Sciencemadness Discussion Board

Xylitol Pentanitrate (question)?

Rich_Insane - 6-6-2009 at 13:31

Has anyone had experience with Xylitol instead of Erythritol or Pentaerythritol? I did a quick search, and couldn't find anything. Where I live, xylitol is a popular replacement for sugar, and is more accessible than Erythritol.

Apparently Xylitol Pentanitrate is a highly viscous liquid energetic, so it wouldn't hurt to use the same nitration process used when preparing ETN.

This thread has a good preparation of MHN (Mannitol Hexanitrate), which I'd think to be similar, and a failed XPN synthesis: http://www.roguesci.org/theforum/showthread.php?t=4437

Perhaps an ETN-style nitration would work, or an NG one (which is posted lower). Basically I'd say it's the same synth as ETN.

[Edited on 6-6-2009 by Rich_Insane]

hissingnoise - 6-6-2009 at 13:52

I'm in Europe and got my erythritol from a US company whose name I forget.
It could be Nutrasweet!
I got mannitol on ebay from a UK seller and I'm not a UK resident. . .
Viscous energetics are maddeningly awkward to handle especially when they're sticky!


[Edited on 7-6-2009 by hissingnoise]

Rich_Insane - 6-6-2009 at 21:06

I can imagine :)

But wouldn't they be a little easier to plasticize?

For me, I may not have searched hard enough, but most health stores (one close to me) sell Xylitol in 5 lb sacks, which is good.

User - 7-6-2009 at 01:10

If iam not mistaking xylitol penta nitrate is a crystalline solid, but only if it is pure enough.
The trouble with these things is that they are not easy to fully nitrate so a sticky mixture is found.So crystallisation is an absolute must.
I believe this is the reason for bad MHN yields only the lower nitrates remain in solution.

Besides this stuff makes runaway like dropping acetone in NA/SA.
Just like a sucrose and friends.

hissingnoise - 7-6-2009 at 04:23

Nutrasweet sell erythritol in 5lb bags---the coarse crystals need to be powdered before nitration. . .

Rich_Insane - 7-6-2009 at 09:36

Hm. I will give a 10 g - 20 g a try sometime using the same Synth as used with ETN.

Unfortunately I don't have a ball mill, and cannot afford one, so I will either grind the crystals with a coffee grinder or with a mortar and pestle.

MWRAY236466 - 12-6-2009 at 09:40

Im from florida, does anybody know where can I get some Xylitol, Erythritol or Mannitol???

No info on web about Xylitol pentanitrate.... But has a good OB!

Did somebody try to get MHN by nitration of mannose??

hissingnoise - 12-6-2009 at 10:11

This is from COPAE, mannitol is prepared by reduction of mannose; nitration of mannose gives mannose pentanitrate, a compound with good OB but poor stability.
It melts at 81*C and it decomposes rapidly at temperatures as low as 50*C. . .


[Edited on 12-6-2009 by hissingnoise]

Rich_Insane - 13-6-2009 at 17:25

Yea, I was worried about preparing this kind of explosive, because I've heard that the stability is poor. I was looking into more liquid explosives, especially very viscous ones that I can plasticize fairly easily.

Unfortunately I cannot do an ETN style nitration just yet, since I have yet to wait for my equipment and chemicals to arrive.

The link I posted had a good synthesis of MHN, however the XPN synthesis there ended up as a failure.

MWRAY236466 - 17-6-2009 at 06:11

I think XPN is s very good HE.... But i didnt hear about someone that finished the nitration. A man posted a video about "XPN" but it was crystals. XPN is a liquid exp.

Rich_Insane - 20-6-2009 at 14:29

Apparently there's been a lot of failure when it comes to XPN. I will give it a shot once my supplies arrive. Make sure it stays ultra-cool though.

LabRatNW - 22-10-2009 at 21:48

If MHN is indeed a viscous liquid, could you mix it readily with something like ETN for a pliable clay? The ETN should be easily soluble in MHN. Not to mention the properties of said solution. Could you safely mix together (by hand, like sugar and shortening) the two components without risking detonation?

hissingnoise - 23-10-2009 at 03:24

MHN, mannitol hexanitrate is a solid explosive m.p. >100*c!
Its stability is less than that of ETN and both are more easily detonated than PETN.

User - 23-10-2009 at 03:41

Still i wouldnt really be scared of unplanned detonation.
Do watch out for the nitro headaches you could get by absorption through the skin, they could be very severe if one would kneed such a mass.
MHN is a fluffy crystal (without recrystalization).
SHN is somewhat liquid as well as the sucrose/fructose etc.
Liquid is not really the right word, its more like a sticky mess :)

[Edited on 23-10-2009 by User]

hissingnoise - 23-10-2009 at 04:40

Quote: Originally posted by User  
Still i wouldnt really be scared of unplanned detonation.

Wtf---if you're being serious, you're an idiot!

