3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid thiodi-2,1-ethanediyl ester
[CAS# 41484-35-9]

Identification

• Classification: Catalysts and additives >> Antioxidant
• Name: 3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid thiodi-2,1-ethanediyl ester
• Synonyms: 2-[2-[3-(4-Hydroxy-3,5-ditert-butyl-phenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(4-hydroxy-3,5-ditert-butyl-phenyl)propanoate
• Molecular Formula: C₃₈H₅₈O₆S
• Molecular Weight: 642.93
• CAS Registry Number: 41484-35-9
• EC Number: 255-392-8
• SMILES: CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)CCC(=O)OCCSCCOC(=O)CCC2=CC(=C(C(=C2)C(C)(C)C)O)C(C)(C)C

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.533, Calc.^*
• Melting Point: 78 °C
• Boiling Point: 659.4±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 352.6±31.5 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Risk Statements: H302+H312-H315-H318-H411
• Safety Statements: P264-P270-P273-P280-P301+P312+P330-P302+P352+P312-P305+P351+P338+P310-P332+P313-P391-P501

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	2	H411

Discovery and Applications

3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid thiodi-2,1-ethanediyl ester, commonly referred to as a thiodiester of a hindered phenolic antioxidant, is a significant compound in the field of polymer chemistry and materials science. The discovery of this compound can be traced back to the ongoing quest for effective stabilizers and antioxidants to enhance the longevity and performance of various materials. As industries began to recognize the detrimental effects of oxidative degradation on polymers, researchers focused on developing antioxidants that could prevent such deterioration.

The synthesis of 3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid thiodi-2,1-ethanediyl ester involves the esterification of a hindered phenolic compound with a thiodiester. Hindered phenols are known for their ability to scavenge free radicals, thus providing excellent oxidative stability. The incorporation of thiodiester functionality enhances the compound’s effectiveness by providing additional sites for radical trapping and stabilizing polymer matrices against thermal and oxidative degradation.

One of the primary applications of this compound is in the stabilization of polymers, particularly in plastics, rubber, and coatings. The presence of the hindered phenolic group contributes to its ability to inhibit oxidation, prolonging the life and maintaining the physical properties of the materials. This is particularly valuable in applications such as automotive parts, electrical insulation, and consumer goods, where durability and resistance to environmental stressors are critical.

In addition to its role as an antioxidant in polymer formulations, 3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid thiodi-2,1-ethanediyl ester is also used in various industrial applications, including lubricants and oils. Its antioxidant properties help in preventing the degradation of these products, thereby ensuring optimal performance and extending their service life. The compound’s stability at elevated temperatures makes it particularly suitable for high-performance lubricants used in automotive and industrial machinery.

Moreover, the compound is being investigated for its potential use in food packaging materials. Its antioxidant properties can help protect food products from oxidative spoilage, thereby enhancing shelf life and maintaining quality. As consumers increasingly demand longer-lasting and safer food products, the incorporation of such antioxidants into packaging materials becomes essential.

Despite its numerous benefits, safety assessments of 3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid thiodi-2,1-ethanediyl ester are crucial. Like many chemical additives, it must be handled with care to minimize potential health risks. Regulatory bodies have established guidelines for the safe use of such compounds in consumer products, ensuring that they do not pose significant risks to human health or the environment.

In conclusion, 3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid thiodi-2,1-ethanediyl ester is a valuable antioxidant with diverse applications in polymer stabilization, lubricants, and food packaging. Its effective radical scavenging ability enhances the durability and performance of various materials, making it an essential compound in multiple industries. As research continues to evolve, the importance of this thiodiester in promoting the longevity and safety of consumer products is expected to grow.

References

1979. Khimicheskaya Promyshlennost, Seriya: Toksikologiya i Sanitarnaya Khimiya Plastmass. Chemical Industry, Series: Toxicology and Sanitation Chemistry of Plastics, (4)(36).

2008. Kinetics of thermolysis of sterically hindered phenols used as polymeric material stabilizers. Russian Journal of Applied Chemistry. DOI: 10.1134/s107042720809022x

2022. The Functionalized UiO-66 Engineering for the Synergistic Enhancement of Mechanical Properties of Polydicyclopentadiene Nanocomposites. Journal of Inorganic and Organometallic Polymers and Materials. DOI: 10.1007/s10904-022-02499-3