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woelen
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Properties of 1,2-dichloroethane, interesting experiments?
I have the option of obtaining quite some CH2Cl-CH2Cl. I still am wondering whether I should get this chemical, or not. This depends on what I can do
with it. Storing another liter of not-used toxic chemical is not what I want, I really should have a use for it.
Are there any specific properties, which make this chemical particularly interesting? Does it have specific solvent properties, which are not covered
by other chlorinated solvents like CH2Cl2, CHCl3, CCl4, CHCl=CCl2? I only can find very sparse and scattered information on 1,2-dichloroethane and
most of it is about its toxicity as a chlorinated solvent.
So, if there are interesting syntheses or experiments (especially less known ones) with this chemical or when it has specific solvent properties, then
I would love to read about them.
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plante1999
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If it was me I would take it rigth now. 1,2-dichloroethane is an industrial building block of importance. I have hard time finding it here, as such I
will need to make mine!!
A very nice experiment is to dissolve sulphur in a boilling sol. of NaOH to make polysulphides, and then add the dichloroethane. Continue boiling
until discoloration. You should get polysulphide rubber, aka fuel line rubber.
I never asked for this.
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killer_lapin
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I agree with plant, diversity of chemical is always apreciated at some point. Dichloroethane is stable so you shouldn't worry about decompositon like
ether or THF.
@plant1999 I had an idea few years ago but never tried it since I had the chance to get DCE. So the idea was to reflux ethylene glycol with
hydrochloric acid in presence of PTC to yield a mixture of 2-chloroethanol and DCE.
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AndersHoveland
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I believe there was a procedure to make ethylene carbonate with it, by refluxing with zinc carbonate.
Ethylene carbonate is a highly polar solvent that can dissolve both ions and hydrophobic compounds, particularly suited for nucleophilic substitution
on organic halogens.
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plante1999
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So, woelen, will you buy it? If yes, please try the rubber.
I never asked for this.
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Nicodem
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Quote: Originally posted by plante1999  | | A very nice experiment is to dissolve sulphur in a boilling sol. of NaOH to make polysulphides, and then add the dichloroethane. Continue boiling
until discoloration. You should get polysulphide rubber, aka fuel line rubber. |
| Quote: | | So, woelen, will you buy it? If yes, please try the rubber. |
Try how? Without the reference? Please give us the reference.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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plante1999
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The Chemical Process Industries
by Norris R. Shreve
and
http://www.chymist.com/Synthetic%20Rubber.pdf
Got it?
[Edited on 29-5-2013 by plante1999]
I never asked for this.
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woelen
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I ordered a liter of CH2ClCH2Cl and when it arrives I'll try the rubber experiment. Another experiment I'll try is making higher chlorinated versions
of ethane.
Besides this, I also ordered 100 ml of methanesulfonic acid. With NaBH4 this allows preparation of B2H6, another interesting chemical to experiment
with.
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garage chemist
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1,2-dichloroethane is also a convenient precursor to vinyl chloride
through thermal dehydrochlorination.
Simply lead pure dichloroethane vapor through a tube heated to 500-550°C with a residence time of 10-20s. Vinyl chloride and HCl are formed, starting
material conversion is around 50%.
The HCl is washed out with water, the vapors condensed through cooling and the vinyl chloride and unreacted dichloroethane separated by fractional
distillation.
I'd like to experiment with vinyl chloride at some point since it is a very reactive monomer which tends to polymerize in a highly exothermic
reaction.
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Dr.Bob
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DCE is often used as a replacement for DCM where you need to heat the reaction hotter than 40C or so. It behaves much like it for the purposes of
a higher boiling chlorinated solvent. But I am sure there are interesting things to do with it, and you can never have too many chlorinated
solvents. :-)
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woelen
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The 1,2-dichloroethane arrived and I'll first try the rubber experiment. It is an easy one and can be done on a test tube scale.
The experiment of making vinyl chloride also sounds very interesting, but heating vapor at 500 C in a suitable tube is something beyond the
capabilities of my equipment. I have no equipment for such high temperature chemistry. I would love to do that, but I consider it too dangerous,
because I have my lab inside the house at the attic and I'm not willing to take the risk of a fire. For me, chemistry is limited to temperatures of
150 C, maybe 200 C and occasionally a test tube scale experiment at somewhat higher temperature (e.g. boiling hot H2SO4).
[Edited on 25-6-13 by woelen]
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AndersHoveland
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Here is the preparation of ethylene carbonate: http://www.bromicacid.com/carbonate.htm
I suspect the reaction would proceed even more readily with ethylene chloride, especially since the transient ZnCl2 that would form would have a
catalytic effect.
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woelen
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I tried the experiment of making rubber. I took a very concentrated solution of NaOH and added some solid sulphur. This mix I heated, until all
sulphur is dissolved. This gives a deep yellow solution, with a tinge of brown/green. I allowed this very hot solution to cool down a little bit (but
still quite hot, near boiling temperature of water) and then I carefully dripped in some C2H4Cl2. The first drops lead to violent boiling, but after
these, the liquid has cooled down sufficiently. A thin layer of C2H4Cl2 remained on top of the yellow aqueous layer (the aqueous layer is more dense,
due to the high concentration of NaOH). The C2H4Cl2 slowly turns yellow, it appears that sulphur dissolves in it.
