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Author: Subject: nitroglycerin
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[*] posted on 1-5-2010 at 09:58


I know about the harmless runaways: nitrogen oxides, heat, no detonation. That's when it goes "good".

In the small scale, the violent runaway probably depends on how much nitro has already accumulated. At the start of nitration or dumping all the glycerin in at once might not allow the nitro to form, or decompose as or before it has even formed, alongside a vigorous oxidation of the glycerin.

Notice the example, from the poster I gave, it was towards the end where there was a runaway, so that means it was actually about 10ml which had formed, and detonated. Whereas your friend dumped all the glycerin in at once. That's not to say this will happen predictably, just my thoughts on the differences.

For: HNO3 + 2 H2SO4 = NO2+ + H3O+ + 2 HSO4-

Water is disadvantageous because of the protonation it causes (NO2+ and H2O form HNO3), and for which the sulfuric acid compensates. Sulfuric acid protonates the HNO3 which is what forms the NO2+. In pure nitric acid there is little NO2+, which is why it's combined with H2SO4. The hydronium sulfate is no good for the conversion to NO2+. With more water and more sulfuric acid, there will be less nitronium.

[Edited on 1-5-2010 by Formatik]
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[*] posted on 25-10-2010 at 11:56


Is it feasible to use a solvent such as DCM or petroleum ether during the synthesis of NG, to dilute it to inertness during the later stages of the reaction and the workup?
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[*] posted on 28-10-2010 at 07:30


Thats a good question. Could you been more specific though? At what point would you dilute it? After it has formed on top of the nitrating mixture?

I know that NG can be transported more safely by diluting it with Acetone to a point where it is extremely hard to detonate, which I think starts somewhere around 70% NG to 30% acetone. I've never thought about trying it during a synthesis though. Sounds like a fun project.

Maybe you could add the acetone or whatever solvent with the NG to dilute before extracting it from the nitrating mixture with your separatory funnel. It could then be washed, neutralized and evaporated for a nice clean product. Being diluted and therefore less sensitive, it could make the synthesis and handling much safer. Any thoughts?





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[*] posted on 28-10-2010 at 13:27


Supposedly, DCM is a very good medium for aromatics nitration. I read somewhere that toluene was quantitatively nitrated to TNT by adding anhydrous nitric acid to a solution of it in DCM at 0 C. I haven't tried it myself though.
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[*] posted on 28-10-2010 at 13:35


Quote: Originally posted by rbick  

I know that NG can be transported more safely by diluting it with Acetone to a point where it is extremely hard to detonate, which I think starts somewhere around 70% NG to 30% acetone. I've never thought about trying it during a synthesis though. Sounds like a fun project.



"BEFORE INVENTING his Dynamite in 1863, Alfred B. Nobel (1833-1896)
proposed a rather safe method of transporting liquid NG. He mixed it
with 15-20 parts of anhydrous methyl alcohol and transported the
resulting nonexplosive mixture in tanks to places of work. There the
NG was precipitated by adding water and the supernatant dilute
methanol removed by decantation. As this method was time-consuming
and rather wasteful (because it did not pay to recover methanol), it
was seldom used in the USA. Here, where everything is done in a hurry
and as cheaply as possible, it was preferred to transport NG in
liquid form, although it was more dangerous. Many accidents occurred
and many lives were lost in connection with NG and as long as most of
the workman were foreigners especially Chinese, the industrialists,
who care only for profits, did not introduce any safety regulations
until they were forced by the Government after establishing in 1910
the Bureau of Mines at Pittsburgh , Pennsylvania."

PATR 2700 me thinks.
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[*] posted on 29-10-2010 at 05:53


Surely, it must be possible to initiate a 15:85 mix of methanol and NG with a suitable detonator (I realize that the technology of detonators weren't very advanced at the time).
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[*] posted on 29-10-2010 at 07:09


Quote: Originally posted by Microtek  
Surely, it must be possible to initiate a 15:85 mix of methanol and NG with a suitable detonator (I realize that the technology of detonators weren't very advanced at the time).



Nobel added methanol to prevent an accidental an explosions.

It wouldn't have been used mixed as an explosive... that would
have required larger bore holes to correct for the expanded
volume. Assuming it could have be detonated, which was
accomplished in the early days by flame only. Black powder
mixed with NG was also used.

