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CAS No: 104-15-4
p-Toluenesulfonic acid (PTSA) is an organic compound with the formula CH3C6H4SO3H. An aromatic sulfonic acid, often used as a strong acid catalyst. p-Toluenesulfonic acid monohydrate has been used as a reducing agent for the reductive amination of ketones and aldehydes. In the presence of p-Toluenesulfonic acid monohydrate novel deazaflavin-cholestane hybrid compounds have been synthesized in a condensation reaction. 2-Phenylethyl alpha-glucoside has also been synthesized in the presence of p-Toluenesulfonic acid monohydrate. p-toluenesulfonic 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.
P-TOLUENESULFONIC ACID; 4-Methylbenzenesulfonic acid; p-Toluenesulphonic acid; 4; Toluenesulfonic acid; Toluene-4-sulfonic acid; Tosic acid; p-Tolylsulfonic acid; Benzenesulfonic acid, 4-methyl-; p-Methylbenzenesulfonic acid; Tosylic acid; p-Toluenesulfonate
Eltesol; p-Methylphenylsulfonic acid; Cyclophil P T S A; ar-Toluenesulfonic acid; p Toluolenesulfonic acid; P-Toluene Sulfonic acid; PARA-TOLUENE SULFONATE; Benzenesulfonic acid, methyl-; Methylbenzenesulfonic acid; Toluene-4-sulphonic acid; PTSA; Nacure 1040; Cyzac 4040; p-Toluene sulfonate; 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); p-toluene sulphonic acid; para-toluenesulfonic acid; HSDB 2026; UNII-QGV5ZG5741; NSC 167068; p-toluensulfonic acid; 2(Or 4)-toluenesulphonic acid;; Toluen-4-sulfonsaeure; toluene-p-sulfonic acid; p-Toluene-sulfonic acid; 4-Toluene sulfonic acid; para-toluenesulphonic acid; paratoluene sulphonic acid; para toluene sulfonic acid; CHEMBL541253; QGV5ZG5741; 4-TOLUENE-SULFONIC ACID; ar-Toluenesulfonic acid (8CI); 4-methylbenzene-1-sulfonic acid; P-Toluene Sulfonic acid(monohydrate); TsOH; WLN: WSQR D1; p-TSA; K-Cure 040; TSU; Kyselina p-toluensulfonova [Czech]; p-Toluenesulfonic acid, pure, 12% in acetic acid; Kyselina p-toluenesulfonova [Czech]; EINECS 203-180-0; BRN 0472690; TosicAcid; 4-sulphotoluene; AI3-26478; pTsOH; TosOH; Tosic acid p-TSA; p-toluenesulfonicacid; p-TsOH; Tos-OH; p-toluenesufonic acid; Ts-OH; p-toluen sulfonic acid; p-toluenesuiphonic acid; p; toluenylsulfonic acid; paratoluenesulfonic acid; PTS ACID; 4-toluenesulphonic 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; ACMC-1C4C9; 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-methyl benzene sulfonic acid; 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; ANW-15037; BBL020095; BDBM50294029; MFCD00064387; MFCD02683442; NSC167068; STL199173; AKOS008966288; AM90497; CS-W019626; DB03120; MCULE-1176533515; NSC-167068; Para-Toluenesulfonic acid-polymer supported
Overview
p-toluene sulfonic acid (Its molecular structural formula is p-CH3C6H4SO3H, also known as TsOH, English name is p-toluene sulfonic acid) 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-monohydrate (TsOHH2O) 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-toluene sulfonic 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. It 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.
Chemical properties
Colorless monoclinic sheet or columnar crystals. Soluble in ethanol and ether, slightly soluble in water and hot benzene.
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.
Production method
By p-toluenesulfonyl chloride hydrolysis derived. Toluene can also be used as raw materials, sulfonated by sulfuric acid derived.
Description
p-Toluene sulfonic acid (PTSA) or tosylic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H. It 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, 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 strong mineral acids (especially nitric acid, sulfuric acid, and per chloric acid), TsOH is non - oxidizing.