LabRatNW - 23-10-2009 at 12:37

Basically what I was trying to get at, is if I can use a binder that's also HE, then the detonation would be that much more powerful.

If ETN and MHN are crystalline, I wouldn't expect XPN (the 5-carbon analog) to be either. I may play around with energies in chem 3d to get a better idea.

[Edited on 10-23-2009 by LabRatNW]

User - 23-10-2009 at 17:56

Yes well what i meant was that it isnt going to explode just by looking at it.
Although it is considered a sensitive substance one still needs a firm hammer blow to actually set it off.
I dont believe that by simply kneading it anything will happen.
From experience i can say that it just isnt That sensitive.
Still it is powerful and needs to be treated with respect.
Clear?

XPN is a sort of liquid sticky mass which evaporates quite quickly.


[Edited on 24-10-2009 by User]

hissingnoise - 24-10-2009 at 03:30

Thanks for clearing that up!
It did appear that you were more concerned by a nitrohead than the possible loss of digits, limbs or organs.

Rich_Insane - 26-10-2009 at 15:17

I know this has been mentioned here, but what are some good places to get xylitol, mannitol, or erythritol for very low prices (like $4/lb). I want to make a small batch of ETN first (I'm a newb to nitrate esters).

hissingnoise - 27-10-2009 at 06:17

Short reply---ebay

[Edited on 27-10-2009 by hissingnoise]

hissingnoise - 28-10-2009 at 08:49

Quote: Originally posted by Rich_Insane  
I want to make a small batch of ETN first (I'm a newb to nitrate esters).

Your first batch should really be very small, <1gm and noting its behaviour will give you some confidence but bear in mind that you're dealing with a solid form of nitro, more or less. . .

LabRatNW - 28-10-2009 at 15:59

I'm actually a fairly experienced chemist, I was planning on my 1st batch being about 5g. Energetic materials are a whole new game for me, so I gotta be super careful. Any recommendations for solvents?

User - 29-10-2009 at 03:38

All these sugar nitrate esters are can be dissolved in (warm) acetone.
It is wise to neutralize while in solution to prevent acid remains to be get trapped withing the crystals.
By adding water and cooling one can recrystallize the product.
Look up the table for PETN solute ability acetone/water/temp in urbanski , I found that at least some of his brothers act in a similar way (sorbitol/mannitol/sucrose).

quicksilver - 4-11-2009 at 13:49

*** Xylitol is a lot like mannitol in that one needs very high quality white - HNO3, 1.50 or better, then use the H2SO4 drop by drop technique that MHN methods employ - and you should have no problems.

Frankly, Erythritol is getting to be sold quite a bit now through a great deal of standard commercial outlets in the US & EU. Start reading brand labels and you'll see! I can think of one of the top of my head in the US called "TRUVIA" that's Erythritol and sold right near where the "Splenda" is sold.

Mannitol is tough to find on occasion & so is Sorbitol but eurythritol is a darn good sugar substitute & is being used more and more xyitol is pretty good but doesn't dissolve in tea or coffee as fast and for cooking in a batter is really tough to get an even sweetness.

hissingnoise - 4-11-2009 at 15:32

All three compounds can be be nitrated in good yield using a mixed acid as is used for glycerol; obviously dissolved NO2 poses some risk of runaway so low temps and slow addition of the finely-ground crystals is recommended. . .
Conc. HNO3 with a slight excess volume of 98% H2SO4, cooled to ~5*C bypasses the need for strong white HNO3.
In each case a large volume of ice-water should be used in drowning!
For efficient mixing of the thickening mixture, a teflon spatula of some sort is a good idea.

[Edited on 4-11-2009 by hissingnoise]

quicksilver - 7-11-2009 at 15:43

PATENTS:
us1850225 Inositol hexanitrate
us1951595 initiation application / related material for Inositol hexanitrate

us2204059 recrystallization methodology; excellent long term storage & pre-neutralize crystal formation info

us2370437 urea used for favorable equilibrium shift (solid alcohol nitration) - works great for tough ones like sorbital that alters into liquid state during nitration, etc.

Older patents will often have less "manufacturing secrets" than material from the 1950's +

hissingnoise - 8-11-2009 at 06:06

Those compounds seem of little interest to the HE hobbyist; the positive OB makes the first more oxidiser that useful HE and sorbitol hexanitrate, though somewhat less oxygen-rich is MHN in a difficult liquid form. . .

LabRatNW - 9-11-2009 at 19:58

"Slight excess volume" sounds like you need more that one equivalent. Try "catalytic amount." Usually a fraction of a percent. I've found that the acidic (HNO3) nitration of sucrose runs away with as little as 2% equivalent H2SO4. I fogged out a lab with NO2 trying to make nitrosucrose, so I know first hand. I'd start with about 1% equivalent and work up or down from there.