Hudson Maxim
Dynamite Stories 1916
(A reprise can be had from www.fireworksnews.com )

HOISTED WITH HIS OWN PETARD
LIQUID nitroglycerin is still used to torpedo the oil-wells when they get old, in order to
give them a new lease on life.

There was one teamster in the old days who had become notorious as a hauler of the
dangerous explosive. The law does not permit the shipment of the liquid by freight or by
express, and for that reason this teamster had plenty to do in hauling nitroglycerin for long
distances. He was a great smoker and his old pipe was always alight, though he might be
riding on a ton of nitroglycerin with a few kegs of black gunpowder clinked into the load.

One day he was carrying, on runners, about two tons of nitroglycerin and a few odd
kegs of gunpowder, when something happened. There had been a fall of several inches of
light snow the evening before, and the scene of the eventuation was an open field which
he was crossing.

There was an enormous crater in the ground; the light snow around the crater was
besprinkled with a few shreds of horse and harness and a sliver or two of sled, but not a
trace of the driver was ever found.

Vist :—

Tallini Tales of Destruction www.logwell.com
..an amazing collection of historical stories involving nitroglycerin use in the oilfields.

For historical info on the early use of NG in the oil fields
consult the every suspenseful/interesting

VAn Gelder & Schlatter
History of the Explosives Industry in America
IME 1927
1132 well indexed pages.

I own a 1972 Arno Press reprint.
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[*] posted on 29-10-2010 at 07:16


Microtek,

I bet it is too. If I'm not mistaken they were using compressed black powder to initiate dynamite until later in the 1800s?

Although I've never read about using Methanol, I know that a 70% NG/30% Acetone can be detonated although a booster must be used. I'm assuming it would be similar with Methanol since NG is listed as miscible with both Methanol, Acetone, and other organic solvents on the MSDS.

I read either a patent or an article (can't remember which if it was an actual patent or not) discussing the use of Acetone to dilute NG for safety reasons but the link and information was lost along with Rogue Sci :(. If anyone has the link, I'd like to see it!

EDIT: The Wizard and I posted at the same time. Looks like he found the info for the use of Methanol. Nice... :cool:

[Edited on 29-10-2010 by rbick]




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[*] posted on 29-10-2010 at 07:58


Quote: Originally posted by rbick  

EDIT: The Wizard and I posted at the same time. Looks like he found the info for the use of Methanol. Nice... :cool:



Actually I found it years ago ...

Newsgroups: rec.pyrotechnics
From: "donald j haarmann" <haa...@mail.idt.net>
Date: 1997/06/01
Subject: Re: expendable labor!

"Before inventing his Dynamite in 1863, Alfred B. Nobel (1833-1896)
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[*] posted on 29-10-2010 at 08:09


Quote: Originally posted by rbick  
Microtek,

I bet it is too. If I'm not mistaken they were using compressed black powder to initiate dynamite until later in the 1800s?



Eric Twitty in his book "Blown to Bits in the Mine: A History of Mining &
Explosvies in the United States, dates usage of RR powder [which version?]
from 1876 to 1930.

A curious version was made by the Giant Powder Company. Twitty cites
US Patent 183,764 of 1876 for the following:-

"Egbert Judson, on the of Giant Powder Company's visionary founding fathers,
duly noted the performance of the mixture of a small volume of nitroglycerine
absorbed in blasting powder, and its possible applications. In 1876 he patented
"Judson Powder", which consisted of a modified blasting powder thinly coated
nitroglycerine. The difference between Judson's product and earlier NG-coated
blasting powder formulas lay in the manufacturing process. Judson melted
the sulfur, added the other powder ingredients to the melt, cooled it, crushed it,
and classified the grains. Melting the ingredients made their surfaces glassy,
decreasing porosity and facilitating an even coat of nitroglycerine. In the making
of true blasting powder, there was no melting of ingredients. Judson's formula
required the grains be coated with 5%, 10%, or 15% nitroglycerine by weight."
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[*] posted on 8-1-2011 at 05:19


I'm aware of the safer alternatives of NG (namely, EGDN/PGDN) but at one point or another, I want to synthesis some nitroglycerin. I simply deflagrate the secondaries I produce, so I'm not after making a large quantity at all. It's more just the experience and notoriety of synthesizing a little NG, so I can add a little first hand experience onto the knowledge I have accumulated from reading about it.

