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Author: Subject: New Energetic Materials - Current Research
chemoleo
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because I thought those novel compounds from the paper Quince dug out fit well into this thread.
Because of the broad nature of this thread, I also moved the details on glyoxal synthesis to this location, as this truly is a subject that merits its own attention.

If the subject on glyoxal condensations and energetics thereof is followed up (i.e. with experiments) I'll be happy to move the respective posts to a new dedicated thread.

So please, any major details/methods relating to particular compound discussed in this thread belong into a dedicated one, else it just gets unmanagable!

Never Stop to Begin, and Never Begin to Stop...
Tolerance is good. But not with the intolerant! (Wilhelm Busch)
Chris The Great
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I was in the middle of making an image of some compounds I found for my post, and when I previewed, everything crashed and I lost my post since you have stuck the topics together! Acck! Anyway, it wasn't that long, so here it is:

I was reading through a recent military document, and found information on two very interesting compounds they are currently researching, DTTO and IsoDTTO. Both have the formula C<sub>2</sub>N<sub>8</sub>O<sub>4</sub>. They have high densities (2.419 and 2.484). high heats of formation (179.5 and 175.7 kcal/mol) and astounding detonation pressures of 131.4 and 131.8 GPa! This puts HMX (38.2GPa) and even tetranitrotetrahedrane (51.2GPa) to shame! These explosives would be brisant to the extreme, and substantially more powerful than any other explosive made!

Here is a picture of their structures:
http://img274.imageshack.us/img274/6791/dtto9sb.jpg

[Edited on 5-9-2005 by Chris The Great]

[Edited on 5-9-2005 by Chris The Great]
((Blasta))
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I too have heard of this explosive as well. But, I am curious how it is manufactured. I remember a physics prof talking about an explosive that was one of the most powerful ever made, but it could not be manufactured in a standard atmosphere---it had to be inside a vaccum.

use caution---explosives in transport
Chris The Great
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It isn't manufactured, and there are lots of possible routes but I personally think none of them will work. I'll put them up into a graphic tommorrow, they all start from glyoxal, interestingly. Again, I don't think they'll work.

The reason is that the nitrogen rings with the two oxygens are very stable (surprisingly). The charges can resonate, forming alternating positive and negative charges around the ring, greatly stabilizing it. The nitrogen ring without oxygen simply doesn't form and if it does it immediatly decomposes into nitrogen and alkynes. With one oxygen, the ring has moderate stability, and with two it turns out to be very stable.
All proposed methods that I am aware of involve the ring or rings having only one oxygen at some point, and so I think the methods will probably fail. Who knows though, perhaps a method will oxidize the ring before it has a chance to decompose?

But, it's late and school starts tommorrow.
Ramiel
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Review Article

<html>I see that an article reviewing the syntheses of DTTO <i>and</i> iso-DTTO has just been approved for public release. Now, if someone can verify that this article; “<a href="http://www.stormingmedia.us/23/2330/A233034.html"> Synthesis of 1,2,3,4-Tetrazines, 1,2,3,4-Tetrazine Di-N-oxides, Pentazole Derivatives, Pentazine Poly-N-oxides, and Nitroacetylenes</a>”<sup> 1</sup>, is what it says it is – a DARPA/AFOSR generated review – then perhaps we can decide if it is worth getting, and if so, find a way to acquire it.