Work out a reaction diagram and calculate your theoretical conversions from reactants to products. If you want ALL of your alcohols to nitrate, then you'll need (in the case of XPN) 5 molar units of nitrate to 1 unit of xylitol. If your calculations come out correctly, for every 1g xylitol, you'll need about 3.32g potassium nitrate and 6.2mg of 96% sulfuric. Keep the reaction in an ice bath as a minimum, and use as little water as possible. (50 ml?)

As for MHN and SHN being more or less oxygen rich than one another? Not a chance. The only difference between sorbitol and mannitol is their absolute configurations, or the way their chiral centers are oriented. As far as quantitative conversion of the alcohol to the nitrate, they are identical, as their molecular formulas are identical. They're just enantiomers of one another.

[Edited on 11-10-2009 by LabRatNW]

hinz - 10-11-2009 at 13:31

Quote:
"Slight excess volume" sounds like you need more that one equivalent. Try "catalytic amount." Usually a fraction of a percent. I've found that the acidic (HNO3) nitration of sucrose runs away with as little as 2% equivalent H2SO4. I fogged out a lab with NO2 trying to make nitrosucrose, so I know first hand. I'd start with about 1% equivalent and work up or down from there.


Forget the idea of making nitric esters of aldehydes (sucrose is a aldehyde) as a beginner. They will oxidize. Ever done the the silver mirror experiment?

The H2SO4 is only one reason for it, as it dehydrates the sugar. The big problem is the trace amount of NO2 in your nitric acid. And as soon as something is oxidized, more NO2 is produced =>runaway.
And aldehydes are easily oxidized as said before.

[Edited on 10-11-2009 by hinz]

hissingnoise - 11-11-2009 at 02:50

Quote: Originally posted by hinz  

Forget the idea of making nitric esters of aldehydes (sucrose is a aldehyde) as a beginner. They will oxidize.

The aldehyde group in sucrose doesn't interfere with nitration by mixed acid provided the temp. is low enough, i.e. ~ 0*C. . .

Question about nitrating poly-alcohols

LabRatNW - 23-11-2009 at 21:05

Does KNO3 work okay? I know most people recommend NH4NO3, but I already have the potassium salt.

User - 24-11-2009 at 03:20

Does KNO3 work for what?
(be more clear in your questions)

This nitration takes something a little more than just SA/XNO3.
These mixtures tend to get very thick thus having a very bad heat transfer, and a sugar so easy oxidized/attacked does not like that.
A runaway is prone to happen if you use KNO3.
NH4NO3/SA is more stir able but still has this issue.


Something that could work is adding DCM to the mixture to make it thinner.

Nitrating a poly alcohol.

LabRatNW - 25-11-2009 at 17:29

I was going to use a sugar-alcohol (similar to Xylitol, maybe? Did you miss the label of the thread?) with H2SO4 and KNO3. All I needed to know is if it will work in place of NH4NO3, I don't see any reason it shouldn't... but if someone that has HE synth experience has had issues with it, I'd like to know.

quicksilver - 1-12-2009 at 13:15

Issues noticed from experimentation:

1.) Mixed solution of H2SO4 and solid nitrate until clear, then refrigerate until at least 10C. Mix the solid nitrate extremely well! DO NOT have materiel floating in solution. One of the stumbling blocks is that often the KNO3 is impure and foreign matter becomes problematic when such a "Big Bertha" activity like a nitration is the objective. If the material is prilled, crush till extremely fine then mix w/ H2SO4 at a slow rate. The result should be a clear solution. This should be maintained at 10-15C.

2.) Most often the addition speed of the material to be nitrated is the contributor to success or a run-a-way. If you need to - use a time keeping mechanism to make sure the addition is not too fast NOR is it too much in weight/quantity. Materials such as these (sugar alcohols) MUST be kept moving with in the cold solution and the addition should be sub-gram level. Suggestion would be the larger stir-bar in oval shape as that will continue to stir when the solution becomes thickened. If that is unavailable, use standard stir-bar at higher speed but be VERY careful to never have nongranular or "lumpy" material. Use old coffee grinder if need be (on both nitrate and material to BE nitrated).

Note that USP grade KNO3 goes into solution quickly and without trace. Test KNO3 and see if coating of clay, etc is seen in nitrate/water solution. If foreign mater exists, clean it out or use another source of nitrate (same for any solid nitrate obviously)

3.) Less NaNO3 is needed than KNO3 & less KNO3 than NH4NO3 to achieve the similar level of mixed acid solution.

AfricanPyro - 30-3-2011 at 04:58

So has anyone successfully synthesized Xylitol Pentanitrate with Xylitol and the same ETN synthesis procedure?

quicksilver - 30-3-2011 at 09:47

There would generally be minute differences in nitration of previously solid polyols. Elements may exist as time of exposure, mixed or direct HNO3 exposure, temperatures, etc. Some maintain solidity while others reach a viscous syrup-like consistency at a certain level of nitration. Check Federoff (PATR): I believe there are specifics therein regarding Xylitol & it's idiosyncrasies.