Benzenesulfonic acid

Benzenesulfonic acid (conjugate base benzenesulfonate) is an organosulfur compound with the formula C6H6O3S. It is the simplest aromatic sulfonic acid. It forms white deliquescent sheet crystals or a white waxy solid that is soluble in water and ethanol, slightly soluble in benzene and insoluble in nonpolar solvents like diethyl ether. It is often stored in the form of alkali metal salts. Its aqueous solution is strongly acidic.

Benzenesulfonic acid[1]
Skeletal formula of benzenesulfonic acid
Ball-and-stick model of the benzenesulfonic acid molecule
Names
Preferred IUPAC name
Benzenesulfonic acid[3]
Other names
Benzene sulphonic acid; Benzenesulphonic acid; Phenylsulfonic acid; Phenylsulphonic acid; Besylic acid[2]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.399 Edit this at Wikidata
EC Number
  • 202-638-7
RTECS number
  • DB4200000
UNII
UN number 2583, 2585, 1803
  • InChI=1S/C6H6O3S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H,7,8,9) checkY
    Key: SRSXLGNVWSONIS-UHFFFAOYSA-N checkY
  • InChI=1/C6H6O3S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H,7,8,9)
    Key: SRSXLGNVWSONIS-UHFFFAOYAJ
  • OS(=O)(=O)c1ccccc1
Properties
C6H6O3S
Molar mass 158.17 g·mol−1
Appearance Colorless crystalline solid
Density 1.32 g/cm3 (47 °C)
Melting point
  • 44 °C (hydrate)
  • 51 °C (anhydrous)
 
Boiling point 190 °C (374 °F; 463 K)
Soluble
Solubility in other solvents Soluble in alcohol, insoluble in non-polar solvents
Acidity (pKa) −2.8[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Corrosive
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H290, H302, H314, H315, H319, H335
P234, P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P363, P390, P403+P233, P404, P405, P501
Flash point > 113 °C
Safety data sheet (SDS) External MSDS
Related compounds
Related sulfonic acids
Sulfanilic acid
p-Toluenesulfonic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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PreparationEdit

Benzenesulfonic acid is prepared from the sulfonation of benzene using concentrated sulfuric acid:

 

This conversion illustrates aromatic sulfonation, which has been called "one of the most important reactions in industrial organic chemistry".[5]

ReactionsEdit

Benzenesulfonic acid exhibits the reactions typical of other aromatic sulfonic acids, forming sulfonamides, sulfonyl chloride, and esters. The sulfonation is reversed above 220 °C. Dehydration with phosphorus pentoxide gives benzenesulfonic acid anhydride ((C6H5SO2)2O). Conversion to the corresponding benzenesulfonyl chloride (C6H5SO2Cl) is effected with phosphorus pentachloride.

It is a strong acid, being almost fully dissociated in water.

Benzenesulfonic acid and related compounds undergo desulfonation when heated in water near 200 °C. The temperature of desulfonation correlates with the ease of the sulfonation:[5]

C6H5SO3H + H2O → C6H6 + H2SO4

Because of that, sulfonic acids are usually used as a protecting group, or as a meta director in electrophilic aromatic substitution.

The alkali metal salt of benzenesulfonic acid was once used in the industrial production of phenol. The process, sometimes called alkaline fusion, initially affords the phenoxide salt:

C6H5SO3Na + 2 NaOH → C6H5ONa + Na2SO3
C6H5ONa + HCl → C6H5OH + NaCl

The process has been largely displaced by the Hock process, which generates less waste.

UsesEdit

Salts of Benzenesulfonic acid such as Sodium benzenesulfonate (Ludigol) and Monoethanolamine benzenesulfonate are used as surfactants in laundry detergent.[6]

A variety of pharmaceutical drugs are prepared as benzenesulfonate salts and are known as besilates (INN) or besylates (USAN).

In a diluted form, it is also used as a polymer remover stripping agent.[clarification needed][citation needed]

ReferencesEdit

  1. ^ Benzenesulfonic acid[dead link], Sigma-Aldrich
  2. ^ Besylic acid, ChemIndustry
  3. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 789. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  4. ^ Guthrie, J. P. Hydrolysis of esters of oxy acids: pKa values for strong acids Can. J. Chem. 1978, 56, 2342-2354. doi:10.1139/v78-385
  5. ^ a b Otto Lindner, Lars Rodefeld (2005). "Benzenesulfonic Acids and Their Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_507.{{cite encyclopedia}}: CS1 maint: uses authors parameter (link)
  6. ^ "Safety Data Sheet - P & G's Tide Simply" (PDF). pg.com. 2014-02-05. Retrieved 2018-04-13.