Bis(1,2,2,6,6-pentamethyl-4-piperidyl) [[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate
[CAS# 63843-89-0]

Identification

• Classification: Food additive >> Stabilizing and coagulating agent
• Name: Bis(1,2,2,6,6-pentamethyl-4-piperidyl) [[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate
• Molecular Formula: C₄₂H₇₂N₂O₅
• Molecular Weight: 685.04
• CAS Registry Number: 63843-89-0
• EC Number: 264-513-3
• SMILES: CCCCC(CC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)(C(=O)OC2CC(N(C(C2)(C)C)C)(C)C)C(=O)OC3CC(N(C(C3)(C)C)C)(C)C

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.531, Calc.^*
• Boiling Point: 644.2±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 343.4±31.5 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Risk Statements: H302-H372-H373-H410-H412
• Safety Statements: P260-P264-P270-P273-P301+P317-P319-P330-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335

• Transport Information: UN 3077

Discovery and Applications

Bis(1,2,2,6,6-pentamethyl-4-piperidyl) [[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate is a specialized organic compound recognized for its role as a hindered amine light stabilizer (HALS) and antioxidant. This complex molecule combines sterically hindered piperidine units with a phenolic moiety, providing it with unique properties to enhance the longevity and performance of polymeric materials. Its discovery and development stem from efforts to improve the durability of materials exposed to environmental stresses, particularly ultraviolet (UV) radiation and oxidative degradation.

The discovery of this compound can be attributed to advances in HALS technology, a field that gained traction in the mid-20th century as synthetic polymers began replacing traditional materials in numerous applications. Researchers aimed to address the susceptibility of these polymers to degradation caused by UV exposure and oxidation. By incorporating the piperidyl and phenolic structures into a single molecule, scientists achieved synergistic stabilization effects that significantly improved polymer performance.

The primary application of bis(1,2,2,6,6-pentamethyl-4-piperidyl) [[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate lies in the plastics and coatings industries. As a HALS, it effectively scavenges free radicals generated during photooxidative processes, thereby preventing chain reactions that degrade polymer structures. Its phenolic group further contributes by neutralizing peroxides and inhibiting oxidative reactions, ensuring long-term stability. This dual functionality makes it an indispensable additive in materials such as polyethylene, polypropylene, polyesters, and polyurethanes.

In the automotive and construction sectors, this compound is widely used in exterior applications where exposure to harsh weather conditions and UV radiation is inevitable. It enhances the lifespan and aesthetic appeal of plastic parts, protective coatings, and sealants. Additionally, its inclusion in agricultural films and packaging materials helps maintain their mechanical properties and transparency, even under prolonged sun exposure.

Research into this compound's environmental impact has underscored the need for sustainable practices in its application. While highly effective, its persistence in the environment has prompted studies into its biodegradability and potential for recycling. Emerging formulations aim to balance performance with environmental considerations, ensuring that this compound continues to support sustainable development.

Overall, bis(1,2,2,6,6-pentamethyl-4-piperidyl) [[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate exemplifies the intersection of molecular design and industrial utility. Its multifaceted stabilizing effects have made it a cornerstone in modern polymer technology, showcasing the potential of tailored chemistry to address both performance and durability challenges.

References

2009. Bis(1,2,2,6,6-pentamethylpiperidin-4-yl) 2-butyl-2-(3,5-di-tert-butyl-4-hydroxybenzyl)malonate (Tinuvin 144). Acta crystallographica. Section E, Structure reports online, 65(10).
DOI: 10.1107/s1600536809035260"