2,4-Di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate
[CAS# 4221-80-1]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 2,4-Di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate
• Molecular Formula: C₂₉H₄₂O₃
• Molecular Weight: 438.66
• CAS Registry Number: 4221-80-1
• EC Number: 224-166-0
• SMILES: CC(C)(C)C1=CC(=C(C=C1)OC(=O)C2=CC(=C(C(=C2)C(C)(C)C)O)C(C)(C)C)C(C)(C)C

Properties

• Melting point: 195-197 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H303-H315-H319
• Safety Statements: P264-P280-P302+P352-P312-P337+P313-P305+P351+P338-P362+P364-P332+P313

Discovery and Applications

2,4-Di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, commonly known as a high-performance antioxidant, plays a critical role in enhancing the stability and longevity of various materials. This compound belongs to the class of phenolic antioxidants, which are widely utilized to prevent the degradation of polymers, plastics, and other materials exposed to oxidative stress.

The discovery of 2,4-Di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate emerged from the ongoing research into improving the stability of polymers and plastics. Researchers sought to develop antioxidants that could provide enhanced protection against thermal and oxidative degradation, thereby extending the lifespan and maintaining the performance of these materials. The synthesis of this compound involved modifying phenolic structures to increase their effectiveness in neutralizing free radicals, which are known to contribute to the degradation of polymers.

In terms of application, this antioxidant is extensively used in the plastics and rubber industries. It functions by scavenging free radicals that can initiate the oxidative degradation process. By inhibiting these radicals, the compound helps in maintaining the mechanical and physical properties of the materials, such as tensile strength, elasticity, and color stability. This makes it particularly valuable in applications where long-term performance and resistance to environmental factors are essential.

One of the primary uses of 2,4-Di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate is in the production of polyolefins, such as polyethylene and polypropylene. These polymers are widely used in packaging, automotive parts, and consumer goods. The inclusion of this antioxidant in their formulation ensures that the final products retain their quality and performance over extended periods, even under harsh conditions.

Additionally, this compound is employed in the stabilization of synthetic rubbers used in tires, seals, and gaskets. The antioxidant properties help in preventing the degradation caused by heat and oxidation, thereby improving the durability and safety of rubber products. It is also used in coatings and adhesives to enhance their resistance to aging and maintain their functionality over time.

The effectiveness of 2,4-Di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate has been demonstrated through extensive research and application. Studies have shown that it provides superior protection against oxidative damage compared to other antioxidants, contributing to the overall performance and reliability of the materials in which it is used. Its role in extending the service life of products and maintaining their properties makes it a valuable additive in various industrial applications.

In summary, 2,4-Di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate is a significant antioxidant used to improve the stability and longevity of polymers, plastics, and rubbers. Its ability to neutralize free radicals and prevent oxidative degradation makes it an essential component in the production of high-performance materials.

References

1980. Plastics from the aspect of hygiene. A contribution to the estimation of ultra-violet absorbers and light stabilizers from the aspect of hygiene. Journal of Hygiene, Epidemiology, Microbiology, and Immunology, 24(3).
URL: https://pubmed.ncbi.nlm.nih.gov/7190986

2014. Analysis of Personal Care Products in Sediments and Soils. Personal Care Products in the Aquatic Environment.
DOI: 10.1007/698_2014_264