Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: HexaChloroEthane Synthesis?
SpiffyVision
Harmless
*




Posts: 1
Registered: 21-1-2004
Member Is Offline

Mood: Bored

[*] posted on 21-1-2004 at 18:59
HexaChloroEthane Synthesis?


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.




All your base are belong to who?
View user's profile View All Posts By User
Pyrovus
Hazard to Others
***




Posts: 241
Registered: 13-10-2003
Location: Australia, now with 25% faster carrier pigeons
Member Is Offline

Mood: heretical

[*] posted on 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...
View user's profile View All Posts By User
Polverone
Now celebrating 21 years of madness
*********




Posts: 3186
Registered: 19-5-2002
Location: The Sunny Pacific Northwest
Member Is Offline

Mood: Waiting for spring

[*] posted on 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.




PGP Key and corresponding e-mail address
View user's profile Visit user's homepage View All Posts By User
chemoleo
Biochemicus Energeticus
*****




Posts: 3005
Registered: 23-7-2003
Location: England Germany
Member Is Offline

Mood: crystalline

[*] posted on 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?



Never Stop to Begin, and Never Begin to Stop...
Tolerance is good. But not with the intolerant! (Wilhelm Busch)
View user's profile View All Posts By User
AngelEyes
Hazard to Others
***




Posts: 187
Registered: 24-1-2003
Location: South of England
Member Is Offline

Mood: Better than it used to be.

[*] posted on 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]
View user's profile View All Posts By User
Theoretic
National Hazard
****




Posts: 776
Registered: 17-6-2003
Location: London, the Land of Sun, Summer and Snow
Member Is Offline

Mood: eating the souls of dust mites

biggrin.gif posted on 22-1-2004 at 07:17


Maybe addition of hydrogen chloride to cyanogen (addition across the triple bind) will help... :D
View user's profile View All Posts By User
BromicAcid
International Hazard
*****




Posts: 3253
Registered: 13-7-2003
Location: Wisconsin
Member Is Offline

Mood: Rock n' Roll

[*] posted on 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.




Shamelessly plugging my attempts at writing fiction: http://www.robvincent.org
View user's profile Visit user's homepage View All Posts By User
guaguanco
Hazard to Others
***




Posts: 216
Registered: 26-11-2003
Member Is Offline

Mood: heterocyclic

[*] posted on 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.
View user's profile View All Posts By User

  Go To Top