Storage and transportation characteristics
Storehouse is ventilates, low temperature and dry; Store with base separately
Chemical Properties
Clear colorless to light yellow solution
Definition
An arenesulfonic acid that is benzenesulfonic acid in which the hydrogen at position 4 is replaced by a methyl group.
Reactions
p-Toluene sulfonic acid 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 it 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.
Preparation and handling
TsOH is prepared on an industrial scale by the sulfonation of toluene. It hydrates readily. Common impurities include benzene sulfonic acid and sulfuric acid. Impurities can be removed by recrystallization from its concentrated aqueous solution followed by azeotropic drying with toluene.
Toluene sulfonic acid finds use in organic synthesis as an "organic - soluble" acid catalyst.
Examples of uses :
Acetalization of an aldehyde.
Esterification of carboxylic acids.
Trans esterification of an ester.
Tosylate esters
Tosylate esters are used as alkylating agents because the tosyl group is electron-with drawing, which makes the tosylate anion a good leaving group. The tosyl group is also a protecting group for alcohols and amines, prepared by combining the alcohol with 4- toluenesulfonyl chloride, usually in an aprotic solvent, often pyridine, the basicity of which activates the reaction. Toluenesulfonate esters undergo nucleophilic attack or elimination. Reduction of tosylate esters gives the hydrocarbon. Thus, tosylation followed by reduction allows for the deoxygenation of alcohols.
Industry Uses
Agricultural chemicals (non-pesticidal)
Catalyst in the manufacture of foam insulation
Corrosion inhibitors and anti-scaling agents
Finishing agents
Industrial Cleaners, Metal Working, Textile Dye Manufacturing, Polymers and Coatings Catalysts
Intermediates
Oxidizing/reducing agents
Paint additives and coating additives not described by other categories
Process regulators
Processing aids,
Consumer Uses
Adhesives and sealants
Agricultural products (non-pesticidal)
Building/construction materials not covered elsewhere
Cleaning and furnishing care products
Fabric, textile, and leather products not covered elsewhere
Paints and coatings
Industry Processing Sectors
Adhesive manufacturing
All other basic organic chemical manufacturing
All other chemical product and preparation manufacturing
Fabricated metal product manufacturing
Oil and gas drilling, extraction, and support activities
Paint and coating manufacturing
Pesticide, fertilizer, and other agricultural chemical manufacturing
Pharmaceutical and medicine manufacturing
Plastic material and resin manufacturing
Soap, cleaning compound, and toilet preparation manufacturing
Textiles, apparel, and leather manufacturing
Toluenesulfonic acid (p-toluenesulfonic acid; TsOH; p TsOH): An aromatic sulfonic acid, often used as a strong acid catalyst. Most commonly refers to para-methylbenzenesulfonic acid monohydrate (CH3C6H4SO3H.H2O; pKa -2), but the anhydrous form may also be used.
p-Toluenesulfonic acid (PTSA or pTsOH) or tosylic acid (TsOH) is an organic compound with the formula CH3C6H4SO3H. It is a white solid that is soluble in water, alcohols, and other polar organic solvents.[5] The CH3C6H4SO2 group is known as the tosyl group and is often abbreviated as Ts or Tos. Most often, TsOH refers to the monohydrate, TsOH.H2O.[5]
As with other sulfonic acids, TsOH is a strong organic acid. It is about one million times stronger than benzoic acid.[5] It is one of the few strong acids that is solid and, hence, conveniently weighed.
Application
Acetylation of Alcohols using Acetylating Reagents and Acid Catalysts
t-Butyldimethylsilylation of Alcohols using TBS Reagents
Trimethylsilylation of Alcohols using TMS Reagents
Acid Catalyzed Acetalization Using p-Toluenesulfonic Acid
About this substance
This substance is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to < 100 000 tonnes per annum.
This substance is used by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Widespread uses by professional workers
This substance is used in the following products: pH regulators and water treatment products and laboratory chemicals. This substance is used in the following areas: health services and scientific research and development. Other release to the environment of this substance is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.