I began to think, nitrating 1ml of glycerin may pose more threat than a larger quantity. Not the consequences obviously, but an increased risk of an accident occuring. It would mean if I manually stirred it, there would probably be an increased chance of stirring rod to side of beaker contact. While I am definitely more inclined to use an aquarium pump, with these quantities it may prove to be a little annoying to do so. It also makes the whole experiment in colloquial language, "more fiddly".

It then brings me to, what glassware would be most suitable? Small beakers that could occupy such a small mix well aren't really abundant in a lab that usually does larger synthesis. I'm not keen to use a 25 x 150mm test tube, either. I gladly will go out and buy smaller beakers and other equipment to do the synthesis safely as I much rather pay with money than with eye loss or digit loss.

I've got my opinion in mind, but another from someone with a more practical knowledge couldn't hurt. I already know if I were to nitrate 20ml of glycerin, I would just use a suitable beaker, an aquarium pump to blow air over to create a whirlpool effect and all the other necessary precautions outlined in this thread and in literature. But for an amount where I only want to use 1ml? Would it just be an easier and safer process increasing it to 3, 4 or 5ml, just to make the whole procedure less of a nuisance?
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[*] posted on 8-1-2011 at 05:41


I use a thermometer as stirring rod and I flinch at every glass-on-glass clink!
Going at it as if you're beating eggs in a bowl is not the way to go.
Gentle (and I mean gentle) stirring shouldn't throw up "surprises" . . .

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[*] posted on 8-1-2011 at 10:18


Can anyone please post a link to the nitroglycerin producing method that was mentioned in the first post?
I can't manage to find it via the search option...
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[*] posted on 8-1-2011 at 11:58


Quote: Originally posted by The WiZard is In  

Eric Twitty in his book "Blown to Bits in the Mine: A History of Mining & Explosvies in the United States, dates usage of RR powder [which version?] from 1876 to 1930.



Snelling and Storm
Bureau of Mines Bulletin 51
The Analysis of Black Powder and Dynamite
1913

GRANULATED NITROGLYCERIN POWDER.

When ordinary dynamite is used in blasting any material of a
consistency resembling that of earth or clay, little of the energy of
the explosive does useful work, because the soft and compressible
nature of the material blasted allows the greater part of the
energy of the explosive to be used in compacting the material and
in producing a cavity. Consequently, gunpowder has been largely
used in all places where earth, clay, or other soft material was to
be dislodged. In the blasting of the banks of railroad cuts there are
often places where a soft, but somewhat consolidated material,
intermediate between earth and hard rock, has to be blasted. Such
a material might be a soft shale, for example, or a friable and
easily crumbled sandstone, and for dislodging it neither ordinary
blasting powder nor ordinary dynamite is particularly suitable. In
the year 1876 E. Judson patented an explosive consisting of a low-
grade gunpowder made by heating and mixing together coal,
sulphur, sodium nitrate, etc., granulating the mixture, and then
coating this nonabsorbent granulated dope with a small amount of
nitroglycerin. The proportion of nitroglycerin used—often as little
as 5 per cent— was such that had it been absorbed by the grains
of explosive it would not have been capable of detonation, but by
remaining wholly or largely upon the surface of the grains the use
of a detonator brought about its explosion and the simultaneous
ignition of the gunpowder base which it covered. Such an
explosive, as a result of the detonation of the nitroglycerin,
produces an initial blow sufficient to crack and fissure the partly
consolidated material in which it is placed. The action of the
gunpowder mixture that forms the larger part of the explosive so
heaves and moves the broken-up mass as to make easy its
removal with steam shovels.

Granulated nitroglycerin powders, or "free-running" explosives,
have been very much used in the excavation of earth and are
commonly known as Judson powder (after the inventor), bank
powder, or railroad powder. In the analysis of low-grade granular
powder, moisture is determined by the standard method, and the
usual method of extracting with ether is followed. In the ether
extract are usually found large proportions of sulphur, rosin, etc.,
besides the nitroglycerin. The proportion of sulphur commonly used
in low-grade granular powder is so considerable that usually it is
not all removed by extraction with ether.

Explosive-DuPont-RR.jpg - 351kB Explosive-Judson-Powder-V&S-338.jpg - 441kB Explosive-Judson-Powder-V&S-681.jpg - 448kB

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DuPont is from the 1928 Edition of DuPont's Blasters Handbook,
the oldest edition I own. It is also in the 1934 ed. Not in the
1942 and following editions.

