Dimethyl suberate
[CAS# 1732-09-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Methyl ester compound
• Name: Dimethyl suberate
• Synonyms: Octanedioic acid dimethyl ester
• Molecular Formula: C₁₀H₁₈O₄
• Molecular Weight: 202.25
• CAS Registry Number: 1732-09-8
• EC Number: 217-059-5
• SMILES: COC(=O)CCCCCCC(=O)OC

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*, 1.016 g/mL (Expl.)
• Boiling point: 268.0 °C 760 mmHg (Calc.)^*, 266 - 268 °C (Expl.)
• Flash point: 111.4±16.9 °C (Calc.)^*
• Index of refraction: 1.431 (Calc.)^*, 1.432 (Expl.)

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

Safety Data

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

Discovery and Applications

Dimethyl suberate is a diester compound derived from suberic acid, which is an eight-carbon linear dicarboxylic acid. Its molecular formula is C₁₀H₁₈O₄, consisting of a suberic acid backbone where both terminal carboxyl groups have been esterified with methyl groups. This symmetric diester belongs to the family of dialkyl esters and is commonly used as an intermediate in organic synthesis and polymer chemistry.

The preparation of dimethyl suberate is typically accomplished through the esterification of suberic acid with methanol, catalyzed by strong acids such as sulfuric acid or p-toluenesulfonic acid. The reaction is usually performed under reflux, with water removal to drive the equilibrium toward ester formation. The purity of the resulting dimethyl suberate can be enhanced by distillation or recrystallization techniques.

Dimethyl suberate is widely employed as a building block in the synthesis of polyesters and other polymers. When reacted with diols, it undergoes polycondensation to form polyester chains, which can be used in fibers, films, coatings, and biodegradable plastics. The eight-carbon chain length of suberate units imparts flexibility and moderate crystallinity to the polymers, influencing their mechanical strength and thermal properties.

Beyond polymerization, dimethyl suberate serves as an intermediate in the synthesis of specialty chemicals, including plasticizers, lubricants, and surfactants. Its ester groups can be selectively transformed through hydrolysis or transesterification, yielding functionalized derivatives for further chemical modifications. The compound’s relatively low volatility and good chemical stability under normal conditions contribute to its utility in formulation chemistry.

Dimethyl suberate exhibits solubility in various organic solvents such as alcohols, ethers, and chlorinated solvents, while being sparingly soluble in water. This solubility profile facilitates its use in diverse synthetic and industrial processes.

Physically, dimethyl suberate is typically a colorless liquid or crystalline solid with a melting point that depends on its purity and sample preparation. It is stable under ambient temperature and pressure but should be stored away from moisture and strong bases to prevent hydrolysis.

The compound’s role in sustainable chemistry is enhanced by the potential to source suberic acid from renewable biomass, such as the oxidative cleavage of fatty acids derived from plant oils. This renewable origin supports the development of bio-based polymers and chemicals, aligning with environmental and economic goals.

In conclusion, dimethyl suberate is a versatile dialkyl ester widely utilized in polymer synthesis, chemical manufacturing, and formulation industries. Its combination of chemical reactivity, physical properties, and potential renewable sourcing continues to support its significance in modern industrial applications.

References

2005. New transformation of cycloalkanone acetals by peracids α,ω-dicarboxylic acids synthesis. Central European Journal of Chemistry.
DOI: 10.2478/bf02479272

2023. 1,12-Dodecanediol-Based Polyesters Derived from Aliphatic Diacids with Even Carbons: Synthesis and Characterization. Journal of Polymers and the Environment, 31(5).
DOI: 10.1007/s10924-023-02884-0

2007. Resins and additives for powder coatings and alkyd paints, based on renewable resources. Journal of Coatings Technology and Research, 4(4).
DOI: 10.1007/s11998-007-9020-5