Triflic acid

Trifluoromethanesulfonic acid, also known as triflic acid, TFMS, TFSA, HOTf or TfOH, is a 3SO3H. It is one of the strongest

Properties

Triflic acid is a DMSO,
With an 14 (pKa ~ −15) mol/kg, HOTf qualifies as a 3SO

−
3

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, known as 4 and HNO3. Further recommending its use, triflic acid does not sulfonate substrates, which can be a problem with not undergo:

C6H6 + H2SO4 → C6H5(SO3H) + H2O

Triflic acid fumes in moist air and forms a stable solid monohydrate, CF3SO3H·H2O, melting point 34 °C.

Health Precautions

Trifluouromethanesulfonic acid is one of the strongest acids known. On eye contact it causes severe eye burns and may cause blindness. With contact with skin it causes severe burns with delayed tissue destruction. On inhalation it causes fatal spasms, inflammation and

Syntheses

Trifluoromethanesulfonic acid was first synthesized in 1954 by Haszeldine and Kidd by the following reaction:
Trifluoromethanesulfonic acid is produced industrially by

CH3SO3H + 4 HF → CF3SO2F + H2O + 1.5 H2

The resulting CF3SO2F is hydrolyzed, and the resulting triflate salt is preprotonated. Alternatively, trifluoromethanesulfonic acid arises by oxidation of trifluoromethyl

CF3SCl + 2 Cl2 + 2 H2O → CF3SO2OH + 4 HCl

Triflic acid is purified by

Uses

In the laboratory, triflic acid is useful in protonations because the conjugate base of triflic acid is non-nucleophilic. It is also used as an acidic titrant in non-aqueous acid-base titration because it behaves as a strong acid in many solvents (2SO4) are only moderately strong.

Salt formation

Trifluoromethanesulfonic acid exothermically reacts with metal 2.

CuCO3 + 2 CF3SO3H → Cu(O3SCF3)2 + H2O + CO2

Chloride ligands can be converted to the corresponding triflates:

3 CF3SO3H + [Co(NH3)5Cl]Cl2 → [Co(NH3)5O3SCF3](O3SCF3)2 + 3 HCl

This conversion is conducted in neat HOTf at 100 °C, followed by precipitation of the salt by the addition of ether.

Organic reactions

Triflic acid reacts with acyl halides to give mixed triflate anhydrides, which are strong acylating agents, e.g. in

CH3C(O)Cl + CF3SO3H → CH3C(O)OSO2CF3 + HCl

CH3C(O)OSO2CF3 + C6H6 → CH3C(O)C6H5 + CF3SO3H

Triflic acid catalyzes the reaction of aromatic compounds with sulfonyl chlorides, probably also via the intermediacy of a mixed anhydride of the sulfonic acid.
Triflic acid promotes other Friedel-Crafts-like reactions including the cracking of alkanes and alkylation of alkenes, which are very important to the petroleum industry. These triflic acid derivative catalysts are very effective in isomerizing straight chain or slightly branched hydrocarbons that can increase the
Triflic acid reacts exothermically with alcohols to produce ethers and olefins.

, also known asor, is a sulfonic acid with the chemical formula CFSOH. It is one of the strongest acids . Triflic acid is mainly used in research as a catalyst for esterification Triflic acid is a hygroscopic , colorless liquid at room temperature. It is soluble in polar solvents such as DMF acetonitrile , and dimethyl sulfone . Addition of triflic acid to polar solvents can however be dangerously exothermic With an Ka = 8.0 ×10(pKa ~ −15) mol/kg, HOTf qualifies as a superacid . Triflic acid owes many of its useful properties to its great thermal and chemical stability. Both the acid and its conjugate base CFSO, known as triflate , resist oxidation/reduction reactions, whereas many strong acids are oxidizing, e.g. HClOand HNO. Further recommending its use, triflic acid does not sulfonate substrates, which can be a problem with sulfuric acid fluorosulfuric acid , and chlorosulfonic acid . Below is a prototypical sulfonation, which HOTf doesundergo:Triflic acid fumes in moist air and forms a stable solid monohydrate, CFSOH·HO, melting point 34 °C.Trifluouromethanesulfonic acid is one of the strongest acids known. On eye contact it causes severe eye burns and may cause blindness. With contact with skin it causes severe burns with delayed tissue destruction. On inhalation it causes fatal spasms, inflammation and edema Trifluoromethanesulfonic acid was first synthesized in 1954 by Haszeldine and Kidd by the following reaction:Trifluoromethanesulfonic acid is produced industrially by electrochemical fluorination (ECF) of methanesulfonic acid:The resulting CFSOF is hydrolyzed, and the resulting triflate salt is preprotonated. Alternatively, trifluoromethanesulfonic acid arises by oxidation of trifluoromethyl sulfenyl chloride Triflic acid is purified by distillation from triflic anhydride In the laboratory, triflic acid is useful in protonations because the conjugate base of triflic acid is non-nucleophilic. It is also used as an acidic titrant in non-aqueous acid-base titration because it behaves as a strong acid in many solvents ( acetonitrile acetic acid , etc.) where common mineral acids (such as HCl or HSO) are only moderately strong.Trifluoromethanesulfonic acid exothermically reacts with metal carbonates and hydroxides . Illustrative is the synthesis of Cu(OTf)Chloride ligands can be converted to the corresponding triflates:This conversion is conducted in neat HOTf at 100 °C, followed by precipitation of the salt by the addition of ether.Triflic acid reacts with acyl halides to give mixed triflate anhydrides, which are strong acylating agents, e.g. in Friedel-Crafts reactions.Triflic acid catalyzes the reaction of aromatic compounds with sulfonyl chlorides, probably also via the intermediacy of a mixed anhydride of the sulfonic acid.Triflic acid promotes other Friedel-Crafts-like reactions including the cracking of alkanes and alkylation of alkenes, which are very important to the petroleum industry. These triflic acid derivative catalysts are very effective in isomerizing straight chain or slightly branched hydrocarbons that can increase the octane rating of a particular petroleum-based fuel.Triflic acid reacts exothermically with alcohols to produce ethers and olefins.

