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Benzenesulfonic acid (conjugate base benzenesulfonate) is an organosulfur compound with the formula C₆H₅SO₃H. 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:

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

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:^[5]

C₆H₅SO₃H + H₂O → C₆H₆ + H₂SO₄

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

Benzensulfonic acid is commonly used as the active ingredient in laundry detergent used in clothes washing machines.^[6]

Benzenesulfonic acid is often used to convert to other specialty chemicals.

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.

References

^ Benzenesulfonic acid^{[dead link]}, Sigma-Aldrich
^ Besylic acid, ChemIndustry
^ 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.
^ Guthrie, J. P. Hydrolysis of esters of oxy acids: pK_a values for strong acids Can. J. Chem. 1978, 56, 2342-2354. doi:10.1139/v78-385
^ ^a ^b Otto Lindner, Lars Rodefeld "Benzenesulfonic Acids and Their Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_507
^ "Safety Data Sheet - P & G's Tide Simply" (PDF). pg.com. 02-05-2014. Retrieved 04-13-2018. Check date values in: |access-date=, |date= (help)

UpToDate Contents

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English Journal

Determination of Enantiomeric Impurity of Levamlodipine Besylate Bulk Drug by Capillary Electrophoresis Using Carboxymethyl-β-Cyclodextrin.

Qi Y1, Zhang X.
Cell biochemistry and biophysics.Cell Biochem Biophys.2014 Dec;70(3):1633-7. doi: 10.1007/s12013-014-0106-2.
A rapid capillary electrophoresis method using carboxymethyl-β-cyclodextrin (CM-β-CD) as chiral selector was developed and validated for the enantiomeric purity determination of levamlodipine besylate bulk drug. Several parameters for were optimized for a satisfactory enantioresolution, including
PMID 25269770

The impact of chirality on the development of robust and stable tablet formulation of (S-) amlodipine besylate.

Hadžidedić S1, Uzunović A, Sehić Jazić S, Kocova El-Arini S.
Pharmaceutical development and technology.Pharm Dev Technol.2014 Dec;19(8):930-41. doi: 10.3109/10837450.2013.840847. Epub 2013 Oct 7.
The aim of this study was to compare the specific characteristics of the S-enantiomer and the racemate of amlodipine besylate (AB) in order to design a robust and stable formulation of the active S-enantiomer which will guarantee continuous performance of the unichiral version of amlodipine. Preform
PMID 24099553

Steady-state and synchronous spectrofluorimetric methods for simultaneous determination of aliskiren hemifumarate and amlodipine besylate in dosage forms.

Ebeid WM1, Elkady EF, El-Zaher AA, El-Bagary RI, Patonay G.
Luminescence : the journal of biological and chemical luminescence.Luminescence.2014 Nov;29(7):878-83. doi: 10.1002/bio.2636. Epub 2014 Mar 31.
Aliskiren hemifumarate (ALS) and amlodipine besylate (AML) were simultaneously determined by two different spectrofluorimetric techniques. The first technique depends on direct measurement of the steady-state fluorescence intensities of ALS and AML at 313 nm and 452 nm upon excitation at 290 and 375
PMID 24687516

Japanese Journal

降圧配合錠の製剤学的性質が成分溶出性に与える影響

分析化学 64(11), 835-844, 2015
NAID 130005129314

透析導入時の薬剤選択に苦慮した急性間欠性ポルフィリン症の1例

日本透析医学会雑誌 48(7), 437-441, 2015
NAID 130005090710

アムロジピンベシル酸塩製剤と酸化マグネシウム製剤の‌同時簡易懸濁による主薬量の変動

医療薬学 40(4), 252-257, 2014
NAID 130005062834

Related Pictures

★リンクテーブル★

リンク元	「ベシル酸」「ベシル酸塩」「ベシレート」「besilate」
拡張検索	「amlodipine besylate」

「ベシル酸」

Benzenesulfonic acid^[1]
Names
	Preferred IUPAC name Benzenesulfonic acid
	Other names Benzene sulphonic acid; Benzenesulphonic acid; Phenylsulfonic acid; Phenylsulphonic acid; Besylic acid
Identifiers
CAS Number	98-11-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:64455;
ChEMBL	ChEMBL1422641;
ChemSpider	7093 ;
ECHA InfoCard	100.002.399
EC Number	202-638-7
PubChem CID	7371;
RTECS number	DB4200000
UNII	685928Z18A ;
UN number	2583, 2585, 1803
	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 c1ccc(cc1)S(=O)(=O)O ;
Properties
Chemical formula	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)
Solubility in water	Soluble
Solubility in other solvents	Soluble in alcohol, insoluble in non-polar solvents
Acidity (pKa)	−2.8
Hazards
Main hazards	Corrosive
Safety data sheet	External MSDS
GHS pictograms
GHS signal word	Danger
GHS hazard statements	H290, H302, H314, H315, H319, H335
GHS precautionary statements	P234, P260, P261, P264, P270, P271, P280, P301+312, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P330, P332+313, P337+313, P362, P363, <abbr class="abbr" title="Error in hazard statements">P390, P403+233, P404, P405
Flash point	> 113 °C
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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	Infobox references