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What is Trifluoromethanesulfonic acid?

Apr 12，2021

Identification

Name: Trifluoromethanesulfonic acid

Synonyms: Fluorad FC-24;Methanesulfonic acid, trifluoro-;trifluoromethanesulfonic;trifluoro-methanesulfonicaci;FC-24;PERFLUOROMETHANESULFONIC ACID;PFC-MS;TRIFLUOROMETHANESULPHONIC ACID

CAS: 1493-13-6

MF: CHF3O3S

MW: 150.08

EINECS: 216-087-5

Properties

Melting point -40 °C

Boiling point 162 °C(lit.)

Density 1.696 g/mL at 25 °C(lit.)

Vapor density 5.2 (vs air)

Vapor pressure 8 mm Hg ( 25 °C)

Refractive index n20/D 1.327(lit.)

RTECS PB2771000

Fp None

Storage temp. ?20°C

Solubility Miscible in H<sub>2</sub>O

pka -14(at 25℃)

Form Fuming Liquid

Color slightly brown

Trifluoromethanesulfonic acid, also known as triflic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is often regarded as one of the strongest acids, and is one of a number of so-called "superacids". it is used in the manufacture of pharmaceuticals, agricultural chemicals and polymers. The anhydrous form is widely used in fine chemical synthesis. It is non-oxidizing, has a high thermal stability, and is resistance to both oxidation and reduction, which makes it one of the more useful compounds in the super acids class. In the pharma industry, it is used to make a number of drug classes, including nucleosides, antibiotics, steroids, proteins and glycosides. Triflic anhydride reacts readily with water and has an unfavorable toxicity profile.

Preparation

Yellow-brown liquid. The boiling point is 167~170 ℃.The refractive index is 1.331.The relative density is 1.708.It is the strongest organic acids, easily soluble in water.Use carbon disulfide as raw material, with the reaction of iodine pentafluoride to produce trifluoromethyl disulfide.(CF3S) 2Hg was obtained when reacting with mercury; Then through oxidation of hydrogen oxide, trifluoromethanesulfonic acid is acquired.

Uses

Trifluoromethanesulfonic acid is used for organic synthesis, widely used in pharmaceutical and chemical industries, such as nucleosides, antibiotics, steroids, protein, sugar, vitamins synthesis, silicone rubber modification.

Trifluoromethanesulfonic acid is used as a catalyst in Friedel-Crafts type acylation, alkylation and polymerization reactions; as a solvent for ESR; as a nonaqueous strong acid titrant; with trifluoroacetic acid, q.v., in solid-phase peptide synthesis. It is used in isomerization and alkylation of the catalyst, the preparation of 2, 3-dihydro-2-indanone, tetralone, glycosides in the removal of glycoproteins.

Reactions

Trifluoromethanesulfonic acid acts as a catalyst for esterification reactions and an acidic titrant in nonaqueous acid-base titration. It is useful in protonations due to the presence of conjugate base triflate is non nucleophilic. It serves as a deglycosylation agent for glycoproteins. In addition, it is a precursor and a catalyst in organic chemistry. It reacts with acyl halides to prepare mixed triflate anhydrides, which are strong acylating agents used in Friedel-Crafts reactions. It acts as a key starting material for the preparation of ethers and olefins by reacting with alcohols as well as to prepare trifluoromethanesulfonic anhydride by dehydration reaction.

Article illustration

Catalyst used in the production of cocoa butter substitute from palm oil. This is a very similar reaction to what would be done if one wanted to create polymers using triflic acid in the synthesis. Other Friedel-Crafts type reactions using triflic acid include 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.

Health Effect

Trifluoromethanesulfonic acid is a corrosive irritant to the skin, eyes, and mucous membranes. A strong acid. Violent reaction with acyl chlorides or aromatic hydrocarbons evolves toxic hydrogen chloride gas. When heated to decomposition it emits toxic fumes of Fand SOx.

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