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Author: Subject: Trinitromelamine
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[*] posted on 10-9-2002 at 20:30
Trinitromelamine


I'm thinking that melamine may be a very fun compound to nitrate. Melamine itself is a very dense compound for an organic molecule - 1.573g/cm3; trinitromelamine may be even denser. l think trinitromelamine may be more powerful than even RDX: better oxygen balance; more carbon, less hydrogen; probably will be more dense; and contains far more nitrogen. I'm also up for any routes to synthesize melamine; currently I'm planning on trying to dehydrate urea with concentrated sulfuric acid; hopefully that will yield melamine.

Any thoughts?




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wink.gif posted on 11-9-2002 at 01:26


Exuse me for asking, but could you please also post the IUPAC name for the compounds instead of their trivials?

Or you could just keep posting to yourself :o
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[*] posted on 11-9-2002 at 09:43
There are alternatives


I've said this in one other post but I'll say it again: IUPAC names *and* trivial names both have their places. IUPAC is systematic and will tell you about structures, sure. On the other hand, trivial names are very common in manufacturing and even chemical research literature, especially if you go back a few decades (even to the 1960s, much less the 1920s or 1860s), are often shorter, and can tell you something of the history of the compound. Try searching the web both for 2-hydroxy-1,3,5-trinitrobenzene and for "picric acid." See which returns more information.

If you really want systematic names, I suggest you register on chemfinder.com (it's free) and then you can find systematic and trivial names for most compounds.

Additionally, if people want to specify without ambiguity what sort of compound they are referring to, I suggest including a CAS number or molecular diagram along with the trivial compound name, both of which are (to me) more elegant than long IUPAC names.
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[*] posted on 11-9-2002 at 17:35
Unfair


Quote:
Try searching the web both for 2-hydroxy-1,3,5-trinitrobenzene and for "picric acid." See which returns more information.


That is a biased search lol. The IUPAC name for picric acid is 2,4,6-trinitrophenol, so typing 2-hydroxy-1,3,5-trinitrobenzene will yield way less results than it should. ;)

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[*] posted on 11-9-2002 at 17:50
Whoops


See, you can tell that I don't really know the IUPAC naming scheme. When I go to chemfinder.com I assume that the longest and most unwieldy synonym for a chemical is its IUPAC name :P
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sad.gif posted on 13-9-2002 at 08:02


Melamine = cyanuric triamide
Or 1,3,5 triamino 2,4,6 triazabenzene!
C3N3(NH2)3
(-N=C(NH2)-)3

Unfortunately MadScientist, trinitromelamine
(-N=C(NHNO2)-)3
has been already done and indeed it outperforms RDX by a little but it is incredibely unstable...it hydrolyses very very fast...probably because of a lack of basicity of the amine part...The dinitramino compound is a bit stabler but of lower power than TNT!
Example:
Ever tought about :
NH2-C6H5 + HNO3 (conc) --> O2N-NH-C6H5 + oxydation products (quinones)
As a mather of facts:
O2N-NH-C6H5 -rearranges-> NH2-C6H5-NO2 (para)
This proves an vicinal to aromatic ring nitramine is unstable!
Now there is a possibility to get a NO2 on a aromatic amine and it is to increase its basicity with a CH3...cf tetryl!
O2NNH-C6H2(NO2)3 is unstable and hydrolyses fast.

CH3-NNO2-C6H2(NO2)3 is stable.

Therefore something really interesting knowing the properties of tetryl vs TNT and TNB would be to make a nitration of C6H3(-N(CH3)2)3 to get
(CH3-NNO2)3C6(NO2)3 (hextryl-just invented the name)
Or to make it via methathesis from
C6Cl3(NO2)3 + 3CH3-NNaNO2 --> hextryl + 3 NaCl

PH Z
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biggrin.gif posted on 29-4-2003 at 21:54


quote:
---------------------------------------------
Unfortunately MadScientist, trinitromelamine
(-N=C(NHNO2)-)3
---------------------------------------------


(-N=C(NHNO2)-)3 --->
2,4,6-trinitramino-1,3,5-triazine

The trinitromelamine should be
(-N=C(NO2)-)3 --->
2,4,6-trinitro-1,3,5-triazine

or the hydronitrazaamino compound

2,4,6-triamino-1,3,5-trinitrotrihydro-1,3,5-s-triazine
2,4,6-triamino-1,3,5-trinitrazatrihydrobenzene
2,4,6-triaminocyclotrimethylenetriaminetrinitrate
>NNO2-CHNH2-NNO2-CHNH2-NNO2-CHNH2->
[triazatrihydroTATB]

