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p-Toluenesulfonic acid (PTSA) or tosylic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H.
p-Toluenesulfonic acid (PTSA) is a white extremely hygroscopic solid that is soluble in water, alcohols, and other polar organic solvents.
The CH3C6H4SO2 group is known as the tosyl group and is often abbreviated as Ts or Tos.
CAS: 104-15-4
MF: C7H8O3S
MW: 172.2
EINECS: 203-180-0
Synonyms
TL65;TL65LS;PARATOLUENE SULPHONIC ACID;p-tolylsulfonicacid;PTSA 70;toluene-4-sulphonic;Toluene-p-sulfonate;toluenesulfonicacid,liquid,withmorethan5%freesulfuricacid
Most often, p-Toluenesulfonic acid (PTSA) refers to the monohydrate, TsOH.H2O.
As with other aryl sulfonic acids, TsOH is a strong organic acid.
p-Toluenesulfonic acid (PTSA) is about one million times stronger than benzoic acid.
p-Toluenesulfonic acid (PTSA) is one of the few strong acids that is solid and therefore is conveniently weighed and stored.
p-Toluenesulfonic acid (PTSA) referred to as PTS, is a non-oxidizing organic acid, white needle or powder crystals, soluble in water, alcohols, ethers and other polar solvents.
Easy deliquescence, easy to make wood, cotton fabric dehydration and carbonization, insoluble in benzene and toluene. generating p-cresol when alkali fusion.
Commonly, p-Toluenesulfonic acid (PTSA) or tetrahydrate (TsOH4H2O) is preferred.
Preparation of methyl p-cresol acid in industry is by using concentrated sulfuric acid on the toluene sulfonation of p-toluenesulfonic acid.
The preparated p-toluenesulfonic acid often contains benzene sulfonic acid and sulfuric acid impurities, can be purified in recrystallization of concentrated hydrochloric acid, azeotropic drying.
p-Toluenesulfonic acid (PTSA) is widely used as catalyst agent in the synthesis of pharmaceuticals, pesticides, polymerization stabilizer and organic synthesis (esters, etc.), paint intermediates and resin curing agent.
And p-Toluenesulfonic acid (PTSA) is also the commonly used acid catalyst in organic synthesis.
p-Toluenesulfonic acid (PTSA) is neutralized with sodium hydroxide and then obtains sodium p-toluene sulfonate, and react with phosphorus pentachloride, can obtains p-toluenesulfonyl chloride.
The latter used in the nucleophilic substitution reaction, also used as alcohol hydroxyl protective group.
p-CH3C6H4SO3Na + PCl5 →p-CH3C6H4SO2Cl.
The use of p-toluenesulfonic acid also catalyzes the protection of dihydrofuran on the alcohol, carboxylic acid esterification, transesterification reaction, making the aldehyde generate acetal.
p-Toluenesulfonic acid (PTSA) or tosylic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H.
p-Toluenesulfonic acid (PTSA) is a white solid that is soluble in water, alcohols, and other polar organic solvents.
The 4-CH3C6H4SO2- group is known as tosyl group and is often abbreviated as Ts or Tos.
Most often, p-Toluenesulfonic acid (PTSA) refers to the monohydrate, TsOH.H2O.
p-Toluenesulfonic acid (PTSA) is a strong organic acid, about a million times stronger than benzoic acid.
p-Toluenesulfonic acid (PTSA) is one of the few strong acids that is solid and, hence, conveniently weighed.
Also, unlike some strong mineral acids (especially nitric acid, sulfuric acid, and per chloric acid), TsOH is non - oxidizing.
p-Toluenesulfonic acid (PTSA) is an arenesulfonic acid that is benzenesulfonic acid in which the hydrogen at position 4 is replaced by a methyl group.
p-Toluenesulfonic acid (PTSA) is a member of toluenes and an arenesulfonic acid.
p-Toluenesulfonic acid (PTSA) is a conjugate acid of a toluene-4-sulfonate.
p-Toluenesulfonic acid (PTSA) is a toluene sulfonic acid with high para-isomer content.
