Chemichael - 4-2-2018 at 10:22
Hello,
Would the following halogenate the alkane? Basically adding fine powdered NaBr to the alkane in a flask and bubbling ozone....with or without water.
Or would the bromoalkane possibly formed be attacked by ozone too? Im not really sure and I cant really find much online.
O3 + NaBr + alkane
I just try to think of possible new reactions sometimes, since I find it interesting.
[Edited on 4-2-2018 by Chemichael]
LearnedAmateur - 5-2-2018 at 04:10
I hope this article help you out a little, I would think that it would be quite difficult to do anything useful starting out with an alkane
(especially a small one, C=<5 or so).
https://www.sciencedirect.com/science/article/pii/0010218063...
Melgar - 6-2-2018 at 00:51
Seems like a good way to produce sodium bromate.
I mean, not an efficient way to produce sodium bromate, but at least a way to do it.
Under acidic conditions with a strong light source, maybe, though.
Chemichael - 6-2-2018 at 03:39
Thanks for the info. I guess there will be a bunch of side reactions if the bromoalkane even forms.
Wouldn't O3 + NaBr = NaO + BrO2 and the BrO2 would be used to halogenate below 0C? Bromine dioxide decomposes at 0C to bromine and oxygen.
Also this might be a bit dangerous since I researched that Chlorine dioxide can explosively decompose, so bromine dioxide would probably do the same
sort of thing.
[Edited on 6-2-2018 by Chemichael]
LearnedAmateur - 6-2-2018 at 04:27
Actually, doing some research, I’ve come to the conclusion that it is possible to halogenate an alkane using this method. According to the
publication below, ozone will oxidise bromide to bromine, and presumably result in the formation of sodium hydroxide as a result (please correct me if
I’m wrong, but 2 O3 + 2 NaBr + H2O -> Br2 + 2 NaOH + 2 O2).
The bromine gas, via free radical substitution, would form a mixture of bromoalkanes. Albeit, I doubt this would be very practical on an amateur scale
and there are far more efficient processes in industry, especially since the formed bromine will react with aqueous hydroxide resulting in
contextually useless bromates assuming the above reaction is correct.
https://pubs.acs.org/doi/abs/10.1021/jp0467346?journalCode=j...
[Edited on 6-2-2018 by LearnedAmateur]
Chemichael - 6-2-2018 at 15:03
That's interesting, thanks! Glad to know it would work. If I were to do this, I think a small scale where you bubble in ozone in the NaBr and alkane
in a small round bottom flask with magnetic stirring would be where to start with this. I would also see products of the reaction when doing this with
or without water and I would use an ice bath with salt added for the reaction without water. The bromine dioxide decomposes at 0C and that's what I
believe forms along with NaO. I wonder how brominated the alkane would be with bromine dioxide.