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{{Chembox {{Chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 396296298 | verifiedrevid = 439470812
| Name = Benzenesulfonic acid | Name = Benzenesulfonic acid
| Reference = <ref>, ]</ref> | Reference = <ref> {{dead link|date=January 2017|bot=medic}}{{cbignore|bot=medic}}, ]</ref>
| ImageFileL1 = Benzenesulfonic-acid-2D-skeletal.png | ImageFileL1 = Benzenesulfonic-acid-2D-skeletal.png
| ImageSizeL1 = 120px | ImageSizeL1 = 145
| ImageNameL1 = Structural formula of benzenesulfonic acid | ImageAltL1 = Skeletal formula of benzenesulfonic acid
| ImageFileR1 = Benzenesulfonic-acid-3D-balls-B.png | ImageFileR1 = Benzenesulfonic acid molecule ball.png
| ImageSizeR1 = 120px | ImageSizeR1 = 145
| ImageNameR1 = Ball-and-stick model | ImageAltR1 = Ball-and-stick model of the benzenesulfonic acid molecule
| PIN = Benzenesulfonic acid<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 789 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
| IUPACName =
| OtherNames = Benzene sulphonic acid; Benzenesulphonic acid; Phenylsulfonic acid | OtherNames = Benzene sulphonic acid; Benzenesulphonic acid; Phenylsulfonic acid; Phenylsulphonic acid; Besylic acid<ref>, ChemIndustry</ref>
⚫ |Section1={{Chembox Identifiers
| Abbreviations = | Abbreviations =
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | Section1 = {{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7093 | ChemSpiderID = 7093
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
Line 25: Line 25:
| StdInChIKey = SRSXLGNVWSONIS-UHFFFAOYSA-N | StdInChIKey = SRSXLGNVWSONIS-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 98-11-3 | CASNo = 98-11-3
| PubChem = | PubChem = 7371
| SMILES = c1ccc(cc1)S(=O)(=O)O | SMILES = OS(=O)(=O)c1ccccc1
| RTECS = DB4200000
| UNNumber = 2583, 2585, 1803
| EINECS = 202-638-7
| ChEBI = 64455
| ChEMBL = 1422641
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=6|H=6|O=3|S=1 | C=6 | H=6 | O=3 | S=1
| Appearance = Colorless crystalline solid | Appearance = Colorless crystalline solid
| Density = 1.32 g/cm<sup>3</sup> (47 °C) | Density = 1.32 g/cm<sup>3</sup> (47 °C)
| MeltingPt = * 44 °C (hydrate) | MeltingPt ={{bulleted list|44 °C (hydrate)|51 °C (anhydrous)}}
| BoilingPtC = 190
* 51 °C (anhydrous)
| BoilingPtC = 190 | Solubility = Soluble
⚫ | SolubleOther = Soluble in alcohol, insoluble in non-polar solvents
| Solubility = Soluble
⚫ | Solvent = other solvents
⚫ | SolubleOther = Soluble in alcohol, insoluble in non-polar solvents
⚫ | pKa = −2.8<ref>Guthrie, J. P. Hydrolysis of esters of oxy acids: p''K''<sub>a</sub> values for strong acids ''Can. J. Chem''. '''1978''', ''56'', 2342-2354. {{doi|10.1139/v78-385}}</ref>
⚫ | Solvent = other solvents
⚫ | pKa = -2.8<ref>Guthrie, J. P. Hydrolysis of esters of oxy acids: pKa values for strong acids. ''Can. J. Chem''. '''1978''', ''56'', 2342-2354.</ref>
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = Corrosive | MainHazards = Corrosive
| ExternalSDS =
| ExternalMSDS =
| FlashPt = >113 °C | FlashPt = >&nbsp;113&nbsp;°C
| Autoignition = | AutoignitionPt =
| GHSPictograms = {{GHS05}}{{GHS07}}
| RPhrases = {{R20}} {{R22}} {{R34}} {{R36}} {{R37}} {{R38}}
| GHSSignalWord = Danger
| SPhrases = {{S26}} {{S36/37/39}} {{S45}}
| HPhrases = {{H-phrases|290|302|314|315|319|335}}
| PPhrases = {{P-phrases|234|260|261|264|270|271|280|301+312|301+330+331|302+352|303+361+353|304+340|305+351+338|310|312|321|330|332+313|337+313|362|363|390|403+233|404|405|501}}
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| OtherFunctn = ]<br>] | OtherFunction = ]<br />]
| Function = sulfonic acids | OtherFunction_label = sulfonic acids
}} }}
}} }}


'''Benzenesulfonic acid''' is an ] with the formula C<sub>6</sub>H<sub>5</sub>SO<sub>3</sub>H. It is the simplest ] ]. '''Benzenesulfonic acid''' (] '''benzenesulfonate''') is an ] with the formula ]<sub>6</sub>]<sub>6</sub>]<sub>3</sub>]. It is the simplest ] ]. It forms white ] sheet crystals or a white waxy solid that is soluble in water and ], slightly soluble in ] and insoluble in nonpolar solvents like ]. It is often stored in the form of ] ]s. Its aqueous solution is ].

Benzenesulfonic acid forms colorless ] sheet crystals or a white waxy solid that is soluble in water and ethanol, slightly soluble in ] and insoluble in ] and ]. It is often stored in the form of alkali metal salts. Its aqueous solution is ]. It has the ability to react violently with bases and attack metals.


