Sciencemadness Discussion Board

HexaChloroEthane Synthesis?

SpiffyVision - 21-1-2004 at 18:59

I've been looking into the possible synthesis of Hexachloroethane for pyrotechnical use (smoke). There is not a lot of information available on the topic, I've searched E&W, rec.pyro, and this place, no luck at all. I was wondering if some could possibly point me in the correct direction, or perhaps a suggestion on its manufacture.

Thanks in advance.

Pyrovus - 21-1-2004 at 21:09

My suggestion would be to use the Kolbe reaction. Starting from a sodium or potassium or whatever salt of trichloroacetic acid, electrolysis would yeild hexachloroethane at the anode as follows:
CCl3COO- -> CCl3COO. +e-
This radical decomposes:
CCl3COO -> CCl3. +CO2
The two carbon trichloride radicals then combine to form hexachloroethane:
2CCl3 -> C2Cl6

Trichloroacetic acid can be formed by reacting acetic acid with chlorine. There's a detailed synthesis for chloroacetic acid, which can also be used for trichloroacetic acid at http://www.roguesci.org/megalomania/synth/synthesis2.html#ch...

Polverone - 21-1-2004 at 22:14

From Ullman's Encyclopedia of Industrial Chemistry:
Quote:
Limited industrial uses of hexachloroethane do not justify large-scale production processes.

A primary source for hexachloroethane is from the production of tetrachloroethylene and carbon tetrachloride by chlorinolysis of hydrocarbons and chlorinated hydrocarbon residues (see page 79 Tetrachloroethylene by Chlorination of Hydrocarbons and Chlorinated Hydrocarbons ). It can be separated from the residues by distillation and fractionated crystallization.

For the intentional production of hexachloroethane, tetrachloroethylene is chlorinated batchwise in presence of iron chloride. The hexachloroethane crystallizes from the mother liquor and is isolated. The mother liquor is recycled and again chlorinated [322].

The photochemical chlorination of tetrachloroethylene is performed similarily [323].

This is within the reach of a determined amateur, since tetrachloroethylene (aka perchloroethylene) is a fairly common solvent, but gaseous chlorine isn't much fun to work with.

chemoleo - 22-1-2004 at 05:32

are there other things you can do with C2Cl6 other than burning it? I mean, it isn't a solvent (MP 187 deg C) or anything... so what could it be used for?

AngelEyes - 22-1-2004 at 06:50

might make a good thermite (of sorts) mix with Aluminium....I read somewhere that CCl<sub>4</sub> also goes up well with Al...

but I guess that is still burning it.

[Edited on 22-1-2004 by AngelEyes]

Theoretic - 22-1-2004 at 07:17

Maybe addition of hydrogen chloride to cyanogen (addition across the triple bind) will help... :D

BromicAcid - 22-1-2004 at 09:24

Quote:

I mean, it isn't a solvent (MP 187 deg C) or anything...


At its melting point it rapidly sublimes. It might do good under reduced pressure but I've yet to test this.

guaguanco - 22-1-2004 at 09:42

Quote:
Originally posted by Theoretic
Maybe addition of hydrogen chloride to cyanogen (addition across the triple bind) will help... :D

Or not.