Glutaric anhydride
[CAS# 108-55-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Carboxylic anhydride
• Name: Glutaric anhydride
• Synonyms: Dihydro-2H-pyran-2,6(3H)-dione
• Molecular Formula: C₅H₆O₃
• Molecular Weight: 114.10
• CAS Registry Number: 108-55-4
• EC Number: 203-593-6
• SMILES: O=C1CCCC(=O)O1

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*, 1.411 g/mL (Expl.)
• Melting point: 51 - 55 °C (Expl.)
• Boiling point: 287.0 °C 760 mmHg (Calc.)^*, 319.9 °C (Expl.)
• Flash point: 120.9±15.9 °C (Calc.)^*, 173 °C (Expl.)
• Index of refraction: 1.463 (Calc.)^*
• Water solubility: hydrolysis

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302+H312-H315-H318-H335
• Safety Statements: P261-P280-P305+P351+P338-P304+P340-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

Glutaric anhydride is an organic compound with the molecular formula C₅H₆O₃. It is the cyclic anhydride derivative of glutaric acid, formed by the dehydration of two carboxyl groups in glutaric acid, resulting in a five-membered anhydride ring. Glutaric anhydride appears as a colorless crystalline solid with a characteristic sharp odor and is moderately soluble in organic solvents such as ether and benzene.

The compound was first synthesized in the 19th century through the thermal dehydration of glutaric acid or by the catalytic cyclization of related dicarboxylic acid derivatives. Its structure and reactivity have since been thoroughly investigated, confirming its role as a typical acid anhydride with reactive carbonyl groups.

Glutaric anhydride is widely used as an intermediate in organic synthesis. Its high reactivity toward nucleophiles allows it to readily undergo ring-opening reactions with amines, alcohols, and water, producing corresponding glutaric acid derivatives, esters, or amides. This reactivity makes it valuable in the preparation of polyesters, polyamides, and other polymeric materials.

In polymer chemistry, glutaric anhydride is employed as a monomer or comonomer to introduce pendant carboxyl groups or crosslinking sites in polymers. It contributes to modifying the physical properties of polymers such as adhesion, flexibility, and chemical resistance.

Glutaric anhydride is also used in the pharmaceutical and agrochemical industries for the synthesis of various intermediates and active compounds. Its ability to form amide and ester linkages facilitates the production of drugs, herbicides, and insecticides with improved performance.

In addition, glutaric anhydride serves as a building block in the synthesis of chelating agents, surfactants, and plasticizers. Its incorporation into chemical formulations can improve solubility, stability, and compatibility of end products.

The compound is generally handled under controlled conditions due to its reactivity and potential to hydrolyze in the presence of moisture, forming glutaric acid. It has a melting point around 73–75 °C and must be stored in airtight containers to maintain stability.

In summary, glutaric anhydride’s discovery and development have made it a key reagent in organic synthesis and polymer chemistry. Its applications span from the production of specialty polymers to the manufacture of pharmaceuticals and agrochemicals, demonstrating its versatility and importance in industrial and research settings.

References

1968. A new method for the synthesis of macrocyclic compounds. Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science, 17(3).
DOI: 10.1007/bf00911609

2023. Super absorbent glutaric anhydride-modified agar: Structure, properties, and application in biomaterial delivery. International Journal of Biological Macromolecules, 232.
DOI: 10.1016/j.ijbiomac.2023.123524

2023. A comparative study of the surface modification of cellulose using glutaric anhydride and succinic anhydride through a greener technique. Cellulose, 30(14).
DOI: 10.1007/s10570-023-05405-3