Tris(2-chloro-1-(chloromethyl)ethyl)phosphate
[CAS# 13674-87-8]

Identification

• Classification: Catalysts and additives >> Plastic rubber additive
• Name: Tris(2-chloro-1-(chloromethyl)ethyl)phosphate
• Synonyms: Tris(1-chloromethyl-2-chloroethyl)phosphate; Tris(1,3-dichloroisopropyl)phosphate; Tri(beta,beta'-dichloroisopropyl)phosphate; Phosphoric acid tris(1,3-dichloro-2-propyl)ester; Fyrol FR 2; PF 38; TCPP; TDCPP
• Molecular Formula: C₉H₁₅Cl₆O₄P
• Molecular Weight: 430.91
• CAS Registry Number: 13674-87-8
• EC Number: 237-159-2
• SMILES: C(C(CCl)OP(=O)(OC(CCl)CCl)OC(CCl)CCl)Cl

Properties

• Density: 1.512
• Melting point: -64 ºC
• Refraction index: 20
• Boiling point: 315 ºC
• Decomposition: 240-280 ºC
• Flash point: 249 ºC
• Water solubility: <0.1 g/100 mL at 24 ºC

Safety Data

• Hazard Symbols: GHS08;GHS09 Warning
• Hazard Statements: H351-H410
• Precautionary Statements: P202-P273-P280-P308+P313-P391-P405

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Carcinogenicity	Carc.	2	H351
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	3	H331

Discovory and Applicatios

Tris(2-chloro-1-(chloromethyl)ethyl)phosphate, commonly referred to as tris(chloroethyl) phosphate (TCEP), is an organophosphate compound that has gained attention for its utility in various industrial applications, particularly as a flame retardant and plasticizer. Its unique structure, characterized by three chlorinated ethyl groups bonded to a phosphate moiety, contributes to its effectiveness in enhancing the fire resistance of materials.

The discovery of TCEP can be traced back to the mid-20th century, during a period of growing interest in the development of chemical compounds that could improve the safety and performance of synthetic materials. Organophosphate esters, including TCEP, were synthesized and studied for their potential applications in fire-retardant formulations due to their ability to inhibit combustion processes. The chlorinated nature of TCEP enhances its flame-retardant properties by promoting the formation of a char layer when exposed to heat, which acts as a barrier to flame propagation.

One of the primary applications of tris(2-chloro-1-(chloromethyl)ethyl)phosphate is in the manufacturing of flexible and rigid polyvinyl chloride (PVC) products. By incorporating TCEP into PVC formulations, manufacturers can significantly improve the material's resistance to ignition and flame spread. This property is particularly valuable in applications where fire safety is a critical concern, such as in building materials, electrical cables, and automotive components. TCEP is often preferred in environments that require stringent fire safety regulations, contributing to the overall safety and compliance of end products.

In addition to its role as a flame retardant, TCEP serves as a plasticizer, enhancing the flexibility and durability of PVC and other polymeric materials. As a plasticizer, TCEP reduces the brittleness of plastics, allowing them to maintain their structural integrity under varying conditions. This dual functionality of TCEP as both a flame retardant and a plasticizer makes it a versatile additive in the plastics industry.

However, concerns have been raised regarding the environmental and health impacts of organophosphate compounds, including TCEP. Studies have indicated that certain organophosphates may pose risks to human health and the environment, particularly in terms of toxicity and bioaccumulation. As a result, regulatory scrutiny has increased, prompting the need for safer alternatives and more sustainable practices in the use of chemical additives.

The investigation of TCEP and similar compounds has led to ongoing research aimed at understanding their long-term effects and exploring safer substitutes. Alternatives such as halogen-free flame retardants and bio-based plasticizers are being developed to mitigate the potential risks associated with organophosphates, while still maintaining the desired performance characteristics in materials.

Tris(2-chloro-1-(chloromethyl)ethyl)phosphate exemplifies the balance between enhancing material safety and addressing environmental concerns. As industries continue to innovate and prioritize sustainability, the future of TCEP and its applications will depend on advances in research and the development of safer, more environmentally friendly alternatives that meet the stringent safety requirements of modern materials.

References

1981. The metabolism and disposition of tris(1,3-dichloro-2-propyl) phosphate (fyrol FR-2) in the rat. Toxicology and Applied Pharmacology, 57(3).
DOI: 10.1016/0041-008x(81)90238-6

2024. A critical review of wastewater-based epidemiology as a tool to evaluate the unintentional human exposure to potentially harmful chemicals. Analytical and Bioanalytical Chemistry, 416(24).
DOI: 10.1007/s00216-024-05596-z

2024. Phosphorous flame-retardant concentration in Finnish daycares dust and children's exposure. Chemosphere, 349.
DOI: 10.1016/j.chemosphere.2024.143820