Originally posted by garage chemist
What made your eyes sting is Chlorosulfonic acid methylester, CH3O-SO2-Cl. A potent lachrymator which has been used as a war gas.
It is commonly prepared by slowly dripping methanol into sulfuryl chloride while cooling with ice, then boiling away the HCl, rapidly washing the
substance with ice water and distilling it in vacuum (I have a procedure).
With water, it hydrolyzes to methylsulfuric acid and if water is present in excess, the methylsulfuric acid hydrolyzes further to sulfuric acid
and methanol.
(Unfortunately, I don't know if it reacts with methanol).
Note that heating methylsulfuric acid in vacuum causes it to decompose into sulfuric acid and dimethyl sulfate, the latter distills over as it is
formed.
Dimethyl sulfate is normally prepared by reacting chlorosulfonic acid with methanol and heating the formed methylsulfuric acid in vacuum as described
above.
I highly recommend to download "The War Gasses" from the Library, it's from there where I got all the above information.
How do you feel? Did you notice any delayed effects of the lachrymatory fumes?
Please be careful with such experiments in the future. Me2SO4 is even more toxic than HF in regard to exposure by skin absorption, and also a lethal
and non- detectable inhalative poison. Working without a fume hood is suicide. |