Cyanuric chloride [2,4,6-Trichloro-1,3,5-triazine]

Cyanuric chloride (C3Cl3N3) is a chemical compound with various industrial and chemical applications. It is associated with mousey irritating odor, dissolves well in organic solvents. It is obtained by trimerization of cyanogen chloride - analogous to acetylene synthesis of benzene, the driving force, of course, is the formation of a resonance-stabilized aromatic 1,3,5-triazine ring.

Properties:

• Chemical Formula: C3Cl3N3
• Molecular Weight: 184.41 g/mol
• Appearance: White crystalline solid
• Melting Point: 146-148 °C
• Boiling Point: Decomposes before boiling
• Solubility: Insoluble in water, but soluble in organic solvents like acetone, benzene, and chloroform.

Uses:

1. Intermediate in Chemical Synthesis:

   • Pesticides and Herbicides: Used in the production of agrochemicals.
   • Pharmaceuticals: Intermediate for the synthesis of various pharmaceutical compounds.
   • Dyes and Pigments: Precursor in the production of certain dyes and pigments.

2. Polymer Production:

   • Resins: Utilized in the manufacture of resins for coatings and adhesives.
   • Stabilizers: Acts as a stabilizing agent in some polymer production processes.

3. Water Treatment:

   • While cyanuric acid (derived from cyanuric chloride) is used in water treatment, cyanuric chloride itself is not typically used directly in this application.

Synthesis:

1. Preparation of Hydrogen Cyanide (HCN):

   • Hydrogen cyanide can be produced by the Andrussow process, which involves the reaction of methane, ammonia, and oxygen over a platinum catalyst: CH4+NH3+1.5O2→HCN+3H2O\text{CH}_4 + \text{NH}_3 + 1.5 \text{O}_2 \rightarrow \text{HCN} + 3 \text{H}_2\text{O}CH4+NH3+1.5O2→HCN+3H2O

2. Reaction with Chlorine:

   • The hydrogen cyanide prouced is then reacted with chlorine gas to produce cyanogen chloride: Cl2+HCN→ClCN+HCl\text{Cl}_2 + \text{HCN} \rightarrow \text{ClCN} + \text{HCl}Cl2+HCN→ClCN+HCl

3. Trimerization:

1.  

   • The cyanogen chloride is passed through a heated catalyst bed, which facilitates the trimerization reaction. Common catalysts for this process include activated carbon or specific transition metal salts.
   • The trimerization typically occurs at temperatures around 180-250°C.

2. Purification:

   • The crude cyanuric chloride produced is purified by distillation or recrystallization to remove any unreacted cyanogen chloride and other impurities.

Reaction Conditions:

• Temperature: 180-250°C
• Catalyst: Activated carbon or transition metal salts
• Pressure: Often carried out under atmospheric pressure, but conditions may vary based on the specific industrial setup.

Safety and Handling:

• Toxicity: Both cyanogen chloride and cyanuric chloride are highly toxic. Proper safety protocols must be followed.
• Protective Equipment: Use appropriate PPE, including gloves, goggles, and respiratory protection.
• Ventilation: Perform reactions in a well-ventilated area or fume hood to avoid inhalation of toxic gases.

Reaction Conditions:

• Temperature: 180-250°C
• Catalyst: Activated carbon or transition metal salts
• Pressure: Often carried out under atmospheric pressure, but conditions may vary based on the specific industrial setup.

Safety and Handling

• Toxicity: Both cyanogen chloride and cyanuric chloride are highly toxic. Proper safety protocols must be followed.
• Protective Equipment: Use appropriate PPE, including gloves, goggles, and respiratory protection.
• Ventilation: Perform reactions in a well-ventilated area or fume hood to avoid inhalation of toxic gases.

Safety Considerations:

• Toxicity: Cyanuric chloride is toxic and can cause severe irritation to the skin, eyes, and respiratory system. It should be handled with care.
• Protective Equipment: Use appropriate personal protective equipment (PPE) such as gloves, goggles, and respiratory protection.
• Storage: Store in a cool, dry, well-ventilated area away from incompatible substances such as strong bases and oxidizing agents.
• Environmental Impact: It is harmful to aquatic life with long-lasting effects. Measures should be taken to prevent its release into the environment.

Handling and Disposal:

• Handling: Handle under a fume hood with adequate ventilation. Avoid direct contact with the substance.
• Disposal: Dispose of in accordance with local, regional, and national regulations. Do not discharge into drains or the environment.

If you have any specific questions or need more detailed information about cyanuric chloride, feel free to ask!