Azelaic acid diethyl ester
[CAS# 624-17-9]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Azelaic acid diethyl ester
• Synonyms: Nonanedioic acid diethyl ester; Diethyl azelaate; Diethyl azelate; Diethyl nonanedioate; NSC 61074
• Molecular Formula: C₁₃H₂₄O₄
• Molecular Weight: 244.33
• CAS Registry Number: 624-17-9
• EC Number: 210-833-3
• SMILES: CCOC(=O)CCCCCCCC(=O)OCC

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*, 0.973 g/mL (Expl.)
• Melting point: -16 - -15.8 ºC (Expl.)
• Boiling point: 291.5 ºC 760 mmHg (Calc.)^*, 326.3 ºC (Expl.)
• Flash point: 129.2±16.9 ºC (Calc.)^*
• Index of refraction: 1.439 (Calc.)^*, 1.435 (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

Azelaic acid diethyl ester is the diethyl ester derivative of azelaic acid, a saturated nine-carbon dicarboxylic acid. Its molecular formula is C₁₄H₂₆O₄. This compound contains two ethyl ester groups attached to both ends of the linear nine-carbon alkyl chain, making it a bifunctional ester widely used in organic synthesis and materials chemistry.

The preparation of azelaic acid diethyl ester typically involves esterification of azelaic acid with ethanol in the presence of acid catalysts such as sulfuric acid or p-toluenesulfonic acid. The reaction is performed under reflux conditions with the continuous removal of water to drive the equilibrium toward ester formation. Alternatively, azelaic acid chlorides may be reacted with ethanol to obtain the diethyl ester.

Azelaic acid diethyl ester serves as an important intermediate in the synthesis of polymers, plasticizers, and surfactants. Its two ester groups facilitate polycondensation reactions with diols or diamines to form polyesters or polyamides, respectively. The nine-carbon alkyl spacer imparts flexibility, hydrophobicity, and moderate crystallinity to the resulting polymers, influencing their mechanical properties and thermal stability.

In the production of plasticizers, azelaic acid diethyl ester derivatives are valued for their ability to impart flexibility and durability to polymeric materials such as polyvinyl chloride (PVC). Additionally, the compound’s chemical structure enables it to act as a precursor in the synthesis of specialty surfactants and lubricants.

Physically, azelaic acid diethyl ester is generally a colorless to pale yellow liquid. It is soluble in common organic solvents including alcohols, ethers, and hydrocarbons but has limited water solubility due to its hydrophobic alkyl chain.

The compound is chemically stable under ambient conditions but may undergo hydrolysis in acidic or basic environments, reverting to azelaic acid and ethanol. Proper storage in a cool, dry place is recommended to maintain its integrity.

Azelaic acid and its derivatives, including diethyl ester, are also sourced from renewable feedstocks such as vegetable oils, supporting green chemistry initiatives and sustainable production practices.

In summary, azelaic acid diethyl ester is a bifunctional diester of azelaic acid used extensively in polymer synthesis, plasticizer production, and specialty chemical manufacturing. Its structural features and chemical reactivity enable diverse applications in industrial and research settings.

References

2021. Diethyl Azelate for the Treatment of Brown Recluse Spider Bite, a Neglected Orphan Indication. In vivo (Athens, Greece), 35(6).
DOI: 10.21873/invivo.12679

2017. Combination of ester biosynthesis and ω-oxidation for production of mono-ethyl dicarboxylic acids and di-ethyl esters in a whole-cell biocatalytic setup with Escherichia coli. Microbial Cell Factories, 16(1).
DOI: 10.1186/s12934-017-0803-9

2013. Acyloin Condensation of Diesters. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-126-00029