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TOSIC ACID

CAS Number: 104-15-4
Chemical formula: C7H8O3S
Molecular Weight: 172.20
Appearance: colorless (white) solid

APPLICATIONS


Tosic acid is prepared on an industrial scale by the sulfonation of toluene.
Common impurities of Tosic acid include benzenesulfonic acid and sulfuric acid.

Tosic acid contains an amount of water.
To estimate the total moisture present as impurity, the Karl Fischer method is used.
Impurities can be removed by recrystallization from its concentrated aqueous solution followed by azeotropic drying with toluene.


Tosic acid finds use in organic synthesis as an "organic-soluble" strong acid.
Examples of such uses include:

Acetalization of an aldehyde.
Fischer–Speier esterification.
Transesterification reactions.

Tosic acid is used in the chemical industry as a catalyst.
Also,  Tosic acid is used in the manufacturing of textile dyes, drugs, cleaning agents, polymers, and paints; 

Some uses of Tosic acid:

Products that remove stains or discoloration of fabric (including color-safe bleaches) used in laundry
Cleaning products and household care
general household cleaning
bleaching products
hydrotrope
produces a reaction
surfactant
solubility enhancer
Acid and Alkali Cleaning of Metals 
Molding and Core Making 
Electroplating 
Working with Glues and Adhesives 
Plastic Composites Manufacturing 
Photographic Processing 
Agricultural chemicals
Catalyst in the manufacture of foam insulation
Corrosion inhibitors
anti-scaling agents
Finishing agents
Industrial Cleaners
Metal Working
Textile Dye Manufacturing
Polymers
Coatings Catalysts
Intermediates
Oxidizing/reducing agents
Paint additives and coating additives 
Process regulators
Processing aids, 
Surface active agents
Adhesives and sealants
Agricultural products 
Building/construction 
Cleaning and furnishing care products
Fabric, textile, and leather products 
Paints and coatings

Tosic acid used in the chemical industry as a catalyst.
Further, Tosic acid is used in the manufacturing of textile dyes, drugs, cleaning agents, polymers, and paints. 

Tosic acid is used in photography (color bleaching)

Tosic acid is used as a catalyst (with applications including resins in foundry cores), as a curing agent for resins, as a descaling agent (industrial metal cleaners), in electroplating bathes, plastics, dyes, pharmaceutical intermediates, food packaging adhesives, and as a coupling and wetting agent.


Tosic acid is used in the synthesis of resveratrol.
Also, 
Tosic acid is used in the synthesis of oxane derivatives as antimalarial agents.

Tosic acid is used as a catalyst in the synthesis of resveratrol, in oxane derivatives as an antimalarial agent, as substituted piperidine and unsymmetrical benzyl.

Tosic acid may be used as a catalyst in the synthesis of unsymmetrical benzils, highly substituted piperidines or 1,3,5-Trisubstituted benzenes by trimerization of alkynes.
Further, Tosic acid may be used as a catalyst in the synthesis of Triazoloquinazolinone and benzimidazoquinazolinone derivatives, 1,3,5-Trisubstituted pyrazoles derivatives or Selenated ketene dithioacetals.

Tosic acid is used in pharmaceuticals, pesticides, dyes and detergents, also used in plastics and printing coatings
Further, Tosic acid is used in the preparation of cresol and Pharmaceutical (such as the preparation of doxycycline), pesticides (such as the preparation of dicofol), dyes and detergents and other industries. It is also used in the plastics and printing coatings industry.

Tosic acid may be used as a catalyst in the synthesis of the following:

Unsymmetrical benzils.
Highly substituted piperidines.
1,3,5-Trisubstituted benzenes by trimerization of alkynes.
Triazoloquinazolinone and benzimidazoquinazolinone derivatives.
1,3,5-Trisubstituted pyrazoles derivatives.
Selenated ketene dithioacetals.

Tosic acid (Its molecular structural formula is p-CH3C6H4SO3H, also known as TsOH, English name is p-toluene sulfonic acid) is a non-oxidizing organic acid, white needle or powder crystals, soluble in water, alcohols, ethers and other polar solvents.

Features of Tosic acid:

Easy deliquescence
easy to make wood
cotton fabric dehydration and carbonization
insoluble in benzene and toluene
generating p-cresol when alkali fusion.

Commonly, Tosic acid is preferred in the industry.

