We are implementing a protocol in wich DMSO must be sonicated for 15 h. After the sonication the DMSO has a very foul smell. Can this be related to thermal decomposition of the DMSO due to the high temperatures generated by the cavitation process? There is black phosphorus suspended in the DMSO. Therefore, in principle the smell might arise from the phosphorus and not from the DMSO.
Dear Sergio,
Dimethylsulfoxide (DMSO) is very stable solvent; has a boiling point of 189 C.
Carbon-S bonds are very strong bonds and are not broken upon ultrasound waves employed for a lengthy time. DMSO vapor has an unpleasant odor. It might be that the combination of the suspended phosphorus and the DMSO vapor gives the smell you have experienced.
Hoping this will be helpful,
Rafik
Be careful with a posible reduction of the sulfone check this web
http://www.organic-chemistry.org/synthesis/S1H/reductionssulfoxides.shtm
There are plenty of methods and some of the layers of black phosphorus could be oxidized...
Thanks Santiago. If I understand the information contained in the link correctly, could dimethyl sulfide and dimethyl disulfide be responsible for the strong smell?
Dears
All the reactions indicated in the link are undertaken in reducing conditions in the presence of certain reagents. As I understood from the question that there are no reagents similar to those in the link are present in the vessel of sergio.
If dimethylsulfide is produced from dimethylsulfoxide a very strong smell (cabbage-like smell) is observed however since its boiling point is 37 it will disappear immediately due to the heat generated by sonication.
Rafik
Phosphorus black is somehow a reducing agent, not very strong this is true, however the Snell may come from a reduction to sulfide in the presence of black phosphorus whose layers may be oxidised
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