Halogenation of Methane (Chlorination)
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CH4 + Cl2 → CH3Cl + HCl
Overview
Methane undergoes free radical substitution with chlorine in the presence of UV light or heat. The mechanism involves initiation (Cl₂ → 2Cl·), propagation (Cl· + CH₄ → CH₃· + HCl, CH₃· + Cl₂ → CH₃Cl + Cl·), and termination. Further substitution can produce CH₂Cl₂, CHCl₃, and CCl₄.
Participants
| Role | Substance | Coefficient | State |
|---|---|---|---|
| Reactant | Methane CH₄ | 1 | (g) |
| Reactant | Chlorine Cl | 1 | (g) |
| Product | Hydrochloric Acid HCl | 1 | (g) |
Everyday Example
Chloroform (CHCl₃), historically used as an anesthetic, is produced by multiple chlorination of methane.
Industrial Importance
Chloromethane (CH₃Cl) is used as a methylating agent and refrigerant. Dichloromethane is a widely used solvent. Chloroform is an important chemical intermediate.
Properties
- Type
- Organic
- Reversible
- No
- Energy
- Exothermic
- ΔH
- -98.0 kJ/mol
- Catalyst
- UV light or heat