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Revision as of 11:03, 12 November 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.← Previous edit Latest revision as of 15:53, 29 December 2024 edit undoZinnober9 (talk | contribs)Extended confirmed users, Pending changes reviewers51,986 edits Restored revision 1265989386 by Zinnober9 (talk): Unexplained changes, breakage.Tags: Twinkle Undo 
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{{Chembox {{Chembox
| Watchedfields = changed
| verifiedrevid = 396119453 | 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 = 7093 | ChemSpiderID = 7093
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 685928Z18A | UNII = 685928Z18A
| InChI = 1/C6H6O3S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H,7,8,9) | InChI = 1/C6H6O3S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H,7,8,9)
| InChIKey = SRSXLGNVWSONIS-UHFFFAOYAJ | InChIKey = SRSXLGNVWSONIS-UHFFFAOYAJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H6O3S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H,7,8,9) | StdInChI = 1S/C6H6O3S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H,7,8,9)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| 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=5|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 = 0.7
}} }}
| 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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