Sciencemadness Discussion Board - Any explosives made with Napthalene?

Any explosives made with Napthalene?

Matsumoto_Hideki - 4-1-2005 at 00:46

??? I just got a pile of napthalene crystals... Is there something I should be making with it?

evilgecko - 4-1-2005 at 00:50

You can make a firebomb. Constructed like a starmine except the bottom of the tube has pure BP, then a mixture of Nap/BP in ratio 60/40, then finiely pure Nap on top. Light through a hole in the side of the cardboard tube. The finer the nap the better. Boy does that stuff stink!!!

Dumb... me no know search button

Joeychemist - 4-1-2005 at 01:05

There are several explosives made with naphthalene, however I'm sure they
have already been talked about to death so maybe a search might prove to be useful. There is a search button for a reason you know?

Try searching tetranitronaphthalene...

mark - 4-1-2005 at 01:10

Tetranitronaphthalin; t ´ etranitronaphthal´ ene; TNN
*The presence of mall amounts of impurities may easily increase the experi-
mental value to above 1000 kcal/kg.ഊyellow crystals
empirical formula:C10H4N4O8
molecular weight:308.2
energy of formation:+23.7 kcal/kg =+99.2 kJ/kg
enthalpy of formation:+8.4 kcal/kg =+35.3 kJ/kg
oxygen balance:–72.7 %
nitrogen balance:18.18%
melting point:
softening of the isomer mixture
begins at 190 °C =374 °F
Tetranitronaphthalene is a mixture of isomer ,which is obtained by
continued nitration of dinitronaphthalenes.
The tetrasubstituted compound can only be attained with difficulty.The
crude product is impure and has an irregular appearance.It can be
purified with glacial acetic acid.

Source:myer and homburg

neutrino - 4-1-2005 at 03:34

Go to EW for anything like this. I seem to vaguely recall something like what you’re looking for (easy explosive from naphaltene) discussed there some time ago.

TeNN

Joeychemist - 4-1-2005 at 03:39

TeNN

First nitration;
-Mix 64g naphthalene powder with 105ml water in beaker, then slowly add 105ml 95% H2SO4, then add 81ml 70%HNO3 and allow the solution to cool to room temp.
-slowly over a three hour period add 150g more powdered naphthalene to the solution above while stirring, this will cause heat, you must regulate the addition of the naphthalene to get the temperature at 50 °C by the end of the addition time, after all the naphthalene is added and dissolved heat to 55°C while constantly stirring the mix for 4-5min.
-Stop stirring and allow the mix to cool. You should be able to see some mononitronaphthalene crystals forming on the surface.
-cool and filter the mononitronaphthalene.

Next nitration bath;
Prepare a mixture of 300ml 55%H2SO4 and 152g KNO3, cool to 25°C in ice bath, then slowly add the mononitronaphthalene from above while stirring and keeping the temp between 38°C and 45°C, you must not let the temperature rise any higher than 45°C during the addition process, this will take about an hour.
-after the addition heat mix to 55°C and hold until dinitronaphthalene crystals form, then cool and filter the solution to remove dinitronaphthalene and wash very good with a lot of cold water and allow to dry.

-add the dinitronaphthalene to boiling acetone until it dissolves, then filter the un-dissolved particles and waste, save and cool the filtrate to lowest temp possible and filter the dinitronaphthalene crystals and save the filtrate.
-boil the filtrate down to half the original volume, allow to cool and filter out the rest of the dinitronaphthalene and allow to dry.

The final nitration;
-prepare in a ice bath a solution of 750ml 99% H2SO4 and 750ml 99%fumeing HNO3 and allow the nitration bath to cool below 20°C.
-slowly add while stirring the dry dinitronaphthalene from the previous steps into the acid solution being careful not to let the temperature fall or rise between 15-20°C during the addition.
-after adding the required amount of dinitronaphthalene heat the mixture slowly over an hour to 80°C (about 1c per min)., then maintain a steady temp between 80-85°C for three hours.
-allow the mix to cool to lowest temp possible, then filter on an acid-filter paper to collect the TeNN, save the filtrate and drown it in ice water to precipitate additional TeNN.

-Wash the crystals with a lot of water then add to 95% ethyl alcohol, let the crystals dissolve, cool the solution in a salt-ice bath to re-crystallize the now pure TeNN, filter and dry this final product.

Axt - 4-1-2005 at 12:54

View Attachment.