Its USD$22.95 to buy a PDF for Joe Citizen, but perhaps there are persons who can legally acquire the document (although I wouldn’t recommend violating EULA-type agreements or committing corporate espionage upon a site that claims to be a Pentagon publisher!) <sup>1</sup> Harold Shechter, M. Venugopal, D. Srinivasulu. 2003, ‘Synthesis of 1,2,3,4-Tetrazines, 1,2,3,4-Tetrazine Di-N-oxides, Pentazole Derivatives, Pentazine Poly-N-oxides, and Nitroacetylenes’, <i>Ohio State University Columbus Dept. of Chemistry</i>, Report Number A233034, 60 p.p. </html> Caveat Orator Chris The Great National Hazard Posts: 463 Registered: 29-10-2004 Location: Canada Member Is Offline Mood: No Mood It is a general overview of the methods that don't work, and what methods they are probably trying right now. It also includes some information on other compounds but the main focus is DTTO and isDTTO. Yes, it is a DARPA/AFOSR related presentation, it is basically the overheads from some presentation. There is lots of writing on it, so there is a fair amount of information. I can also access it for free from a undisclosed source, but I'd rather it not went the way of the kewl-swarmed source, sorry guys (but feel free to PM if you need something specific, I'll try to get it for you) http://rapidshare.de/files/4807062/Synthesis_of_High_Energy_... 1,671KB Here are some other files related to the subject of recent high energy materials (non-DARPA/AFOSR stuff, originally from a roguesci torrent). Here is a review on recent energetic materials, it was an interesting read, and is a good way to see what has been going on recently in the field: http://rapidshare.de/files/4807149/New_Energetic_Materials.p... 1,989KB Another similar journal, with some other energetic materials. http://rapidshare.de/files/4807181/A_review_of_energetic_mat... 283KB [Edited on 6-9-2005 by Chris The Great] akinmad Hazard to Others Posts: 245 Registered: 24-7-2003 Member Is Offline Mood: No Mood tetranitro-propane diurea I don't know if this substance is covered here (UTFSE yields no results). But while I was reviewing the New Energetic Materials.pdf I saw a substance called tetranitro-propane diurea (p16 shows the structure). The last column states that it's easy to prepare and has a very high VOD (9030) and good thermal stability. While searching the net, I came across an article about the preparation of this substance. http://doi.wiley.com/10.1002/1521-4087(200104)26:2%3C63::AID-PREP63%3E3.3.CO;2-V Name of the article is Synthesis, Characterization and Thermal Behaviour of 2,4,6,8-Tetranitro-2,4,6,8-Tetraazabicyclo[3.3.1]Nonane-3,7-Dione (TNPDU) and one of its Methylene Analogues A. K. Sikder, G. M. Bhokare, D. B. Sarwade, J. P. Agrawal * Its abstract states that : 2,4,6,8 - Tetranitro - 2,4,6,8 - tetraazabicyclo[3.3.1]nonane-3,7-dione (TNPDU) has been synthesized from propane diurea by nitration with nitric acid-acetic anhydride with a yield of 85 %. The molecular structure of the compound has been determined by elemental analysis, IR and 1H-NMR spectroscopy. Some of the properties including thermal and explosion delay behaviour of the compound and its mixtures with high explosives, are reported. An analogous compound 2,5,7,9-tetranitro-2,5,7,9-tetraazabicyclo[4.3.0]nonane-8-one (TNABN) has also been evaluated for some of the explosive properties considering its good stability and insensitiveness as compared to other nitrodiurea derivatives. What is the cons and pros of this substance and can somebody who has access to this article upload it to the rapidshare? S.C. Wack bibliomaster Posts: 2169 Registered: 7-5-2004 Location: Cornworld, Central USA Member Is Offline Mood: Enhanced here A short time after I last mentioned PEP, it was removed from the library catalog and the list of journals, and UTFSE there is fruitless. Other Wiley journals are not affected, leaving me to wonder if they got an email from Wiley, I don't see how else this could have happened. It is still obtainable, however. DUHHHHHHHHH!!!!!!!!!!!!!!!: It has been pointed out to me that I uploaded the wrong pdf, starting on page 75 instead of 63. It has been corrected. The S.C. stands for "Space Cadet" and although this name was chosen as a sort of homage to Wack, I will be the first to admit that it applies, perhaps more often than for most people. [Edited on 8-9-2005 by S.C. Wack] franklyn International Hazard Posts: 3027 Registered: 30-5-2006 Location: Da Big Apple Member Is Offline Mood: No Mood Octanitrocubane http://cst-www.nrl.navy.mil/%7Erichards/projects/slr1.html . deiki Harmless Posts: 8 Registered: 14-3-2006 Location: a random manifold Member Is Offline Mood: chaotic I had found this few months ago, but I never seen it mentionned here: http://www.dtic.mil/descriptivesum/Y2000/OSD/PE0603225D.pdf "Polymeric carbon monoxide, the first of a new and potentially very interesting class of metastable High Energy Density Materials (HEDM) was synthesized under very high pressure and temperature in the laboratory and recovered for characterization at ambient conditions. Energy content of this class of materials is predicted to exceed that of known high explosives by a factor of 2 to 4." franklyn International Hazard Posts: 3027 Registered: 30-5-2006 Location: Da Big Apple Member Is Offline Mood: No Mood Polycarbonyl monomer is metastable at ambient conditions and is synthesized by compressing liquid carbon monoxide at pressures exceeding 5GPa , that's 50,000 atmospheres. Fairly straight forward and easier to make than suboxide of carbon ( C3O2 ). Now