Dimethyl azelate
[CAS# 1732-10-1]

Identification

• Classification: Catalysts and additives >> Plastic rubber additive
• Name: Dimethyl azelate
• Synonyms: Dimethyl nonanedioate; Azelaic acid dimethyl ester
• Molecular Formula: C₁₁H₂₀O₄
• Molecular Weight: 216.27
• CAS Registry Number: 1732-10-1
• EC Number: 217-060-0
• SMILES: COC(=O)CCCCCCCC(=O)OC

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*, 1.007 g/mL (Expl.)
• Melting point: 18 ºC (Expl.)
• Boiling point: 276.0 ºC 760 mmHg (Calc.)^*, 301.2 ºC (Expl.)
• Flash point: 117.4±16.9 ºC (Calc.)^*, 113 ºC (Expl.)
• Index of refraction: 1.434 (Calc.)^*, 1.435 (Expl.)

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

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H318
• Precautionary Statements: P264+P265-P280-P305+P354+P338-P317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318

Discovory and Applicatios

Dimethyl azelate is a dialkyl ester derived from azelaic acid, a nine-carbon dicarboxylic acid with the molecular formula C₁₁H₂₀O₄. Structurally, dimethyl azelate consists of a linear nine-carbon chain terminated at both ends by methyl ester groups. It is commonly referred to as the dimethyl ester of azelaic acid and belongs to the class of dialkyl esters frequently used in polymer and organic synthesis.

The synthesis of dimethyl azelate is typically achieved by the esterification of azelaic acid with methanol in the presence of acid catalysts such as sulfuric acid or p-toluenesulfonic acid. This reaction is conducted under reflux conditions, with the continuous removal of water to shift the equilibrium toward ester formation. Purification methods include distillation or recrystallization to obtain the compound in high purity.

Dimethyl azelate serves as an important intermediate in the production of polyesters, plasticizers, lubricants, and surfactants. Its bifunctional ester groups enable polycondensation reactions with diols to form polyesters exhibiting flexibility, chemical resistance, and varying degrees of crystallinity. The nine-carbon aliphatic chain influences the physical properties of the polymers, such as melting temperature, tensile strength, and biodegradability.

In the plastics and polymer industries, dimethyl azelate is valued for its role in synthesizing materials with improved softness and elasticity. The polymers derived from azelate esters can be designed to have applications ranging from fibers to coatings and biodegradable packaging materials. Additionally, ester groups can undergo selective transformations such as hydrolysis or transesterification, facilitating the production of derivatives with tailored functionalities.

Beyond polymer synthesis, dimethyl azelate is employed in the formulation of plasticizers and lubricants, where its chemical stability and hydrophobic character enhance the performance and longevity of these materials. It is also used as a chemical intermediate in the manufacture of surfactants and emulsifiers, where modifications of its ester groups lead to amphiphilic molecules.

Dimethyl azelate has favorable solubility characteristics, being soluble in many organic solvents such as alcohols, ethers, and chlorinated hydrocarbons, but only sparingly soluble in water. This allows its use in various organic synthesis and formulation processes.

The compound is typically a colorless to pale yellow liquid or solid at room temperature, depending on its purity and preparation method. It is chemically stable under ambient conditions but sensitive to hydrolysis in the presence of strong acids or bases.

Azelaic acid and its derivatives, including dimethyl azelate, are notable for their derivation from renewable resources. Industrial production often involves the oxidative cleavage of unsaturated fatty acids, such as oleic acid from vegetable oils, making dimethyl azelate a bio-based chemical. This renewable sourcing aligns with growing emphasis on sustainable and green chemistry practices.

In summary, dimethyl azelate is a versatile and widely used dialkyl ester that functions as a key intermediate in polymer chemistry, plasticizer manufacture, and specialty chemical synthesis. Its favorable chemical properties and renewable origins contribute to its ongoing relevance in industrial and environmental applications.

References

2023. Biodegradable polyester-polybutylene succinate (PBS): a review. Polymer Bulletin, 80(9).
DOI: 10.1007/s00289-023-04998-w

2024. Poly(butylene Succinate-co-butylene Brassylate) Derived from Brassylic Acid: Structures and Properties. Journal of Polymers and the Environment, 32(6).
DOI: 10.1007/s10924-024-03330-5

2021. Identification and quantification of dicarboxylic fatty acids in head tissue of farmed Nile tilapia (Oreochromis niloticus). European Food Research and Technology, 247(7).
DOI: 10.1007/s00217-021-03747-5