Formulation or re-packing
This substance is used in the following products: metal surface treatment products and non-metal-surface treatment products.
Release to the environment of this substance can occur from industrial use: formulation of mixtures and formulation in materials.
Uses at industrial sites
This substance is used in the following products: coating products, polymers and lubricants and greases.
This substance is used for the manufacture of: chemicals, fabricated metal products, plastic products and machinery and vehicles.
Release to the environment of this substance can occur from industrial use: as processing aid, as an intermediate step in further manufacturing of another substance (use of intermediates), for thermoplastic manufacture and as processing aid.
Use of the substance/preparation
Identified uses basic Intermediates
Restriction on
Use not for food or drug use, for laboratory use only
Nandadeep is one of the largest manufacturer and leading exporter of Para Toluene Sulfonic Acid (PTSA). We can manufacture PTSA monohydrate with several different specifications as per the need of the customer. PTSA is available both in crystalline form as well as a solution and has a wide range of application. Nandadeep offers PTSA grades with as low as 0.1% free sulfuric acid, resulting in lower corrosion of end user's machinery and reactors.
In Addition to above, there are many customer specific grades available
Applications :
1. Used as a catalyst in the following processes:
o Cross linking reactions
o Ethly Acetate, Butyl Acetate
o Plasticizer manufacturing DOP, DBP, DEP
o Unsymmetrical benzils
o Highly substituted piperidines
o 1,3,5-Trisubstituted benzenes by trimerization of alkynes
o Triazoloquinazolinone and benzimidazoquinazolinone derivatives
o Selenated ketene dithioacetals
o Coating industry
o Electronic polymers
2. Used as Intermediate in
o Fine chemical manufacture
o Dye/pigment
o Metal working
o Pharmaceutical intermediates (tetra cycline drugs, antiviral)
3. As a curing agent in bulk quantities in thermosetting resin systems, varnishes, acrylic resins, foundry resins.
4. As a neutralizing agent for acrylonitrile production.
5. Used in paints, paper chemicals, API, detergent, cosmetics.
6. Anionic surfactants (clear liquid detergent, luxury shampoo).
7. Performance additives for paint & coating.
8. Esterification /condensation /acetylation / polymerization/ alkylation/ hydrolysis /dehydration.
9. Also applicable for use in food packaging adhesives.
PTSA Application:
• PTSA is comparable in strength to mineral acids such as Sulphuric acid, but are especially suitable for organic reactions where an inorganic, mineral acid could cause charring, oxidation, or an unwanted chemical reaction.
• It is most useful as acid-catalyst reaction such as esterification /condensation /acetylation / polymerization/ alkylation’s/ hydrolysis /dehydration. · As a hardening agent of furan resin which is applied in foundry Industry (Sand Casting).
• In Plasticizers industries mainly for DEP/ DOP/ DBP – As esterification catalyst .· It is also used as curing agent for many resin system such as mino/phenolic/acrylic resins/resoles / epoxies / amino-Plastics and furniture lacquers.
• As an anti-stress additive for electroplating baths additive, plastics, coatings, dyes, pharmaceutical intermediates, hydrotrope, coupling agent and as a wetting agent.
• Also applicable for use in food packaging adhesives.
• As intermediate of dye chemistry
• In Butyl Acrylate manufacturing – As catalyst.· In Pharmaceutical industries is used for manufacturing of below product – As catalyst. CIPROFLOXACIN , Persantin, Naproxen DOXYCYCLIN SULPHAMETHAXAZOLE . And produce the intermediates of Amoxicillin , Cefadroxil .
