Tetradecanedioic acid dimethyl ester
[CAS# 5024-21-5]

Identification

• Classification: Analytical chemistry >> Food safety >> Fatty acid, fatty acid methyl ester
• Name: Tetradecanedioic acid dimethyl ester
• Synonyms: 1,12-Dodecanedicarboxylic acid dimethyl ester; Dimethyl tetradecanedioate; NSC 9505
• Molecular Formula: C₁₆H₃₀O₄
• Molecular Weight: 286.41
• CAS Registry Number: 5024-21-5
• EC Number: 225-711-5
• SMILES: COC(=O)CCCCCCCCCCCCC(=O)OC

Properties

• Solubility: Practically insoluble (0.034 g/L) (25 ºC), Calc.^*
• Density: 0.955±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: 54-58 ºC^**
• Boiling point: 326.6±10.0 ºC 760 mmHg (Calc.)^*
• Flash point: 146.4±17.4 ºC (Calc.)^*
• Index of refraction: 1.445 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

^** Motoki, Shinichi; Nippon Kagaku Zasshi 1960, V81, P665-7.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Tetradecanedioic acid dimethyl ester is the dimethyl ester derivative of tetradecanedioic acid, a saturated dicarboxylic acid with a fourteen-carbon linear chain. The molecular formula of tetradecanedioic acid dimethyl ester is C₁₆H₃₀O₄. This compound contains two methyl ester functional groups located at both ends of the aliphatic chain, making it a bifunctional ester useful in organic synthesis and polymer chemistry.

The synthesis of tetradecanedioic acid dimethyl ester is typically accomplished through the esterification of tetradecanedioic acid with methanol in the presence of acid catalysts such as sulfuric acid or p-toluenesulfonic acid. The reaction is conducted under reflux with removal of water to drive the equilibrium toward ester formation. Alternative methods may involve transesterification or reaction of tetradecanedioyl chloride with methanol.

Tetradecanedioic acid dimethyl ester is a key intermediate in the preparation of polyesters and other polymers. The presence of two ester groups at the termini of the fourteen-carbon alkyl chain enables its participation in polycondensation reactions with diols or diamines, resulting in materials with enhanced flexibility, hydrophobicity, and thermal stability. Compared to shorter-chain esters, polymers derived from tetradecanedioic acid dimethyl ester typically exhibit lower crystallinity and increased chain mobility, which influence mechanical properties.

In addition to polymer synthesis, this dimethyl ester serves as a precursor for specialty chemicals, plasticizers, and surfactants. Chemical modifications such as hydrolysis, reduction, or transesterification provide access to a variety of derivatives tailored for specific applications. Its relatively low volatility and chemical stability under ambient conditions make it suitable for incorporation in formulation processes.

Physically, tetradecanedioic acid dimethyl ester is generally a colorless to pale yellow liquid or waxy solid depending on purity and temperature. It exhibits good solubility in organic solvents such as alcohols, ethers, and hydrocarbons, but limited solubility in water due to its hydrophobic alkyl chain.

The compound is chemically stable under normal storage conditions but can undergo hydrolysis in strongly acidic or basic environments. Proper storage in a cool, dry place away from moisture is recommended to maintain its integrity.

Tetradecanedioic acid and its esters can be derived from renewable resources such as plant oils or microbial fermentation products, supporting sustainable chemical manufacturing and green chemistry initiatives.

In summary, tetradecanedioic acid dimethyl ester is a bifunctional diester with two methyl ester groups on a fourteen-carbon alkyl chain. It is widely used as an intermediate in polymer synthesis, specialty chemical production, and materials science. Its structural features and chemical reactivity enable diverse applications in industrial and research contexts.

References

2009. Kolbe Electrolysis. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-048-00023

1975. Generation of ω-carbomethoxyalkyl radicals and syntheses based on them. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 24(11).
DOI: 10.1007/bf00921653

1968. Isolation of tetradecan-1,14-dioic acid from the comstock mealybug,Pseudococcus comstocki Kuwana (Homoptera: Pseudococcidae). Lipids, 3(3).
DOI: 10.1007/bf02531741