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Rosco Bodine
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Quote: Originally posted by woelen  | Methyl hypochlorite does exist, actually, it is very easy to make it. Mix 0.5 ml of methanol with 1 ml of conc. acetic acid (80% or better). Mix this
with a few ml of 10% bleach, slowly. You get a colorless gas, it bubbles nicely. If you keep a flame near the gas, then you get a deafening report! Be
careful with igniting the gas, its explosions are powerful and can cause a test tube to shatter. It is best if you do this in a petri dish or
hourglass.
I also tried to make methyl chlorite in the same way with 10% NaClO2, but that does not work. You get slow production of ClO2, just a little bit is
formed, it makes the mix pale yellow. No colored gas can be observed above the liquid. |
Hazards for the organic hypochlorites include light !
They are photo sensitive.
Wonder if methyl hypochlorite would react with urea solution, possibly with some MEK to form the azine.
I'm thinking hydrazine or methyl hydrazine.
There is an old thread here linked
http://www.sciencemadness.org/talk/viewthread.php?tid=1896
Also this reports isopropyl hypochlorite by same method as tert-butyl hypochlorite.
http://www.orgsyn.org/demo.aspx?prep=CV5P0184
Potentially there would be chloroform as a byproduct from bleach reacting with ethanol, isopropanol, or acetone. This a nasty reaction in terms of
toxic and explosion hazards.
[Edited on 3/19/2018 by Rosco Bodine]
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woelen
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I also did the experiment with ethanol and propanol. With ethanol you get a yellow liquid, but this liquid is VERY volatile. You see it evaporate, a
big drop of this liquid on a piece of glass evaporates in half a minute or so. The propanol ester is much less volatile.
The ethanol and propanol esters are not explosive like the methanol ester. The vapor burns very quickly, with an orange flame and production of some
soot. The liquids burn like nitrated cotton. They produce a WHOOSH sound and a very fast burn, but there is no report. The methyl ester really
explodes with a loud report, so there is quite some difference.
Production of chloroform is virtually none, as long as you use sufficient acid. For this reason, you must mix your alcohol with twice its volume of
acetic acid of high concentration and this mix must be added to the bleach. If you don't use lots of acid, then with ethanol and isopropanol you may
end up with chloroform. If you first add the acid to the bleach, then you get a lot of chlorine and no ester is formed at all.
This reaction indeed is not very safe, that's why I told to use very small amounts, do not scale up.
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Tdep
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I too managed to make some (what I believed to be) ethyl hypochlorite, present as a green liquid that would float to the surface of the water solution
it was made from transiently, before evaporating away into nothing, escaping capture and analysis. I'm amazed these compounds exist, there's very
little information online about them
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Rhodanide
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| Quote: Originally posted by Tdep | | I too managed to make some (what I believed to be) ethyl hypochlorite, present as a green liquid that would float to the surface of the water solution
it was made from transiently, before evaporating away into nothing, escaping capture and analysis. I'm amazed these compounds exist, there's very
little information online about them |
You didn't try and light it?
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Tdep
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Ya I mean what good is a synthesis if you don't end with trying to light it on fire, but it was in a water ethanol mix and there was a lot of chlorine
and a lot going on... so none of it made it to the flames (that's really what I mean by '''further analysis''')
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Bert
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Having seen what tiny drops of the somewhat related ethyl perchlorate do, and given the description of the violent explosion of small bubbles? I am
quite willing to limit the ammounts of methyl hypochlorite to a few ml...
I certainly agree that anything we make which includes a potential for explosion MUST be tested in a flame, for science! Also for entertainment value,
if you're anything like me.
Also ran across this bit about trimethyl Perchlorate while searching for Blasters spoon photo, attached below.
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Another unusual ester was made in 1930 - trichloromethyl perchlorate from anhydrous carbon tetrachloride and AgClO4. It was so explosive that it could
only be made in minute quantities and couldn't be completely isolated as it detonated with extreme violence when the CCl4 was evaporated off.
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http://www.sciencemadness.org/talk/viewthread.php?tid=1081
I note Blaster has been absent from the forum since February of 2013. Hope he is still above the ground-
Not sure I am feeling lucky today, and carbon tetrachloride is depressingly hard to come by OTC in USA these days.
[Edited on 19-3-2018 by Bert]
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woelen
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I know of the ethyl perchlorate. It is very powerful.
Ethyl hypochlorite is much less powerful, it burns like nitrocotton when liquid. Maybe liquid methyl hypochlorite is as powerful as ethyl perchlorate,
but I do not have the equipment to make this in liquid form. When you mix the chemicals it simply bubbles away as a gas. The gas, however, is very
powerful already.
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Rhodanide
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| Quote: Originally posted by Bert | Having seen what tiny drops of the somewhat related ethyl perchlorate do, and given the description of the violent explosion of small bubbles? I am
quite willing to limit the ammounts of methyl hypochlorite to a few ml...
I certainly agree that anything we make which includes a potential for explosion MUST be tested in a flame, for science! Also for entertainment value,
if you're anything like me.
Also ran across this bit about trimethyl Perchlorate while searching for Blasters spoon photo, attached below.
| Quote: |
Another unusual ester was made in 1930 - trichloromethyl perchlorate from anhydrous carbon tetrachloride and AgClO4. It was so explosive that it could
only be made in minute quantities and couldn't be completely isolated as it detonated with extreme violence when the CCl4 was evaporated off.
|
http://www.sciencemadness.org/talk/viewthread.php?tid=1081
I note Blaster has been absent from the forum since February of 2013. Hope he is still above the ground-
Not sure I am feeling lucky today, and carbon tetrachloride is depressingly hard to come by OTC in USA these days.
[Edited on 19-3-2018 by Bert] |
Yeah, that's EXACTLY the thread I was thinking of when I said that Alkyl Perchlorates are absolutely INSANE chemicals.
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Bert
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I noted the description of Silver hypochlorite a few posts up.
Could Carbon tetrachloride and Silver hypochlorite react as Carbon tet and Silver perchlorate do?
[Edited on 19-3-2018 by Bert]
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woelen
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A few posts up there was writing about silver chlorite, not silver hypochlorite.
Silver chlorite is stable, a yellow compound: AgClO2
Silver hypochlorite does not exist it seems. I once tried making that, but if you add a silver salt to bleach you get a black precipitate, most likely
a higher oxide of silver. I myself have done experiments with peroxodisulfate and silver(I) salts and these lead to formation of a mixed
silver(I)/silver(III) oxide, Ag2O2. Hypochlorite most likely also produces this, but the result is much more messy than with peroxodisulfate, due to
the high pH involved and due to the presence of chloride. No clean simple product.
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