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Author: Subject: 1,2 Dichloroethane
Db33
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[*] posted on 13-3-2017 at 20:46
1,2 Dichloroethane


does anyone know a place that sells this stuff for a reasonable price? eBay sellers are asking about a dollar per mg 30ml for $30, not worth it. Im looking for like 500ml or even a liter so if anyone can PM me or tell me a good place to get some for solvent use please let me know.
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Yttrium2
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[*] posted on 13-3-2017 at 21:42


No ideas?
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[*] posted on 14-3-2017 at 01:27


A quick search says that it is not too tricky to buy -- depending on location. Prices quoted seem to be better than the eBay offerings you describe. I can't vouch for these suppliers personally though.
http://www.sciencestuff.com/prod/Chem-Rgnts/C1675
http://www.rightpricechemicals.com/buy-1-2-dichloroethane-re...
https://www.google.com.au/webhp?sourceid=chrome-instant&...


But, if you can't buy it, you could always make some. Hit some ethylene with chlorine gas and it should condense out.
Prepchem has a procedure involving antimony trichloride. My naive thinking suggests this could be simplified.

Of course getting hold of a cylinder of ethylene has its own issues. Because, although it is widely used in industry and agriculture, I suspect it is not readily available to the amateur.
Wikipedia says it can be made from dehydrating ethanol with concentrated sulfuric acid. Prepchem has this procedure and another as well.

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Db33
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[*] posted on 14-3-2017 at 11:27


i did see Science Stuff buy i also though they only delivered to schools and businesses? I have a good friend on this site that has offered to sell me some of his personal supply so i might take that route but yeah this isnt a watched chem at all is it? I dont think it is.
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adk
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[*] posted on 14-3-2017 at 12:35


Thermo Fisher sell it. In Australia it's about $200 for 2.5L



https://www.argentscientific.com/
sales@argentscientific.com
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Amos
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[*] posted on 14-3-2017 at 13:29


For solvent use? Dichloromethane or chloroform would probably work just as well.
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Db33
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[*] posted on 14-3-2017 at 13:32


i know DCM is preferred and i remember a friend either told me or i read it in literature there was a reason that DCE was preferred for this particular reaction.
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JJay
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[*] posted on 14-3-2017 at 15:53


You can get antimony by the truckload from eBay. It's not very expensive. If you dissolve common lead alloys (from bullets, anchors, fishing weights, etc.) in nitric acid, antimony oxide should precipitate out.



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macckone
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[*] posted on 14-3-2017 at 20:18


Chloroform is going to have a slightly lower boiling point
and will be much easier to make. It is also significantly
less flammable which matters.
Carbon tetrachloride is very close in boiling point but harder
to make than chloroform.
Tetrachloroethylene is readily available as break cleaner.
However, it may react and has a higher boiling point.
It can be used to make carbon tetrachloride though.
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[*] posted on 15-3-2017 at 07:27


Likely a bit simpler, you could probably do an SN2 on ethylene glycol with hydrochloric acid to form the product if you don't need very large amounts.
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Amos
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[*] posted on 15-3-2017 at 08:06


Quote: Originally posted by Db33  
i know DCM is preferred and i remember a friend either told me or i read it in literature there was a reason that DCE was preferred for this particular reaction.


If you were willing to let us know what reaction you have planned you would probably find some helpful suggestions on how to avoid using such an uncommon solvent.

Quote: Originally posted by macckone  

Tetrachloroethylene is readily available as break cleaner.
However, it may react and has a higher boiling point.
It can be used to make carbon tetrachloride though.


Hold on now, carbon tetrachloride can be made from tetrachloroethylene how?
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[*] posted on 15-3-2017 at 09:14


Quote: Originally posted by Amos  
Hold on now, carbon tetrachloride can be made from tetrachloroethylene how?

Yeah, I'm pretty sure you can just add two molecules of Cl2 to it at elevated temperatures, and that'll do it. No hydrogen required, and thus no HCl to dispose of.
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[*] posted on 15-3-2017 at 09:28


That'd be news to me. It's pretty easy to go to hexachloroethane, but breaking that C-C single bond, with chlorine? Pretty sure you'd need to do free-radical substitution catalyzed by UV light for that.
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[*] posted on 15-3-2017 at 11:11


Quote: Originally posted by Melgar  
Quote: Originally posted by Amos  
Hold on now, carbon tetrachloride can be made from tetrachloroethylene how?

Yeah, I'm pretty sure you can just add two molecules of Cl2 to it at elevated temperatures, and that'll do it. No hydrogen required, and thus no HCl to dispose of.


This is how one gets hexachloroethane, not carbon tetrachloride.
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Melgar
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[*] posted on 17-3-2017 at 12:04


Quote: Originally posted by PirateDocBrown  
That'd be news to me. It's pretty easy to go to hexachloroethane, but breaking that C-C single bond, with chlorine? Pretty sure you'd need to do free-radical substitution catalyzed by UV light for that.

It's definitely a free-radical reaction, but elevated temperatures are all that's needed. The first step of the reaction is reversible, but the second step wouldn't be.

