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S.C. Wack
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And once you do have the hypochlorite, what can you do with it, other than chlorinating amines as in OS? Well, you can chlorinate alkanes.
[Edited on 21-7-2005 by S.C. Wack]
Attachment: jacs_82_6108_1960.pdf (673kB)
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S-Bursic
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Me and my friend tried to make C2H5OCl and it didn't work. We didn't measure anything so is that the reason that it didn't work? We put in about 50 ml
of H2O and then then about 8 ml of conc. NaOH solution. After that we added the same amount of C2H5OH. At that point a white precipitate was formed.
We think that was sodim ethoxide. Then we bubbled chlorine though the solution for 5 to 10 min. Nothing was formed. The only thing was that the sodim
ethoxide dissolved. Can you please tell me what went wrong except the measurment?
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Zinc
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| Quote: | Originally posted by Axt
Ethyl hypochlorite also seperates readily from a solution of NaOCl/ethanol/acetic acid.
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Axt Did you try it? If yes what ratios did you use?
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Axt
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| Quote: | Originally posted by Zinc
Axt Did you try it? If yes what ratios did you use? |
Yeh I tried it, it worked but I dont remember anymore about it. Other then it seperates quickly as the yellow top layer, and decomposes pretty quickly
as well. Forget the ratios. try 20ml glacial acetic acid, 80ml 12.5% NaOCl and less then stoichiometric EtOH.
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Zinc
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| Quote: | Originally posted by Axt
try 20ml glacial acetic acid, 80ml 12.5% NaOCl and less then stoichiometric EtOH. |
Can I use 80% acetic acid instead of glacial acetic acid?
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Sauron
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t-Butyl hypochlorite is in Org.Syn, which see.
Maybe they will have comments and references pertinent to the others.
First of two Org.Syn procedures attached below
[Edited on 13-1-2007 by Sauron]
Attachment: CV4P0125[1].pdf (140kB)
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Sauron
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Second Org.Syn procedure:
In both cases let me call your special attention to the safety precautions
Good hood is mandatory.
Dim lighting is required
Total avoidance of contact with rubber is required.
Do not heat above boiling point.
Etc etc.
[Edited on 13-1-2007 by Sauron]
[Edited on 13-1-2007 by Sauron]
Attachment: CV5P0184[1].pdf (144kB)
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Zinc
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Does anyone know how to prepare amyl hypochlorite and what are its properties?
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tr41414
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GAA obivously is diluted when mixed with hypochlorite solution...
Is it possible to use another/maybe inorganic acid, or does acetic acid work as some kind of solvent/protectant?
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Norrys
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I tested Axt`s Method, with 80% acetic acid instead, and it worked very well.
I also tried to ignite some EtOCl. In my first test I put some drops on a piece of paper and touched it with a match. It made a big orange fireball,
as it schould do. But when I droped a little bit on a stone, I observed a selfignition, and the flames burned the EtOCl, which was left in the
pipet. Because it was confined, it exploded and destroyed the glass-part of the
pipet completely. Luckily I wasnt hit by a schrapnell.
But how could it ignite by only beeing droped on a stone?
[Bearbeitet am 14-1-2008 von Norrys]
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halogen
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Perhaps something was on the stone?
F. de Lalande and M. Prud'homme showed that a mixture of boric oxide and sodium chloride is decomposed in a stream of dry air or oxygen at a red heat
with the evolution of chlorine.
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Norrys
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lol, maybe, but what would be able to make the EtOCl explode?
Has anyone data about sensitivity and uncompability with other materials?
I am afraid, that this could happen again.
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Norrys
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| Quote: | Ursprünglich verfasst von Zinc
What ratios did you use? |
Look at Axt's Synthesis:
80ml NaOCl to 20ml Acetic acid and less than stoichiometric ethanol.
But I made a smaller batch, ~20ml NaOCl and ~5-6ml Acid, usw. Although that was a very small batch, it worked well and was enough to make my ears
ring, when it exploded
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Bromine
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Today try synthesis of EtOCl two times by bubbling chlorine trough NaOH H2O EtOH solution. Chlorine was generated with TCCA + HCl.
In first try all EtOCl vapourized before I could extract it with droper. In second atempt I provided better cooling and got few small self detontions
when bubbling chlorine troug soultion.
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Norrys
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| Quote: | Ursprünglich verfasst von Zinc
What conc. of NaClO did you use? |
Roughly 13%. Nearly the same concentration, as the bleach, which was used in Axt's synthesis. Please dont ask, how much ethanol I used, I didn't
measure it, because it was a pretty litle amount, just some ml, maybe two or three.