Preparation of methyl p-cresol acid in industry is by using concentrated sulfuric acid on the toluene sulfonation of Tosic acid.
The preparated Tosic acid often contains benzene sulfonic acid and sulfuric acid impurities, can be purified in recrystallization of concentrated hydrochloric acid, azeotropic drying.

Tosic acid 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 it is also the commonly used acid catalyst in organic synthesis.

Tosic acidt 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 Tosic acid also catalyzes the protection of dihydrofuran on the alcohol, carboxylic acid esterification, transesterification reaction, making the aldehyde generate acetal.

Tosic acid is used for:

(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.

DESCRIPTION

Tosic acid is an organic compound with the formula CH3C6H4SO3H.
Further, Tosic acid is a white solid that is soluble in water, alcohols, and other polar organic solvents.

Tosic acid, is an inexpensive and easy to handle organic catalyst used in organic synthesis.

As with other aryl sulfonic acids, Tosic acid is a strong organic acid.
Tosic acid is about one million times stronger than benzoic acid.

Tosic acid, liquid, with more than 5% free sulfuric acid appears as colorless to black solid. Odorless or nearly odorless.

Further, Tosic acidis an arenesulfonic acid that is benzenesulfonic acid in which the hydrogen at position 4 is replaced by a methyl group.
Tosic acid is a member of toluenes and an arenesulfonic acid.

Tosic acid is a conjugate acid of a toluene-4-sulfonate.

Tosic acid is a useful research chemical. 

Tosic acid is an organic compound with the formula CH3C6H4SO3H.
More to that, Tosic acid is an aromatic sulfonic acid, often used as a strong acid catalyst.

Tosic acid has been used as a reducing agent for the reductive amination of ketones and aldehydes.
In the presence of Tosic acid novel deazaflavin-cholestane hybrid compounds have been synthesized in a condensation reaction.

2-Phenylethyl alpha-glucoside has also been synthesized in the presence of Tosic acid.
Tosic acid esters, are a common class of reagents used in the pharmaceutical industry as alkylating agents, catalysts, and in purification steps of the chemical synthesis of a drug substance.

Tosic acid is in a class of strong acids used in different fields of synthetic organic chemistry, used as an acid catalyst for Fischer-Speier estherification provides excellent conversion and the most common use is likely for 'Catch and Release' purifications.

Tosic acidt is widely used for the scavenging of amines and other basic functionalities including weakly basic anilines,borohydrides and metals such as Ni and Ag.
Further, Tosic acid can also be used as an acid catalyst for organic reactions. .

Tosic acid has been specially optimized for use in organic applications and will not dissolve in methanol or any other solvents. It delivers much higher recovery and has better flow characteristics than corresponding polymer.

Tosic acid is is a strong organic acid.
Moreover, Tosic acid is a non-oxidizing chemical compound.
Tosic acid finds use in organic synthesis as an "organic-soluble" acid catalyst.

The reaction flask is heated with reflux for 5-6 h at 160° C.
When the reaction begins the droplets of water start to form.
From time to time the water from the dean stark collector is lowered into a small measuring cylinder.

After five hours of 12.5 ml of water is collected, the reaction continues until no more water is forming.
When the reaction is complete heating is removed and reaction mixture is allowed to cool.

After addition of few ml of water, Tosic acid immediately crystallizes.
The reaction product is filtered, washed with small amount of water.

The purification is performed by dissolving in small amount of hot water and and treating with activated charcoal, then filtered into a conical flask and cooled with ice-salt.
To this strongly cooled solution gaseous hydrogen chloride is passed leading to the formation of white crystals which are filtered and dried.
Tosic acid crystallizes with one molecule of water and melts at 104-105 °C. Yield about 25 g.

Tosic acid is prepared by sulfonation using toluene as a raw material and heating and boiling with sulfuric acid. The mother liquor of the production process of Tosic acid contains uncrystallized methyl benzene sulfonic acid and free sulfuric acid.
After neutralization, sodium methylbenzenesulfonate can be produced.

Tosic acid is a strong organic acid, about a million times stronger than benzoic acid.

Tosic acid 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), Tosic acid is non-oxidizing.

Tosic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H.

The screening assessment focused on Tosic acid, also referred to as benzenesulfonic acid, 4-methyl-.
It was assessed under the third phase of the Chemicals Management Plan (CMP).

