Dilauryl thiodipropionate
[CAS# 123-28-4]

Identification

• Classification: Food additive >> Antioxidants
• Name: Dilauryl thiodipropionate
• Synonyms: Didodecyl 3,3'-thiodipropionate
• Molecular Formula: C₃₀H₅₈O₄S
• Molecular Weight: 514.84
• CAS Registry Number: 123-28-4
• EC Number: 204-614-1
• SMILES: CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*, 0.915 g/mL
• Melting point: 40-42 °C
• Index of Refraction: 1.472, Calc.^*
• Boiling Point: 580.8±35.0 °C (760 mmHg), Calc.^*
• Flash Point: 264.8±14.0 °C, Calc.^*, >110 °C

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

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Risk Statements: H302-H319-H372-H410
• Safety Statements: P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Dilauryl thiodipropionate, commonly abbreviated as DLTD, is an organosulfur compound with the molecular formula C26H50O4S. This chemical belongs to the class of thiodipropionic acid esters and is characterized by its structure, which features two lauryl (dodecyl) groups attached to a thiodipropionate backbone. The discovery of dilauryl thiodipropionate dates back to the mid-20th century when researchers began exploring the potential of thiodipropionic acid esters as antioxidants in various applications.

The synthesis of dilauryl thiodipropionate typically involves the esterification of thiodipropionic acid with lauryl alcohol in the presence of an acid catalyst. This process results in the formation of the ester compound while releasing water as a byproduct. The resulting product is a pale yellow, oily liquid that is soluble in organic solvents but has limited solubility in water.

One of the primary applications of dilauryl thiodipropionate is as an antioxidant in the polymer industry. Its ability to scavenge free radicals and inhibit oxidative degradation makes it a valuable additive in the formulation of plastics, rubber, and other polymeric materials. By incorporating dilauryl thiodipropionate into polymer compositions, manufacturers can enhance the thermal stability and prolong the shelf life of their products. This is particularly important for materials that are exposed to heat, light, or oxygen, as these factors can accelerate oxidative reactions that lead to discoloration, loss of mechanical properties, and overall degradation.

In addition to its role as an antioxidant in polymers, dilauryl thiodipropionate is utilized in the production of lubricants and greases. Its properties allow it to improve the oxidative stability of lubricants, thereby extending their service life and performance under high-temperature conditions. This application is especially beneficial in automotive and industrial machinery, where lubrication is critical for reducing friction and wear between moving parts.

Moreover, dilauryl thiodipropionate has been explored for its potential as a stabilizer in cosmetic formulations. Its antioxidant properties can help protect sensitive ingredients from degradation due to exposure to air and light, ensuring the efficacy and longevity of cosmetic products. This application is particularly relevant in the formulation of creams, lotions, and other personal care products that may contain oils and other susceptible components.

While dilauryl thiodipropionate offers significant benefits, safety considerations must be taken into account. Although it is generally regarded as safe for use in industrial applications, exposure to concentrated forms can cause irritation to the skin and eyes. Proper handling and safety measures, including the use of personal protective equipment, are recommended when working with this compound in manufacturing settings.

In summary, dilauryl thiodipropionate is an important compound with diverse applications in the polymer, lubricant, and cosmetic industries. Its discovery as a thiodipropionic acid ester has led to the development of various products that benefit from its antioxidant properties. As research continues to explore new applications and formulations, dilauryl thiodipropionate will likely play a vital role in enhancing the stability and performance of a wide range of materials.

References

2010. Final Safety Assessment of Thiodipropionic Acid and Its Dialkyl Esters as Used in Cosmetics. International Journal of Toxicology.
DOI: 10.1177/1091581810373150

2014. Antioxidant synergism between synthesised alkylated diphenylamine and dilauryl thiodipropionate in polyolefin base fluid. Journal of Thermal Analysis and Calorimetry.
DOI: 10.1007/s10973-014-3808-1

2016. Comparative evaluation of free radical scavenging activities and cytotoxicity of various solvent fractions of Sandong Sageretia thea (Osbeck) M.C. Johnst. branches. Food Science and Biotechnology.
DOI: 10.1007/s10068-016-0259-4