woelen
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Stability of cyanuric chloride at room temperature?
I finally have the reagent C3N3Cl3 (one of Sauron's favorites  ), not to be
confused with the easy to obtain TCCA which is C3N3O3Cl3.
This afternoon I received the bottle with the material and it is a very fine free flowing powder, which slightly fumes in air and has a strong
peculiar smell. But what concerns me is that the label on the bottle states that the material must be kept at a temperature between 0 C and 4 C, and
that is something which I do not like at all. I have no refrigerator for storing chemicals and I do not want to keep this huge bottle (2.5 liters, it
contains 1 kg of reagent) in my normal food-storage fridge. It would be sad if the material is not stable at room temperature. I paid over EUR 40 for
the material and for that amount of money I really want a stable chemical, which also is good after years of storage.
If I look at MSDS's, then none of them mentions that it is necessary to keep this material in a fridge. Can anyone shed some light on this? Why is
this?
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Jor
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Woelen did you buy this at Labstuff? I have also been thinking of buying it, but I wasn't sure if it is restriced...
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Nicodem
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At work we have this reagent stored at room temperature. It is old well over 20 years judging by the state of the label and the old package style, but
it was still efficient for the syntheses performed recently (though nobody ever bothered to check its purity). There is no reason to believe it
unstable at room temperature. The only thing that can easily deteriorate is moisture, so if you think it is poorly packed just wrap the stopper with
parafilm and it should be OK for decades.
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woelen
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Nicodem, thanks for the response. That takes away my concerns. I have not yet done any experiments with it, because it is nastier than I expected. The
smell is very sticky, hours after, I still can smell it, while I just have had the bottle open and closed it again. I even think that it is nastier
than SOCl2 or CH3COCl, simply because it leaves non-volatile remains which can be smelt for a long time. So, this is a typical outside-only chemical.
I also have to rebottle it into a smaller bottle, the bottle which I now have is huge, with a fairly thin layer of powder at the bottom, and that is
not practical at all. So, I also am in the process of finding a suitable bottle for repackaging this chemical.
@Jor: Yes, I purchased this at Labstuff. It is not restricted like PCl5, PCl3 and SOCl2. Keep in mind though that this is nasty stuff and you
certainly need to repackage it for practical use.
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Sauron
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Oh, it's useful stuff, particularly for alkyl chlorides and bromides, and acyl chlorides.
The only reasons I no longet see it as a near panacea are:
workup can be a pain
and I have found ways to get to what were "denied" reagents like SOCl2, PCl3, POCl3, PCl5 etc. so CC (TCT) is not quite so strategic.
Also I am less ethusiastic about oxalyl chloride than before and that domoshes the significance of CC as a reagent for making (COCl)2. Not that
oxalyl chloride doesn't have its uses.
What will you be using the CC for?
Sic gorgeamus a los subjectatus nunc.
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woelen
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I intend to use it in general for making organic chlorides. One of the first things I want to do is making CH3Cl, simply by adding TCT to methanol. I
like experimenting with gases and CH3Cl is just one of the gases which I did not have any opportunity to experiment with.
Another project is making CH3CH2Cl and maybe acyl chlorides like CH3CH2COCl and CF3COCl.
I also like the idea that TCT does not give off gases like SO2 and/or HCl, which may be quite annoying when other gaseous or low-boiling compounds are
made.
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woelen
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Btw, I have another question. Is there any chance that TCT reverts to the monomeric form CNCl under certain conditions? That also would be a great
risk, I certainly don't want to have CNCl around. I cannot find anything about this on Internet, but you never know. Especially when this reaction can
occur on storage that would be really scary, having a huge bottle of stuff around with CNCl in it under high pressure 
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Sauron
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The short answer is No,
Don't heat it to decomposition.
Read Ullmann.
Sic gorgeamus a los subjectatus nunc.
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benzylchloride1
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Our research group at the university uses cyanuric chloride to synthesize complex molecules called dendrimers, by reacting it with amines with careful
temperature control. Tetrahydrofuran is a good solvent for derivatives of these compounds. We clean objects that have contacted cyanuric chloride with
aqueous ammonia, it works fairly well. I am going to purchase some for my own use as it is very useful for making acid chlorides.
Amateur NMR spectroscopist
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