Tosic acid does not occur naturally in the environment.
According to information gathered by the Government, Tosic acid is mainly used in Canada in the manufacture of paints and coatings, and of plastic and rubber materials, among other uses.

Tosic acid, also known as tosylate or para-toluene sulfonate, is a member of the class of compounds known as p-methylbenzenesulfonates.
p-Methylbenzenesulfonates are benzenesulfonic acids (or derivative thereof) carrying a methyl group at the para- position.
Tosic acid is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa).

Tosic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H.

Tosic acid is a white solid that is soluble in water, alcohols, and other polar organic solvents.

Belongs to the class of organic compounds known as p-methylbenzenesulfonates. These are benzenesulfonic acids (or derivative thereof) carrying a methyl group at the para- position.

As with other aryl sulfonic acids, Tosic acid is a strong organic acid.
Tosic acid is about one million times stronger than benzoic acid.

Tosic acid is one of the few strong acids that is solid and therefore is conveniently weighed and stored.

Tosic acid is an arenesulfonic acid that is benzenesulfonic acid in which the hydrogen at position 4 is replaced by a methyl group.

Tosic acid is a member of toluenes and an arenesulfonic acid.
Thus, Tosic acid is a conjugate acid of a toluene-4-sulfonate.

Tosic acid is a catalyst frequently used in nonpolar media; effective in carbonyl protection–deprotection; selectively cleaves N-Boc, other amine protecting groups; superior for enol ether, acetate preparation; used in esterifications, dehydrations, isomerizations, rearrangements.
Further, Tosic acid is a colorless hygroscopic solid.

Tosic acid is a colorless black solid with no or little odor.

Tosic acid, an oxonium salt, is an inexpensive and easy to handle organic catalyst used in organic synthesis.
The study of the crystalline structure of Tosic acid shows that it is monoclinic with P21/c space group. 

PROPERTIES


Water Solubility:    2.3 g/L
logP:    -0.88
logP:    1.67
logS:    -1.9
pKa (Strongest Acidic):    -2.1
Physiological Charge:    -1
Hydrogen Acceptor Count: 3
Hydrogen Donor Count:    1
Polar Surface Area:    54.37 Ų
Rotatable Bond Count:    1
Refractivity:    41.72 m³·mol⁻¹
Polarizability:    16.55 ų
Number of Rings: 1
Bioavailability: Yes
Rule of Five:    Yes
Ghose Filter:    No
Veber's Rule:    No
MDDR-like Rule:    No
Physical State: Crystals
Color: white
Odor: none reported
pH: Not applicable.
Vapor Pressure: 0.0000027 mm Hg @ 25 deg C
Viscosity: Not available.
Boiling Point: 140 deg C @ 20 mmHg
Freezing/Melting Point: 103 deg C
Autoignition Temperature: 350 deg C ( 662.00 deg F)
Flash Point: 180 deg C ( 356.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Soluble.
Specific Gravity/Density: Not available.
Molecular Formula: C7H8O3S.H2O
Molecular Weight: 190.22

FIRST AND AID


Eyes:

In case of contact, immediately flush eyes with plenty of water for at least 15 minutes.
Get medical aid immediately.

Skin:

In case of contact, flush skin with plenty of water.
Remove contaminated clothing and shoes.
Get medical aid if irritation develops and persists.
Wash clothing before reuse.

Ingestion:

If swallowed, do not induce vomiting unless directed to do so by medical personnel.
Never give anything by mouth to an unconscious person.
Get medical aid.

Inhalation:

If inhaled, remove to fresh air.
If not breathing, give artificial respiration.
If breathing is difficult, give oxygen. Get medical aid.

SAFETY AND HANDLING


li has moderate toxicity.
Irritation of the skin, eyes and mucous membranes.
Tosic acid used in the production process is toxic and has damage to the liver and hematopoietic system as well as the nervous system of the human body.
Concentrated Tosic acid is extremely corrosive, so the production system equipment should maintain good tightness, to prevent leakage, the operator should wear protective equipment.

The use of plastic bags plus wooden boxes packaging, storage in a cool, ventilated, dry place.
According to the provisions of the storage and transportation of toxic chemicals.


Handling:

Wash thoroughly after handling.
Remove contaminated clothing and wash before reuse.
Use with adequate ventilation.

