Benzyltriethylammonium chloride

Details:

Benzyltriethylammonium chloride (BTEAC or TEBAC) is a quaternary ammonium salt with the chemical formula C??H??ClN. It is widely recognized for its role as a phase-transfer catalyst (PTC) in organic synthesis. Here's a structured overview:

Chemical Structure

• Components:

  • A benzyl group (C?H?CH??) attached to a nitrogen atom.

  • Three ethyl groups (C?H?) bonded to the same nitrogen.

  • A chloride (Cl?) counterion.

• Molecular Formula: C??H??ClN.

• Appearance: Typically a white crystalline solid.

Key Properties

Solubility: Hydrophilic due to the ionic chloride and lipophilic due to organic groups, enabling it to bridge aqueous and organic phases.

Stability: Stable under standard conditions but may decompose at high temperatures or with strong oxidizers.

Synthesis

Reaction: Produced by alkylating triethylamine with benzyl chloride:

C?H?CH?Cl + N(C?H?)? → [C?H?CH?N(C?H?)?]?Cl?C?H?CH?Cl + N(C?H?)? → [C?H?CH?N(C?H?)?]?Cl?

Process: The tertiary amine (triethylamine) reacts with benzyl chloride, forming a quaternary ammonium salt.

Applications

1. Phase-Transfer Catalysis:

   • Facilitates reactions between reactants in immiscible phases (e.g., aqueous NaOH and organic substrates).

   • Common in SN2 reactions, esterifications, and nucleophilic substitutions.

2. Industrial Uses:

   • Surfactant in emulsions.

   • Potential use in ionic liquids and polymer chemistry.

3. Biochemical Applications:

   • May disrupt cell membranes due to cationic nature, though less common than other quaternary ammonium disinfectants.

Safety and Handling

Toxicity: Can irritate skin, eyes, and respiratory systems.

Precautions: Use gloves, goggles, and adequate ventilation. Store in a dry environment.

Alternate Names

Abbreviated as BTEAC, TEBAC, or benzyltriethylammonium chloride.

Summary

BTEAC is a versatile catalyst enhancing reaction efficiency in multiphase systems. Its structure allows it to mediate between polar and nonpolar environments, making it invaluable in organic synthesis and industrial processes. Proper handling is essential due to its irritant properties.