2-(2-Hydroxy-3-tert-butyl-5-methylbenzyl)-4-methyl-6-tert-butylphenyl acrylate
[CAS# 61167-58-6]

Identification

• Classification: Catalysts and additives >> Antioxidant
• Name: 2-(2-Hydroxy-3-tert-butyl-5-methylbenzyl)-4-methyl-6-tert-butylphenyl acrylate
• Synonyms: Irganox 3052; 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) monoacrylate; 2-tert-Butyl-6-(3-tert-butyl-2-hydroxy-5-methylbenzyl)-4-methylphenyl acrylate
• Molecular Formula: C₂₆H₃₄O₃
• Molecular Weight: 394.55
• CAS Registry Number: 61167-58-6
• EC Number: 262-634-6
• SMILES: CC1=CC(=C(C(=C1)C(C)(C)C)O)CC2=C(C(=CC(=C2)C)C(C)(C)C)OC(=O)C=C

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*
• Boiling point: 491.6±44.0 ºC 760 mmHg (Calc.)^*
• Flash point: 185.0±21.2 ºC (Calc.)^*
• Index of refraction: 1.538 (Calc.)^*

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

Safety Data

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovory and Applicatios

2-(2-Hydroxy-3-tert-butyl-5-methylbenzyl)-4-methyl-6-tert-butylphenyl acrylate is a high-performance hindered phenol acrylate antioxidant and stabilizer, developed to provide excellent protection against thermal and oxidative degradation in polymeric and elastomeric materials. This compound belongs to the class of multifunctional acrylate derivatives of sterically hindered phenols and is especially valuable due to its dual-functionality, combining antioxidant properties with the ability to chemically bond into polymer networks via its acrylate moiety.

The molecule consists of two substituted phenolic rings, both featuring tert-butyl groups in the ortho positions, enhancing steric hindrance around the hydroxyl group and thereby increasing oxidative resistance. One of these phenols carries a hydroxybenzyl group that links to the other phenol through a methylene bridge. The acrylate group is attached to the 4-methyl-6-tert-butylphenyl ring, enabling the compound to copolymerize with unsaturated monomers during processing. This structural configuration allows the antioxidant functionality to be permanently incorporated into the polymer backbone, minimizing migration and leaching during use.

This compound was developed in response to limitations of conventional phenolic antioxidants, which, while effective, are often physically blended with the polymer matrix and may leach out or bloom to the surface over time. Such migration can reduce long-term stabilization and cause compatibility or regulatory issues, particularly in sensitive applications such as food packaging, medical devices, or automotive interiors. In contrast, acrylated phenols like 2-(2-hydroxy-3-tert-butyl-5-methylbenzyl)-4-methyl-6-tert-butylphenyl acrylate can be covalently integrated into the polymer, thus enhancing permanence and stability without sacrificing antioxidant efficacy.

Applications of this compound are primarily in acrylate and methacrylate polymer systems, UV-curable coatings, adhesives, elastomers, and high-performance thermoplastics. It is particularly useful in UV- and heat-sensitive formulations, where its combined stabilizing and reactive capabilities help protect polymers during both processing and end-use conditions. The acrylate group ensures excellent compatibility with acrylate-functional resins, enabling efficient dispersion and co-curing under UV light or thermal initiation.

In industrial formulations, it may be used alone or synergistically with other stabilizers, such as phosphites or thioethers, which can provide secondary stabilization through hydroperoxide decomposition. The overall effect is improved color retention, extended service life, and enhanced resistance to yellowing, embrittlement, and mechanical degradation over time.

Its synthesis typically involves the acylation of the hindered bisphenol with acryloyl chloride or a similar acrylic acid derivative, under conditions that preserve the integrity of the phenolic structure and ensure selective functionalization. The final product is a viscous liquid or crystalline solid, depending on its purity and formulation, and is soluble in a variety of organic solvents and reactive diluents.

Due to its ability to be immobilized within the polymer, this compound is also suitable for use in regulatory-sensitive applications where low extractables and leachables are required. By reducing the risk of antioxidant migration, it can improve product safety and regulatory compliance, especially in applications involving human contact or environmental exposure.

As demand increases for advanced materials with improved longevity and environmental performance, multifunctional stabilizers like 2-(2-hydroxy-3-tert-butyl-5-methylbenzyl)-4-methyl-6-tert-butylphenyl acrylate are gaining importance. Their utility in high-performance coatings, biomedical devices, and automotive materials highlights the shift toward integrated solutions that offer both performance and permanence within the polymer matrix.

References

2022. Medical Device Contact Allergy: Glucose Monitors and Insulin Pumps. Current Dermatology Reports.
DOI: 10.1007/s13671-021-00352-3

2024. Lignin-Based Rubber Composites and Bionanocomposites. Rubber Based Bionanocomposites.
DOI: 10.1007/978-981-10-2978-3_8

No publication date available. https://www.epa.gov/tsca-inventory. EPA TSCA Inventory.
URL: https://www.epa.gov/tsca-inventory