Naphthalene diozonide seems like one of the more isolatable explosive ozonides, I would try a commercial ozone generator through naphthalene in hexane cooled in a freezer. Since it precipitates as it forms it could well work. Problem will be keeping bubbler unplugged.

<center><img src="http://www.sciencemadness.org/scipics/axt/napdiozonide.jpg"></center>

[Edited on 9-12-2005 by Axt]

Attachment: naphthalene_ diozonide.pdf (873kB)
This file has been downloaded 1847 times

Joeychemist - 5-1-2005 at 02:06

There are several isomers of tetranitronaphthalene, 1,2,4,6-; 1,2,5,8-; 1,2,6,8-; 1,3,5,7-; 1,3,5,8-; 1,4,5,8-; and1,3,6,8-tetranitronaphthalene. 1,3,6,8-tetranitronaphthalene forms in abundance over the other isomers, which is good because that is the desired isomer.

While on the subject here, does anyone know how to synthesize Naphthylamineperchlorate?

evilgecko - 6-1-2005 at 00:49

lol and there I was thinking you wanted a simple firebomb

thalium - 6-1-2005 at 01:23

If you want something evil to do with it just smell it. Or give it to others to smell

Cloner - 8-1-2005 at 06:29

You can mix the naphtalene with toluene or fuel or such and use it in a plastic bag firebomb (yes I know this is kewl). This gives sooty flaming fireballs. It's of course very dangerous since there's liquid fuel overheating.

nitration of naphtalene goes reasonable to the third nitration I think. This I could achieve with less acids of less strength. While trinitronaphtalen is an explosive, it is not as powerful as tnt or TNN. I wonder why the recipy given above doesn't let the nitration go in four steps because this wastes way too much acids (99% fuming nitric for gossake

)

[Edited on 8-1-2005 by Cloner]

Insolent fool!

Joeychemist - 8-1-2005 at 07:10

Quote:

Originally posted by Cloner
You can mix the naphtalene with toluene or fuel or such and use it in a plastic bag firebomb (yes I know this is kewl). This gives sooty flaming fireballs. It's of course very dangerous since there's liquid fuel overheating.

Quote:

Yep that is K3wL.

nitration of naphtalene goes reasonable to the third nitration I think. This I could achieve with less acids of less strength. While trinitronaphtalen is an explosive, it is not as powerful as tnt or TNN. I wonder why the recipy given above doesn't let the nitration go in four steps because this wastes way too much acids (99% fuming nitric for gossake

)

That is the procedure to designed to target and synthesize the isomer 1,3,6,8- of tetranitronaphthalene (TeNN) *NOT* trinitronaphthalene (TNN) you misguided silly fool, and if you think that you can come up with a better more efficaint way I’d like to see it.

You probably might want to actually try a procedure before you criticize it as well as read up on WTF you’re talking about.
:mad:

I am open to criticism and will accept *any* help or ideas from anyone, except for the copy and paste, skim through 2 pages on google, un-informed uneducated self proclaimed know it all newbie kewl types like yourself. If you wish to impress anyone here by acting like you know what you’re talking about you’re in for a lot of flaming because not only can we see right through you to the kewl within but we love to flame on kewls.

[Edited on 9-1-2005 by Joeychemist]

Cloner - 14-1-2005 at 04:35

I am not at all afraid to sink to *your* level, at least for the duration of this post.

Half of your post is flaming, and hence useless. Please refrain from this dribble in the future, at least when talking to me.

Anyway, the procedure of flashbangboom and posted here are questionable, since the implication is that the third and fourth nitration step are equal in status, which the are absolutely not. The fourth step requires definitely more nitrating power. I am not saying you didn't get that product, but the overkill you use to get it is not necessary. Check urbanski on the TNN issue and you will find one of the typical nitration triangles for naphtalene which will help you derive the necessary concentrations.

Now as for the product, I am pretty sure that the product you get using insufficient acid strength is trinitro and dinitro mixed together but perhaps I will throw a purified sample of trinitro in the NMR when I am there for legit purposes, to prove my point.

[Edited on 14-1-2005 by Cloner]

Joeychemist - 14-1-2005 at 04:56

My level, ha, laying down you still couldn’t bring yourself to my level.

Please go on? Or even better, you write out a synth.

, as I said before, If you can do better???

There are a lot of impurities that can affect this explosive and its performance that is why the final nitration uses large amounts of the purest of acids, among other reasons.

