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Nicodem
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[*] posted on 12-9-2013 at 11:00


Another new study:

Impact insensitive dinitromethanide salts
J. M. Shreeve, Ling He, Damon A. Parrish and Guo-Hong Tao
Chem. Commun., 2013, Accepted Manuscript
DOI: 10.1039/C3CC46518G
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[*] posted on 9-11-2013 at 08:13


Quote: Originally posted by franklyn  
That is a gem of a paper.

The essential reaction scheme irrespective of the *azole , is the oxidation of the
acetic acid functional group into trinitroformate in a rather fascile manner. It begs
the question if this will work generally on any R-CH2COOH. A likely candidate to
investigate would be aromatic derivatives such as ,1,3,5- benzene triacetic acid.



www.chemspider.com/Chemical-Structure.309530.html
www.guidechem.com/products/4435-67-0-p1.html
http://datasheets.scbt.com/sc-252412.pdf
a bit expensive at ~ $130 per 500 gm.
http://www.scientificlabs.co.uk/product/17383-500MG

The intended result of this would be
1,3,5-Tris (trinitromethyl)- Benzene , CAS 210053-27-3
oxygen balance is , - 4.6
2 C6H3{C(NO2)3}3 => 15 CO2 + 3 CO + 3 H20 + 9 N2



Apart from Arylacetic acids other candidates are Alkyl Dicarboxylic acids.
http://en.wikipedia.org/wiki/Dicarboxylic_acid
By this process Succinic Acid would yield Hexanitroethane.

Succinic Acid (Butanedioic Acid) HOOC.(CH2)2.COOH
http://en.wikipedia.org/wiki/Succinic_Acid
Glutaric Acid (Pentanedioic Acid) HOOC.(CH2)3.COOH
http://en.wikipedia.org/wiki/Glutaric_acid
Adipic Acid (Hexanedioic Acid) HOOC.(CH2)4.COOH
http://en.wikipedia.org/wiki/Adipic_acid
Pimelic Acid (Heptanedioic Acid) HOOC.(CH2)5.COOH
http://en.wikipedia.org/wiki/Pimelic_acid
Pimelic can be synthesized from salicylic acid
http://www.orgsyn.org/orgsyn/pdfs/CV2P0531.pdf

Carboxylic acids can be made by oxidizing an alcohol group.
A typical reaction is:


Syntheses of Tetracarboxylic Acids
Boris I Zapadinskii et al 1973 Russ. Chem. Rev. 42 939
http://iopscience.iop.org/0036-021X/42/11/R04

Ethylene Diamine Tetraacetic acid (EDTA) is available over the counter
from your health food store around $ 15 for 125 grams in capsules.
http://en.wikipedia.org/wiki/EDTA

.

[Edited on 3-4-2012 by franklyn]


What about the trioxane version of this ?

I have read about 135 trinitromethyl triazene, it has a very good positive oxygen balance but its unstable. So i wonder if the trioxane, although might be less energetic, is stable.
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[*] posted on 3-1-2014 at 06:03


Quote: Originally posted by franklyn  

Who knew that a seeming inert ceramic , Boron Nitride , can serve as fuel
in a sprengel admixture. This is literally OTC but details are sparingly available.
It appears that BN powder soaked with fuming nitric acid is comparable to
some blends of aromatics with tetranitromethane.

The Future of Warheads Armor & Ballistics
mentiond on page 7
http://www.mater.upm.es/ISB2007/Proceedings/PDF/Volume_1/Vol.I(1)GS01.pdf

Reaction Mechanisms in Shocked, Intercalated Graphite and Boron Nitride
http://hal.archives-ouvertes.fr/docs/00/25/37/51/PDF/ajp-jp4...

related thread _
http://www.sciencemadness.org/talk/viewthread.php?tid=13189

.


