Sodium 2,2'-methylene-bis-(4,6-di-tert-butylphenyl)phosphate
[CAS# 85209-91-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphonate / phosphonate
• Name: Sodium 2,2'-methylene-bis-(4,6-di-tert-butylphenyl)phosphate
• Synonyms: 2,4,8,10-Tetrakis(1,1-dimethylethyl)-6-hydroxy-12H-dibenzo[d,g][1,3,2]dioxaphosphocin 6-oxide sodium salt
• Molecular Formula: C₂₉H₄₂NaO₄P
• Molecular Weight: 508.61
• CAS Registry Number: 85209-91-2
• EC Number: 286-344-4
• SMILES: CC(C)(C)C1=CC2=C(C(=C1)C(C)(C)C)OP(=O)(OC3=C(C2)C=C(C=C3C(C)(C)C)C(C)(C)C)[O-].[Na+]

Properties

• Melting point: >300 °C (Expl.)

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H332-H411-H412
• Safety Statements: P261-P271-P273-P304+P340-P317-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H332
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Reproductive toxicity	Repr.	2	H361

• Transport Information: UN 3077

Discovery and Applications

Sodium 2,2'-methylene-bis-(4,6-di-tert-butylphenyl)phosphate is a prominent organophosphate compound known for its antioxidant properties and its application in polymer stabilization. The compound, characterized by its bulky tert-butyl-substituted phenyl groups and a sodium phosphate moiety, plays a critical role in preserving the integrity of materials subjected to oxidative stress, particularly polymers and plastics. Its discovery and development reflect the ongoing advancements in additive chemistry aimed at enhancing material performance.

The synthesis of sodium 2,2'-methylene-bis-(4,6-di-tert-butylphenyl)phosphate can be traced to research in the mid-20th century, which focused on organophosphates as stabilizers. Researchers identified the compound's ability to scavenge free radicals effectively, a property derived from its sterically hindered phenolic groups. This functionality inhibits oxidation processes that degrade polymers, making the compound a key ingredient in stabilizer formulations.

In industrial applications, sodium 2,2'-methylene-bis-(4,6-di-tert-butylphenyl)phosphate is widely used as an antioxidant additive in the production of plastics, rubbers, and elastomers. Its role is particularly significant in polyolefins such as polyethylene and polypropylene, where it prevents thermal and oxidative degradation during manufacturing and prolonged use. The compound's high thermal stability and low volatility make it suitable for high-temperature processing, ensuring consistent protection throughout the material's lifecycle.

The compound also finds applications in coatings, adhesives, and lubricants, where oxidative stability is crucial. In these formulations, sodium 2,2'-methylene-bis-(4,6-di-tert-butylphenyl)phosphate enhances product durability and maintains performance under harsh environmental conditions, such as exposure to heat and UV radiation. Additionally, its compatibility with other stabilizers, such as hindered amine light stabilizers (HALS), allows for synergistic effects that further extend the longevity of materials.

Recent research has explored the environmental and health aspects of using sodium 2,2'-methylene-bis-(4,6-di-tert-butylphenyl)phosphate. Studies indicate that the compound is effective in very low concentrations, minimizing its environmental footprint. Efforts are also underway to develop biodegradable analogs and alternative synthetic routes that align with green chemistry principles.

The versatility and effectiveness of sodium 2,2'-methylene-bis-(4,6-di-tert-butylphenyl)phosphate ensure its continued use across multiple industries. As demand for durable and sustainable materials grows, this compound remains a cornerstone of modern material science, contributing to innovation in polymer technology and beyond.

References

2024. Influence of nucleating agent on the mechanical and thermal properties of neat isotactic polypropylene/reprocessed polypropylene blends. Iranian Polymer Journal, 33(10).
DOI: 10.1007/s13726-024-01369-8

2020. Non-isothermal crystallization behavior of isotactic polypropylene/copper nanocomposites. Journal of Thermal Analysis and Calorimetry, 141(5).
DOI: 10.1007/s10973-020-09512-2

2015. Preparation and foaming mechanism of foamable polypropylene based on self-assembled nanofibrils from sorbitol nucleating agents. Journal of Materials Science, 50(22).
DOI: 10.1007/s10853-015-9402-5