V&S is Vangelder and Schatler, History of the Explosives Industry
in America. IME 1927.


V&S

"[Egbert Putman] Judson [b. 9 August 1812 patented Giant Powder
No. 2* in 1873] was a self-made man who had no use for
theorists, among whom he classed all chemists. Although he was
the proprietor of the largest chemical or acid works in San
Francisco, he never employed one of these creatures. Since the
first Judson powder was rather sticky and would not run readily
down bore holes, he conceived the idea of drying the grains or
"driving the nitroglycerine into the grains" by heating them to
about 200o F. He built a jacketed iron pan, about 5 by 12 feet in
size which held about a ton of powder and was heated by steam to
the desired temperature. The powder was then shovelled into the
pan with wooden scoops and stirred by a white man with a
wooden rake until the grains appeared dry. Next it was shovelled
out on the floor to cool. Several charges had been made when the
workman who was doing the work was taken sick with a headache,
caused, so he said, by the red fumes coming from the powder. As
he was alone, Judson having just gone, be went to tell Judson and
get some fresh air. This saved his life. He had not gone two
hundred feet when there was a flash. All that remained of the
building was the iron pan."

* 40pts NG , 40 sodium nitrate, 6 rosin, 6 sulphur 8 kieselguhr.

As one wag noted some years ago when I posted this in
Sci.Chem... A chemist would have blow up the iron pan.

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[*] posted on 12-1-2011 at 05:47
NG neutralization


I have noticed NG can be difficult to properly neutralize.

Two times have I put NG under a NaHCO3 solution (once for 12 h, and once for more than 24 h, I have posted about the first attempt in this thread some time ago). After the time has elapsed I tested both the solution over NG, and the NG itself with litmus paper. The solution was basic but the NG was still acidic. Both times was the NG periodically swirled under the solution (not too much but quite a bit).

The second time I tried, after 12 h of staying under the NaHCO3 solution, I removed most of the solution, and added cca. 60 ml of acetone to the cca. 17-18 ml of NG and a small amount of the solution that remained over the NG (cca. 10 ml). The acetone and NG mixed and formed a layer that floated above the aqueous solution. After that I added cca. 150 ml of a NaHCO3 solution, swirled a minute or two, noticed some CO2 evolving, and added 500 ml of water. The water removed some acetone from the NG, but some (around half the volume) still remained mixed with the NG, so I added again the same amount of water. This removed almost all of the acetone. Then the third wash with half the volume of water was performed and the NG was tested with litmus paper, showing that it is non-acidic. After that I put the NG under an almost saturated NaCl solution to remove the water dispersed in the NG (it is milky-white). I forgot to write that all the water washes were performed with relatively warm water (hot tap water, how hot is it? Around 50 C?), in the hope that the extra heat would remove at least a small amount acetone through evaporation, and that the NaHCO3 solutions were both times moderately concentrated (don't know the exact conc. because I didn't weigh the NaHCO3), in the second attempt they were luke-warm, in the first room-temperature. I would also like to say that all of the washings reduced the final yield of NG (I don't know how much exactly because I never measured it, only eyeballed it. After the nitration I had around 20-23 ml (the batch was 200 ml of conc. H2SO4, 100 g of AN and 25 ml of glycerin), after the washings around 15-17 I believe.

All in all I can say that NG if more difficult to neutralize than I thought.

Are there some more effective methods? I do believe that constant stirring of the NG while under the basic solution would be much better, but I don't have the equipment for that. Perhaps simply letting it sit under the solution for several days would also work, but I would take a long time (not that I'm in a hurry but still :P)
Maybe it the problem where to dilute NaHCO3 solutions?




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[*] posted on 12-1-2011 at 06:28


Quote:

Are there some more effective methods? I do believe that constant stirring of the NG while under the basic solution would be much better, but I don't have the equipment for that.

What lack of equipment could possibly prevent you swirling the mixture by hand?
Wash water won't worm its way into the interior of the nitro by itself, you know!
And the bicarbonate solution should be no more than 5% . . .


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[*] posted on 12-1-2011 at 08:36


Quote: Originally posted by hissingnoise  

What lack of equipment could possibly prevent you swirling the mixture by hand?


Indeed, but don't think I could hand swirl it for several hours. It seems at the moment that the best thing to do would it be to leave it under a NaHCO3 solution for several days with periodic swirling.