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tr41414
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I have tried a modified synth today... I tried using oxalic and formic acid, with bad (no)results.
Oxalic is not a good choice as it isn't realy soluble in the mix, so it is a bit problematic to add and forms insoluble oxalate which makes the rxn
"dirty". Even if there was some product it couldn't be isolated.
The reaction with the formic acid foamed quite a lot... After addition the testtube was shaken a bit which resulted in a geyser of
hypochlorite/water/chlorine/co2(?) going into air  The tube got very warm...
Maybe the formic is oxidised to co2 or sth like that...
@Norrys: Does the AcOH rxn foam? Did you use cooling and at what rate did you mix the reactants?
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Norrys
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| Quote: | Ursprünglich verfasst von tr41414
@Norrys: Does the AcOH rxn foam? Did you use cooling and at what rate did you mix the reactants? |
No I didn't use any cooling, but ist frosty cold (~3°C) in my lab. It didnt foam much, but it would have done so, if I had put all the acid at once
into the cylinder.
I firstly mixed a little amount of ethanol with 20ml 13% NaOCl and added then ~5-6ml of 80% acetic acid dropwise with a pipet. When I aded it a bit
too fast, gas evolved, but no foam formed.
Formic acid is said to be an reducing agent. So you can't mix it with an oxidiser, such as sodium hypochlorite solution.
[Bearbeitet am 15-1-2008 von Norrys]
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tr41414
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I made ethyl and isopropyl hypochlorite today using that metod  There is
absolutely no foam made and the hypochlorite readily separates as yellowish oil, although i didn't get much of the ethyl- product (isopropyl went much
better)...
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Zelot
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Do the reactants have to be pure? It would be a real money-saver if I could buy bleach, rubbing alcohol, and white vinegar to make this. Otherwise I
would have to shell out for lab-grade chems.
So... what did you do over the weekend?
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tr41414
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Acetic acid should be bought I think (lab/photo chemical), I used lab grade GAA... You could also concentrate it by yourself using solvent extraction
or make acetate, dry it and then free the acid using H2SO4...
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Zelot
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*sigh*
It's just that a gallon of 5% vinegar only costs $4. Maybe I'll try it with low concentrations first. If it doesn't, then I guess I'll boil some down
to 30%. Wait, how do you salt the water out? I just don't like to try experiments that no one else has done before, because it might blow up in my
face.
[edit]
In one of the links previously provided, it said to bubble chlorine through a mixture of alcohol and lye. This would produce sodium hypochlorite. So,
is the acetic acid really needed? Also, doesn't sodium hypochlorite react with acetic acid to give chlorine gas?
[Edited on 1/28/2008 by Zelot]
So... what did you do over the weekend?
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tr41414
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You can't distil acetic acid without a very good column, also solvent extraction is way quicker... Add IPA (say 2ml per 10ml of 5% vinegar), salt to
your acid, then separate IPA+acid layer, after removal of IPA, you should be left with quite high conc. acid...
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Zelot
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How would you remove the IPA? By heating? Would it be about 80%? Wait, I wouldn't need to remove the IPA, because I'm making isopropyl hypochlorite.
D'oh!
Also, is it able to DDT, or do you have to use a primary?
What temperature does the reaction have to take place to avoid it being in a gaseous state? I thought I would do it outside, where it never goes above
50 degrees F, but no oily liquid was recovered.
[Edited on 1/29/2008 by Zelot]
[Edited on 1/30/2008 by Zelot]
So... what did you do over the weekend?
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PHILOU Zrealone
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| Quote: | Originally posted by Norrys
lol, maybe, but what would be able to make the EtOCl explode?
Has anyone data about sensitivity and uncompability with other materials?
I am afraid, that this could happen again. |
With sensitive unstable materials it is not unusual to have surface catalysed decompositions...so what need to be present is a finely divided solid
compound and...it goes booom.
One of the main example that comes to my mind is diazomethane...glas rod may allow this to self decompose catalytically to D2D.
It is also the case with sensitive radicalar reactions like Cl2/H2 and H2/O2, under certain circumstances on unpolished glas reaction is catalysed, it
heats up, then speed of reaction becomes higher what heats further and faster up into runnaway, flame and sometimes explosion.
Hypochlorite ester are prone to radicalar reactions...
[Edited on 30-1-2008 by PHILOU Zrealone]
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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Zelot
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Sorry to bring this thread up again, but I thought this might be a bit interesting:
http://books.google.com/books?id=y5mZrW1KB_AC&pg=PA239&a...
On page 242, It has a diagram showing the electrochemical preparation of isopropyl hypochlorite.
So... what did you do over the weekend?
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