if we can only peroxidate this http://arxiv.org/PS_cache/physics/pdf/0112/0112068.pdf and same here _ http://www.i-b-r.org/docs/polycarweb.pdf#search=%22polycarbo... http://www.ictp.trieste.it/~pub_off/preprints-sources/1998/I... . franklyn International Hazard Posts: 3027 Registered: 30-5-2006 Location: Da Big Apple Member Is Offline Mood: No Mood Yup works with CO2 also CO2 glass http://www.newscientisttech.com/article.ns?id=dn9339&fee... . Sauron International Hazard Posts: 5351 Registered: 22-12-2006 Location: Barad-Dur, Mordor Member Is Offline Mood: metastable The REALLY amazing thing about that article is that some gullible reporter bought the notion that an explosive based on hydrazine, proven human carcinogen, is somehow environmentally friendly, what a laugh. TOXIC Al2O3!! that's alumina. Toxic alumina and green hydrazine. ROTF! Or that a propellant mix that is LESS detectable by radar or satellite is somehow a Good Thing. It might be someone's good thing and someone else's Very Bad Thing all depending on which way it in pointed! Axt International Hazard Posts: 778 Registered: 28-1-2003 Member Is Offline Mood: No Mood  Quote: Originally posted by Axt I'm attaching the article relating to NM-glyoxal condensation to dinitroinositol. Which is run at low temp, excess NM and precipitates from methanol solution. Hopefully that means further condensation is possible. In the very least it does present an easy method for retrieving a pure product from the condensation reaction. Cyclizations of Dialdehydes with Nitromethane. VII. Preparation of neo-Inosadiamine- 1,4 OK, just ran across the nitration product of dinitroinositol in <a href="http://www.sciencemadness.org/talk/viewthread.php?tid=7518">Organic Chemistry of Explosives</a>, yeh it will form the tetranitrate but the book contradicts its reference, the patent reference GB1107907 says only 1 nitrate group can be introduced via HNO3/H2SO4 and four with HNO3/AcO, where the book says both give the tetranitrate. Supposedly the tetranitrate is too sensitive for practical use but the dinitrate has "significantly better properties" and must have been interesting enough to be studied by Lawrence Livermore Labs as its designated "LLM-101". It can be made by HNO3/chloroform nitration. It doesnt look it, but accordring to LLNL its energy is estimated to be simular to HMX Must be more dense then it looks (though they dont define "energy". Its a simple reaction but crappy yields of dinitroinositol from NM + glyoxal. [Edited on 2-6-2007 by Axt] Mardec Harmless Posts: 33 Registered: 29-5-2007 Location: In a Lab Member Is Offline Mood: No Mood  Quote: Originally posted by Axt It can be made by HNO3/chloroform nitration. [Edited on 2-6-2007 by Axt] Is a chloroform / HNO3 nitration the same as a DCM/HNO3 nitration? And can CHCl3 extract HNO3 from a watery solution like DCM? Or did I misunderstood? I am currently working on HNO3 100% through DCM, but DCM is a problem for me, where as Chloroform is easely available form me. [Edited on 3-6-2007 by Mardec] Axt International Hazard Posts: 778 Registered: 28-1-2003 Member Is Offline Mood: No Mood Yes and Yes, though HNO3 is less soluble in chloroform then DCM, you will still need a dehydrating agent as I assume water is more soluble in DCM/HNO3 then DCM alone. A progress report by LLNL mentions that diluting the HNO3 helps prevent the tetranitrate but not entirely and that the tetranitrate "is a very sensitive material and should never be isolated dry". Though the dinitrate is insensitive and of interest because "of its energy, which is estimated to be simular to that of HMX. LLM-101 also has an exceptionally high temperature at the Chapman-Jouguet state". Its also a potential precursor to high energy polymers. [Edited on 4-6-2007 by Axt] The_Davster A pnictogen Posts: 2861 Registered: 18-11-2003 Member Is Offline Mood: No Mood  Quote: Originally posted by Axt Organic Chemistry of Explosives, I have just spent the last couple days reading that pretty much cover to cover, seeing as this is the 'New energetic materials' thread, that book covers much of the weird and wonderful energetics. Best overview of the recent developments I have seen. Fascinating sections on nitrogen heterocycles. [Edited on 5-6-2007 by The_Davster] woelen Super Administrator Posts: 7293 Registered: 20-8-2005 Location: Netherlands Member Is Offline Mood: interested The link you quoted does not work. It asks for a password and both the whimsy and references passwords do not work. After login it tells me this is a non-existent subforum. Could you (or Axt) give a working link of that book? The art of wondering makes life worth living... Want to wonder? Look at https://woelen.homescience.net Axt International Hazard Posts: 778 Registered: 28-1-2003 Member Is Offline Mood: No Mood Link work for me but kmno4 originally found and uploaded it to here: http://mihd.net/g4c6io The_Davster A pnictogen Posts: 2861 Registered: 18-11-2003 Member Is Offline Mood: No Mood http://mihd.net/g4c6io How strange, at the time I found that link it took me to the right place. The link has now been edited h0lx Hazard to Self Posts: 64 Registered: 31-12-2005 Member Is Offline  Quote: Originally posted by Sauron ...that an explosive based on hydrazine, proven human carcinogen, is somehow environmentally friendly, what a laugh... it is. It decomposes to H2O and N2, when burned. A crash would be a whole another thing. DeAdFX National Hazard Posts: 339 Registered: 1-7-2005 Location: Brothel Member Is Offline Mood: @%&$ing hardcore baby