Minimize dust generation and accumulation.
Keep container tightly closed.

Avoid breathing dust.
Do not get in eyes.
Avoid contact with skin and clothing.

Storage:

Store in a cool, dry, well-ventilated area away from incompatible substances.

SYNONYMS


P-TOLUENESULFONIC ACID
4-Methylbenzenesulfonic acid
104-15-4
4-Toluenesulfonic acid
p-Toluenesulphonic acid
Toluene-4-sulfonic acid
Tosic acid
p-Tolylsulfonic acid
Tosylic acid
p-Methylbenzenesulfonic acid
Toluenesulfonic acid
Benzenesulfonic acid, 4-methyl-
p-Methylphenylsulfonic acid
p-Toluenesulfonate
Eltesol
PARA-TOLUENE SULFONATE
PTSA
Cyclophil P T S A
ar-Toluenesulfonic acid
p-Toluolenesulfonic acid
p-Toluene sulfonate
P-Toluene Sulfonic acid
Methylbenzenesulfonic acid
Nacure 1040
Benzenesulfonic acid, methyl-
Cyzac 4040
Toluene-4-sulphonic acid
Kyselina p-toluenesulfonova
Manro PTSA 65 E
Manro PTSA 65 H
TSA-HP
TSA-MH
Manro PTSA 65 LS
Kyselina p-toluensulfonova
Toluene-p-sulfonate
K-Cure 1040
Toluenesulfonic acid (VAN)
Toluen-4-sulfonsaeure
p-toluene sulphonic acid
para-toluenesulfonic acid
HSDB 2026
UNII-QGV5ZG5741
NSC 167068
p-toluensulfonic acid
2(Or 4)-toluenesulphonic acid
toluene-p-sulfonic acid
p-Toluene-sulfonic acid
para-toluenesulphonic acid
paratoluene sulphonic acid
para toluene sulfonic acid
4-Toluene sulfonic acid
CHEMBL541253
QGV5ZG5741
4-TOLUENE-SULFONIC ACID
4-methylbenzene-1-sulfonic acid
CHEBI:27849
TsOH
WLN: WSQR D1
p-TSA
K-Cure 040
TSU
Kyselina p-toluensulfonova [Czech]
Kyselina p-toluenesulfonova [Czech]
EINECS 203-180-0
BRN 0472690
TosicAcid
4-sulphotoluene
AI3-26478
pTsOH
TosOH
Tosic acid p-TSA
p-toluenesulfonicacid
P-Toluene Sulfonic acid(monohydrate)
p-TsOH
Tos-OH
p-toluenesufonic acid
4-Toluenesulfonicacid
p-toluene sulfonicacid
p-toluene-sulfonicacid
p-toluensulphonic acid
paratoluensulfonic acid
Ts-OH
p-toluen sulfonic acid
p-toluenesuiphonic acid
p-toluenylsulfonic acid
paratoluenesulfonic acid
PTS ACID
4-toluenesulphonic acid
p -toluenesulfonic acid
p- toluenesulfonic acid
p-tolu-enesulfonic acid
p-toluyl sulphonic acid
toluene p-sulfonic acid
para-toluensulfonic acid
rho-toluenesulfonic acid
paratoluenesulphonic acid
p-toluene-sulphonic acid
toluene 4-sulfonic acid
toluene p-sulphonic acid
toluene-p-sulphonic acid
para toluenesulfonic acid
paratoluene sulfonic acid
paratoluene-sulfonic acid
SCHEMBL34
4-toluene sulphonic acid
4-toluene-sulphonic acid
rho-toluene sulfonic acid
para toluenesulphonic acid
para-toluene sulfonic acid
para-toluene-sulfonic acid
4methylbenzenesulfonic acid
DSSTox_CID_6701
4-methylphenylsulfonic acid
para toluene sulphonic acid
para-toluene sulphonic acid
EC 203-180-0
4-methylphenylsulphonic acid
DSSTox_RID_78188
NCIOpen2_002932
NCIOpen2_003096
4-methylbenzenesulphonic acid
DSSTox_GSID_26701
4-methyl-benzenesulfonic acid
4-methylbenzene sulfonic acid
4-methylbenzene-sulfonic acid
4-11-00-00241 (Beilstein Handbook Reference)
70788-37-3
4-methyl benzene sulfonic acid
