1,3-Propane sultone explained

1,3-Propane sultone is the organosulfur compound with the formula (CH₂)₃SO₃. It is a cyclic sulfonate ester, a class of compounds called sultones.^{[1] [2]} It is a readily melting colorless solid.

Synthesis

It may be prepared by the acid catalyzed reaction of allyl alcohol and sodium bisulfite.

Reactions

1,3-propane sultone is an activated ester and is susceptible to nucleophilic attack. It hydrolyzes to the 3-hydroxypropylsulfonic acid.

It has been used in the synthesis of specialist surfactants, such as CHAPS detergent.^[3]

Safety

Typical of activated esters, 1,3-propane sultone is an alkylating agent. 1,3-Propane sultone is toxic, carcinogenic, mutagenic, and teratogenic.^{[4] [5]}

See also

• 1,4-Butane sultone
• Dimethyl sulfate
• Vinylsulfonic acid
• Isethionic acid
• Sulfolane

Notes and References

1. Book: R. J. Cremlyn . An Introduction to Organosulfur Chemistry . John Wiley and Sons . Chichester . 1996 . 0-471-95512-4.
2. Morimoto . Yoshiki . Kurihara . Hajime . Kinoshita . Takamasa . Can α-sultone exist as a chemical species? First experimental implication for intermediacy of α-sultone . Chemical Communications . 2000 . 3 . 189–190 . 10.1039/A909094K.
3. Hjelmeland. LM. A nondenaturing zwitterionic detergent for membrane biochemistry: design and synthesis.. Proceedings of the National Academy of Sciences of the United States of America. November 1980. 77. 11. 6368–70. 6935651. 10.1073/pnas.77.11.6368. 350285. 1980PNAS...77.6368H. free.
4. Web site: Scorecard Chemical Profile for Propane Sultone. 2008-11-17. 2008-09-23. https://web.archive.org/web/20080923100823/http://www.scorecard.org/chemical-profiles/summary.tcl?edf_substance_id=1120-71-4#hazards. dead.
5. Web site: NIOSH Pocket Guide to Chemical Hazards. 2013-11-13.