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N,N-dimethylformamide (DMF)

  • Category:
    Aliphatic Amines

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Product Profile

1. Chemical Structure and Properties

Molecular Formula:

C₃H₇NO

Structural Formula:

HCON(CH₃)₂

A polar aprotic solvent with a formamide core and two methyl groups attached to the nitrogen atom.

Physical Properties:

  • Appearance: Clear, colorless liquid with a faint amine-like odor.
  • Boiling Point: 153°C; Density: 0.94 g/cm³; Vapor Pressure: 3.7 mmHg at 25°C.
  • Solubility: Miscible with water, alcohols, ethers, and most organic solvents.

Chemical Properties:

  • High Polarity: Dipole moment of 3.8 D, enabling dissolution of polar and nonpolar compounds.
  • Thermal Stability: Decomposes above 350°C, releasing CO, NOₓ, and methylamines.
  • Reactivity: Acts as a catalyst in reactions like Vilsmeier–Haack formylation and Ullmann couplings.

2. Industrial Applications

Polymer Production:

  • Solvent for polyurethane (PU) and polyacrylonitrile (PAN) production.
  • Example: Dissolves PU precursors for synthetic leather manufacturing (e.g., Clarino® fabrics).

Pharmaceuticals:

  • Reaction Medium: Key solvent for peptide synthesis, antibiotic production, and anticancer drugs.

Electronics:

  • Photoresist Stripper: Removes resist layers in semiconductor fabrication.

Agrochemicals:

  • Solvent for pesticides and herbicide formulations.

Petrochemicals:

  • Extractive distillation agent for separating acetylene from hydrocarbon mixtures.

3. Safety and Toxicology

Health Hazards:

  • Hepatotoxicity: Linked to elevated liver enzymes and fibrosis.
  • Reproductive Toxicity: Potential teratogenic effects (H360D).
  • Inhalation (≥10 ppm): Respiratory irritation, headache, nausea.
  • Skin Contact: Penetrates gloves; causes hepatotoxicity and reproductive harm.
  • Ingestion: Highly toxic; damages liver and kidneys.

Fire & Explosion:

Combustible liquid (flash point: 58°C); forms explosive peroxides upon storage.

Protection Measures:

  • PPE: Silver Shield® gloves, full-face respirators with organic vapor cartridges.
  • Storage: Inert gas blanket to prevent peroxide formation.

4. Environmental & Regulatory Compliance

Environmental Impact:

  • Aquatic Toxicity: LC50 (fish): 1,000–5,000 mg/L; EC50 (daphnia): 500 mg/L.
  • Biodegradability: Slow (40% in 28 days); persistent anaerobically.
  • Atmospheric Fate: Reacts with hydroxyl radicals (half-life ~5 days).

Regulatory Frameworks:

  • GB 13690-2009: Class 3.3 Flammable, Hazardous Chemical.
  • OSHA PEL: 10 ppm (skin); EPA TRI-listed.
  • CLP: Repro. Tox. 1B, Acute Tox. 4, Skin Irrit. 2.
  • REACH: Restricted; requires industrial authorization.

Transport:

UN 2265; Class 3 Flammable Liquid, Packing Group III.

5. Case Studies & Insights

Case 1: Polyurethane Synthetic Leather

Process: DMF dissolves PU resins for textile coatings (e.g., Clarino®).

Efficiency: 95% recovery via distillation; 80% emission reduction.

Case 2: Semiconductor Photoresist Stripping

Application: DMF-based strippers for EUV resist removal in 3nm fabrication.

Performance: 99.9% residue removal without substrate damage.

Comparative Analysis:

  • Pros: High solvency for polar polymers.
  • Cons: DMAc less toxic but 30% higher cost.