:P




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mad.gif posted on 2-6-2003 at 09:37


Nope trinitromelamine is triazine (C3N3H3) and not triazane (C3N3H9) related; there is only C availability for a linkage.
(-CCl=N-)3 when reacted with NaN3 provides cyanuric triazide (-C(N3)=N-)3; when reacted with NH3, you get melamine (-C(NH2)=N-)3 which can also be obtained from dehydration reaction of urea.
(NH2)2C=O + NH2-CO-NH2 --> (NH2)2C=N-CO-NH2 or NH2-C(NH2)=N-C(NH2)=O + H2O
NH2-C(NH2)=N-C(NH2)=O + NH2-CO-NH2 --> NH2-C(NH2)=N-C(NH2)=N-C(NH2)=O + H2O
A final condensation of the final =O and NH2- close the aromatic ring.To make triaminocyanuric ring -melamine!

Action of AgNO2 in an appropriate solvant allows cyanuric iodide (-CI=N-)3 to form in a very exothermic reaction the trinitro brother of TNB (-C(NO2)=N-)3 and AgI.
Reduction of 2,4,6 trinitro cyanuric ring forms melamine too; but reduction of, N, N', N" trinitromelamine give trihydrazino derivative.The later upon HNO2 reaction yields the triazide!This shows that the NO2 is wel linked to the external NH2's and not on the aromatic C's.

(-N=C(NO2)-)3 -H-> (-N=C(NH2)-)3
(-N=C(NH-NO2)-)3 -H-> (-N=C(NH-NH2)-)3
(-N=C(NH-NH2)-)3 -HNO2->(-N=C(NH-NH-NO)-)3 -> (-N=C(N3)-)3 + 3 H2O

The compounds you speak about are more like:
(-CH(NO2)-N(NH2)-)3, (-CH(NH2)-N(NO2)-)3
and (-CH(NO2)-N(NO2)-)3

The first could be done by mixing CHBr2-NO2 and refluxing with equimolar amounts of NH2-NH2, in pyridine.
The second one by reduction of melamine and subsequent nitration of (-CH(NH2)-NH-)3.
Finally mixing CHBr2-NO2 with equimolar amounts of NaNH-NO2 in pyridine.
No doubt interesting compounds; the last one being a dream since containing more NO2's than RDX.
(-CH2-N(NO2)-)3 vs (-CHNO2-NNO2-)3
Better OB (slightly positive but it is ideal with negative OB plasticisers), higher density (no doubt), higher energy output and thus much higher VOD (over the 10 km/s).




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biggrin.gif posted on 3-6-2003 at 16:31


Trinitromelamine is trinitromelamine.
I think important is how maked. ;)

Why should the compounds not exist ?

Here some exambles:

Excuse me when i writing some errors, i can correct it later.

2,4,6-trinitro-1,3,5-tiazine
(melaminetrinitrate)
[>N=CNO2-N=CNO2-N=CNO2->]

2,4,6-trinitramino-1,3,5-triazine
(trinitraminomelamine)
[>N=CNHNO2-N=CNHNO2-N=CNHNO2->]

2,4,6-trinitroxy-1,3,5-triazine
(cyanurtrinitrate)
[>N=CONO2-N=CONO2-N=CONO2->]

1,3,5-trinitro-1,3,5-triaza-s-triazine
(triazacyclohexanetrinitrate) - RDX
[>NNO2-CH2-NNO2-CH2-NNO2-CH2->]

1,3,5-trinitro-1,3,5-triaza-2,4,6-triamino-s-triazine
(triaminotriazacyclohexanetrinitrate) - triamino-RDX
[>NNO2-CHNH2-NNO2-CHNH2-NNO2-CHNH2->]

1,3,5-trinitro-1,3,5-triaza-2,4,6-trinitramino-s-triazine
(trinitraminotriazacyclohexanetrinitrate) - - trinitramino-RDX
[>NNO2-CHNHNO2-NNO2-CHNHNO2-NNO2-CHNHNO2->]

1,3,5-trinitro-1,3,5-triaza-s-triazine-2,4,6-trione
(hydroisocyanurtrinitrate)
[>NNO2-(C=O)-NNO2-(C=O)-NNO2-(C=O)->]

1,3,5-trinitramino-1,3,5-triaza-1,3,5-s-triazine-2,4,6-trione
(trinitraminohydroisocyanur)
[>NNHNO2-(C=O)-NNHNO2-(C=O)-NNHNO2-(C=O)->]

1,3,5-trinitro-1,3,5-triaza-s-triazine-2,4,6-trione tri-sodium salt
(hydroisocyanurtrinitrate tri-sodium salt)
[>NNO2-CHONa-NNO2-CHONa-NNO2-CHONa->]