Quote:
This is how one gets hexachloroethane, not carbon tetrachloride.

Yes, that is what happens when you add ONE molecule of chlorine. The other is added in a free-radical reaction at higher temperatures. It's not that hard to break a carbon-carbon bond when one or more of the carbons is attached to three large halogen atoms. Think of the haloform reaction, for example.

[Edited on 3/17/17 by Melgar]
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Corrosive Joeseph
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[*] posted on 17-3-2017 at 18:18


"Refux ethylene glycol with an excess of zinc chloride and conc. hydrochloric acid
Distill out the lower boiling 1,2-Dichloroethane from the reaction mixture'

Taken from - http://www.sciencemadness.org/talk/viewthread.php?tid=64518

Anyone know anything more about this one...............? Looks promising..............


/CJ

https://www.thevespiary.org/rhodium/Rhodium/Vespiary/talk/in...

[EDIT] - Added link for extra info............. Hmmm.............

@ macckone - Tetrachloroethylene is not in ANY brake cleaner in my country

@Neuro-- why do you say "if you don't need large amounts". I'm smelling a catch here.

@everyone - How does this material compare to other chlorinated solvents..............? Interesting compound. Potential for easy synthesis. I must know more.................. :o

[EDIT2] - Questions and additional musings

[Edited on 18-3-2017 by Corrosive Joeseph]

[Edited on 18-3-2017 by Corrosive Joeseph]




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[*] posted on 18-3-2017 at 11:20


I have a small bottle of 1,2-dichloroethane,
it came with a special offer £1 rubber synthesis kit
http://www.ebay.co.uk/itm/232180462901?_trksid=p2057872.m274...




CAUTION : Hobby Chemist, not Professional or even Amateur
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Corrosive Joeseph
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[*] posted on 18-3-2017 at 19:34


Quote: Originally posted by Sulaiman  
I have a small bottle of 1,2-dichloroethane,
it came with a special offer £1 rubber synthesis kit
http://www.ebay.co.uk/itm/232180462901?_trksid=p2057872.m274...


I dunno how 'small' that is but I was thinking more in terms of litre batches............

Chlorinated solvents are more or less gone from the shelves now days.
DCE from antifreeze, zinc and HCl is very interesting................


Further reading for synthesis -

Weygand and Hilgetag - Preparative Organic Chemistry (1972)

Pages 214-231 "Replacement of Alcohol OH by Halogens"

Much text, refs and experimentals................ Hmm, I see what Neuro means now


1,2 Dichloroethane can also be aminated in the classic 'pipe bomb' to ethylenediamine 'under pressure at 180C in an aqueous medium' according to https://en.wikipedia.org/wiki/Ethylenediamine

This is two VERY amazing solvents from 4 OTC ingredients............ Am I the only one getting excited here..................?? :D


/CJ



[Edited on 19-3-2017 by Corrosive Joeseph]

[Edited on 19-3-2017 by Corrosive Joeseph]




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Db33
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[*] posted on 22-3-2017 at 11:35


I dunno if anyone else has found this to be the case but i have a source now that sells it to me for $26 for 500ml. This is by far the cheapest i have found it. Most others have it at least double or triple. So if anyone ever needs a good cheap source for this product just pm me.
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[*] posted on 15-7-2021 at 11:04


I haven't figured it out by my own and this is a classic beginner's question, but perhaps someone more savvy could shed some light.

How interchangeable DCM and DCE are in general? This is because I've got a full bottle of DCM, so I wouldn't want to order DCE just to realize it was unnecessary.
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[*] posted on 15-7-2021 at 11:21


The major advantage of DCE over DCM is generally its higher boiling point. Very often when a paper calls for DCE you will find additional instructions like "60 C" which is not achievable with DCM. I can't think of any other practical differences.



[Edited on 04-20-1969 by clearly_not_atara]
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[*] posted on 15-7-2021 at 11:28


That is an excellent point. Didn't even think about it, even I have had to deal with some reactions with poorly chosen solvents with big reflux issues.
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[*] posted on 15-7-2021 at 11:31


Sodium triacetoxyborohydride is a general, mild, and selective reducing agent for the reductive amination of various aldehydes and ketones. 1,2-Dichloroethane (DCE) is the preferred reaction solvent, but reactions can also be carried out in tetrahydrofuran and occasionally in acetonitrile.


is one of the many uses of DCE.
The reduction is faster than in THF.
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[*] posted on 15-7-2021 at 15:20


As far as I know, that solvent can easily be switched out with DCM or chloroform as well or similar solvents.
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[*] posted on 26-7-2021 at 07:51


I did some reductions with STAB. Using DCM one would need to cool the reaction flask, in most cases an Erlenmeyer. The addition of STAB to the solvent and substrate is exothermic not dramatically but sufficient to raise the temperature to appr. 50 C. Way too high for DCM and even chloroform has quite a high vapour pressure at these elevated temperatures.

DCE is the first choice, however, since its on the REACH list of dangerous substances, its much harder to obtain. I used THF, so actually i have no comparison if DCE would enhance yields. It definitely shortens the reaction (reduction) time.
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