Dimethyl dodecanedioate
[CAS# 1731-79-9]

Identification

• Classification: Analytical chemistry >> Food safety >> Fatty acid, fatty acid methyl ester
• Name: Dimethyl dodecanedioate
• Synonyms: Dimethyl 1,10-Decanedicarboxylate; Dodecanedioic acid dimethyl ester
• Molecular Formula: C₁₄H₂₆O₄
• Molecular Weight: 258.36
• CAS Registry Number: 1731-79-9
• EC Number: 217-050-6
• SMILES: COC(=O)CCCCCCCCCCC(=O)OC

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*
• Melting point: 30 - 32 ºC (Expl.)
• Boiling point: 300.9±10.0 ºC 760 mmHg (Calc.)^*, 356.5 - 357.8 ºC (Expl.)
• Flash point: 135.0±17.4 ºC (Calc.)^*
• Index of refraction: 1.441 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P264-P270-P301+P312-P330

Discovory and Applicatios

Dimethyl dodecanedioate is a diester derived from dodecanedioic acid, a saturated aliphatic dicarboxylic acid with a twelve-carbon linear chain. Its molecular formula is C₁₄H₂₆O₄, and its structure consists of a dodecane backbone terminated at both ends by methyl ester groups. As a symmetric molecule, it is classified as a dialkyl ester and is commonly referred to as the dimethyl ester of dodecanedioic acid.

The synthesis of dimethyl dodecanedioate typically involves the esterification of dodecanedioic acid with methanol in the presence of an acid catalyst such as sulfuric acid or p-toluenesulfonic acid. The reaction proceeds under reflux conditions, often with removal of water to drive the equilibrium toward ester formation. High-purity dimethyl dodecanedioate can also be obtained by transesterification of other esters or by direct catalytic processes utilizing renewable feedstocks.

This compound serves as an important intermediate in the production of specialty polymers, plasticizers, and lubricant additives. Its bifunctional ester groups enable it to undergo polycondensation reactions with diols to form polyesters with desirable thermal and mechanical properties. The long hydrocarbon chain provides flexibility and hydrophobicity to the polymer backbone, influencing crystallinity and durability. Polyesters derived from dimethyl dodecanedioate find applications in fibers, films, coatings, and biodegradable materials.

In addition to polymer synthesis, dimethyl dodecanedioate is used as a precursor for producing various specialty chemicals. Reduction or hydrolysis of the ester groups yields corresponding alcohols or acids, which can then be further functionalized. It is also utilized in the manufacture of plasticizers, where its ester moieties contribute to plastic flexibility and compatibility with polymer matrices. Its chemical stability and low volatility make it suitable for use in high-performance lubricant formulations, providing enhanced viscosity and oxidative resistance.

Due to its relatively long carbon chain and ester functionality, dimethyl dodecanedioate exhibits good solubility in organic solvents such as alcohols, ethers, and chlorinated hydrocarbons, while being practically insoluble in water. This property facilitates its use in solvent-based synthesis and formulation processes.

The compound is generally a colorless liquid or low-melting solid, stable under ambient conditions but sensitive to strong hydrolytic or basic environments which can cleave the ester bonds. Handling requires standard precautions for ester compounds, including storage in dry, cool conditions to prevent degradation.

Dimethyl dodecanedioate’s role in industrial chemistry is closely linked to sustainable and green chemistry trends, as dodecanedioic acid itself can be obtained from renewable sources such as biomass-derived fatty acids or microbial fermentation. This bio-based origin enhances the attractiveness of dimethyl dodecanedioate as a feedstock in environmentally friendly polymer and chemical production.

In summary, dimethyl dodecanedioate is a valuable dialkyl ester intermediate widely used in polymer chemistry, plasticizer manufacture, and lubricant formulation. Its chemical versatility, structural symmetry, and derivation from renewable feedstocks support its continued relevance in advanced materials and sustainable industrial applications.

References

2016. Castor oil as a potential renewable resource for the production of functional materials. Sustainable Chemical Processes, 4(1).
DOI: 10.1186/s40508-016-0055-8

2010. Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol. Biotechnology Letters, 32(10).
DOI: 10.1007/s10529-010-0311-z

2005. Copolymeric polythioesters by lipase-catalyzed thioesterification and transthioesterification of alpha,omega-alkanedithiols. Applied Microbiology and Biotechnology, 68(3).
DOI: 10.1007/s00253-005-027-5