Propane-1,3-sultone Hydrolysis
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1,3-Propane sultone is the
organosulfur Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfur ...
compound with the formula (CH2)3SO3. It is a cyclic sulfonate ester, a class of compounds called
sultone In organosulfur chemistry, a sulfonate is a salt or ester of a sulfonic acid. It contains the functional group , where R is an organic group. Sulfonates are the conjugate bases of sulfonic acids. Sulfonates are generally stable in water, non-o ...
s. It is a readily melting colorless solid.


Synthesis

It may be prepared by the acid catalyzed reaction of
allyl alcohol Allyl alcohol ( IUPAC name: prop-2-en-1-ol) is an organic compound with the structural formula . Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a raw material ...
and
sodium bisulfite Sodium bisulfite (or sodium bisulphite, sodium hydrogen sulfite) is a chemical mixture with the approximate chemical formula NaHSO3. Sodium bisulfite in fact is not a real compound, but a mixture of salts that dissolve in water to give solutions ...
.


Reactions

1,3-propane sultone is an activated ester and is susceptible to nucleophilic attack. It
hydrolyzes Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysi ...
to the acid. : It has been used in the synthesis of specialist surfactants, such as
CHAPS detergent CHAPS is a zwitterionic surfactant used in the laboratory to solubilize biological macromolecules such as proteins. It may be synthesized from cholic acid and is zwitterionic due to its quaternary ammonium and sulfonate groups; it is structurall ...
.


Safety

Typical of activated esters, 1,3-propane sultone is an
alkylating agent Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effectin ...
. 1,3-Propane sultone is toxic, carcinogenic, mutagenic, and teratogenic.


See also

*
1,4-Butane sultone 1,4-butane sultone is a six-membered δ-sultone and the cyclic ester of 4-hydroxybutanesulfonic acid. As a sulfo-alkylating agent, 1,4-butanesultone is used to introduce the sulfobutyl group (–(CH2)4–SO3−) into hydrophobic compounds posses ...
* Dimethyl sulfate * Vinylsulfonic acid *
Isethionic acid Isethionic acid is an organosulfur compound containing an alkylsulfonic 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 18 ...
* Sulfolane


References

{{DEFAULTSORT:Propane sultone, 1,3- Sultones