility Soluble in water, freely soluble in absolute alcohol, ether, soluble in benzene, chloroform, and slightly soluble in petroleum ether. Hydrogen Bond Donor Count  2 Hydrogen Bond Acceptor Count  4  Rotatable Bond Count   4...

Uses of Glutaric Acid

Glutaric acid is used as a precursor in organic synthesis. For example, uvitonic acid is produced by the action of ammonia on glutaric acid. It is also used in the preparation of its anhydride and esters. Glutaric diester can be used for the production of pyrogallol.  It is also used in the manufacture of various polymers such as polyamides and polyesters. Through the hydrogenation of glutaric acid and its derivatives, 1,5-Pentanediol is produced, which is a common plasticizer and precursor to polyesters....

Health Hazards

Glutaric acid may irritate the skin and eyes. Some chronic hazards of this compound are that it might be harmful when inhaled, ingested, or absorbed through the skin. On heating for decomposition, it may emit acrid smoke, irritating fumes, and toxic fumes of carbon dioxide and carbon monoxide....

FAQs on Glutaric Acid

Question 1: What is glutaric acid?...