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TRIETHYLAMINE (TEA)

  • Category:
    Aliphatic Amines

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Product Profile

1. Chemical Structure and Properties

Molecular Formula:

C₆H₁₅N

Structural Formula:

N(CH₂CH₃)₃

A tertiary amine composed of a central nitrogen atom bonded to three ethyl groups.

Physical Properties:

  • State: Colorless liquid with a strong, ammonia-like odor.
  • Boiling Point: 89°C; Density: 0.73 g/cm³; Vapor Pressure: 54 mmHg at 20°C.
  • Solubility: Miscible with organic solvents (e.g., ethanol, ether); slightly soluble in water (1.2 g/100 mL).

Chemical Properties:

  • Basicity: Strong base (pKa = 10.75 in water), reacts exothermically with acids to form salts (e.g., triethylamine hydrochloride).
  • Reactivity: Participates in nucleophilic substitutions and catalytic reactions; flammable (flash point: -7°C).

2. Industrial Applications

Chemical Synthesis:

  • Catalyst: Widely used in polyurethane foam production to accelerate isocyanate-polyol reactions.
  • Neutralizing Agent: Neutralizes acids in pharmaceutical synthesis (e.g., penicillin production).

Pharmaceuticals:

  • Intermediate for antimalarials (e.g., chloroquine) and local anesthetics (e.g., lidocaine).

Agrochemicals:

  • Key component in herbicide formulations (e.g., glyphosate stabilization).

Polymer Industry:

  • Acts as a chain extender in epoxy resin curing and silicone rubber production.

Electronics:

  • Etching agent in semiconductor manufacturing for silicon wafer processing.

3. Safety and Toxicology

Hazard Profile:

  • Inhalation (≥25 ppm): Irritates respiratory tract, causes headache, dizziness (TLV-TWA: 1 ppm).
  • Skin/Eye Contact: Severe irritation and chemical burns (rabbit skin LD50: 460 mg/kg).
  • Ingestion: Highly toxic (oral LD50 rat: 460 mg/kg); induces gastrointestinal damage.

Acute Exposure:

  • Chronic Effects: Potential liver/kidney toxicity (animal studies).

Flammability:

Highly flammable liquid (NFPA 704: Health 3, Flammability 3).

Protection Protocols:

  • Engineering Controls: Explosion-proof ventilation, vapor detectors.
  • PPE: Chemical-resistant gloves (e.g., neoprene), goggles, and respirators with organic vapor cartridges.

Regulatory Limits:

OSHA PEL: 25 ppm (8-hour TWA); NIOSH IDLH: 200 ppm.

4. Environmental and Regulatory Compliance

Ecotoxicology:

  • Aquatic Toxicity: LC50 (fish, 96h): 12 mg/L; EC50 (daphnia): 8 mg/L.
  • Biodegradation: Moderate (60% degradation in 28 days, OECD 301B).
  • Atmospheric Impact: Reacts with ozone to form secondary pollutants (half-life ~6 hours).

Global Regulations:

  • EU: Classified as Flammable Liquid (Category 2) and Acute Tox. 3 (H331) under CLP.
  • US EPA: Listed on the Toxic Release Inventory (TRI); regulated under CERCLA.
  • China: GB 13690-2009 categorizes TEA as a Class 3.2 flammable liquid.

Transport:

UN 1296; Class 3 (Flammable Liquid), Packing Group II.

5. Case Studies and Application Insights

Case 1: Polyurethane Foam Production

Process: Dow Chemical uses TEA as a catalyst in flexible foam manufacturing for mattresses.

Efficiency: Reduces curing time by 40% vs. non-catalytic methods.

Case 2: Pharmaceutical Neutralization

Application: Pfizer employs TEA to neutralize HCl during ciprofloxacin synthesis, achieving 98% yield.

Comparative Analysis:

  • Cost: TEA is 30% cheaper but requires stricter odor control.
  • Performance: Pyridine offers lower flammability but higher toxicity (TLV: 0.1 ppm).