Trifluoroacetic acid

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Trifluoroacetic acid

Trifluoroacetic acid (TFA) is the most simple perfluorinated carboxylic acid

Perfluorinated carboxylic acid

Perfluorinated carboxylic acids , or perfluorocarboxylates are fluorocarbon-based chemical compounds with carboxylic acid or carboxylate functional groups....
chemical compound

Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
with the formula CF₃CO₂H. It is a strong carboxylic acid

Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
due to the influence of the three very electronegative

Electronegativity

Electronegativity, symbol χ, is a chemical property that describes the ability of an atom to attract electrons towards itself in a covalent bond....
fluorine

Fluorine

Fluorine is the chemical element with the symbol F and atomic number 9. Fluorine forms a single bond with itself in elemental form, resulting in the diatomic F2 molecule....
atoms. Relative to acetic acid

Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
, TFA is almost 100,000-fold more acidic. TFA is widely used in organic chemistry

Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
.

trofluorination of acetic acid

Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
by the Simons method is the best way to obtain trifluoroacetic acid. The anodic reaction of the electrolysis

Electrolysis

In chemistry and manufacturing, electrolysis is a method of separating Chemical bond chemical compound by passing an electric current through them....
of a mixture of hydrogen fluoride

Hydrogen fluoride

Hydrogen fluoride is a chemical compound with the chemical formula HF. It is the principal industrial source of fluorine, often in the aqueous form as hydrofluoric acid, and thus is the precursor to many important compounds including pharmaceuticals and polymers ....
and acetic acid below the voltage at which elemental

Chemical element

A chemical element is a type of atom that is distinguished by its atomic number; that is, by the number of protons in its atomic nucleus. The term is also used to refer to a pure chemical Chemical substance composed of atoms with the same number of protons....
fluorine

Fluorine

Fluorine is the chemical element with the symbol F and atomic number 9. Fluorine forms a single bond with itself in elemental form, resulting in the diatomic F2 molecule....
(F₂) develops is a mild reaction which leaves the carboxylic group intact.

is a reagent

Reagent

A reagent or reactant is a substance or compound consumed during a chemical reaction. Solvents and catalysts, although they are involved in the reaction, are usually not referred to as reactants....
used frequently in organic synthesis

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
because of a combination of convenient properties: volatility, solubility in organic solvents, and its strength.

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Synthesis

Electrofluorination of acetic acid

Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
by the Simons method is the best way to obtain trifluoroacetic acid. The anodic reaction of the electrolysis

Electrolysis

In chemistry and manufacturing, electrolysis is a method of separating Chemical bond chemical compound by passing an electric current through them....
of a mixture of hydrogen fluoride

Hydrogen fluoride

Chemical element

Fluorine

Uses

TFA is a reagent

Reagent

Organic synthesis

Sulfuric acid

Sulfuric acid, hydrogen2sulfuroxygen4, is a strong mineral acid. It is soluble in water at all concentrations. Sulfuric acid has many applications, and is one of the top products of the chemical industry....
but more readily available in anhydrous form than hydrochloric acid

Hydrochloric acid

Hydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong acid mineral acid and has major industrial uses....
. One complication to its use is that TFA forms an azeotrope

Azeotrope

An azeotrope is a mixture of two or more liquids in such a ratio that its composition cannot be changed by simple distillation. This occurs because, when an azeotrope is boiled, the resulting vapor has the same ratio of constituents as the original mixture....
with water with a boiling point of 105 °C.

It is also used as a ion pairing agent in liquid chromatography for separation of organic compounds, particularly peptides and small proteins. It is a versatile solvent for NMR spectroscopy

NMR spectroscopy

Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is the name given to a technique which exploits the magnetic properties of certain nuclei....
(for materials stable in acid).

The derived acid anhydride, trifluoroacetic anhydride

Trifluoroacetic anhydride

Trifluoroacetic anhydride is the acid anhydride of trifluoroacetic acid. In particular, trifluoroacetic anhydride is the perfluorinated derivative of acetic anhydride....
(TFAA), [CF₃C(O)]₂O, is a common reagent for introducing the trifluoracetyl group.

TFA is also commonly used to produce thin film ceramic functional materials through chemical solution deposition (CSD). Particularly, in materials with barium such as YBa₂Cu₃O (YBCO), which acts as a fluorinated source to avoid undesired barium carbonate

Barium carbonate

Barium carbonate , also known as witherite, is a chemical compound used in rat poison, bricks, ceramic glazes and cement.Witherite crystallizes in the orthorhombic system....
(BaCO₃).