This is interesting because it has high gas production and very high density. Aluminum nitride also seen to be able to be used since it has a similar heat of formation however having a much higher density of 3.26 Can it be added in powdered form in rocket propellants ?
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[*] posted on 23-1-2014 at 12:18


Hi

I read about DiNitroGuadinine and NitroGuadinineNitrate and both can be made by the nitration of nitroguanidine (NGN needs only 60% HNO3 and DNG needs 100%+H2SO4/oleum)...but i dont want to waste such many H2SO4 on DNG and dont want to make oleum (to expensive and much much work - and fucking dangerous btw) so i wonder if it is possible to make a too step nitration like the RDX synthesis with hexamine dinitrate...

hexamine (+HNO3)-> hexaminedinitrate (+HNO3)-> RDX
nitroguanidine (+60%HNO3)-> nitroguanidinenitrate (+HNO3+"a bit" of H2SO4)-> dinitroguanidine ??????

could that work?


other question, there is not much information about NGN...only some translation that says it would be more powerful than DNG or ammoniumdinitroguanidine...can this be? if yes, <nevermind>@first question :D
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[*] posted on 11-9-2014 at 21:48
NGN


NGN prepare a like RDX?
The answer will learn the following: Check it out. Try it. It's the fastest way. Fastest response. A completely accurate. A write how it turned out.
LL
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[*] posted on 8-1-2015 at 06:02


did anyone succeed in synthesis any of these new EM ? I went through some papers posted here and found them very complex.
if yes , please share your experience.
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[*] posted on 20-2-2015 at 11:33


4,4,8,8-Tetranitroadamantane-2,6-diyl Dinitrate: A High-Density Energetic Material
Yifei Ling, Xiaoli Ren, Weipeng Lai and Jun Luo
European Journal of Organic Chemistry, 2015; An ASAP article first published online (22. Jan. 2015)
DOI: 10.1002/ejoc.201403449




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[*] posted on 22-2-2015 at 12:23


Quote: Originally posted by Nicodem  
4,4,8,8-Tetranitroadamantane-2,6-diyl Dinitrate: A High-Density Energetic Material
Yifei Ling, Xiaoli Ren, Weipeng Lai and Jun Luo
European Journal of Organic Chemistry, 2015; An ASAP article first published online (22. Jan. 2015)
DOI: 10.1002/ejoc.201403449

Thanks Nicodem,

Just for those curious about it:
Quoted from the link:
Abstract:
The novel high-performance energetic material, 4,8,8-tetranitroadamantane-2,6-diyl dinitrate has been synthesized and fully characterized. The synthetic strategy features the construction of the adamantane skeleton with different functional groups at adjacent methylene carbon atoms to overcome the problems associated with the ortho effect and steric crowding, and is amenable to the synthesis of other polynitroadamantanes. The experimentally determined physical properties as well as the calculated detonation properties indicate that this compound exhibits high thermal stability (220 °C), high density (1.852 g /cm³), and excellent detonation velocities (8529 m /s) and pressures (33.43 GPa).

And for those who likes it with images:
4,4,8,8-Tetranitroadamantane-2,6-diyl Dinitrate
4488-Tetranitroadamantane-26-diyl-dinitrate.jpg - 14kB

I think the 2,2,4,4,6,6,8,8-octanitroadamantane would be also interesting and there are two methylene left free that would render possible the making of a tetranitroadamantane-tetrayl-tetranitrate or a dodecanitroadamantane with each methylene holding two nitro groups...




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[*] posted on 20-3-2015 at 12:03


Quote: Originally posted by PHILOU Zrealone  
Quote: Originally posted by Nicodem  
4,4,8,8-Tetranitroadamantane-2,6-diyl Dinitrate: A High-Density Energetic Material
Yifei Ling, Xiaoli Ren, Weipeng Lai and Jun Luo
European Journal of Organic Chemistry, 2015; An ASAP article first published online (22. Jan. 2015)
DOI: 10.1002/ejoc.201403449

Thanks Nicodem,

Just for those curious about it:
Quoted from the link:
Abstract:
The novel high-performance energetic material, 4,4,8,8-tetranitroadamantane-2,6-diyl dinitrate has been synthesized and fully characterized. The synthetic strategy features the construction of the adamantane skeleton with different functional groups at adjacent methylene carbon atoms to overcome the problems associated with the ortho effect and steric crowding, and is amenable to the synthesis of other polynitroadamantanes. The experimentally determined physical properties as well as the calculated detonation properties indicate that this compound exhibits high thermal stability (220 °C), high density (1.852 g /cm³), and excellent detonation velocities (8529 m /s) and pressures (33.43 GPa).

