Sciencemadness Discussion Board

Nitrocellulose peroxide

Hunterman2244 - 30-6-2018 at 07:48

Peroxides of cellulose have been shown to form(e.g.
https://onlinelibrary.wiley.com/doi/abs/10.1002/app.1979.070...), would this also apply to nitrocellulose?

UC235 - 30-6-2018 at 11:11

No, they're using cellulose that's been chemically modified to break rings open with the formation of aldeydes. The peroxides are present as relatively unstable (with respect to loss of H2O2) aldehyde peroxy-hydrates. Nitration of cellulose blocks the hydroxyl groups needed for the ring-opening oxidation to happen. If you tried to do the peroxidation first, I don't think any of the introduced peroxy groups would survive nitration and the aldehyde groups replacing hydroxyl groups could no longer be nitrated.

Laboratory of Liptakov - 30-6-2018 at 11:51

It seems that many researchers are fascinated in a peroxides of any types. By the way, result will only and again organic peroxide. If ever something. ...:cool:

Hunterman2244 - 30-6-2018 at 16:37

Quote: Originally posted by UC235  
No, they're using cellulose that's been chemically modified to break rings open with the formation of aldeydes. The peroxides are present as relatively unstable (with respect to loss of H2O2) aldehyde peroxy-hydrates. Nitration of cellulose blocks the hydroxyl groups needed for the ring-opening oxidation to happen. If you tried to do the peroxidation first, I don't think any of the introduced peroxy groups would survive nitration and the aldehyde groups replacing hydroxyl groups could no longer be nitrated.

Thanks!

Hunterman2244 - 30-6-2018 at 20:20

How about using dinitrogen pentoxide?

hissingnoise - 1-7-2018 at 02:15

No! Even if you could prepare the anhydride it will do no more than nitrate the cellulose.

Hunterman2244 - 1-7-2018 at 11:54

Quote: Originally posted by hissingnoise  
No! Even if you could prepare the anhydride it will do no more than nitrate the cellulose.

Ok, was really just wondering the reaction.

Rocinante - 2-7-2018 at 14:50

Liptakov: geminal hydroxyperoxides are quite stable and worthwile to look at

DubaiAmateurRocketry - 2-7-2018 at 17:33

Quote: Originally posted by Rocinante  
Liptakov: geminal hydroxyperoxides are quite stable and worthwile to look at


From TATP's 0.5J/1N sensitivities to around 1-5J and 3-5N.

A good improvement, but the friction sensitivity is still too high to be practical.

Laboratory of Liptakov - 2-7-2018 at 21:40

Rocinate, I looked on geminal peroxides. Great propertties. Easy synthesis. But start precursor will some unavailable. Is not clear from text what is it. ..:cool:

Rocinante - 3-7-2018 at 02:59

Lead azide is like 0.5 N, 3 N is plenty enough for blasting caps and such.

nitro-genes - 3-7-2018 at 15:52

Noticed an existing thread on geminal hydroperoxides --> http://www.sciencemadness.org/talk/viewthread.php?tid=63440

Would (similar to terephtalic acid) trimesic acid also be able to form a geminal hydroperoxide? Couldn't help thinking of the legendary DPPP patent... :P (Although condensation of acetone all the way to mesitylene doesn't seem likely under these conditions though)

Laboratory of Liptakov - 3-7-2018 at 22:44

A series of geminal hydroperoxides were synthesized from their corresponding ketones or aldehydes (see Fig.1) and 30-50 wt% hydrogen peroxide (H2O2) in the presence of molecular iodine (I2) or hydrogen chloride as catalyst.

OK ....:cool:...What is it corresponding keton and aldehyde...?

nitro-genes - 4-7-2018 at 09:44

Oops, the carboxilic acid is not the starting point it seems indeed, thanks Liptakov. :D The aldehyde could be one of the oxidation intermediates from mesitylene though...but then again, direct oxidation of methyl groups for any potential mesitylene formed would probably not be favorable anyway, instead ring chlorination or hydroxylation being more likely.

Laboratory of Liptakov - 5-7-2018 at 05:21

For amateur examinations is important using some precursor, which is available, or is possible his easy preparation from available compounds. Or else, his atractivity is ending in the passage of history.