| p-Toluenesulfonic acid[1] | |
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| IUPAC name | 4-methylbenzenesulfonic acid |
| Other names | Tosylic acid p-toluenesulfonic acid tosic acid PTSA |
| Identifiers | |
| CAS number | 104-15-4 6192-52-5 (monohydrate) |
| SMILES | Cc1ccc(S(=O)(O)=O)cc1 |
| Properties | |
| Molecular formula | C7H8O3S |
| Molar mass | 172. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 20 g/mol 190. 22 g/mol (monohydrate) |
| Appearance | colorless (white) solid |
| Melting point |
106-107 °C |
| Boiling point |
140 °C at 20 mmHg |
| Solubility in water | 67g/100 ml |
| Acidity (pKa) | -2. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. 8 |
| Structure | |
| Molecular shape | tetrahedral at S |
| Hazards | |
| Main hazards | skin irritant |
| R-phrases | 36/37/38 |
| S-phrases | 26 |
| Related compounds | |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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p-Toluenesulfonic acid (PTSA) is an organic compound with the formula CH3C6H4SO3H. Molecular geometry or molecular structure is the three- Dimensional arrangement of the Atoms that constitute a Molecule. Occupational safety and health is a cross-disciplinary area concerned with protecting the Safety, Health and welfare of people engaged in R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly An organic compound is any member of a large class of Chemical compounds whose Molecules contain Carbon. In Chemistry, a methyl group is a Hydrophobic Alkyl Functional group named after Methane (4 Benzene, or benzol, is an organic Chemical compound and a known Carcinogen with the molecular formula C 6 H 6 Sulfonic acid is an unstable Acid with the formula H-S(=O2-OH TsOH, as it is abbreviated, is a white solid that is soluble in water, alcohols, and other polar organic solvents. In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon "Polar molecule" and "Non-polar" redirect here Most often, TsOH refers to the monohydrate, TsOH. Hydrate is a term used in Inorganic chemistry and Organic chemistry to indicate that a substance contains Water. H2O.
TsOH is a strong organic acid, about a million times stronger than benzoic acid. An organic acid is an Organic compound with Acidic properties Benzoic acid, C7H6O2 (or C6H5COOH is a colorless crystalline solid and the simplest Aromatic Carboxylic 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. Nitric acid ( H[[nitrate NO3]] also known as Aqua fortis and spirit of nitre, is a highly corrosive and Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid. Perchloric acid, HClO4 is an Oxoacid of Chlorine and is a colorless liquid soluble in water.
Contents |
Preparation and handling
TsOH is prepared on an industrial scale by the sulfonation of toluene. Sulfonic acid is an unstable Acid with the formula H-S(=O2-OH Toluene, also known as methylbenzene or phenylmethane, is a clear water -insoluble liquid with the typical smell of Paint thinners redolent of 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. Hydrochloric acid is the Solution of Hydrogen chloride ( H[[Chlorine Cl]] in water An azeotrope (pronounced [2]
Toluenesulfonic acid finds use in organic synthesis as an "organic-soluble" acid catalyst. Organic synthesis is a special branch of Chemical synthesis and is concerned with the construction of Organic compounds via Organic reactions Organic Examples of uses:
- Acetalization of an aldehyde. An acetal is a Molecule with two single bonded oxygens attached to the same carbon atom An aldehyde is an organic compound containing a terminal Carbonyl group. [3]
- Esterification of carboxylic acids. Esterification is the general name for a Chemical reaction in which two reactants (typically an alcohol and an acid form an Ester as the reaction product Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H [4]
- Transesterification of an ester. In Organic chemistry, transesterification is the process of exchanging the Alcohol group of an Ester compound with another Alcohol. Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least [5]
See also
It is also used as a catalyst with 3,4 dihydro-2H pyran in alcohol protection. A tosyl group (abbreviated Ts or Tos) combines the Toluene and Sulfonyl Functional groups. Collidine p-toluenesulfonate or CTPS is a salt between ''p''-toluenesulfonic acid and Collidine (246-trimethylpyridine
References
- ^ Merck Index, 11th Edition, 9459.
- ^ Perrin, D. D. and Armarego, W. L. F. , Purification of Laboratory Chemicals, Pergamon Press: Oxford, 1988.
- ^ H. Griesser, H. ; Öhrlein, R. ; Schwab, W. ; Ehrler, R. ; Jäger, V. (2004). "3-Nitropropanal, 3-Nitropropanol, and 3-Nitropropanal Dimethyl Acetal". Org. Synth.; Coll. Organic Syntheses is a Scientific journal that since 1921 has provided the Chemistry community with annual collections of detailed and checked procedures Vol. 10: 577.
- ^ Furuta, K. Gao, Q. -z. ; Yamamoto, H. (1998). "Chiral (Acyloxy)borane Complex-catalyzed Asymmetric Diels-Alder Reaction: (1R)-1,3,4-Trimethyl-3-cyclohexene-1-carboxaldehyde". Org. Synth.; Coll. Organic Syntheses is a Scientific journal that since 1921 has provided the Chemistry community with annual collections of detailed and checked procedures Vol. 9: 722.
- ^ Imwinkelried, R. ; Schiess, M. ; Seebach, D. (1993). "Diisopropyl (2S,3S)-2,3-O-isopropylidenetartrate". Org. Synth.; Coll. Organic Syntheses is a Scientific journal that since 1921 has provided the Chemistry community with annual collections of detailed and checked procedures Vol. 8: 201.
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