1,3,5-trinitramino-1,3,5-triaza-1,3,5-s-triazine-2,4,6-trione tri-sodium salt
(trinitraminohydroisocyanur tri-sodium salt)
[>NNHNO2-CHONa-NNHNO2-CHONa-NNHNO2-CHONa->]

and

1,3,5-triazine-2,4,6-triazide
(cyanurtriazide)
[>N=(C-NNN)-N=(C-NNN)-N=(C-NNN)->]

1,3,5-triaza-s-triazine-1,2,3,4,5,6-hexazide
1,3,5-triazidamine-s-triazine-2,4,6-triazide
(hydromelaminehexaazide)
[>(N-NNN)-(CH-NNN)-(N-NNN)-(CH-NNN)-(N-NNN)-(CH-NNN)->]

1,3,5-triaza-s-triazine-1,2,2,3,4,4,5,6,6-nonaazide
1,3,5-triazidamine-s-triazine-2,4,6-tri(diazide)
(hydromelaminenonaazide)
[>(N-NNN)-(C(NNN)2)-(N-NNN)-(C(NNN)2)-(N-NNN)-(C(NNN)2)->]

:P




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smile.gif posted on 5-6-2003 at 14:55


If you read wel in my previous posts about 1/5 of the molecules you have mentionned exist already (So why asking if they could be done...EXISTING = MADE).
The others, you should patent them really but you will only earn money in a century or two :)!
I will let you discover which doesn't exist, because too unstable.
Some tips:
-What is the higher Azides amount practically introduceable in a molecule?
-Does gemdiazide exist?
-Does vicinal azide exist?
-Does nitrohydrazide exist?
-Are mixed nitrate acid anhydride stable?
-Are nitrogroup introduced on an acidic H stable?
-Is nitrourea stable, what happens to dinitrourea stability?What to expect of higher multimers?
-Does CH3-NNO2-CH3 or RDX stand NaOH?
-Does CH3-N(N3)-CH3 exist and be stable at 20°C?

Where is the fun if I reply to all your questions and that you don't experimentate anymore or don't read what people (me included because it is the second time today that I notice you don't read correctly what is written prior :mad: ) have already done in the field?
Ahh pleasure of exploding glassware, schrapnels and burned mustach :P:P:P!

Anyway, despite your way of writting molecules, I have been able to understand everything and on a theorical writting level...all your formulas are correct :o:o:o

Let see in how much seconds you will answer my questions...shouldn't be a problem for such a fast working brain ;) ;) ;especially with all the tips I gave you (piece of cake) :P:P:P;););):):):):D:D:D




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smile.gif posted on 5-6-2003 at 16:04


I want give only some tips what the people understnd when they read the thread ! :)
I think you have a to compact knowledge for a normally studyed person, or ? :P




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smile.gif posted on 6-6-2003 at 09:09


You simply ask too many questions at a time in one post...one question per post and if possible per tread would be better.
I answered to Madscientist interrogation about melamine? You put in doubt my explanations, and I proved you the name and formula was right owing to experimental related facts.Then you came with something else and started to diverge from the subject of this tread.
Sometimes it is good to do so to revive the tread when it goes down, but you have to put clear questions at max 2 or 3 otherwise everybody goes crazy.I can't take proper time to reply then and it is sometimes too condensed and compact.Also let the time to people to react to your questions:

Ex Absurde demonstrandi of what's happening:
Q1-Is it possible to cook porc in sunbeams?
P-Sunbeams is heat and when well localised can produce enought heat to cook proteins (what meat is).
K-What happens if there is rain...and if...and in that case...
P-Well it depends fo this..., that ... and in that case.
K-Hey and this..., and that ... why does it work or why doesn't it work ... and if I do this it should work, but when I did it didn't why..and why the sky is blue...and who came first the frog the egg of the kitchen?
-..... :( :mad: :( :mad: fear of exponential questions.

You were asking for answer about stability and possibility of existance of 15 compounds what would make me use too much "virtual paper" for this tread... of course less if I explain it in scientific terms (by definition compact and concise)...and much more if it is for "normal studied person" (average educated people) because it would need much more explanations and turns to go to the points.
:cool:




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[*] posted on 22-7-2003 at 18:49


melamine is cyanamide cyclic trimer. and nitrocyanamide is trinitromelamine monomer. it is made from alkalinization of N-metyl-N-nitroso-N'-nitroguanidine. a synthesis route of it, its salts & its primary materials can be found on swedish infomania.
O<sub>2</sub>NNHC(=NH)N(CH<sub>3</sub>;)NO + NaOH => NaNNO<sub>2</sub>CN + H<sub>2</sub>CNN + H<sub>2</sub>O
obviously trinitromelamine can form salts similarly, as density of electron cloud is very low on hydrogen atoms in TNmelamine. lead salt of TNmelamine detonation reaction:
Pb<sub>3</sub>C<sub>6</sub>N<sub>18</sub>O<sub>12</sub> => 3Pb + 6CO<sub>2</sub> + 9N<sub>2</sub>
trinitrotrinitratomethylmelamine is very interesting if exists ;). various nitratoethylnitramino compounds have been patented (include trinitratoethyltrinitromelamine with a VOD of 8700 m/s) but I don't remember any nitratomethylnitramine derivative, may be they polymerize before nitration. anyway it will have 0 OB and a VOD that is considerably higher than 8700 m/s !
trimethylol melamine is probably commercially available as starting material for melamine resins. it's kind of material u can order without raising any suspicion, there is no illegal usage for it as far as I know (well, except the one we gonna create ;):D:D)
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[*] posted on 23-3-2007 at 20:00
trimethylolmelamine


It would be easy enough to make the trimethylolmelamine .

According to US4525520 Example 1 :
Quote:

Preparation of trimethylolmelamine 37% Aqueous solution of formaldehyde (14.9 parts) was diluted with water to 100 parts and adjusted to pH 6.5 to 6.8 using 0.1N aqueous NaOH solution. Into this solution, 23.1 parts of melamine was added and completely dissolved by stirring with the temperature gradually raised to 75 DEG C. After being held at 75 DEG C. for 5 minutes, the solution was rapidly cooled to 0 DEG C. and allowed to stand without stirring for 24 hours. This separates out white crystals.

The crystals were filtered out, washed with methanol several times, and air-dried, giving 25.7 parts of trimethylolmelamine crystals.


Its polyol hydroxyls should nitrate easily enough
to provide a trinitroester .

Whether it would add three more nitro groups to the ring ,
I don't really know ....but it would probably be a damn powerful explosive just with the trinitroester structure .
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[*] posted on 23-3-2007 at 22:53


Quote:
Originally posted by Rosco Bodine
trimethylolmelamine polyol hydroxyls should nitrate easily enough to provide a trinitroester

[img]http://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?t=l&cid=70549[/img]
Interesting thought , but why make it if its available in industrial quantities as a wood
adhesive among other uses Its even used as a pharmaceutical Cealysin, and Cilag 61.
This is a water proof resinous polymer so it presents different challenges for solvation.
Other derivatives _
http://pubs.acs.org/cgi-bin/abstract.cgi/iechad/1952/44/i11/...

[Edited on 24-3-2007 by franklyn]

[Edited on 19-7-2007 by franklyn]

Methylolmelamine resin (small).jpg - 151kB
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[*] posted on 23-3-2007 at 23:23


You would want to make it because for nitration you would want the intact hydroxyls of the crystalline ,
undehydrated , monomer , which is unstable even at room temperature . So you would want to prepare
the material fresh and then nitrate it .

It is very likely that rather than nitration occuring ,
the acid will simply catalyze polymerization ......

I honestly don't know .

BTW , your attached image is too large , maybe reduce it
by about 30% and it won't foul up the page formatting .

[Edited on 24-3-2007 by Rosco Bodine]
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[*] posted on 3-4-2007 at 22:30


Quote:
Extract from Ind. Eng. Chem: 33(6); 770

<b>Methylolmelamines</b>. Melamine reacts with alcohols, simple sugars such as glucose (66), and phenol (6). But of greater importance to the resin chemist is the reaction of both alkyl and aromatic aldehydes and ketones with melamine. These condensations are so extensively used that they warrant particular consideration.

The most important of this large group of condensation products are the methylol compounds. They are produced in good yields when melamine is reacted with neutral or slightly alkaline formaldehyde, or with some substance producing formaldehyde. Of the six products possible from the condensation of these two compounds, the most stable and readily isolated is hexamethylolmelamine (10, 82). This compound may be produced either by heating melamine with an excess of neutral formaldehyde to 90" C. (194" F.), or by allowing the melamine to react with neutral formaldehyde at room temperature over a period of 15 to 18 hours. Elemental analysis indicates that the product formed in both cases is the same and contains one molecule of water of crystallization per molecule of hexamethylolmelamine.

Though the trimethylol compound is not so stable as the hexamethylol compound, it has also been prepared. If one mole of melamine is reacted with three moles of neutral or slightly alkaline formaldehyde in the cold for 15 hours, the trimethylol compound is obtained. The entire separation and purification of this material must be carried out with extreme rapidity and at very low temperatures to prevent further reaction. Elemental analysis shows that under these conditions the compound crystallizes from aqueous solution with two molecules of water of crystallization. Owing to its extreme reactivity, the material has no definite melting point and is not stable on standing.


