P-Toluenesulfonic acid

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P-Toluenesulfonic acid

p-Toluenesulfonic acid (PTSA) is an organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
with the formula CH₃
Methyl group

In chemistry, a methyl group is a hydrophobic alkyl functional group named after methane . It has the chemical formula -3 and is often abbreviated -Me....
C₆H₄
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
SO₃H
Sulfonic acid

Sulfonic acid usually refers to a member of the class of organic acids with the general formula R-S2-OH, where R is usually a hydrocarbon side chain....
. TsOH, as it is abbreviated, is a white solid that is soluble in water, alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s, and other polar
Chemical polarity

In chemistry, polarity refers to the dipole-dipole intermolecular forces between the slightly electric charge end of one molecule to the negative end of another or the same molecule....
organic solvents. Most often, TsOH refers to the monohydrate
Hydrate

Hydrate is a term used in inorganic chemistry and organic chemistry to indicate that a substance contains water. The chemical state of the water varies widely between hydrates, some of which were so labeled before their chemical structure was understood....
, TsOH^.H₂O.

TsOH is a strong organic acid
Organic acid

An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acids whose acidity is associated with their carboxyl group -COOH....
, about a million times stronger than benzoic acid
Benzoic acid

Benzoic acid, C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for 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
Nitric acid

Nitric acid , also known as aqua fortis and spirit of nitre, is a highly corrosion and toxic strong acid that can cause severe burns....
, sulfuric acid
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....
, and perchloric acid
Perchloric acid

Perchloric acid, HClO4, is an oxoacid of chlorine and is a colorless liquid soluble in water . It is a strong acid comparable in strength to sulfuric acid and nitric acids....
), TsOH is non-oxidizing.

is prepared on an industrial scale by the sulfonation of toluene
Toluene

Toluene, also known as methylbenzene or phenylmethane, is a clear, Water -insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene....
.

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Encyclopedia

p-Toluenesulfonic acid (PTSA) is an organic compound
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
with the formula CH₃
Methyl group

In chemistry, a methyl group is a hydrophobic alkyl functional group named after methane . It has the chemical formula -3 and is often abbreviated -Me....
C₆H₄
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
SO₃H
Sulfonic acid

Sulfonic acid usually refers to a member of the class of organic acids with the general formula R-S2-OH, where R is usually a hydrocarbon side chain....
. TsOH, as it is abbreviated, is a white solid that is soluble in water, alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s, and other polar
Chemical polarity

In chemistry, polarity refers to the dipole-dipole intermolecular forces between the slightly electric charge end of one molecule to the negative end of another or the same molecule....
organic solvents. Most often, TsOH refers to the monohydrate
Hydrate

Hydrate is a term used in inorganic chemistry and organic chemistry to indicate that a substance contains water. The chemical state of the water varies widely between hydrates, some of which were so labeled before their chemical structure was understood....
, TsOH^.H₂O.

TsOH is a strong organic acid
Organic acid

An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acids whose acidity is associated with their carboxyl group -COOH....
, about a million times stronger than benzoic acid
Benzoic acid

Benzoic acid, C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for 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
Nitric acid

Nitric acid , also known as aqua fortis and spirit of nitre, is a highly corrosion and toxic strong acid that can cause severe burns....
, sulfuric acid
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....
, and perchloric acid
Perchloric acid

Perchloric acid, HClO4, is an oxoacid of chlorine and is a colorless liquid soluble in water . It is a strong acid comparable in strength to sulfuric acid and nitric acids....
), TsOH is non-oxidizing.

Preparation and handling
TsOH is prepared on an industrial scale by the sulfonation of toluene
Toluene

Toluene, also known as methylbenzene or phenylmethane, is a clear, Water -insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene....
. It hydrates readily. Common impurities include benzenesulfonic acid and sulfuric acid. Impurities can be removed by recrystallization from concentrated 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....
followed by azeotropic
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....
drying.

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

An acetal is a molecule with two single bonded oxygens attached to the same carbon atom.Traditional usages distinguish ketal from acetal . Current accepted terminology classifies ketals as a subset of acetals....
ization of an aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
.
Esterification
Esterification

Esterification is the general name for a chemical reaction in which two reactants form an ester as the product . Esters are common in organic chemistry and biological materials, and often have a characteristic pleasant, fruity odor....
of 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....
s.
Transesterification
Transesterification

In organic chemistry, transesterification is the process of exchanging the alcohol group of an ester compound with another alcohol. These reactions are often catalyst by the addition of an acid or base ....
of an ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
.

Reactions
p-Toluenesulfonic acid may be converted to p-toluenesulfonic anhydride by heating with phosphorus pentoxide
Phosphorus pentoxide

Phosphorus pentoxide is a chemical compound with formula Phosphorus2Oxygen5. This white crystalline solid is the anhydride of phosphoric acid....
.

See also

Tosyl
Tosyl

A tosyl group is CH3C6H4SO2. This group is usually derived from the compound 4-Toluenesulfonyl chloride, CH3C6H4SO2Cl, which forms esters and amides of toluenesulfonic acid....
Collidine p-toluenesulfonate
Collidine p-toluenesulfonate

Collidine p-toluenesulfonate or CTPS is a salt between P-Toluenesulfonic acid and collidine .External links ...

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

External links