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Author: Subject: TeNN (tetra-nitronaphtalene)
Madog
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[*] posted on 21-9-2002 at 13:14
TeNN (tetra-nitronaphtalene)


hey. recently the explosive TeNN was brought to my attention and i made calculations for the nitration of napthelene to MNN then TeNN via H2SO4 and NaNO3. here are the amounts

the amount of H2SO4 was just kinda guessed

MNN
12.8g napthelene
8.5g NaNO3
15ml H2SO4
theoroetical yield = 17.3g

TeNN
17.3g MNN
25.5g NaNO3
40ml H2SO4
theoretical yield = 30.8g

today i added 17g of NaNO3 to 20ml of H2SO4 and then added 25.6g of napthelene. then i let it nitrate for just over an hour, drownded it, washed, then added the dark, brownish product to 30g of KNO3 and 40ml of H2SO4

(yes, i made an idiotic mistake, i used the amount of nitrateing mix for 17.3g MNN, i probaly had around 20g anyways, and i didnt have any more crushed NaNO3 so i used KNO3 with a little extra to compinsate.)

i cant believe i made such a dumb mistake. but anyways, i let it start to nitrate,and realised my mistake then whent down and added more KNO3, which caused it to run away(ugh, should have used an ice bath, i realy wasnt thinking today) i promptly drownded it with water and added the contents to a 1000ml beaker full of water. then i noticed something weird, the product was liquid!! so i grabbed a pipet and extracted it and put it in a test tube.

the liquid has a density of ~1.2g/ml, then density of napthelene is 1.16g/ml, the density of TeNN is something like 1.6g/ml

my theory is htat it is the trinitrate and that the NO2 grounps made the molecule polar causeing it to become liquid, but of course im probaly wrong. anybody have a clue what it is?

[Edited on 14-12-2005 by chemoleo]




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[*] posted on 22-9-2002 at 03:37


Probably dinitronaphtalene, because trinitronaphtalene seems to unsymmetric and would be polar.



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[*] posted on 22-9-2002 at 04:45
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The naphthalene system is highly aromatic, and all electrons are delocalized. The ring is not going to become polar by addition of a couple EWGs.

With each further nitration, the molecule becomes harder to nitrate, because the electronegativity of the ring system decreases, and is less attracted to the nitronium attacking species.

Plus, since the substitution pattern is highly meta, the ring crowds faster, making steric hindrance a threat after di- and trinitration.

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[*] posted on 22-9-2002 at 08:02


If it's a liquid, it's not a nitronapthalene! Also, if you did make napthalene more polar then it would not be liquid - polar molecules would be attracted to each other more strongly, so it would be solid with a higher melting/boiling point than napthalene.

You probably oxidised it to something during the little runaway that you had, IIRC phthalic anhydride is made by oxidising napthalene, I don't know what it's physical state is though.

Start slow, and add nitro groups gradually! When you have the di-/tri- nitro, then you can get it hot to add the last one or two (80*C+), but I think mono- might be too fragile to survive these conditions for long.
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[*] posted on 22-9-2002 at 17:08


i knew i musta been way off.

but this is strange now, it gradualy solidified! but it wasnt hot when i had it liquid, and it waqs liquid for a while. i dont know what could have happend.

i will try melting it and stuff later, when i get a chance, i am gona be busy this week as usual

i think i will try to nitrate the product further or try the whole thing over again.




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[*] posted on 23-9-2002 at 00:34


This is typical of mono-nitro naphthalene. It has a melting point of around 50-55 C, but either a lot of impurities are introduced when nitrating naphthalene at home, or else the compound simply has a great capacity for under-cooling. You will see that the same happens if you dissolve it in acetone and then drown it in water.
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[*] posted on 23-9-2002 at 13:41


ok, thanks, i might just make cheddites from this.

i measured the density to be 1.2g/cc but i expect it to be off by at least .1g

i realy couldnt think straight that day.




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[*] posted on 23-9-2002 at 13:51


sorry, i meant 0.01g



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[*] posted on 3-1-2003 at 14:43


today i took the product from the last time i tried this and nitrated it with 60 grams of NaNO3 and 80ml of H2SO4, it was heated and nitrated all day with a coffee pot hotplate. the product is lighter in color and in small pieces, not chunks. doesn anyone think this is TeNN? or TNN? ill weigh it when it drys



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[*] posted on 4-1-2003 at 09:43


weight is 50 grams, it is light brownish yellowish, kinda burns



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[*] posted on 4-1-2003 at 09:58


Try to detonate some. If you press a few grams into a 1cm pipe with a gram of PETN on top, it would definitely detonate if it's TeNN.
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[*] posted on 13-12-2005 at 11:42


Sorry to dig up an old thread, but I've been trying to work out the correct numbers for MNN using H2SO4 and NH4NO3. I've made MNN before but I know the numbers I used were off.

I assume that
12.8g napthelene
8.5g NaNO3
15ml H2SO4
was used for the purpose of creating .1 molesof nitric acid to nitrate .1 mole of naphthalene.

From what I understand, excess nitric is preferred when nitrating. Using ~35% excess nitric, the numbers I have worked out are 8g naphthalene, 8g NH4NO3, and about 20ml H2SO4.

Does that seem correct or am I missing something? Thank you in advance.
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smile.gif posted on 13-12-2005 at 12:27


1°)Under liquid form density is lower than under solid form.
A few exceptions exist but most of the time solid of a compound fall to the bottom of the liquid phase of that compound (except for water and for a low melting metal I dont recal and...)...Icebergs doesnt always floats :)!
Benzen icebergs doesn't float on benzene...

2°)Impure compound have lower mp than pure compound...and so a mix of naphtalene, dinitronaphtalenes and trinitronaphtalenes will be oily-liquid.

3°)Such impure mixes tends to get eutectic effect and so cristallisation is not easy ..."surfusion" effect (french) Maybe "overfusion" in english?
Temperature must be wel under the mp temp to allow a cristal germination.




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[*] posted on 29-1-2006 at 12:21


Sorry to post the same thing again in the thread, but just wondering if anyone could take a look at my numbers. Thank you.
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