Heres article on yet to be sythesized(?) 2,4,6-Trinitro-1,3,5-triazine. Another article from Los-Alamos predicts 9280m/s @ 1.98g/cm3.

[Edited on 4-4-2007 by Axt]

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[*] posted on 4-4-2007 at 20:43
Deja Vu all over again


Thanks for that Axt " Attachment: 2,4,6-Trinitro-1,3,5-triazine.pdf "
Given what it say's " Surprisingly, there seems to be only one obscure reference
to this compound in - Finger, H. J. Prakt. Chem. 2 1907, 75, 103
"
makes me wonder if explosives and propellant chemists don't do their best work
sitting on their hands. Its nice to know I'm not a lone crackpot , this occured to me
http://www.sciencemadness.org/talk/viewthread.php?tid=6717#p...
and I'm not even that well informed on the subject. Critiqued by Chemoleo
http://www.sciencemadness.org/talk/viewthread.php?tid=6717#p...

.
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[*] posted on 7-4-2007 at 21:39


The direct nitration of melamine produces dinitroammeline aka 4,6-Dinitramino-1,3,5-triazine-2(1H)-one C3H3N7O5, its a dense explosive (1.95g/cm3) though liable to hydrolyse to cyanuric acid. The nitration requires acetic anhydride. In modern literature its designated DNAM for whatever reason, see the attachment for synthesis.

A relation to the theoretical nitration product of trimethylolmelamine, one that has been studied is N,N’,N’’Tris(ethyl-2-nitrato)-N,N’,N’’-trinitromelamine (aka. Tris-X, picture <a href="http://www.sciencemadness.org/talk/viewthread.php?tid=8027">pentryl</a> with CNO2's replaced with N's). I don't have synthesis info though I expect its produced simularly to pentryl, though condensing ethanolamine with cyanuric trichloride. Or if your lucky by condensing melamine with ethyleneglycol under heat/pressure then nitration.

Literature gives Tris-X's properties as being 8700m/s @ 1.73g/cm3, MP 69°C and about as sensitive as RDX. A nice castable explosive however a little thermally unstable.

Melamine itself can be produced by fusing urea with sulphamic acid at about 250°C for 1.5hr or so, this goes through a guanidine intermediate. Leach the fused mass with water which leaves the melamine and a water solution of ammonium and guanidine sulphates. I've done this.

The reference to Tris-X, which I dont have is:

R. W. Millar,N. C. Paul,D. H. Richards, P. Bunyan, P. Golding, and J. A. Rowley, "Tris-X, A New High Energy Polynitramine Explosive: Synthesis Using Dinitrogen Pentoxide Technology, Characterization, and Thermal Stability and Hazard Assessment" <i>Propellants, Explos., Pyrotech.</i> 1993, 18(1), 55.

[Edited on 8-4-2007 by Axt]

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[*] posted on 7-4-2007 at 22:10


That citation for PEP is :

Propellants, Explos., Pyrotech. 1993, 18(2), 55-61

Tris-X(1), A New High Energy Polynitramine Explosive: Synthesis using dinitrogen pentoxide (n2O5) technology(2), characterization, and thermal stability and hazard assessment (p 55-61)
R. W. Millar, N. C. Paul, D. H. Richards (deceased), P. Bunyan, P. Golding, J. A. Rowley
Published Online: 14 Sep 2004
DOI: 10.1002/prep.19930180202

Abstract
This paper describes the synthesis and characterization of two novel heterocyclic trinitramines from readily available starting materials, as well as the evaluation of one of them (Tris-X) as a high explosive. The syntheses, which utilize the ability of dinitrogen pentoxide (N2O5) to cleave aziridine rings to yield vicinal nitramine-nitrates, proceed in high yield to give crystalline products with melting point below 100°C. The characterization of the products by IR, NMR (1H and 13C), mass spectrometry and elemental analysis is described, and whilst possessing high explosive power (the Pcj for Tris-X is calculated at ca 300 kbar) they were found to exhibit acceptable hazard properties (impact sensitivity, temperature of ignition etc). The thermal stability measurements (by DSC and chemiluminescence) however indicated only marginally acceptable stability.

[Edited on 8-4-2007 by Rosco Bodine]
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egloskerry
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[*] posted on 15-4-2007 at 16:46


I know this is off-topic somewhat, but I was thinking melamine as in the plastic plates are made out of, or what formica is made out of. Lol.
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