Hydrazine is rather reactive towards oxygen shouldn't the stuff convert to H2O/N2 after a few weeks or so?
Phel
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The Sila-Explosives Si(CH2N3)4 and Si(CH2ONO2)4: Silicon Analogues of the Common Explosives Pentaerythrityl Tetraazide, C(CH2N3)4, and Pentaerythritol Tetranitrate, C(CH2ONO2)4
Thomas M. Klapötke, Burkhard Krumm, Rainer Ilg, Dennis Troegel, and Reinhold Tacke

attached

Attachment: ja071299p.pdf (951kB)

franklyn
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 Quote: Originally posted by Phel The Sila-Explosives : Silicon Analogues of the Common Explosives

That's really cool , I thought for a long time about attaching oxy radicals to
silicones. To bad these " are extremely shock-sensitive materials and very
difficult to handle
".

.
franklyn
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Alternate Propulsion Energy Sources

Take a walk on the wild side and read about speculative schemes for energetic materials
Metastable Helium , Free radical Hydrogen , Ultra cold neutron cataylsed fission , and so on.

AFRPL-TR-72-31 , JUN 1972 , AD0750554
or here _

Abstract:
A study was conducted by an ad hoc group within the Air Force Rocket
Propulsion Laboratory during the calendar year of 1970 in an attempt to predict
the major propulsion developments that may occur in the next 30 to 40 years.
The report evaluates the future of conventional chemical rocketry based on
thermodynamic principles and revolutionary conceptual approaches to system
Field and Photon Propulsion are evaluated to a degree necessary to define their
potential.

The above was an earlier assessment of ongoing research in propulsion schemes which
reminds me ( though somewhat off topic ) of the subsequent Breakthrough Propulsion
Physics investigation that follows _

http://www.nasa.gov/centers/glenn/research/warp/warp.html

http://www.grc.nasa.gov/WWW/bpp/index.html

ABSTRACT:
In 1996, NASA established the Breakthrough Propulsion Physics program to seek the ultimate
breakthroughs in space transportation: propulsion that requires no propellant mass, propulsion
that attains the maximum transit speeds physically possible, and breakthrough methods of
energy production to power such devices. Topics of interest include experiments and theories
regarding the coupling of gravity and electromagnetism, vacuum fluctuation energy, warp
drives and wormholes, and superluminal quantum effects. Because these propulsion goals are
presumably far from fruition, a special emphasis is to identify affordable, near-term, and
credible research that could make measurable progress toward these propulsion goals. The
methods of the program and the results of the 1997 workshop are presented.
http://www.grc.nasa.gov/WWW/bpp/1997-J_AIAA_SpaceDr.pdf
1 9 9 8
http://gltrs.grc.nasa.gov/reports/1998/TM-1998-208400.pdf
2 0 0 5
http://www.grc.nasa.gov/WWW/bpp/2005-J_ANYAS_AssessBPP.pdf

A lighter primer on some proposals _
http://en.wikipedia.org/wiki/Breakthrough_Propulsion_Physics...
Alcubierre Warp drive _
http://en.wikipedia.org/wiki/Alcubierre_drive
Unproven or discounted ideas _
Go here _
http://web.archive.org
and enter this
http://www.grc.nasa.gov/WWW/bpp/ComnErr.html
Jun 03, 2004 , is the last update

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 Sciencemadness Discussion Board » Special topics » Energetic Materials » New Energetic Materials - Current Research Select A Forum Fundamentals   » Chemistry in General   » Organic Chemistry   » Reagents and Apparatus Acquisition   » Beginnings   » Responsible Practices   » Miscellaneous   » The Wiki Special topics   » Technochemistry   » Energetic Materials   » Biochemistry   » Radiochemistry   » Computational Models and Techniques   » Prepublication Non-chemistry   » Forum Matters   » Legal and Societal Issues   » Detritus   » Test Forum