ar-Toluenesulfonic acid (8CI)
4-methyl-benzene sulphonic acid
4-methyl-benzene-sulphonic acid
DTXSID0026701
NSC2167
4-Toluenesulfinic acid sodium salt
(2r,4s)-toluene-4-sulfonic acid
NSC-2167
ZINC6427042
Tox21_202364
AC-794
BDBM50294029
MFCD00064387
MFCD02683442
NSC167068
STL199173
AKOS008966288
AM90497
AT27303
CS-W019626
DB03120
MCULE-1176533515
NSC-167068
NCGC00248146-01
NCGC00248146-02
NCGC00248146-03
NCGC00259913-01
AS-82150
BP-31081
CAS-104-15-4
Para-Toluenesulfonic acid-polymer supported
DB-050363
FT-0648905
T0267
X8700
EN300-16830
C06677
273T276
A800907
AE-848/00887005
Q285878
SR-01000944854
J-001117
Q-200514
SR-01000944854-1
Toluene sulfonic acid (INCI) 4-Toluenesulfonic acid
F1908-0079
p-Toluenesulfonic acid, polymer-supported, 1.0-2.0 mmol/g on polystyrene
25231-46-3
536747-74-7
p-toluenesulfonic acid, p-toluenesulphonic acid, 4-toluenesulfonic acid, tosic acid, p-tolylsulfonic acid, toluene-4-sulfonic acid, toluenesulfonic acid, tosylic acid, benzenesulfonic acid, 4-methyl, p-methylbenzenesulfonic acid
Toluene sulfonic acid; 4-Methylbenzenesulfonic acid; 4-Toluenesulfonic acid; Benzenesulfonic acid, 4-methyl-; Benzenesulfonic acid, methyl-; Cyclophil P T S A; Cyzac 4040; Eltesol; K-Cure 040; K-Cure 1040; Kyselina p-toluenesulfonova [Czech]; Kyselina p-toluensulfonova [Czech]; Manro PTSA 65 E; Manro PTSA 65 H; Manro PTSA 65 LS; Methylbenzenesulfonic acid; Nacure 1040; TSA-HP; TSA-MH; Toluenesulfonic acid; Tosic acid; p-Methylbenzenesulfonic acid; p-Methylphenylsulfonic acid; p-Toluene sulfonate; p-Toluolenesulfonic acid; p-Tolylsulfonic acid; Toluene-4-sulphonic acid; ar-Toluenesulfonic acid (8CI); [ChemIDplus] UN2583; UN2585 (not more than 5% free sulfuric acid)
Methylbenzenesulfonic acid
Toluenesulfonic acid
Tosic acid
P-Toluene Sulfonic Acid
P-Toluene Sulphonic Acid
para toluene sulfonic acid
para toluene sulphonic acid
PARATOLUENE SULPHONIC ACID
PTS ACID
4-methylbenzenesulfonic acid
ParaTolune Sulfonic Acid
p-toluenesulfonic acid
4-methylbenzenesulfonic acid
4-toluenesulfonic acid
benzenesulfonic acid, 4-methyl-
benzenesulfonic acid, 4-methyl-, hydrate
benzenesulfonic acid, 4-methyl-, monohydrate
p-toluenesulfonic acid monohydrate
toluene-4-sulfonic acid
toluene-4-sulfonic acid monohydrate
Ar-Toluenesulfonic acid; p-Methylbenzenesulfonic acid; p-Methylphenylsulfonic acid; p-Toluenesulfonate; p-Toluenesulfonic acid; p-Toluolenesulfonic acid; p-Tolylsulfonic acid; Benzenesulfonic acid, methyl-; Cyclophil P T S A; Eltesol; Methylbenzenesulfonic acid; Toluene-p-sulfonate; Toluene-4-sulfonic acid; Toluenesulfonic acid; Tosic acid; 4-Methylbenzenesulfonic acid; 4-Toluenesulfonic acid; p-Toluenesulphonic acid; Kyselina p-toluenesulfonova; Kyselina p-toluensulfonova; Manro PTSA 65 E; Manro PTSA 65 H; Manro PTSA 65 LS; Tsa-hp; Tsa-mh; PTSA; Tosylic acid; Cyzac 4040; K-Cure 1040; NSC 167068; Nacure 1040; toluene-4-sulphonic acid


 

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