Thioacetone

Thioacetone
Names
IUPAC name
2-Propanethione
Identifiers
4756-05-2
ChemSpider 557043
Jmol interactive 3D Image
PubChem 641811
Properties
C3H6S
Molar mass 74.14 g·mol−1
Appearance brown liquid
Melting point -40 °C
Boiling point 80-90 °C
Hazards
Main hazards Odour, skin irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Thioacetone is an organosulfur with the chemical formula (CH3)2CS. It is a lightly studied compound. The compound has been isolated as an orange or brown liquid at low temperatures.[1] Above -20 °C, thioacetone readily converts to a polymer and a trimer.[2]

Preparation

The compound is usually obtained by "cracking" the cyclic trimer [(CH3)2CS]3. The trimer is prepared by pyrolysis of allyl isopropyl sulfide or by treating acetone with hydrogen sulfide in the presence of Lewis acids.[3][4] The trimer cracks at 500-600 °C to give the thione.[5][1]

Thioacetone trimer

The trimer of thioacetone is a white solid (CAS#828-26-2) with a disagreeable odor.[2] It is also known as 1,1,3,3,5,5-hexamethyltrithiane.

Odor

A remarkable property of thioacetone is its odor (or perhaps the odor of oligomerization or degradation products). The smell is so potent it can be detected several hundred metres downwind mere seconds after a container is opened.[6] In 1889, an incident involving the chemical forced the evacuation of Swiss city of Fribourg due to the smell. The soap manufacturer Whitehall Soap Works later noted in a 1890 report that dilution seemed to make the smell worse and described the smell as "fearful".[7]

See also

Thiobenzophenone, a thioketone that can be isolated as a solid.

References

  1. 1 2 V.C.E. Burnop, K.G. Latham "Polythioacetone Polymer" 1967, Volume 8,, Pages 589–607.
  2. 1 2 R. D. Lipscomb; W. H. Sharkey "Characterization and polymerization of thioacetone" Journal of Polymer Science Part A-1: Polymer Chemistry 1970, Volume 8, Issue 8, pages 2187–2196. doi:10.1002/pol.1970.150080826
  3. ↑ Bailey, William J.; Chu, Hilda "Synthesis of polythioacetone" A.C.S. Polymer Preprints 1965, vol. 6, pp. 145-55.
  4. ↑ Bohme, Horst; Pfeifer, Hans; Schneider, Erich"Dimeric thioketones" Berichte der Deutschen Chemischen Gesellschaft 1942, vol. 75B, pp. 900-9. This early report mistakes the trimer for the monomer.
  5. ↑ "The photoelectron and microwave spectra of the unstable species thioacetaldehyde, CH3CHS, and thioacetone, (CH3)2CS" Kroto, H. W.; Landsberg, B. M.; Suffolk, R. J.; Vodden, A. Chemical Physics Letters 1974, volume 29, 265. doi:10.1016/0009-2614(74)85029-3
  6. ↑ http://blogs.sciencemag.org/pipeline/archives/2009/06/11/things_i_wont_work_with_thioacetone
  7. ↑ https://books.google.ca/books?id=MSDOAAAAMAAJ&pg=RA3-PA6&lpg=RA3-PA6&dq=smell+thioacetone&source=bl&ots=X0UH-GWpAa&sig=5wmkE-x9ZTWlWq5mCb6aQ9Argvw&hl=en&ei=14IoSoXQAtuptgeX0-jWBQ&sa=X&oi=book_result&ct=result#v=onepage&q=smell%20thioacetone&f=false/ CHemical News and Journal of Industrial Science, Volume 61, page 209

External links

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