Isethionic acid

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Isethionic acid
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Isethionic acid
Names
Preferred IUPAC name
2-Hydroxyethane-1-sulfonic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.169 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6) Yes check.svgY
    Key: SUMDYPCJJOFFON-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6)
    Key: SUMDYPCJJOFFON-UHFFFAOYAO
  • O=S(=O)(O)CCO
Properties
C2H6O4S
Molar mass 126.13 g/mol
Density 1.63 g/cm3
Acidity (pKa)1.39 (predicted)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Isethionic acid is an organosulfur compound containing an alkyl sulfonic acid located beta to a hydroxy group. Its discovery is generally attributed to Heinrich Gustav Magnus, who prepared it by the action of solid sulfur trioxide on ethanol in 1833. [1] It is a white water-soluble solid used in the manufacture of certain surfactants and in the industrial production of taurine. It is most commonly available in the form of its sodium salt (sodium isethionate).

Contents

Synthesis

The original synthesis of the compound, involving the reaction of sulfur trioxide with ethanol, has largely been replaced by more advanced methods. An alternative production method involves the hydrolysis of carbyl sulfate, which is derived from the sulfonation of ethylene.

Isethionic acid 2-step.svg

However the most common route is the reaction of ethylene oxide with aqueous sodium bisulfite, which produces the sodium salt (sodium isethionate):

Sodium isethionate EO.svg

Reactions

Isethionic acid is used as a starting material in the industrial production of taurine.

Dehydration of isethionic acid gives vinylsulfonic acid. [2]

Derivatives

Fatty acid esters of isethionic acid (such as sodium lauroyl isethionate and sodium cocoyl isethionate) are used as biodegradable anionic surfactants. [3] These materials are much milder to skin that other sulfate based surfactants (i.e. sodium lauryl sulfate) [4] making them popular for use in make-up, shampoos and detergent bars including those made by Dove.

Isethionic acid is also used as a counter ion in certain pharmaceutical formulations, including the antimicrobials hexamidine and pentamidine. [5]

Biological importance

Studies made on dog heart slices suggested that heart tissue may be capable of converting taurine to isethionic acid, further experiments demonstrated that this tissue may synthesize taurine from cystine. [6]

See also

Related Research Articles

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<span class="mw-page-title-main">Sulfonic acid</span> Organic compounds with the structure R−S(=O)2−OH

In organic chemistry, sulfonic acid refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

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Sulfation is the chemical reaction that entails the addition of SO3 group. In principle, many sulfations would involve reactions of sulfur trioxide (SO3). In practice, most sulfations are effected less directly. Regardless of the mechanism, the installation of a sulfate-like group on a substrate leads to substantial changes.

<span class="mw-page-title-main">Organosulfate</span> Organic compounds of the form R–O–SO₃ (charge –1)

In organosulfur chemistry, organosulfates are a class of organic compounds sharing a common functional group with the structure R−O−SO−3. The SO4 core is a sulfate group and the R group is any organic residue. All organosulfates are formally esters derived from alcohols and sulfuric acid although many are not prepared in this way. Many sulfate esters are used in detergents, and some are useful reagents. Alkyl sulfates consist of a hydrophobic hydrocarbon chain, a polar sulfate group and either a cation or amine to neutralize the sulfate group. Examples include: sodium lauryl sulfate and related potassium and ammonium salts.

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<span class="mw-page-title-main">Pyrosulfate</span>

In chemistry, disulfate or pyrosulfate is the anion with the molecular formula S
2
O2−
7
. Disulfate is the IUPAC name. It has a dichromate-like structure and can be visualised as two corner-sharing SO4 tetrahedra, with a bridging oxygen atom. In this anion, sulfur has an oxidation state of +6. Disulfate is the conjugate base of the hydrogen disulfate (hydrogen pyrosulfate) ion HS
2
O
7
, which in turn is the conjugate base of disulfuric acid (pyrosulfuric acid).

<span class="mw-page-title-main">Alkylbenzene sulfonate</span> Class of chemical compounds

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<i>N</i>-Methyltaurine Chemical compound

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α-Olefin sulfonates are a group of anionic surfactants, which are used as detergents. The compounds contain a - mostly linear, primary - alkyl R and a monovalent cation M, preferably sodium. The most frequently used example of this group of substances is sodium α-olefin sulfonate.

References

  1. Magnus, G. (1833). "Ueber die Weinschwefelsäure, ihren Einfluss auf die Aetherbildung, und über zwei neue Säuren ähnlicher Zusammensetzung". Annalen der Physik und Chemie. 103 (2): 367–388. Bibcode:1833AnP...103..367M. doi:10.1002/andp.18331030213. ISSN   0003-3804.
  2. Kosswig, Kurt (2000). "Sulfonic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a25_503. ISBN   3-527-30673-0.
  3. Petter, P. J. (1984). "Fatty acid sulfoalkyl amides and esters as cosmetic surfactants". International Journal of Cosmetic Science. 6 (5): 249–260. doi:10.1111/j.1467-2494.1984.tb00382.x. ISSN   0142-5463. PMID   19467117. S2CID   41819056.
  4. Tupker, R. A.; Bunte, E. E.; Fidler, V.; Wlechers, J. W.; Coenraads, P. J. (1999). "Irritancy ranking of anionic detergents using one-time occlusive, repeated occlusive and repeated open tests". Contact Dermatitis. 40 (6): 316–322. doi:10.1111/j.1600-0536.1999.tb06082.x. ISSN   0105-1873. PMID   10385334. S2CID   418996.
  5. Wicho, H, ed. (2009). Austria-Codex Stoffliste (in German) (42 ed.). Vienna: Österreichischer Apothekerverlag.
  6. W.O Read and J.D.Welty (1961). "Synthesis of Taurine and Isethionic Acid by Dog Heart Slices". The Journal of Biological Chemistry. 237 (5): 1521–1522. doi: 10.1016/S0021-9258(19)83734-1 . PMID   14490797.