There is a thread around here about *TeNN*, I believe a different procedure is described; maybe this might appeal to you.

Quote:

Originally posted by ClonerWhile trinitronaphtalen is an explosive, it is not as powerful as tnt or TNN.

You better figure out the difference between TNN and TeNN too.

Of course I will be here when you're ready to continue this.

[Edited on 14-1-2005 by Joeychemist]

Cloner - 28-1-2005 at 09:06

Preliminary work starting out from the dinitro compound has been performed. The MRCOOL procedure was followed to obtain a mixture which was quenched in water. Recrystallisation from ethanol seemed wrong becuase of the large mass that did not dissolve. Later analysis showed that this mass would likely be trinitro compound. The dissolved compound came out after recristallisation from a deep red solution. The dissolved compound seems to be indeed TeNN, but the yield is rather small.

Thus, ethanol is the right recrystallization solvent however the base yield of this reaction was very poor due to a majority of byproduct.

A red coloration is present, I will evaporate the ethanol later. But after partial evaporation another crop of TeNN (or at least I hope so) was formed.

The next step will be analysis of each fraction from the ethanol, and subsequently nitration of the compound that I suspect to be TNN.

[Edited on 28-1-2005 by Cloner]

Glad you're atleast trying the synth out

Joeychemist - 28-1-2005 at 22:15

Cloner you might want to check out the chapter in urbanski (vol,1.) tilted Nitro derivatives of Naphthalene for more detailed info on the process of nitrating naphthalene.

Cloner - 30-1-2005 at 15:11

It makes one wonder how valid our findings are does it now?

In any case, I see these triangles and conclude they must be for temperatures other than the ones I used. Temperature must alter the position of the nitration limits.

For now, I conclude naphtalene is best used in dinitrated form mixed with oxidators as a cheapass (but effective and storage friendly) explosive.

tom haggen - 6-12-2005 at 21:37

Does anyone have the mechanism for this reaction? Also I would like to see a balanced equation for each step in the nitration. I would try and figure it out myself but I'm not quite sure on what side products are formed in the reaction. I was just trying to figure out if you could use nitric acid on the dinitronaphthalene step instead of KNO3.

Joeychemist - 6-12-2005 at 22:28

I could try to explain it you, Tom. But to save myself some time, you better just look in volume 1 of Urbanski (page 422), the answers to you questions are there.

70% nitric acid can be used for the mono and di nitrations of Naphthalene without injuriously affecting the final product and the first two nitro groups can be introduced to the Naphthalene molecule in one step, but the final steps do need stronger nitric acid!

PHILOU Zrealone - 8-12-2005 at 11:12

First of all to get mononitronaphtalene you don't need H2SO4.
Simply mix HNO3 (70% is fine) and naphtalene...then warm it slowly...
I have done this in the past when I had to get nitronaphtalene oils for chedite like explosives...
:cool:

You then get a yellow to orange oily solid...this is a mix of alfa en beta nitronaphtalene with unreacted naphtalene...

Note that the cold proces with HNO3 conc allows one to get one of the two forms and the warm proces allow to isolate the other as major product...
Alfa is simply the 1-nitronaphtalene and Beta the 2-nitronaphtalene...you thus have a simple way to isolate selectively the kinetic or the thermodynamic product by variation of the heat...
Sadly I don't remember clearly wich one is formed (and my books are in boxes)...following me it was the beta under warm conditions.

Secondly, appart TeNN, one can also use naphtalene...
1) as mono or dinitrocompound in cheddites explosives (mixes of nitroaromatics and potassium chlorates)...be carreful product must be acid free!!!!
2)naphtalene has the good idea to be quite resistant to oxydation due to its aromatic power...but this is lower than benzene...and solid with a low melting/sublimating point.
So one could mix it with oxydisers like NH4ClO4, NH4NO3, ... as plain naphtalen or nitrocompound.
3)As mentionned someone amine perchlorate is a good point!
The mononitrocompound can be easily reduced to amine (Fe/HCl or SnCl2/HCl or sulfure proces) and the later amine then reacted with HClO4.
4)From amino naftalene one can easily get naphtol and so activated naftalene will provide polynitronaphtols and polynitronaphtylamines.
5)Amines allows conversion to explosive naphtyldiazonium perchlorate...highly unstable!But also to hydrazino naftalene...the later provides easy way to azidonaphtalene...
6) etc etc etc..