And for those who likes it with images:
4,4,8,8-Tetranitroadamantane-2,6-diyl Dinitrate


I think the 2,2,4,4,6,6,8,8-octanitroadamantane would be also interesting and there are two methylene left free that would render possible the making of a tetranitroadamantane-tetrayl-tetranitrate or a dodecanitroadamantane with each methylene holding two nitro groups...


Article is to be found here
4488-tetranitroadamantane-26-diyl dinitrate
Thanks to Mayko via request in References/ Wanted References :D



[Edited on 20-3-2015 by PHILOU Zrealone]




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[*] posted on 2-4-2015 at 11:20


A few early view Angewangte articles:

Sulfates-Based Nanothermites: An Expanding Horizon for Metastable Interstitial Composites
Comet, M., Vidick, G., Schnell, F., Suma, Y., Baps, B. and Spitzer, D.
Angew. Chem. Int. Ed., (2015) 54: 4458–4462.
doi: 10.1002/anie.201410634

The Many Faces of FOX-7: A Precursor to High-Performance Energetic Materials
Gao, H. and Shreeve, J. M.
Angew. Chem. Int. Ed. (2015).
doi: 10.1002/anie.201501973

Energetic Materials with Promising Properties: Synthesis and Characterization of 4,4′-Bis(5-nitro-1,2,3-2H-triazole) Derivatives
He, C. and Shreeve, J. M.
Angew. Chem. Int. Ed. (2015).
doi: 10.1002/anie.201412303




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[*] posted on 3-4-2015 at 09:47


Thanks Nicodem!

The abstract on sulfate based nano thermite article mentions burn rates in a range, high end is given at 2,500 meters/second?! That's faster than several ammonium nitrate based high explosives in common use- Whee! And water of crystalization is considered a FEATURE by author, not a bug?

Time to re-consider sulfate oxidizers, The WiZ may not have covered all possibilities...

What's possible to achieve as an amateur using OTC materials for a reasonably low cost, easily cast/worked DENSE refractory material. I have a little modification of the pyronol torch/linear thermite steel cutting charge family of devices in mind.

(edit)
How to convince micro scale particles of Aluminum to behave like nano scale?
http://www.dtic.mil/get-tr-doc/pdf?AD=ADA534332


[Edited on 3-4-2015 by Bert]




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[*] posted on 3-4-2015 at 11:12


Bert, the 2500 m/s nano thermite mentioned in Sulfates-Based Nanothermites is probably a CuO/Al mix:
Quote:
While in the literature CuO/Al thermites have not been prepared by reactive
milling or sol-gel methods, unique to CuO/Al thermite is a new synthesis
methodology by Shubhra Gangopadhyay called self-assembly [17]. In this
method, the authors coated copper nanorods (20x100 nm) with a coordinating
polymer (P4VP) followed by coating the coated rods with 80 nm aluminum
powder. The result of this self-assembly process is the thermite with the highest
combustion velocity known of 2400 m/s.

Nanoscale Aluminum - Metal Oxide (Thermite) Reactions for Application in Energetic Materials
Piercey, D. G. and Klapötke, T. M.
http://www.wydawnictwa.ipo.waw.pl/cejem/2-2010/full/klapotke...

The water of crystalization was a problem when I made CuSO4/Mg flash powder. The hydrated mixture surely burns, but the anhydrous mixture explodes with immense violence when heated. The water lowers the ignition point and increases energy content of the mixture though, so why not. If it wasn't for the slow oxidation of magnesium in water, this mixture could have some use:
https://youtu.be/ix-OTDv0i8s?t=1m8s
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[*] posted on 10-4-2015 at 09:25


hi community

somebody mentioned the Energetic Nitrate Ester : / 2,3-Bis-hydroxymethyl-2,3-dinitro-1,4-butanediol tetranitrate / the synthesis isn't that difficult if you have / 2,2-Dimethyl-5-nitro-1,3-dioxan-5-yl)methanol / needed for the first synthesis.