Next, I stoppered the test tube and shook violently for quite some time, in the meantime heating it such that it remained quite hot (but not so hot
that the C2H4Cl2 started boiling). After several minutes, a white flocculent material appeared, which forms a dirly-looking layer of foamy material on
top of the aqueous layer. Most of the C2H4Cl2 is gone at that time.
Finally, I diluted the liquid with 20 times its own volume of tap water and allowed the precipitate to settle. The material is only slightly more
dense than the aqueous solution, even after several days still quite some flocculent solid is floating around in the liquid. Most of it, however, has
settled at the bottom.
The material is off-white. It has a funny smell, somewhat sulphurous, but very different from the smell of hot sulphur. I now allow some of the
material to dry and will try what happens if I heat the material. More will follow...
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plante1999
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maybe try to melt in in one piece with an oil bath.
very interesting woelen, continue!
I never asked for this.
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mr.crow
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Thanks for the link, ethylene carbonate sounds very useful! Can prepare dimethyl carbonate, a safe methylating reagent, from it.
I'm just guessing but if you used 1,2-dichloroethane then ammonium chloride would form instead of driving off ammonia gas and this would ruin the
equilibrium
Double, double toil and trouble; Fire burn, and caldron bubble
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papaya
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I wanted to ask if that rubber("thiokol"?) obtained by woelen is soluble in anything?
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plante1999
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Nope, thats the point of using it as fuel line rubber.
I never asked for this.
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bfesser
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<a href="http://en.wikipedia.org/wiki/Thiokol" target="_blank">Thiokol</a> <img src="../scipics/_wiki.png" /> makes <a
href="http://en.wikipedia.org/wiki/Space_Shuttle_Challenger_disaster" target="_blank">O-Rings</a> <img src="../scipics/_wiki.png" />,
too. 
[Edited on 7/14/13 by bfesser]
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papaya
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As I may try this particular synthesis what is the ratio/concentrations of components for the highest yield ? Also reaction of sulphur with lye seems
to be not as simple as it looks like, there can be many different products (I searched and found different results from different sources: some state
that thiosulfate and [poly]sulfides are formed, others that sulfite and polys). Look into this
www.iapws.jp/Proceedings/Symposium05/365Lin.pdf
as it is what I could find for free. At the end if you look you'll see that if overdone you get no polysulfides at all.
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woelen
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The reaction between sulphur and NaOH in solution is somewhat comparable to the reaction between chlorine and NaOH. The element disproportionates.
The main reaction is as follows: S8 + 12 OH(-) ---> 4 S(2-) + 2 S2O3(2-) + 6 H2O
Once some sulfide is in solution, you get further reaction of S8 with S(2-), giving polysulfides. This reaction competes with the reaction with
hydroxide. So, once you have some S(2-) in solution, it is very hard to obtain a clean reaction. The net effect is that you get a solution with
hydroxide, thiosulfate, sulfide and polysulfides. The solution is deep yellow. You get a mix, hard to obtain a clean product.
You need to heat quite strongly (nearly boiling temperature of water), sulfur and hydroxide do not react that easily. Once you have some sulfide in
solution though, the reactions becomes more and more easy.
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papaya
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Thank you woelen, and what is recomemded ratio of NaOH to S to take (to get more polys, rather than thiosulphate). Also isn't it possible to perform
reaction by melting them together rather than do it in solution, because I want to start with bicarbonate+sulfur instead of NaOH and think this way
they'll react better, is there any difference ? Also, how much dichloroethane do you need and is it possible to perform in an open vessel or you must
cap it (actually pressurize when heated) ?
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woelen
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Bicarbonate plus sulphur most lkely does not work. You need highly alkaline conditions for the reaction. If you want a lot of polysulfides, then use
excess amounts of sulphur. Just add sulphur till no more sulphur dissolves and you get a deep yellow liquid with solid material remaining (which is
unreacted sulphur).
In my experiment I added the C2H4Cl2 to the deep yellow solution and heated the mix such that the C2H4Cl2 was just on the edge of boiling. I did not
cap the test tube. I was shaking frequently and quite violently. It may take some practice to shake a lot without spilling the liquid out of the test
tube  The reaction with the C2H4Cl2 is not fast, but after several minutes you
already have some off-white solid.
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papaya
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I meant to melt sulfur and bicarbonate together, won't that work ? (I've heard ''liver of sulfur'' was made ancient times that way).
Also if sulfur soluble in dichloroethane,it may be worth to add that solution to NaOH for example (who knows how this affects polyS length and
properties) as a possible alchemical modification.. 
[Edited on 17-7-2013 by papaya]
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ScienceSquirrel
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This is a recipe for sulphur rubber from the Royal Society of Chemistry;
http://media.rsc.org/Classic%20Chem%20Demos/CCD-95.pdf
My apologies if it has been posted before.
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papaya
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Thanks, from that I learned that NaOH used was only about 5%, rather small, I expected more..
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