Quote: Originally posted by hissingnoise  

And the bicarbonate solution should be no more than 5% . . .


Interesting. I thought the concentrated the better. Why is diluted better (I know strong bases would hydrolyze NG, but I don't think even a saturated solution of NaHCO3 is enough to do that, but I could be wrong)?




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[*] posted on 12-1-2011 at 13:25


Low bicarb concentrations lessen the possible contamination of nitro!
In practice, it's about 3%!
When you're swirling, time slows to a crawl . . .
Just reconnect with your dogged side and don't let your attention wander!


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[*] posted on 12-1-2011 at 14:02


Many kitchen appliances are made precisely for stirring, so I suggest that you buy a cheap hand mixer and use that. Just make sure that the rotating bits don't hit the sides of the vessel (mount the mixer in a fixed position eg. a drill press) and use a relatively soft plastic vessel just to be safe.
According to Urbanski, an emulsion of NG in relatively little water (on the order of equal volumes of water and NG IIRC; this is not a stable emulsion obviously) cannot be initiated even with a strong blasting cap.

Simply letting the NG stand under a bicarb soln is an excercise in futility. Try looking up diffusion and random walk. Even though you probably can't find diffusion coefficients for acid residue in NG, you can still get an idea of how long it could take. Depending on the batch size and the geometry of your vessel, it could take months or years for it to approach a neutralized state.
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[*] posted on 13-1-2011 at 10:18


…..or just use ordinary & improvised magnetic stirrer and soft plastic vessel.
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[*] posted on 13-1-2011 at 10:34


Quote: Originally posted by hissingnoise  
I use a thermometer as stirring rod and I flinch at every glass-on-glass clink!
Going at it as if you're beating eggs in a bowl is not the way to go.
Gentle (and I mean gentle) stirring shouldn't throw up "surprises" . . .



Get an aquarium aerator and use those bubbles! Safe and will still keep your mix appropriate. In fact, if you take your time and bring your hose to the bottom of the beaker allow it to form a semi-circle around the bottom-base and you'll get a tiny gentle Whirlpool: perfect for continued mixing. By bringing the tubing to a smaller opening you can make a bubblier into a mild jet.
Take a few dollars and invest in a digital thermometer - much safer: sharper results.
Or take some tape and put VERTICAL & THIN stripes on a glass thermometer (all the way to the bulb!) to keep that banging from becoming a tragedy.

Never glass to glass because even if you're the "genteel hand in the West" the thermometer may weigh enough so that an accidental drop from your paw may do enough to start the train rolling; especially those real long ones because they naturally focus (in the bulb) at a point of sorts. Tape won't throw your readings off if you use very thin (vertical) strips.

If you should use a magnetic stir device - periodically examine the stir-bar. Occasionally the Teflon will wear down to the metal. A small piece of tape there is a good "peace of mind" utility.




[Edited on 13-1-2011 by quicksilver]




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[*] posted on 14-1-2011 at 03:05


Ive always wondered about the potential effect of the stirbar..
2 of my stirrers carry very strong magnets, some scratching effect may occur.
Probably not enough to do serious damage , still there is no real way of actually knowing.

[Edited on 14-1-2011 by User]




What a fine day for chemistry this is.
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[*] posted on 14-1-2011 at 08:57


Air has been used in plant production for decades and is more than just a "peace of mind" issue for most. It's a very flexible methodology and is "wear resistant".

We know that the majority of these materials are not as sensitive as characterized but both the fluids and the solid polyols / esters CAN provide a gateway to a tragedy from their very characteristics: fluids can seep into tight places, particulate can grind against itself.
If I were ever to synthesis NG I would ALWAYS err on the side of over-caution.



[Edited on 14-1-2011 by quicksilver]




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[*] posted on 16-1-2011 at 05:37


My NG has now been 4 days under the NaCl solution. Already after the first day it almost completely cleared.

But I notice there are quite a lot of bubbles in the NG. How much do they sensitize the NG? And what would be the best way of removing them?

I was thinking perhaps simple swirling and decantation to an another container would work?




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[*] posted on 16-1-2011 at 07:06


I'd be a bit concerned if I saw lots of bubbles appearing . . .
I'd wash it further; simply tilting the container, which could be fairly large, so that the blob of NGl rolls around the bottom is probably as good as swirling, not to mention safer.

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