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Glutaric Acid Formula

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  • Last Updated : 17 Oct, 2022
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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.

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.

Structure of Glutaric Acid

 

Preparation of Glutaric Acid

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

 

  • 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.

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 
Rotatable Bond Count  

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?

Answer:

Glutaric acid, also termed pentanedioic acid or n-pyrotartaric acid, is an alpha, omega-dicarboxylic acid with the formula C3H6(COOH)2.  It is composed of 5 carbon atoms, 8 hydrogen atoms, and 4 oxygen atoms. The body naturally produces glutaric acid as a by-product during the metabolism of some amino acids, such as lysine and tryptophan.

Question 2: How is glutaric acid prepared?

Answer:

Glutaric acid can be synthesized from malonic ester synthesis, where diiodomethane reacts with the two-molar equivalent of diethyl malonate. It can be manufactured by ring-opening butyrolactone with potassium cyanide which results in a mixed potassium carboxylate-nitrile which is further hydrolyzed to the diacid. It can also be prepared by the oxidative ring fission of cyclopentane with 50% of nitric acid in the presence of vanadium cyanide.

Question 3: What are the properties of glutaric acid?

Answer:

Glutaric acid is a linear five-carbon dicarboxylic acid that has a chemical formula of C5H8O4. Its molecular weight is 132.12 g/mol and it has a density of 1.4 g/cm3. It appears as colorless crystals or white solid. Its boiling point is 200 °C at 20 mmHg, while its melting point is between 95 to 98 °C.

Question 4: Mention some hazards of glutaric acid.

Answer:

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.

Question 5: What are the uses of glutaric acid?

Answer:

Glutaric acid is used as a precursor in organic synthesis. For example, uvitonic acid is produced by the action of ammonia on glutaric acid. 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.

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