Sciencemadness Discussion Board

Thionyl Chloride

Xveckthorn - 7-3-2011 at 03:56

Could Thionyl Chloride be obtained from Thionyl Chloride/Lithium batteries by extraction with chloroform? I realize that TC is soluble in chloroform, so by mixing the paste up in chloroform, the TC dissolves therein, and the chloroform containing TC can then be filtered off?

Chaoschemist - 7-3-2011 at 04:04

Should be possible, as long as you're removing all the Li metal surely.
Don't come up with the idea to dissolve the whole battery-content in CHCl3, remember the violent reaction of alkali metals with chlorinated hydrocarbons.
At least I guess it's not really effective to obtain SOCl2 this way. Quantities in the battery should be pretty low.

hissingnoise - 7-3-2011 at 05:15

remember the violent reaction of alkali metals with chlorinated hydrocarbons.

And Chaoschemist is somewhat understating the reaction here!
They explode violently on contact!

blogfast25 - 7-3-2011 at 07:20

Hmmm… not wanting to encourage Xveckthorn to do ‘bad things’ here but while the dangers of combining hydrocarbon halides with alkali metals are well known and documented, I observed no such explosion when subjecting small amounts of potassium metal to dichloromethane (DCM) at RT. The metal underwent no appreciable change. But when heating the test tube carefully to the BP of DCM, the surface of the potassium metal quickly turned dark blue/black (carbon?) No explosion of otherwise violent reaction occurred though. Later I rinsed the metal with kerosene and melted it down to shiny new metal.

hissingnoise - 7-3-2011 at 11:06

He was talking about chloroform not DCM . . .

6CHCl<sub>3</sub> + 6Na---> 6NaCl + 6HCl + C<sub>6</sub>Cl<sub>6</sub>

[Edited on 7-3-2011 by hissingnoise]

Xveckthorn - 7-3-2011 at 12:12

I actually read somewhere that the portion of the battery that contains the thionyl chloride is like... a 'porous' carbon conductor encasement.

I would think that removing this, cleaning it up a bit, and then soaking it in chloroform for a bit would soak up all the SOCl2.

Just to put your minds at ease, I'm not out to do anything illegal with this info; I'm just studying chlorinations (home chemist, no formal education), and in lieu of phosphorus pentachloride, which I've been unable to obtain, I've decided to go with thionyl chloride which doesn't muddy up the compound being chlorinated as its byproducts are gaseous (or so I've read).

hissingnoise - 7-3-2011 at 12:35

Acetyl chloride for prep. of acetic anhydride, perhaps?

Melgar - 8-3-2011 at 05:24

I've heard TCCA can do some chlorinations too, and that's 99% pure as a swimming pool chemical.