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Author: Subject: methyl nitrate
Boomer
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Ethyl nitrate *is* a bitch, it tends to oxidize rather than nitrate. But if you use fuming nitric free of NOx and work in a freezing mix instead of a simple ice bath, it works like a charm. Crushed ice with the right salt added goes to -30C, the nitration is easily held below -10C.
Rock salt is barely sufficient, but doable with enough patience. Just never let it get above -5C. Once isolated, the ethyl variety is tamer both due to higher bp (less headache) and lower sensitivity.

Oh I almost forgot, adding urea nitrate to the nitric helps too. Not urea for purging of the acid, but the nitrate added to the nitration. Also recommended for RDX, but we're far enough OT.
Just my two cent.
Bromine
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I heard that methyl nitrate is carciogenic.
I was thinking that this could be true because it is methylating reagent. But on the other side i didn't found that information nowhere alse. So what do you think about it ?

Oh and how safe is to use 2 days old methyl nitrate?

[Izmenjeno 28-12-2007 Bromine]

[Izmenjeno 28-12-2007 Bromine]

Mason_Grand_ANNdrews
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TNX -- Intergalactic_Captain. I dont understand what you commenting to my "small" incursions. I dont want
give a commentary to the Me-NO2 synthesis. When you nitrate a strong chilled Me-OH, i will tell you the synthesis
will come like a opended flask of mineral-water after a short time. Every hydrogen ion is replaced wiht an (NO2)-ion and
this produces "somewhat" heat with the concentrated H2SO4 they will convert it to dilute H2SO4 and H2O/NO2. The
Et-ONO2 or more than CH2(NO2)-ONO2 will chauses a lot of heat what block the reacion into dilute H2SO4/HNO3
and evaporated "Oil" of CH3-NO2 (CH2-(CH-OH2)2). Maybe the water is picked up with acetic acid anhydride, the yield is
much more better because the converting of -H into H2SO4 causes not so much heat and something more.

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[Edited on 3-1-2008 by Mason_Grand_ANNdrews]
SecretSquirrel
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 Quote: Originally posted by Bromine I heard that methyl nitrate is carciogenic. I was thinking that this could be true because it is methylating reagent. But on the other side i didn't found that information nowhere alse. So what do you think about it ?

Here is some toxicity info on methyl nitrate
http://physchem.ox.ac.uk/MSDS/ME/methyl_nitrate.html

And the fact that it can be used as methylating agent has nothing to do with its toxicity. Dimethyl carbonate for example is a very good methylating agent and is not carcinogenic.
tr41414
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A bit offtopic... so what is it that makes a methylating agent carcinogenic? As far as i know the mutation comes from methylating dna. If so, is the resistance to hydrolysis an important factor?

Does maybe anyone have a ref (interested in procedure, not only mentioned) to using alkyl nitrates as alkylating agents?
tr41414
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tr41414 just made himself a few mls of EtONO2 (don't have any MeOH handy). It is a clear colorless liquid with chloroform like smell. It didn't detonate with hammer and burned with yellowish-white flame.

PS:Adding some H2SO4 to ethanol and chilling that prior to rxn helps with runaway, also mech. stirring...
Zinc
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Can you describe the details how you made it please?

SecretSquirrel
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I belive the adaptation of this synthesis can be used. Just use EtOH instead of MeOH and proceed with the synthesis as written.

[Edited on 5-1-2008 by SecretSquirrel]

[Edited on 5-1-2008 by SecretSquirrel]
franklyn
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Recipe from Fownes Manual of Chemistry Theoretical & Practical
as it was done in 1878 _
Methyl nitrate is prepared by distilling 50 grams of NaNO3 with 50 grams of
Methyl alcohol and 100 grams of sulfuric acid, in a retort without external
heating.
( presumably if the heat of nitration is enought to boil it , a larger quantity
can easily run away. The Na2SO4 formed serves to keep water in the retort )
It is a colorless liquid density 1.182 at 20 ºC (68 ºF); boils at 60 ºC (140 ºF);
has a faint ethereal oder. It's vapor detonates when heated to 150 ºC (302 ºF).
Heated with alcoholic ammonia, it yields methylamine nitrate. CH3NH2.HNO3

.
tr41414
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The first try was using 7 ml of H2SO4, 4 ml of 60% HNO3 and 3 ml EtOH. A few granules of urea was added to the nitration mix, probably not the best idea as it didn't dissolve and seemed to give of bubbles? It went well until last drops of EtOH were added. The mixture started to give of NOx and turn black. It was dumped in ice/water, from where only a ~0.5ml blob of EtONO2 could be rescued...

