Propane-1,3-sultone Hydrolysis
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1,3-Propane sultone is the
organosulfur Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...
compound with the formula (CH2)3SO3. It is a cyclic sulfonate ester, a class of compounds called sultones. 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 precursor to ...
and
sodium bisulfite Sodium bisulfite (or sodium bisulphite, sodium hydrogen sulfite) is a chemical mixture with the approximate chemical formula NaHSO3. Sodium bisulfite is not a real compound, but a mixture of salts that dissolve in water to give solutions compose ...
.


Reactions

1,3-propane sultone is an
activated ester In organic chemistry, an active ester is an ester functional group that is highly susceptible toward nucleophilic attack. Activation can be imparted by modifications of the acyl or the alkoxy components of a normal ester, say ethyl acetate. Typical ...
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 reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
to the 3-hydroxypropylsulfonic acid. : It has been used in the synthesis of specialist
surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...
s, 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 structurally ...
.


Safety

Typical of activated esters, 1,3-propane sultone is an
alkylating agent Alkylation is a chemical reaction that entails transfer of an alkyl group. 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 effecting ...
. 1,3-Propane sultone is toxic, carcinogenic, mutagenic, and teratogenic.


See also

* 1,4-Butane sultone *
Dimethyl sulfate Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as ( CH3)2 SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agen ...
*
Vinylsulfonic acid Vinylsulfonic acid is the organosulfur compound with the chemical formula CH2=CHSO3H. It is the simplest Unsaturated sulfonic acids, unsaturated sulfonic acid. The C=C double bond is a site of high reactivity. Polymerization gives polyvinylsulfon ...
*
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 Sulfolane (also tetramethylene sulfone, IUPAC nomenclature, systematic name: 1λ6-thiolane-1,1-dione) is an organosulfur compound, formally a cyclic sulfone, with the formula . It is a colorless liquid commonly used in the chemical industry as a s ...


References

{{DEFAULTSORT:Propane sultone, 1,3- Sultones IARC Group 2A carcinogens