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Author: Subject: Organic Hypochlorites
woelen
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[*] posted on 25-3-2018 at 11:30


This stuff is not explosive, but if you ignite it, it will burn very fast. Try this with half a ml or so in a petri dish. Keep the rest of the stuff far away from flame!



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theAngryLittleBunny
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[*] posted on 26-3-2018 at 05:36


Quote: Originally posted by woelen  
This stuff is not explosive, but if you ignite it, it will burn very fast. Try this with half a ml or so in a petri dish. Keep the rest of the stuff far away from flame!


Thanks for that information, I'am on to making t-butyl hypochlorite next, because I heard that burns even faster.
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[*] posted on 26-3-2018 at 12:07


Okay, I tried something and I feel like it's worth posting. I just made a little isopropyl hypochlorite by mixing 50g of 14% NaOCl with isopropanol and acetic acid, and a green layer immediately seperated on top. But as I went to get a pipette, it suddenly violently decomposed with a crackling sound O.o pretty scary, but also kinda fun. So for anyone playing with hypochlorite esters, just be a bit careful, they might blow up in your face.

[Edited on 26-3-2018 by theAngryLittleBunny]
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26-3-2018 at 12:59
woelen
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[*] posted on 18-2-2020 at 14:46


I just tried making the isopropyl ester, but apparently this is much more unstable than the other esters I tried (methyl, ethyl and tert-butyl). I prepared approximately 0.5 ml, but within one minute of its preparation, it made a very loud crackling noise. Then it became silent again, then it made crackling noise again, and so on. I decided not to wait and see what happens further. I took a towel, wrapped it around my hand (thick layer of a few cm) and then grabbed the test tube and dumped its content in the sink.

The reason I made this is for making a nice video for my website, and I decided to take isopropyl, because that is cheap and very common where I live. I'll refrain from that, however. I'll try the tert-butyl variation again. That one is more stable.

[Edited on 18-2-20 by woelen]




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[*] posted on 18-2-2020 at 15:05


Hypochlorites are commonly used to oxidize alcohols to ketones....why wouldn't you just get acetone from this reaction?



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[*] posted on 19-2-2020 at 08:50


Under certain conditions, you can make hypochlorite esters, instead of ketones (or aldehydes).

If you add a mix of an alcohol and a weak acid (acetic acid or propionic acid is fine) to a solution of sodium hypochlorite, then you get the hypochlorite ester and not the oxidized alcohol, e.g. ethanol yields CH3CH2OCl.

These hypochlorite esters are quite interesting and reactive compounds. E.g. CH3OCl is a gas, which on ignition explodes, CH3CH2OCl is a volatile yellow liquid, which burns very fiercely when ignited. C(CH3)3OCl also is a yellow liquid, less volatile, but also very flammable. The isopropyl ester apparently is more unstable than the others and decomposes spontaneously.

It is quite interesting to perform the experiments of making CH3OCl or CH3CH23OCl, by adding a mix of acetic acid and the alcohol with 4 to 5 times its volume of concentrated bleach (10+ % of active chlorine). Only try this with small quantities (e.g. 0.5 ml of alcohol and 0.8 ml of acetic acid). Scaling up may lead to very violent reactions and explosions.




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