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Author: Subject: Interacting Compounds with Ozone
DFliyerz
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[*] posted on 2-1-2015 at 10:28
Interacting Compounds with Ozone


I'm aware that ozone is an extremely powerful oxidizer, and possible to create, which begs the question; how would one go about combining a compound with ozone? Simply put the two reactants in a sealed container together?
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mayko
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[*] posted on 2-1-2015 at 11:01


Quote: Originally posted by DFliyerz  
how would one go about combining a compound with ozone?


Very carefully; ozonides are unstable explosives comparable to organic peroxides.

More: ozonolysis




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franklyn
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[*] posted on 2-1-2015 at 12:02


It's best just to follow a written process. Saturated ( no double bonds present ) Chlorocarbons or Fluorocarbons ( Freons ) are used for a solvent in some proceedures. This is mainly for safety when separating the product. O3 will oxidize almost anything but organic ozonide products are dangerously sensitive. The bigger problem is working at the cryogenic temperarues required in many cases. At room temperature, the gathered amount will degrade very quickly, providing it has not spontaneously exploded.

http://ww2.valdosta.edu/~tmanning/research/ozone



Attachment: Inorganic Ozonides.pdf (138kB)
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Attachment: Safer ozonolysis reactions- A compilation of laboratory experience.pdf (192kB)
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Attachment: Ozone+Amine=Nitro.pdf (455kB)
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Attachment: Ozonation of Naphthalene in Water.pdf (337kB)
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franklyn
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[*] posted on 3-1-2015 at 19:39


My interest in these compounds is as explosives , but there is a rich ever widening general application of ozonolysis as an oxidant reagent.

http://www.ozonolysis.com/ozonolysis/web.nsf/wp/Attachment%2...

- Ozonolysis of Bicyclic Bridged 1,2-Dioxines
http://digital.library.adelaide.edu.au/dspace/bitstream/2440...

Synthesis of five- and six-membered cyclic organic peroxides
www.beilstein-journals.org/bjoc/content/pdf/1860-5397-10-6.p...


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Shob dhillon
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[*] posted on 10-1-2017 at 23:24


I'm interested in seeing if I can make percarboxylic acids from reacting Ozone with the corresponding carboxylic acid but
I don't know what reaction conditions and setup are required, but I think that bubbling Ozone into chilled 99.7% pure acetic acid might generate the peroxyacetic acid in some percentage. I know that peroxy acids can be produced by adding concentrated (~70%) Hydrogen peroxide to either the acid anhydride or carboxylic acid, but the hazards and very scarcity of that stuff make it impossible for my amateur use.

http://www.prepchem.com/synthesis-peracetic-acid/
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Tsjerk
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[*] posted on 11-1-2017 at 03:46


I think ozone won't form the peroxy acid, but oxidize the acid or form the probably very explosive ozonide variant of the peroxy acid.
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Tetra
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[*] posted on 11-1-2017 at 08:30


Be careful...
And don't condense it! It's been reported to "Decompose explosively upon rapid heating to boiling point".
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Tsjerk
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[*] posted on 11-1-2017 at 10:16


Always cool with a boiling point of -112!
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Tetra
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[*] posted on 11-1-2017 at 11:55


Quote: Originally posted by Tsjerk  
Always cool with a boiling point of -112!


I wouldn't go as far to say that LO3 is "Chill", though... :P
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Ok, that was disgraceful, I'll leave.
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PHILOU Zrealone
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[*] posted on 11-1-2017 at 14:47


You have to be prepared for a severe blast:
-Peracids in high concentration are very sensitive explosive (to friction, shock and heat)...especially those with a closer to 0 oxygen balance like performic acid (HCO3H performs very wel :P with its perfect OB of zero) and like peracetic acid.
-Ozon is explosive on its own.
-Condensed phase ozon and fuel must be like LOX (liquid oxygen) explosives but worst.




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Melgar
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[*] posted on 12-1-2017 at 05:49


Ozone is especially selective for C=C double bonds, and will typically replace each side's double bond to a C with a double bond to an O, splitting the molecule in a reaction termed "ozonolysis". Normally, this has to be done at very low temperatures, and even then can result in explosions. However, if you want to perform a much safer version of the ozonolysis reaction, you can use the reaction described here with terminal alkenes (alkenes that terminate in a double-bonded carbon):

http://www.sciencemadness.org/talk/files.php?pid=201968&aid=...

IIRC, ozonides are only formed when ozone adds across double bonds, otherwise you just get typical partial oxidation products for that compound.

[Edited on 1/12/17 by Melgar]
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