==Preparation== ==Preparation==
Benzenesulfonic acid is prepared from the ] of ] by concentrated ]: Benzenesulfonic acid is prepared from the ] of ] using concentrated ]:
⚫ :]


This conversion illustrates ], which has been called "one of the most important reactions in industrial organic chemistry".<ref name=Ullmann>{{Ullmann |author=Otto Lindner |author2=Lars Rodefeld|title=Benzenesulfonic Acids and Their Derivatives|year=2005|doi=10.1002/14356007.a03_507}}</ref>
⚫ :]


==Uses== ==Reactions==
⚫ Benzenesulfonic acid exhibits the reactions typical of other aromatic ]s, forming sulfonamides, sulfonyl chloride, and esters. The sulfonation is reversed above 220&nbsp;°C. Dehydration with ] gives benzenesulfonic ] ((C<sub>6</sub>H<sub>5</sub>SO<sub>2</sub>)<sub>2</sub>O). Conversion to the corresponding benzenesulfonyl chloride (C<sub>6</sub>H<sub>5</sub>SO<sub>2</sub>Cl) is effected with ].
The alkali metal salt of benzenesulfonic acid is used in the production of ] and ]. Benzenesulfonic acid is also used as an acidic catalyst in ] and ]s.


It is a strong acid, being almost fully dissociated in water.
⚫ Benzenesulfonic acid reacts with ] to form benzenesulfonic ] (C<sub>6</sub>H<sub>5</sub>SO<sub>2</sub>OSO<sub>2</sub>C<sub>6</sub>H<sub>5</sub>), and may be converted to the corresponding ] ] (C<sub>6</sub>H<sub>5</sub>SO<sub>2</sub>Cl) with ].


Benzenesulfonic acid and related compounds undergo desulfonation when heated in water near 200&nbsp;°C. The temperature of desulfonation correlates with the ease of the sulfonation:<ref name=Ullmann/>
A variety of pharmaceutical drugs are prepared as ] of benzenesulfonic acid and are known as besylates or besilates.
:C<sub>6</sub>H<sub>5</sub>SO<sub>3</sub>H + H<sub>2</sub>O → C<sub>6</sub>H<sub>5</sub>OH + H<sub>2</sub>SO<sub>4</sub>

For that reason, sulfonic acids are usually used as a ], or as a ] in ].

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

:C<sub>6</sub>H<sub>5</sub>SO<sub>3</sub>Na + 2 NaOH → C<sub>6</sub>H<sub>5</sub>ONa + Na<sub>2</sub>SO<sub>3</sub>
:C<sub>6</sub>H<sub>5</sub>ONa + HCl → C<sub>6</sub>H<sub>5</sub>OH + NaCl
The process has been largely displaced by the ], which generates less waste.

==Uses==
Salts of benzenesulfonic acid such as ] and monoethanolamine benzenesulfonate are used as surfactants in laundry detergent.<ref>{{Cite web|url=https://www.pg.com/productsafety/msds/fabric_and_homecare/detergents/Tide_Simply_-_updated_02-05-2014.pdf|title=Safety Data Sheet - P & G's Tide Simply|date=2014-02-05|website=pg.com |access-date=2018-04-13}}</ref>

A variety of ]s are prepared as benzenesulfonate salts and are known as '''besilates''' (]) or '''besylates''' (]).


==References== ==References==
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] ]
]

]
]
]
]
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Latest revision as of 15:53, 29 December 2024

Benzenesulfonic acid
Skeletal formula of benzenesulfonic acid
Ball-and-stick model of the benzenesulfonic acid molecule
Names
Preferred IUPAC name Benzenesulfonic acid
Other names Benzene sulphonic acid; Benzenesulphonic acid; Phenylsulfonic acid; Phenylsulphonic acid; Besylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.399 Edit this at Wikidata
EC Number
  • 202-638-7
PubChem CID
RTECS number
  • DB4200000
UNII
UN number 2583, 2585, 1803
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H6O3S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H,7,8,9)Key: SRSXLGNVWSONIS-UHFFFAOYSA-N
  • InChI=1/C6H6O3S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H,7,8,9)Key: SRSXLGNVWSONIS-UHFFFAOYAJ
SMILES
  • OS(=O)(=O)c1ccccc1
Properties
Chemical formula C6H6O3S
Molar mass 158.17 g·mol
Appearance Colorless crystalline solid
Density 1.32 g/cm (47 °C)
Melting point
  • 44 °C (hydrate)
  • 51 °C (anhydrous)
Boiling point 190 °C (374 °F; 463 K)
Solubility in water Soluble
Solubility in other solvents Soluble in alcohol, insoluble in non-polar solvents
Acidity (pKa) −2.8
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Corrosive
GHS labelling:
Pictograms GHS05: CorrosiveGHS07: Exclamation mark
Signal word Danger
Hazard statements H290, H302, H314, H315, H319, H335
Precautionary statements 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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

Preparation

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

Aromatic sulfonation of benzene

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

Reactions

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:

C6H5SO3H + H2O → C6H5OH + H2SO4

For that reason, 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.

Uses

Salts of benzenesulfonic acid such as sodium benzenesulfonate (Ludigol) and monoethanolamine benzenesulfonate are used as surfactants in laundry detergent.

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

References

  1. Benzenesulfonic acid , 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. ^ 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. ISBN 978-3527306732.
  6. "Safety Data Sheet - P & G's Tide Simply" (PDF). pg.com. 2014-02-05. Retrieved 2018-04-13.
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