I found a chinese PDF about this explosiv Attachment: phpJ8WtHo (540kB)
This file has been downloaded 553 times
started from Nitromethan nitromethan-.PNG - 22kB


Maybe someone is able to write a synthesis???:)



Star from 2,2-Dimethyl-5-nitro-1,3-dioxan-5-yl)methanol
Attachment: Synthesis of an Energetic Nitrate Ester.pdf (2.5MB)
This file has been downloaded 936 times





[Edited on 10-4-2015 by Mr.Greeenix]
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[*] posted on 10-4-2015 at 12:47


Synthesis of 2,2-Dimethyl-5-nitro-1,3-dioxan-5-yl)methanol is very easy if you have nitromethane and 2,2-dimethoxypropane (the dimethyl acetal of acetone) along with some (para)formaldehyde and a few common reagents. There are patents for making the 2,2-dimethoxypropane from acetone and the alcohol, but I never got it to work beyond trace amounts (enough to smell, but nothing more).
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[*] posted on 10-4-2015 at 14:25


The synthesis is even easier from 1.2-dinitroethane and formaldehyde...
O2N-CH2-CH2-NO2 + 4 CH2=O -base-> (HOCH2)2C(NO2)-C(NO2)(CH2OH)2

Based on the same principle as nitroisobutyl-triol from nitromethane and formaldehyde...
CH3-NO2 + 3 CH2=O -base-> (HOCH2)3C-NO2




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[*] posted on 10-4-2015 at 22:59


But then, where to get the DNE? I haven't seen this for sale anywhere, and IIRC it is unstable in storage. I haven't come across a reasonable synthesis either.
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[*] posted on 11-4-2015 at 05:08


from ethylene dibromide:
Br-CH2-CH2-Br + AgNO2 --> O2N-CH2-CH2-NO2 (36%) + ONO-CH2-CH2-ONO (16%) + ONO-CH2-CH2-NO2 (48%)

from tartric acid fumaric acid or maleic acid:
HO2C-CHOH-CHOH-CO2H -halogenation-> HO2C-CHX-CHX-CO2H
HO2C-CH=CH-CO2H (cis or trans) + X2 -->HO2C-CHX-CHX-CO2H
HO2C-CHX-CHX-CO2H + NaNO2 + urea -DMF-or-DMSO->HO2C-CH(NO2)-CH(NO2)-CO2H + HO2C-CH(ONO)-CH(NO2)-CO2H + HO2C-CH(ONO)-CH(ONO)-CO2H

alfa nitro carboxylic acid performs spontaneous decarboxylation...
HO2C-CH(NO2)-CH(NO2)-CO2H --> O2N-CH2-CH2-NO2 + 2 CO2(g)
HO2C-CH(ONO)-CH(NO2)-CO2H --> O2N-CH2-CH(ONO)-CO2H + CO2(g)

in mild acidic media, only the dinitro compound will be unsoluble

Urea increases solubility of nitrite and avoid side nitrosation reaction of the nitrocompound otherwise you would get aswel nitrolic acids...
R-CH2-NO2 + R'-ONO --> R-CH(-N=O)(NO2) + R'OH
R-CH(-N=O)(NO2) <--==> R-C(NO2)(=N-OH)



[Edited on 11-4-2015 by PHILOU Zrealone]




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[*] posted on 11-4-2015 at 13:24


With those extra steps, I think that the litterature path is about as good, but it would certainly be an interesting experiment.
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[*] posted on 12-4-2015 at 13:08


There is also an electrolytic dimerization of secondary nitrocompounds ammonium salts... :cool:
2 (R)2C(NO2)NH4 -electrolysis-> (R)2C(NO2)-C(NO2)(R)2

Based on that principle:
CH3-NO2 + 2 CH2=O --> (HOCH2)CH-NO2
(HOCH2)CH-NO2 + NH3 --> (HOCH2)C=N(O)-ONH4
2 (HOCH2)C=N(O)-ONH4 -electrolysis-> (HOCH2)C(NO2)-C(NO2)(CH2OH)2

Maybe the alcool function has to be protected first against electro-oxydation by acetylation...the resulting dinitro-tetraacetyl ester would then be unsoluble while the ammonium salt would be soluble, yielding and easier isolation.


