Chemical compound
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.[2][3] 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.[4]
Safety
Typical of activated esters, 1,3-propane sultone is an alkylating agent. 1,3-Propane sultone is toxic, carcinogenic, mutagenic, and teratogenic.[5][6]
See also
References
- ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0525". National Institute for Occupational Safety and Health (NIOSH).
- ^ R. J. Cremlyn (1996). An Introduction to Organosulfur Chemistry. Chichester: John Wiley and Sons. ISBN 0-471-95512-4.
- ^ Morimoto, Yoshiki; Kurihara, Hajime; Kinoshita, Takamasa (2000). "Can α-sultone exist as a chemical species? First experimental implication for intermediacy of α-sultone" (PDF). Chemical Communications (3): 189–190. doi:10.1039/A909094K.
- ^ Hjelmeland, LM (November 1980). "A nondenaturing zwitterionic detergent for membrane biochemistry: design and synthesis". Proceedings of the National Academy of Sciences of the United States of America. 77 (11): 6368–70. Bibcode:1980PNAS...77.6368H. doi:10.1073/pnas.77.11.6368. PMC 350285. PMID 6935651.
- ^ "Scorecard Chemical Profile for Propane Sultone". Archived from the original on 2008-09-23. Retrieved 2008-11-17.
- ^ "NIOSH Pocket Guide to Chemical Hazards". Retrieved 2013-11-13.