IUPAC Names:
4-methyl benzenesulphonic acid
4-methylbenzene-1-sulfonic acid
4-methylbenzene-1-sulfonic acid hydrate
4-Methylbenzenesulfonic acid
4-methylbenzenesulfonic acid
4-methylbenzenesulfonic acid hydrate
4-methylbenzenesulfonic acid hydrate
4-Methylbenzenesulfonic acid monohydrate
4-Methylbenzolsulfonsäure
4-Toluenesulfonic acid monohydrate
acide para toluene sulfonique
acido 4-metilbenzensulfonico
Benzenesulfonic acid, 4-methyl-
Benzenesulfonic acid, 4-methyl-, monohydrate
p-Toluenesulfonic acid
p-Toluenesulfonic acid
p-Toluenesulfonic Acid Monohydrate
p-Toluenesulfonic acid, Tosylic acid, Tosic acid, PTSA
p-Toluenesulphonic acid
p-toluenesulphonic acid
p-Toluenesulphonic acid
p-toluenesulphonic acid (containing a maximum of 5 % H2SO4)
p-toluenesulphonic acid hydrate
p-toluenesulphonic acid, containing a maximum of 5% H2SO4
Para Toluene Sulfonic Acid (PTSA)
Reaction mass of sulphuric acid and 7732-18-5
toluen 4-sulfonová kyselina
Toluene sulphonic acid
toluene-4-silphonic acid
TOLUENE-4-SULPHONIC ACID
Toluene-4-sulphonic acid
toluene-4-sulphonic acid
toluene-4-sulphonic acid
TOLUENESULFONIC ACID
Toluenesulfonic acid, p-
Toluol-4-sulfonsäure
Toluol-4-sulfonsäure Monohydrat
TSA
ácido 4-metilbenzenosulfónico
TRADE Names:
4-Methylbenzenesulfonic Acid
4-Methylbenzolsulfonsaeure, Monohydrat
4-Methylbenzolsulfonsäure
4-Toluenesulfonic acid
Acide benzènesulfonique, 4-méthyl-
Acide benzènesulfonique, 4-méthyl- (< 5 % acide sulfurique)
Acide toluene-4-sulfonique
acido tolueno-4-sulfonico
Benzenesulfonic acid, 4-methyl-
Benzenesulfonic acid, 4-methyl- (9CI)
Benzolsulfonsaeure, 4-methyl
Benzolsulfonsäure, 4-Methyl-
Cyzac 4040
Eltesol TA
Eltesol TA 65
Eltesol TSX/SF
K-Cure 1040
LAS 4-methyl, p-
LAS 4-methyl, p- (max 5 % sulfuric acid); <5% Schwefelsaeure
Manro PTSA/95
Manro PTSA/C
MANRO PTSA/C; 60-100% Active Matter; active substance
Manro PTSA/E
Manro PTSA/LG
Manro PTSA/LS
Methylbenzolsulfonsäure, 4-
Nacure 1040
p-Methylbenzenesulfonic acid
p-Methylphenylsulfonic acid
p-Toluene sulfonate
p-TOLUENE SULFONIC ACID
p-Toluene Sulfonic Acid Monohydrat
p-Toluenesulfonic acid
p-Toluenesulphonic acid
p-Toluolsulfonsaeure
p-Toluolsulfonsäure
p-Toluolsulfonsäure in ca.65%iger wässriger Lsg.; 65% Active Matter; active substance
p-Tolylsulfonic acid
P.T.S.A
PARA-TOLUENESULFONIC ACID CC5U
PARATOLUOLSULFONSAEURE
PTSA 70
Reworyl T 65
Stepanate PTSA-C; 60-100% Active Matter; active substance
Sulframin TX
Toluene Sulfonic Acid
Toluene sulfonic acid (INCI)
Toluene sulphonic acid (65% in water) TL65LS; 65% Active Matter; active substance
toluene-4-sulphonic acid
Toluenesulfonic acid
TOLUENESULFONIC ACID, HI-PARA
Toluenesulfonic acid, p-
Toluenesulfonic acid, p- 65%; 65% Active Matter; active substance
Toluensulfonic acid; 95% Active Matter; active substance
Toluol-4-sulfonsaeure
Toluol-4-sulfonsäure
Toluol-p-sulfonsäure
Toluolsulfo säure, p- 65 %; 65% Active Matter; active substance
Toluolsulfo säure, para
Toluolsulfonic acid, para
Tosic acid
TSA
Wilconate TX Acid
Witco TX Acid
