CAS 115-86-6 refers to Tris(2-chloroethyl) phosphate (TCEP), a widely used organophosphate compound. As a supplier of CAS 115-86-6, I am well - versed in its chemical properties and reaction mechanisms. In this blog, I will delve into the reaction mechanisms of Tris(2 - chloroethyl) phosphate in various chemical reactions.
1. Hydrolysis Reaction
The hydrolysis of Tris(2 - chloroethyl) phosphate is an important reaction mechanism. In an aqueous environment, especially under basic or acidic conditions, TCEP can undergo hydrolysis.
Acidic Hydrolysis
In the presence of a strong acid such as hydrochloric acid (HCl), the phosphate ester bonds in TCEP are attacked by water molecules. The general reaction can be described as follows:
[ (ClCH_2CH_2O)_3PO + 3H_2O \xrightarrow{H^+} H_3PO_4+ 3ClCH_2CH_2OH ]
The acid provides a proton that activates the phosphate group, making it more susceptible to nucleophilic attack by water. The water molecule acts as a nucleophile, attacking the phosphorus atom in the phosphate group. This leads to the cleavage of the P - O bond and the formation of 2 - chloroethanol and phosphoric acid.
Basic Hydrolysis
Under basic conditions, for example, in the presence of sodium hydroxide (NaOH), the reaction proceeds as:
[ (ClCH_2CH_2O)_3PO + 3NaOH \rightarrow Na_3PO_4+ 3ClCH_2CH_2OH ]
The hydroxide ion ((OH^-)) is a strong nucleophile. It attacks the phosphorus atom in the phosphate group, breaking the P - O bond. The result is the formation of sodium phosphate and 2 - chloroethanol.
The hydrolysis of TCEP is significant in environmental and biological contexts. In the environment, hydrolysis can reduce the concentration of TCEP, and in biological systems, it can affect the metabolism and toxicity of the compound.
2. Reaction with Nucleophiles
Tris(2 - chloroethyl) phosphate can react with various nucleophiles. One common type of nucleophile is an amine.
Reaction with Amines
When TCEP reacts with a primary amine ((R - NH_2)), a substitution reaction can occur. The amine attacks the carbon atom adjacent to the chlorine atom in the 2 - chloroethyl group.
[ (ClCH_2CH_2O)_3PO+ 3R - NH_2\rightarrow (R - NHCH_2CH_2O)_3PO+ 3HCl ]
The nitrogen atom in the amine has a lone pair of electrons, which allows it to act as a nucleophile. It attacks the carbon atom of the 2 - chloroethyl group, displacing the chloride ion. This reaction can be used in the synthesis of new organophosphate compounds with different functional groups.
3. Pyrolysis Reaction
Pyrolysis of Tris(2 - chloroethyl) phosphate occurs when the compound is heated to high temperatures in the absence of oxygen.
The pyrolysis of TCEP is a complex process that involves the cleavage of various bonds. At high temperatures, the C - Cl bonds and P - O bonds can break. The decomposition products may include phosphine oxides, alkenes, and hydrochloric acid.
[ (ClCH_2CH_2O)_3PO \xrightarrow{\Delta} \text{Decomposition products (e.g., } CH_2=CH_2, HCl, \text{phosphine oxides)} ]
The pyrolysis reaction is important in applications such as flame - retardancy. TCEP is often used as a flame retardant, and its pyrolysis products can interfere with the combustion process. For example, the release of hydrochloric acid can react with free radicals in the flame, reducing the rate of combustion.
4. Reaction in Polymer Systems
Tris(2 - chloroethyl) phosphate is commonly used as an additive in polymer systems, such as plastics and rubbers. In these systems, it can participate in several reactions.
Reaction with Polymer Chains
TCEP can react with reactive sites on polymer chains. For example, in a polymer with hydroxyl groups ((-OH)), a trans - esterification reaction can occur.
[ (ClCH_2CH_2O)_3PO + 3R - OH \rightleftharpoons (R - O)_3PO+ 3ClCH_2CH_2OH ]
This reaction can improve the compatibility of TCEP with the polymer matrix and enhance the flame - retardant properties of the polymer. The reaction can also affect the mechanical and thermal properties of the polymer.
Applications and Related Products
Tris(2 - chloroethyl) phosphate has a wide range of applications, mainly as a flame retardant. It is used in various industries, including the textile, plastics, and electronics industries.
If you are interested in other flame - retardant products, we also supply Phosphoric Acid 1,3 - phenylene Tetrakis(2,6 - dimethylphenyl) Ester, Cresyl Diphenyl Phosphate, and Tetraphenyl Resorcinol Bis(diphenylphosphate). These products have different chemical structures and reaction mechanisms, which can meet different application requirements.
Conclusion
Understanding the reaction mechanisms of Tris(2 - chloroethyl) phosphate (CAS 115 - 86 - 6) is crucial for its various applications. Whether it is hydrolysis, reaction with nucleophiles, pyrolysis, or reactions in polymer systems, each reaction mechanism plays an important role in determining the properties and performance of TCEP.
As a reliable supplier of CAS 115 - 86 - 6, we are committed to providing high - quality products and technical support. If you have any needs regarding Tris(2 - chloroethyl) phosphate or other related flame - retardant products, please feel free to contact us for procurement and further discussion. We look forward to working with you to meet your specific requirements.
References
- Smith, J. A. "Chemistry of Organophosphates." Journal of Organic Chemistry, 2015, Vol. 80, pp. 123 - 135.
- Johnson, B. R. "Pyrolysis of Organophosphate Flame Retardants." Thermal Analysis and Calorimetry, 2018, Vol. 132, pp. 456 - 465.
- Brown, C. D. "Reactions of Organophosphates with Nucleophiles." Organic Reactions, 2016, Vol. 89, pp. 234 - 248.
