Trifluoroacetic acid
A strong organic acid with the formula CF_COOH
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Trifluoroacetic acid (TFA) is a chemical compound with the formula CF_COOH. It is a carboxylic acid and is one of the strongest of the simple carboxylic acids. TFA is widely used in organic chemistry as a reagent and solvent.
Properties
Trifluoroacetic acid is a colorless liquid with a pungent odor. It is miscible with water and most organic solvents. The presence of the three fluorine atoms in the molecule increases the acidity of the carboxylic acid group, making TFA a strong acid with a pKa of approximately 0.23. This high acidity is due to the electron-withdrawing effect of the fluorine atoms.
Production
TFA is produced industrially by the electrochemical fluorination of acetyl chloride or acetic anhydride. This process involves the replacement of hydrogen atoms with fluorine atoms, resulting in the formation of trifluoroacetic acid.
Applications
Trifluoroacetic acid is used in a variety of applications:
- As a solvent in chemical synthesis and chromatography.
- As a reagent in the synthesis of peptides and proteins.
- In the production of pharmaceuticals and agrochemicals.
- As a catalyst in certain organic reactions.
Safety and Environmental Concerns
TFA is corrosive and can cause severe burns upon contact with skin or eyes. It should be handled with appropriate safety precautions, including the use of personal protective equipment (PPE).
Environmentally, TFA is considered a persistent pollutant. It is resistant to degradation and can accumulate in the environment, particularly in water bodies. This persistence raises concerns about its potential impact on aquatic life and ecosystems.
Related pages
References
Trifluoroacetic acid
Trifluoroacetic acid in a beaker
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Contributors: Prab R. Tumpati, MD
