Tris(2,2,2-trifluoroethyl) phosphate
[CAS# 358-63-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphonate / phosphonate
• Name: Tris(2,2,2-trifluoroethyl) phosphate
• Synonyms: NSC 191836
• Molecular Formula: C₆H₆F₉O₄P
• Molecular Weight: 344.07
• CAS Registry Number: 358-63-4
• EC Number: 807-105-8
• SMILES: C(C(F)(F)F)OP(=O)(OCC(F)(F)F)OCC(F)(F)F

Properties

• Solubility: Slightly soluble (4.1 g/L) (25 ºC), Calc.^*
• Density: 1.564±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: -22 ºC^**
• Boiling point: 186-189 ºC^**
• Refractive index: 1.3200 (20 ºC)^***
• Flash point: 60.4±27.3 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

^** Chugunov, V. S.; Zhurnal Obshchei Khimii 1968, V38(2), P416.

^*** Goryunov, E. I.; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya 1990, (4), P878-86.

Safety Data

• Hazard Symbols: GHS02;GHS07 Warning
• Hazard Statements: H226-H302+H312+H332-H302-H312-H315-H319-H332-H335
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Tris(2,2,2-trifluoroethyl) phosphate (C₆H₉F₉O₄P) is an organophosphate compound that contains three 2,2,2-trifluoroethyl groups attached to a central phosphate core. The trifluoroethyl group is a highly fluorinated alkyl chain, characterized by the presence of three fluorine atoms attached to a carbon backbone, which imparts unique properties to the compound, such as enhanced chemical stability, low surface energy, and hydrophobicity. These properties make tris(2,2,2-trifluoroethyl) phosphate highly useful in a variety of industrial applications, particularly in materials science and chemical manufacturing.

Tris(2,2,2-trifluoroethyl) phosphate was first developed as a high-performance flame retardant. Organophosphate esters are known for their ability to disrupt combustion processes, and the addition of trifluoroethyl groups further enhances these flame-retardant properties. The fluorinated groups help lower the volatility and improve the thermal stability of materials, making them ideal for use in high-temperature environments. The compound is used in a wide range of applications, including coatings, resins, and specialty plastics, where flame resistance is a key requirement.

This chemical compound is often incorporated into polymers to provide flame resistance without compromising the overall physical properties of the material. Its effectiveness as a plasticizer in polymers also helps improve the processability of rigid or brittle polymer systems. For example, it can be found in the production of coatings and paints, where it enhances both the fire resistance and durability of the finished product. The combination of thermal stability, resistance to oxidative degradation, and excellent compatibility with other polymer components makes tris(2,2,2-trifluoroethyl) phosphate a valuable additive in the development of high-performance materials.

In addition to its use as a flame retardant, tris(2,2,2-trifluoroethyl) phosphate has found applications in the electronics and automotive industries, particularly in the formulation of high-performance materials used in cables, connectors, and other components exposed to high temperatures. The compound is also employed in some medical devices where resistance to heat and chemical degradation is essential. The stability provided by the trifluoroethyl groups helps extend the longevity and performance of these materials in demanding environments.

The compound is also useful in chemical synthesis, where it serves as a reagent or intermediate in the preparation of other fluorinated compounds. The trifluoroethyl groups can be transferred to other molecules in various synthetic processes, enabling the development of new fluorinated materials. The solvation properties of tris(2,2,2-trifluoroethyl) phosphate have also been explored in electrolyte systems, particularly in lithium-ion and other rechargeable batteries. Its role as a stabilizing agent for the electrolytes in these systems has been of interest in improving the efficiency and lifespan of battery components.

Despite its usefulness, tris(2,2,2-trifluoroethyl) phosphate must be handled with care due to potential environmental and health concerns. Phosphate esters, in general, are known to be toxic to aquatic life, and long-term exposure may have adverse effects on the environment. As a result, it is important to ensure that the compound is disposed of properly and that industrial processes involving its use adhere to environmental regulations. Additionally, the compound's stability in the presence of moisture can be a consideration, as hydrolysis of the phosphate ester may occur under certain conditions, leading to the formation of by-products that may affect its performance.

In summary, tris(2,2,2-trifluoroethyl) phosphate is a valuable chemical compound with a broad range of applications. Its role as a flame retardant and plasticizer, coupled with its chemical stability, makes it an essential component in the development of high-performance materials used in various industries, including electronics, automotive, and coatings. Furthermore, its use as a reagent in chemical synthesis and its application in electrolyte systems continue to make it a versatile compound in modern material science. However, like all chemical substances, its environmental and health impacts must be carefully managed to ensure safe use and disposal.

References

2024. Anion-cation interactions dictate safe and stable electrolytes for sodium-ion batteries. Communications Materials, 5(1).
DOI: 10.1038/s43246-024-00556-7

2021. Improved stability of highly concentrated LiBF4/fluorinated ethyl acetate-based electrolyte solutions with a co-solvent for LiNi0.8Co0.1Mn0.1O2 positive electrodes in lithium ion batteries. Journal of Applied Electrochemistry, 51(9).
DOI: 10.1007/s10800-021-01590-w

2010. Electrochemical performance of tris(2-chloroethyl) phosphate as a flame-retarding additive for lithium-ion batteries. Metals and Materials International, 16(4).
DOI: 10.1007/s12540-010-0811-3