Possibilities are thus nearly infinite as long as you know organic chemistry and especially the aromatic one...

Marvin - 9-12-2005 at 00:53

Tri and tertra nitronapthalenes wern't that stable chemically, I thought. Also lousey oxygen balence.

I think Philou is on the right track with cheddites, but he's holding out on us clearly. Mononitronapthalene, Sodium or Potassium chlorate and caster oil as a desensitiser is often called 'Explosive S'. Its very efficient for low availability of nitric acid. Depending on the mixing and amount of caster oil, its probably quite sensitive to initiation.

PHILOU Zrealone - 9-12-2005 at 09:24

How strange I dit quote my message and the quoting is away and stil I have checked and it was right

now it has disappeared

"...then warm it slowly..."
-I dit it until 80°C without troubles...no risk of runnaway with 70% HNO3!!!

Sadly I don't remember clearly wich one is formed (and my books are in boxes)...following me it was the beta under warm conditions.
-It was the beta under cold condition (0-20°C) and the alfa above 50
°C or so.

2)naphtalene has the good idea to be quite resistant to oxydation due to its aromatic power...but this is lower than benzene...and solid with a low melting/sublimating point.
-I don't know why I did write power instead of character...

6) etc etc etc..
:cool:

-Mix of naphtalene or nitronaphtalene (or naphtol, naphtylamine perchlorate/nitrate)... with:
a)liquid N2O4 (panclastite like explosives)
b)concentrated HNO3
c)Last but not least...with C(NO2)4 TeNM...

All those a),b) and c) are shock and heat sensitive mixes...note that they do perform very good explosives outputs ... especially the last one...two solids with low melting points....that can be molten to achieve a perfect molecular mix of a high density oxydiser and a high energy unoxydised fuel...

C10H8 + 2C(NO2)4 --> 12 CO + 4 H2O + 4 N2
This mix will thus have a comparable power to a chimeric hexanitro dimethylnitro naphtalene C10(NO2)6(CH2NO2)2 ...but with the heat of reaction ready to contribute to the explosion heat...

C10H8 + 4C(NO2)4 --> 14 CO2 + 4 H2O + 8 N2
This mix will thus have a higher energy output...

Both can achieve without troubles the 8.5 km/s VOD
It is listed in a few books that benzene/TeNM can reach the 9.5 km/s VOD ...

This time reply is right

Cheddites, yeah great stuf...I have made a bunch of it when I was 17 years old...My mother was disgusted by the smel of nitronaphtalenes reactions running into my room under a heat lamp...
I was crazy about the smel...but I haven't abused of it ... no no no

I made the trials with toluene too...but naphtalene is really something appart...because it was half solid and waxy

kazaa81 - 10-11-2008 at 10:41

Ozonation of Naphthalene with Water as Participating Solvent

http://article.pubs.nrc-cnrc.gc.ca/ppv/RPViewDoc?issn=1480-3...

Taoiseach - 11-11-2008 at 00:03

@Axt

The Naphthalene diozonide looks interesting.
Have you tried making potassium ozonide? I have some papers claiming there is a modification/ crystal structure that is actually stable. Another modification is said to be dangerously unstable and decompose quickly. The water content in KOH used could play a role in the formation of these two species.

Ozonides could be an exciting field of exploration because little is known about them, and ozone should be easy to make in a home lab using an old microwave ofen transformer (MOT).

Paddywhacker - 26-3-2009 at 02:22

Yes, it looks interesting. Maybe an easy way to get the di-aldehyde of phthalic acid.

But a lookup of ozonolysis suggests that it would have to be done at an unreasonably low temperature.
See http://www.ozonolysis.com/ozonolysis/web.nsf/wp/Attachment%2...

edit: oops. I looked at Axt's reference and it seems I spoke too soon. The experimenters weren't able to get the di-aldehyde.

[Edited on 26-3-2009 by Paddywhacker]

grndpndr - 9-6-2009 at 21:02

Melt/ cast picric acid-mononitronapthalene.Called Trimonite
likely about the time our great great grandfathers migh have been Miners.Still listed in the VOD MPS lists.7048 MPS 1.6gr cc3.Might be some info in Davis or Urbanski.The only brief reference Ive seen i believe dated from the late 19th century.Although i believe its mentioned in Urbanski vol 3?.
PA/DNN?

[Edited on 10-6-2009 by grndpndr]

[Edited on 10-6-2009 by grndpndr]