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Author: Subject: Effects of amines on C-NO2 bonds
Ral123
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[*] posted on 18-9-2013 at 06:33
Effects of amines on C-NO2 bonds


We all know how stable nitromethane is, but this video http://www.youtube.com/watch?v=br-f1Ls9hZ0 shows it can be efficiently sensitised with DETA. The first question that comes to me is, if it sensitises so well, how well can it store in mixed condition? Can this be used to sensitise other nitro compounds, for example mixture of DNT/HDN?
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AndersHoveland
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[*] posted on 18-9-2013 at 15:08


I am not entirely sure, but I think one of the reasons nitromethane is sensitized is because that these amines are basic, and promote a small portion of the nitromethane converting into its aci- tautomer, which is much more sensitive.

In contrast, typically amines reduce sensitivity when they are in the same aromatic system as the nitro group, an example being TNTAB.

Another possible reason for the sensitization may be that the N-H is more easily oxidized than a C-H bond, due to its polar nature, despite the fact that it is less energetic. So the barrier to reaction could be lower.
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killswitch
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[*] posted on 18-9-2013 at 15:32


What about hexamine? Does that dissolve in NM?
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[*] posted on 18-9-2013 at 20:46


Addition of bases (not only DETA) increases the sensitivity of nitromethane (NM) towards shocks. Experiments shows [1] that addition of 0.05 wt% of DETA to NM increase the detonation velocity and pressure and decreases the critical diameter of the explosive. Acids and water have similar but weaker effect on failure diameter of this explosive.

it is not advisable to store sensitized nitromethane. The addition of amine to NM is performed on site. Indeed the addition, of bases to nitromethane decreases the thermal stability of the mixture. other nitroaromatics (picric acid, tetryl and TNT) have similar effect (decreases of thermal stability) when various bases are added which is obvious from their DSC (Differential Scanning Calorimetry) curves [2]. read the two paper below (and references therein) for more information on sensitized nitromethane and nitroaromatics by the addition of amine.

[1] Zeman, S. Accounts of the New Aspects of Nitromethane Initiation Reactivity, Cent. Eur. J. Energ. Mater. 2009, 6(1), 119-133.

[2] C. P. Constantinou and M. M. Chaudhri, MEASUREMENT OF THE SENSITIZATION OF NITROCOMPOUNDS BY AMINES USING DIFFERENTIAL SCANNING CALORIMETRY, J. Therm. Anal., 1995, 45, 1301-1311.

Dany.



Attachment: Accounts of the New Aspects of Nitromethane Initiation Reactivity.pdf (457kB)
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Attachment: MEASUREMENT OF THE SENSITIZATION OF NITROCOMPOUNDS BY AMINES USING DIFFERENTIAL SCANNING CALORIMETRY.pdf (516kB)
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[Edited on 20-9-2013 by Dany]
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[*] posted on 18-9-2013 at 23:02


Quote: Originally posted by killswitch  
What about hexamine? Does that dissolve in NM?
i have tried in the past and hexamine wont dissolve in nitromethane. i think a solvent that is miscible with NM that also dissolves the hexamine may be the way to go.



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Ral123
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[*] posted on 19-9-2013 at 03:03


I've heard about NaOH sensitising TNT before. What's your opinion, can NM be sensitised with hydrazine(hydrate)? This would be elegant way if it works, non corrosive and more powerful then the inert stuff.
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[*] posted on 19-9-2013 at 11:03


Quote: Originally posted by Ral123  
I've heard about NaOH sensitising TNT before. What's your opinion, can NM be sensitised with hydrazine(hydrate)? This would be elegant way if it works, non corrosive and more powerful then the inert stuff.

-Red ammonium picrate (vs the yellow one) (from NH4OH and TNP)
-Deep red TNT sodium nitronate (vs pale yellow one) (from TNT and concentrated NaOH)
-Brown methylnitronate of Na of NH3 or of N2H4 (from CH3-NO2 and NaOH, NH4OH or N2H5OH

All are based on nitro-nirtonic equilibrium; in basic media nitronic is more present and this sensitizes the stuff!
-For picric acid (I have left aside the uninvolved part of the aromatic ring in the equation)
HO-C=C-NO2 + NH4OH --> O=C-C=N(O)-ONH4 + NH4-C=C-NO2 + H2O
-For TNT (I have left aside the uninvolved part of the aromatic ring in the equation)
CH3-C=C-NO2 + NaOH --> CH2=C-C=N(O)-ONa + H2O
-For NM
CH3-NO2 + NaOH --> CH2=N(O)-ONa + H2O
CH3-NO2 + NH4OH --> CH2=N(O)-ONH4 + H2O
CH3-NO2 + N2H5OH --> CH2=N(O)-ON2H5 + H2O




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AndersHoveland
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[*] posted on 19-9-2013 at 14:00


Would that mean trinitrobenzene would not be sensitized by base?
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killswitch
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[*] posted on 19-9-2013 at 19:16


Forming the aci-nitro of TNB would introduce an sp3 carbon and destroy aromaticity.
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Antiswat
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[*] posted on 20-9-2013 at 07:54


there is this ''field manufactured explosives''
a scanned book, you probably know the kind
i remember reading that sawdust mixed with NM have been used, and the product was an actually functional secondary.. how about that?




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Ral123
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[*] posted on 22-9-2013 at 01:11


But who would do that, it's going to be weak, flammable, volatile and hard to set off.
Can someone suggest a practical way to sensitise NM with N2H4.H2O. I promise a test if the concept is good.
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[*] posted on 23-9-2013 at 10:11


Wow, here discuss my test :D Besides DETA I managed to sensitize nitromethane and with 30% aluminum http://www.youtube.com/watch?v=tCcH8pmXShw
Obtained not only with a DETA and EDA, ethanolamine and others amines :)




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Ral123
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[*] posted on 23-9-2013 at 11:48


I wonder how much dimethyl aniline would do the trick also :D
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