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Description

Triflic acid (Trifluoromethanesulfonic acid) is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest acids and is mainly used in research as a catalyst for esterification[1]. Triflic acid is a hygroscopic, colorless liquid at room temperature. It is soluble in polar solvents such as DMF, DMSO, acetonitrile, and dimethyl sulfone. Triflic acid is a nonoxidizing, thermally stable compound resistant to oxidation and reduction. In the laboratory, triflic acid is helpful in protonations because the conjugate base of triflic acid is non-nucleophilic. Triflic acid promotes other Friedel-Crafts-like reactions, including the cracking of alkanes and alkylation of alkenes, which are very important to the petroleum industry[2].

Chemical Property

Trifluoromethanesulfonic acid has often been acclaimed as the strongest of all known monoprotic organic acids. Fluorosulfonic acid has also been given the same status. Trifluoromethanesulfonic acid and its conjugate base have extreme thermal stability and resistance to reductive and oxidative cleavage. They do not provide a source of fluoride ions, even in the presence of strong nucleophiles. The nonoxidizing nature of trifluoromethanesulfonic acid can be beneficial in minimizing or eliminating side reactions in some instances, and it reduces the hazards associated with strong oxidizing acids such as perchloric acid.

Pure trifluoromethanesulfonic acid is a clear, colorless liquid that boils at 162 ℃ (760 Torr). By comparison, methanesulfonic acid boils at 165 ℃ (8.5 Torr), reflecting a much higher intermolecular association. Trifluoromethanesulfonic acid fumes in moist air until it is converted to a stable monohydrate, which is a solid at room temperature (mp 34 ℃). The monohydrate is more correctly termed hydronium trifluoromethanesulfonate since water is quite a good base in such a strong acid. Like the analogous hydronium perchlorate, this salt is very hygroscopic and will liquefy upon contact with a moist atmosphere. An x-ray crystallographic study showed that its structure comprises oxonium ions, which are hydrogen-bonded to three sulfonate groups in a pyramidal arrangement.

Synthesis method

The first reported syntheses of trifluoromethanesulfonic acid appeared in 1954. Haszeldine and Kidd obtained the acid by oxidation of bis(trifluoromethy1thio)mercury with aqueous hydrogen peroxide. This process was later modified by the direct formation of bis- (trifluoromethy1thio)mercury from carbon disulfide and mercuric fluoride. Haszeldine and Kidd have also described an alternative route to the acid via trifluoromethane sulfonyl chloride. Commonly, the hygroscopic salts of trifluoromethanesulfonic acid are dehydrated at about 100 ℃ under vacuum before adding sulfuric acid[3].

Methyltrifluoromethyl sulfide is another intermediate that has been employed in the synthesis of trifluoromethanesulfonic acid. The sulfide is most conveniently prepared by the reaction of trifluoroiodomethane with sodium methanethiolate, but even higher yields are obtained from a photochemical reaction. The oxidation of methyl trifluoromethyl sulfide to the sulfonate salt was successfully carried out under various conditions.

The disclosure that trifluoromethanesulfonic acid, as well as higher homologous perfluoroalkanesulfonic acids, can be prepared by electrochemical fluorination (ECF) of alkanesulfonyl fluorides (or chlorides) was also made in 1954.

References

[1] Philip A. Staniland. “29-Poly(ether ketone)s.”Comprehensive Polymer Science and Supplements 5 (1989): 483-497.

[2] Keki Hormusji Gharda. “A process for the manufacture of triflic acid.”2011.

[3] Sudip Mukhopadhyay. “Synthesis of Trifluoromethanesulfonic Acid from CHF3.” Organic Process Research & Development 8 4 (2004): 660–662.

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