Tris(4-nonylphenyl) phosphite
[CAS# 3050-88-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphorous compound
• Name: Tris(4-nonylphenyl) phosphite
• Synonyms: Tri(nonaphenyl) phosphite ester
• Molecular Formula: C₄₅H₆₉O₃P
• Molecular Weight: 689.00
• CAS Registry Number: 3050-88-2
• EC Number: 247-759-6
• SMILES: CCCCCCCCCC1=CC=C(C=C1)OP(OC2=CC=C(C=C2)CCCCCCCCC)OC3=CC=C(C=C3)CCCCCCCCC

Properties

• Index of Refraction: 1.526-1.528, (Expl.)
• Boiling Point: 692.0±54.0 °C (760 mmHg), Calc.
• Flash Point: 470.5±31.5 °C, Calc.

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08;GHS09 Danger
• Risk Statements: H315-H317-H318-H361-H400-H410
• Safety Statements: P201-P202-P261-P264-P272-P273-P280-P281-P302+P352-P305+P351+P338+P310-P308+P313-P333+P313-P362-P391-P405-P501

Discovery and Applications

Tris(4-nonylphenyl) phosphite is an organophosphite compound widely used as a stabilizer and antioxidant in polymers and other materials. The compound features three 4-nonylphenyl groups attached to a central phosphorous atom, forming a structure that provides excellent oxidative and thermal stabilization properties. Its versatility and efficiency make it a crucial additive in various industrial applications.

The discovery of tris(4-nonylphenyl) phosphite emerged from the need to improve the performance and longevity of polymers exposed to oxidative conditions. Early research focused on identifying additives capable of scavenging free radicals and decomposing hydroperoxides, two primary causes of polymer degradation. The synthesis of this compound involves the reaction of phosphorus trichloride with 4-nonylphenol in the presence of a base, yielding a highly effective stabilizing agent with good solubility and compatibility in polymer matrices.

One of the primary applications of tris(4-nonylphenyl) phosphite is in the plastics industry, where it is incorporated into polymers such as polyethylene, polypropylene, and polyvinyl chloride. It acts as a secondary antioxidant, complementing hindered phenols by decomposing hydroperoxides formed during processing and end use. This function prevents chain scission and discoloration, enhancing the durability and appearance of finished products.

In addition to polymer stabilization, tris(4-nonylphenyl) phosphite is used in the production of lubricants and adhesives. Its ability to prevent oxidative degradation in these materials ensures consistent performance under high-temperature and high-stress conditions. This capability is particularly important in automotive and industrial applications, where reliability and efficiency are critical.

Environmental considerations have driven research into the compound's biodegradability and potential for eco-friendly formulations. While tris(4-nonylphenyl) phosphite is effective in stabilizing materials, its environmental impact has prompted efforts to develop derivatives with improved safety profiles. This ongoing work aims to balance performance with sustainability, ensuring its continued relevance in modern industries.

References

2023. A “dilute-and-shoot” column-switching UHPLC-MS/MS procedure for the rapid determination of branched nonylphenol in human urine: method optimisation and some fundamental aspects of nonylphenol analysis. Analytical and Bioanalytical Chemistry, 415(5).
DOI: 10.1007/s00216-022-04495-5

2014. LC-MS/MS analytical procedure to quantify tris(nonylphenyl)phosphite, as a source of the endocrine disruptors 4-nonylphenols, in food packaging materials. Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment, 31(4).
DOI: 10.1080/19440049.2014.896481

2011. Most Plastic Products Release Estrogenic Chemicals: A Potential Health Problem That Can Be Solved. Environmental Health Perspectives, 119(7).
DOI: 10.1289/ehp.1003220