Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate
[CAS# 2082-79-3]

Identification

• Classification: Catalysts and additives >> Antioxidant
• Name: Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate
• Synonyms: 3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid octadecyl ester
• Molecular Formula: C₃₅H₆₂O₃
• Molecular Weight: 530.87
• CAS Registry Number: 2082-79-3
• EC Number: 218-216-0
• SMILES: CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Melting point: 50-52 °C
• Index of Refraction: 1.487, Calc.^*
• Boiling Point: 568.1±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 196.3±21.5 °C, Calc.^*, 273 °C

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317
• Safety Statements: P261-P272-P280-P302+P352-P321-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovery and Applications

Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, commonly known as antioxidant 1010 or by its trade name Irganox 1010, is a synthetic compound that has gained prominence in various industrial applications due to its excellent antioxidant properties. The discovery of this compound can be traced back to the research efforts in the 1970s aimed at developing effective stabilizers for polymers and other materials susceptible to oxidative degradation. Its unique chemical structure, which includes a long hydrocarbon chain and a phenolic hydroxyl group, contributes to its effectiveness in protecting materials from oxidative stress.

The synthesis of octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate involves the esterification of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with octadecanol. This process yields a compound that exhibits a high degree of thermal stability, making it particularly useful in applications where heat and light exposure can lead to the degradation of materials.

One of the primary applications of octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is in the plastic and polymer industry. It is widely used as an antioxidant additive in polyolefins, polyvinyl chloride (PVC), and other thermoplastic materials. By incorporating this antioxidant into polymer formulations, manufacturers can significantly extend the shelf life and performance of their products, reducing the risk of discoloration, brittleness, and loss of mechanical properties over time.

In addition to its use in plastics, octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate finds applications in the production of lubricants, oils, and coatings. In these formulations, it acts to inhibit the oxidative degradation of base oils and other components, ensuring that the products maintain their performance characteristics under various operating conditions. This property is particularly valuable in automotive and industrial lubricants, where oxidative stability is critical for optimal functionality and longevity.

Moreover, the compound is utilized in the formulation of food packaging materials. Its antioxidant properties help prevent the oxidation of food products, thus preserving flavor, color, and nutritional value. As consumer awareness regarding food safety and quality continues to rise, the demand for effective antioxidants in packaging materials has increased, further solidifying the importance of octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate in this sector.

Despite its widespread use, safety considerations regarding octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate have prompted ongoing research into its environmental impact and potential health effects. Regulatory agencies have established guidelines for its safe use, and manufacturers are required to adhere to these standards to minimize risks associated with its application.

In conclusion, octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is a vital antioxidant compound with diverse applications in the plastics, lubricants, and food packaging industries. Its discovery marked a significant advancement in the development of materials that are more resistant to oxidative degradation, ultimately leading to enhanced product performance and longevity. Continued research into its properties and applications will likely yield further innovations in material science and product formulation.

References

2024. Nanosponge hydrogel of octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl) propanoate of Alcaligenes faecalis. Applied Microbiology and Biotechnology, 108(1).
DOI: 10.1007/s00253-023-12819-3

2018. Chemo-Enzymatic Synthesis of Renewable Sterically-Hindered Phenolic Antioxidants with Tunable Polarity from Lignocellulose and Vegetal Oil Components. International Journal of Molecular Sciences, 19(11).
DOI: 10.3390/ijms19113358

2020. Synthesis of Fatty Alcohol based Sterically Hindered Esters as Potential Antioxidants for Bioadditives. Petroleum Chemistry, 60(11).
DOI: 10.1134/s0965544120110110