Numerous specialty applications utilize Pilot® PTSA-65 as a catalyst and chemical intermediate.
p-Toluenesulfonic acid (PTSA) is manufactured in a glass lined reactor to ensure a minimum of metallic impurities.
p-Toluenesulfonic acid (PTSA) is CFR 21 approved.
Ideal for industrial specialty applications.
p-Toluenesulfonic acid (PTSA) is a toluene sulfonic acid with high para-isomer content.
Numerous specialty applications utilize Pilot PTSA-65 as a catalyst and chemical intermediate.
p-Toluenesulfonic acid (PTSA) is manufactured in a glass lined reactor to ensure a minimum of metallic impurities.
p-Toluenesulfonic acid (PTSA) is CFR 21 approved. Ideal for industrial specialty applications.
p-Toluenesulfonic acid (PTSA) Chemical Properties
Melting point: 106~107℃
Boiling point: 116 °C
Density: 1.07
Vapor pressure: 69.8Pa at 20℃
Refractive index: 1.3825-1.3845
Fp: 41 °C
Storage temp.: Inert atmosphere,Room Temperature
Solubility: DMSO (Slightly), Methanol (Slightly)
Form: Solution
pka: -0.43±0.50(Predicted)
Color: Clear colorless to light yellow
Odor: pungent odor
Water Solubility: soluble
LogP: 0.41 at 25℃
CAS DataBase Reference: 104-15-4(CAS DataBase Reference)
NIST Chemistry Reference: p-Toluenesulfonic acid (PTSA)(104-15-4)
EPA Substance Registry System: p-Toluenesulfonic acid (PTSA) (104-15-4)
Reactions
p-Toluenesulfonic acid (PTSA) may be converted to p-toluene sulfonic anhydride by heating with phosphorus pentoxide.
When TsOH is heated with acid and water, a hydrolysis reaction takes place and toluene is formed:
CH3C6H4SO3H + H2O → C6H5CH3 + H2SO4
This reaction is general for aryl sulfonic acids, but the rate at which p-Toluenesulfonic acid (PTSA) occurs depends upon the structure of the acid, the temperature and the nature of the catalyzing acid.
For example p- TsOH is unaffected by cold concentrated hydrochloric acid, but hydrolyzes when heated to 186°C in concentrated phosphoric acid.
Uses
(1) For chemical reagents, but also for dyes, organic synthesis.
(2) Used as the intermediates of medicine (such as doxycycline), pesticides (such as dicofol), dyes.
Also used in detergents, plastics, coatings and so on.
(3) For medicine, pesticides, dyes and detergents, but also for plastics and printing coatings.
(4) Widely used in the catalyst synthetic medicine, pesticides, polymerization of the stabilizer and organic synthesis (esters, etc.).
Also used as medicine, paint intermediates and resin curing agent.
p-Toluenesulfonic acid (PTSA) Hydrate (Lisinopril EP Impurity B) is used in the synthesis of resveratrol.
Also used in the synthesis of oxane derivatives as antimalarial agents.
Production method
By p-toluenesulfonyl chloride hydrolysis derived.
Toluene can also be used as raw materials, sulfonated by sulfuric acid derived.
Preparation and uses
p-Toluenesulfonic acid (PTSA) is prepared on an industrial scale by the sulfonation of toluene.
Common impurities include benzenesulfonic acid and sulfuric acid.
p-Toluenesulfonic acid (PTSA) is most often supplied as the monohydrate, and it may be necessary to remove the complexed water before use.
Impurities can be removed by recrystallization from its concentrated aqueous solution followed by azeotropic drying with toluene.
p-Toluenesulfonic acid (PTSA) finds use in organic synthesis as an "organic-soluble" strong acid. Examples of uses include:
Acetalization of an aldehyde.
Fischer–Speier esterification
Transesterification reactions
