Octyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate
[CAS# 125643-61-0]

Identification

• Classification: Food additive >> Antioxidants
• Name: Octyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate
• Synonyms: 3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid C7-9-branched alkyl esters; Antioxidant 1135; Evernox 1135
• Molecular Formula: C₂₅H₄₂O₃
• Molecular Weight: 390.60
• CAS Registry Number: 125643-61-0
• EC Number: 406-040-9
• SMILES: CCCCCCCCOC(=O)CCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C

Properties

• Solubility: 0.0007351 mg/L (25 °C water)
• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.493, Calc.^*
• Melting point: 178.58 °C
• Boiling Point: 444.4±40.0 °C (760 mmHg), Calc.^*, 444.78 °C
• Flash Point: 159.2±20.1 °C, Calc.^*

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

Safety Data

• Risk Statements: H413
• Safety Statements: P273-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

Octyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate, commonly known as Irganox 1076, is a phenolic antioxidant widely used in the polymer industry to prevent the oxidative degradation of plastics and other materials. The discovery of this compound was driven by the need for more effective stabilizers that could extend the lifespan and maintain the properties of polymers exposed to environmental factors such as heat, light, and oxygen.

The synthesis of octyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate involves the esterification of 3,5-di-tert-butyl-4-hydroxyhydrocinnamic acid with 2-ethylhexanol. The presence of the bulky tert-butyl groups in the molecule provides steric hindrance, which protects the phenolic hydroxyl group from reacting with free radicals, thus enhancing the compound’s antioxidant properties. The octyl group, derived from 2-ethylhexanol, increases the lipophilicity of the molecule, improving its compatibility with various polymer matrices and ensuring its uniform distribution within the material.

One of the primary applications of octyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate is in the stabilization of polyolefins such as polyethylene and polypropylene. These polymers are prone to oxidative degradation, which can lead to discoloration, brittleness, and loss of mechanical properties. By incorporating this antioxidant into the polymer matrix, manufacturers can significantly improve the material's resistance to oxidation, thereby extending its service life and maintaining its aesthetic and mechanical properties over time.

The use of octyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate is not limited to polyolefins; it is also effective in other polymers such as polyurethanes, polyamides, and polyesters. In these materials, the antioxidant helps to prevent the degradation that can occur during processing at high temperatures, as well as during the material’s use in end applications. The effectiveness of this compound in various polymer systems makes it a versatile and widely used additive in the plastics industry.

Another significant application of octyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate is in the stabilization of lubricants and oils. The compound is used in automotive and industrial lubricants to prevent the oxidation of the base oil, which can lead to the formation of sludge, varnish, and acidic by-products that degrade the performance of the lubricant. By preventing oxidative degradation, this antioxidant helps to maintain the viscosity, color, and overall performance of the lubricant over extended periods of use.

In addition to its antioxidant properties, octyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate also provides light stabilization, making it useful in applications where materials are exposed to UV radiation. The combination of light and thermal stability makes this compound particularly valuable in outdoor applications, where materials are subjected to harsh environmental conditions.

Research into octyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate continues as scientists explore its potential in new applications and improve its performance in existing ones. The compound’s ability to stabilize a wide range of materials makes it an essential component in the production of high-performance polymers, lubricants, and other materials that require long-term stability and durability.

References

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