Diethyl 3,5-di-tert-butyl-4-hydroxybenzyl phosphate
[CAS# 976-56-7]

Identification

• Classification: Catalysts and additives >> Antioxidant
• Name: Diethyl 3,5-di-tert-butyl-4-hydroxybenzyl phosphate
• Synonyms: Antioxidant 1222
• Molecular Formula: C₁₉H₃₃O₄P
• Molecular Weight: 356.44
• CAS Registry Number: 976-56-7
• EC Number: 213-551-9
• SMILES: CCOP(=O)(CC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)OCC

Properties

• Melting point: 122 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

Diethyl 3,5-di-tert-butyl-4-hydroxybenzyl phosphate is an important chemical compound, primarily known for its role as an antioxidant. It is a phosphite ester derivative of 4-hydroxybenzyl, modified with di-tert-butyl groups, which enhances its stability and efficiency in protecting materials from oxidative degradation. This compound's structure, combining a phenolic antioxidant with a phosphate group, makes it highly effective in both neutralizing free radicals and stabilizing various organic materials exposed to thermal or oxidative stress.

The discovery of Diethyl 3,5-di-tert-butyl-4-hydroxybenzyl phosphate can be traced to efforts in the chemical industry to create more effective antioxidants that provide long-term protection, particularly for polymers and plastics. Antioxidants are crucial in extending the life of products exposed to heat, UV light, and air, as they prevent the breakdown of chemical bonds in materials. The incorporation of di-tert-butyl groups in this compound helps to create steric hindrance around the reactive center, thus increasing its resistance to oxidation.

One of the key applications of Diethyl 3,5-di-tert-butyl-4-hydroxybenzyl phosphate is in the stabilization of plastics, such as polypropylene, polyethylene, and polyvinyl chloride (PVC). These materials, commonly used in packaging, automotive parts, and consumer goods, are prone to degradation due to environmental exposure. When added as an antioxidant, this compound helps to maintain the mechanical properties and appearance of these polymers, preventing yellowing, brittleness, and surface cracking.

In addition to its use in plastic stabilization, Diethyl 3,5-di-tert-butyl-4-hydroxybenzyl phosphate is also applied in lubricants and oils. In these systems, it serves to protect the lubricants from oxidative breakdown during use, which helps maintain their performance over extended periods. This is particularly important in high-temperature or high-pressure applications, such as automotive engines, where the longevity of lubricants is critical for reducing wear and tear on engine components.

Furthermore, the compound finds utility in adhesives, coatings, and elastomers, where it acts as an effective stabilizer in formulations that are exposed to heat, light, or mechanical stress. It helps these materials retain their flexibility, strength, and resistance to environmental factors, which extends their useful life in industrial and consumer applications.

As the demand for more durable and sustainable materials grows, the use of antioxidants like Diethyl 3,5-di-tert-butyl-4-hydroxybenzyl phosphate will continue to be important. Its ability to safeguard polymers and other materials from premature degradation contributes to the production of higher-quality, longer-lasting products, thus supporting efforts to reduce material waste and improve sustainability.

References

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