p-Toluenesulfonic acid (PTSA) is an organic compound with the formula CH₃C₆H₄SO₃H. TsOH, as it is abbreviated, is a white solid that is soluble in water, alcohols, and other polar organic solvents. Most often, TsOH refers to the monohydrate, TsOH^.H₂O.

TsOH is a strong organic acid, about a million times stronger than benzoic acid. It is one of the few strong acids that is solid and, hence, conveniently weighed. Also, unlike some of the strong mineral acids (especially nitric acid, sulfuric acid, and perchloric acid), TsOH is non-oxidizing.

Preparation and handling

TsOH is prepared on an industrial scale by the sulfonation of toluene. It hydrates readily. Common impurities include benzenesulfonic acid and sulfuric acid. Impurities can be removed by recrystallization from concentrated hydrochloric acid followed by azeotropic drying.^[1]

Toluenesulfonic acid finds use in organic synthesis as an "organic-soluble" acid catalyst. Examples of uses:

• Acetalization of an aldehyde.^[2]
• Esterification of carboxylic acids.^[3]
• Transesterification of an ester.^[4]

See also

• Tosyl
• Collidine p-toluenesulfonate

It is also used as a catalyst with 3,4 dihydro-2H pyran in alcohol protection.

References

External links

• MSDS for toluenesulfonic acid

de:Toluolsulfonsäure fr:Acide paratoluènesulfonique nl:P-Tolueensulfonzuur ja:P-????????? pt:Ácido p-toluenossulfônico