[Edited on 12-4-2015 by PHILOU Zrealone]




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[*] posted on 22-4-2015 at 05:14


I put the detailed syn. of / 2,2-Dimethyl-5-nitro-1,3-dioxan-5-yl)methanol / from the chines paper in a translater.
That's my result.
(sorry for the realllly bad English) Maybe someone can translate it into good English;)

methyl nitro-methane (TN):
In the bottom flask fitted to 37% of the formaldehyde in water (327.5 G, 4
mol), and water bath heated to 50 degrees C, add the appropriate amount baking soda to adjust
pH 8.0 sites, increase the temperature to 55 degrees C, drop the nitro-methane (76.9 G, 1.25
mol), and maintain pH sites 8.5, the contribution that the agitation response 40 min to drop to a 10%
of the sulfuric acid adjustment response fluid pH sites 5, heating the reaction fluid temperature up to
80 degrees C, reducing enrichment, cooling, and by a large white needle-like crystals, the
Filter, vacuum drying, and in 3 of methyl nitro-methane 160.8 G / yield 85.2%. / m.p. 152~153 Celsius / C4H9NO5

2,2-Dimethyl-5-nitro-1,3-dioxan-5-yl)methanol:
Adds three methylol nitromethane in the round flask (120.8 g, 0.8 mol), acetone (176.4 mL), stirring,
heating in water bath to 60 degrees Celsius. After three hydroxy A base nitromethane dissolve
completely, ices the water bath to make the solution cool to 10 degrees Celsius by below, the
separation massive acicular crystals. Adds by drops the boron trifluoride etherate solution
(189.8 g, 0.84 mol), Canada finishes, responded 5 min the heating in water bath to
50~55 degrees Celsius, will respond that the fluid poured into the sodium hydrogencarbonate in the
ice water saturated solution, stirring, regulator solution pH close neutrality, pulled out filters
the white solid, the ice water washed 2 times, after the vacuum drying,
2,2- dimethyl - 5- methylol - 5- nitro groups - 1,3- two oxygen mixed hexamethylene 133.1 g,
yield 87.1%. m.p. 130~131 degrees Celsius; C7H13NO5


The only problem is "Boron trifluoride diethyl etherate" but I think some are able to buy it.
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[*] posted on 22-4-2015 at 12:54


If you use 2,2-dimethoxypropane instead of acetone as I mentioned above, there is no need for BF3. Of course, 2,2-DMP isn't exactly OTC either...

Anyway, the article can be had in english and is also discussed elsewhere on this site, so you don't have to go through a machine translation.

Edit: Now I'm confused: You posted the article in english yourself just a few posts back, so what is it you are asking?

[Edited on 22-4-2015 by Microtek]
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[*] posted on 23-4-2015 at 03:29


I posted 2 articels.

1 is in English and starts from 2,2-Dimethyl-5-nitro-1,3-dioxan-5-yl)methanol
and the 2 one is the chinese paper were one synthesis route ist improved from 85->95% and it starts from Nitromethan.
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[*] posted on 23-4-2015 at 08:11


Oh, OK. Tris-nitro (tris(hydroxymethyl)nitromethane) is easy to make in high yield. It is used as a biocide, and there are lots of patents on its preparation.

The second step, I found to be not so easy. In the end I just ordered the 2,2-DMP through Sigma-Aldrich after having tried (unsuccesfully) to synthesize it myself. There are patents about that part also, but in my experience they didn't work as advertized.
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[*] posted on 25-4-2015 at 13:33



It was mentioned before but here is the pdf of Tetranitro-propane diurea and
an other very insensitiv compound
Attachment: TNPDU.pdf (110kB)
This file has been downloaded 1097 times


[Edited on 25-4-2015 by Mr.Greeenix]
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[*] posted on 20-5-2015 at 07:08


Hydrazinium 5-Aminotetrazolate

* incredible high value (9516 m/s) was obtained for the detonation velocity
* it is incredibly insensitiv
* easy preparation

Attachment: Hydrazinium 5-Aminotetrazolate.pdf (498kB)
This file has been downloaded 913 times

What do you think?


[Edited on 20-5-2015 by Mr.Greeenix]
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