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Trifluoroacetic acid

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Trifluoroacetic acid


Trifluoroacetic acid (TFA) is an organic chemistry for various purposes.

Synthesis

TFA is prepared industrially by the electrofluorination of acetyl chloride and acetic anhydride, followed by hydrolysis of the resulting trifluoroacetyl fluoride:[2]

CH
3
COCl
+ 4 HFCF
3
COF
+ 3 H
2
+ HCl
CF
3
COF
+ H
2
O
CF
3
COOH
+ HF

Where desired, this compound may be dried by addition of trifluoroacetic anhydride.[3]

An older route to TFA proceeds via the oxidation of 1,1,1-trifluoro-2,3,3-trichloropropene with potassium permanganate. The trifluorotrichloropropene can be prepared by Swarts fluorination of hexachloropropene.

TFA occurs naturally in sea water, but only in small concentrations (<200 ng/L).[4][5]

Uses

TFA is the precursor to many other fluorinated compounds such as [6] TFA is also less oxidizing than sulfuric acid but more readily available in anhydrous form than many other acids. One complication to its use is that TFA forms an azeotrope with water (b. p. 105 °C).

TFA is popularly used as a strong acid in t-butoxycarbonyl protecting group.[7][8]

At a low concentration, TFA is used as an ion pairing agent in peptides and small proteins. TFA is a versatile solvent for NMR spectroscopy (for materials stable in acid). It is also used as a calibrant in mass spectrometry.[9]

TFA is used to produce trifluoroacetate salts.[10]

Safety

Trifluoroacetic acid is a corrosive acid but it does not pose the hazards associated with hydrofluoric acid because the carbon-fluorine bond is not labile. Toxic.

See also

References

  1. ^ Note: Calculated from Ka ratio of TFA and acetic acid
  2. ^ a b
  3. ^
  4. ^
  5. ^
  6. ^
  7. ^
  8. ^
  9. ^
  10. ^
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