Second try was using double the reagents, improvised overhead stirring and addition funnel also ~2ml of H2SO4 were premixed with ethanol and chilled (mixing 0degC reagents resulted in fairly warm mixture). Addition was done at about 1 drop per second. Product was separated using separating funnel. I got around 5ml of product which was neutralized using bicarbonate and then dried using CaCl2. Half an houf after spent nitration mixture started to give of NOx and turned completely black (after rxn it was removed from cooling bath; there was probably some EtOH/EtONO2 still in there). After a day it was again almost colorless.

In both tries 0degC water + AN bath was used...

The EtONO2 seems to be pretty damn inert...

[Edited on 7-1-2008 by tr41414]
Zinc
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What concentration of ethanol did you use? And could a mixture of NaNO3 and H2SO4 be used?

So ethyl nitrate is not very sensitive?

tr41414
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Ethanol was food grade 94% i think (you can dehydrate it to get better yields)... I guess that mix should work also...
With being inert I meant i couldnt detonate it /w hammer and it also didn't react with NaOH prill... On heating a drop simply vaporised (vapor goes of with less of a woof than AP if you light it). But on the other hand i have done this with small drops of it and there are warnings about it oxidising in explosive manner on contact with nitrating mixture...
garage chemist
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There is a synthesis of ethyl nitrate that uses no H2SO4, but ethanol and 68% nitric acid at 120- 130°C. A mixture of those two, with addition of urea nitrate, is distilled and the distillate washed with water and soda solution.
http://www.lambdasyn.org/synfiles/ethylnitrat.htm
As you can see, the nitration is much, much less sensitive to temperature when there is no H2SO4.

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Boomer
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I still dislike methods where nitric esters are heated (or their precursors, which is the same after some product has formed). Note orgsyn mentions "frequent explosions" for the distillation method if used for MeOH instead of EtOH.

Plus, using fuming nitric + conc. sulfuric is more satisfying to the eyes. Where else do you have the pleasure to see more product than spent reagents? I once had approx. 20ml of EtONO2 sitting on top of 18ml spent acid.

(OK it's less dense, and dissolves up to 10% of nitric, but still.)
Zinc
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Did anyone had an accident while making ethyl nitrate?

Mason_Grand_ANNdrews
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At first, i must to excuse me for the written formula (CH2-(CH-OH2)2).
I cant find it elsewhere. Ive written down this answer in the topic
after a nice night with some friends. I mean the somewhat incorrect
nomenclatura of something like dimethanolmethane (correct formula
CH2-(CH2-OH) is not a allday available stuff.

Some more examples of my writing errors are:

2,2-isopropanoldimethanol
1,2-isopropylalcoholdimethanol
1,3-isopropylalcoholdimethanol
and so on.

Something more what give a little diversity of the stuff.
I would mean, nitrated in a AAA(TFAA)/HNO3 solution it gives some easy nitrates
when dissolved in the water converter and the HNO3 is slowly stirred in over some
hours into the solution.
Concentated H2SO4 should work too, but i mean its can not easy form a -CH2-NO2
nitrate without developing of to much heat or destroying the material.

1,1-isopropyldimethanol tetranitrate (O2N-CH2)2-C(ONO2)-CH2-NO2
1,2-isopropyldimethanol trinitrate (O2N-CH2)-(CH-ONO2)-CH2-NO2
1,3-isopropyldimethanol trinitrate (O2N-CH2)-(CHONO2)2-(CH2ONO2)
and something more.

Any simple formulas to some unkown stuff, maybe for guys they know how it
can get from suppliers or prepared or have a way to prepare. Amines and more
stuff here not mentioned here.

I mean what my expieriences told, this nitrates are very insensitive and i think
they are more than good to make a insensible solvent for a high explosive in ratio 60:40. (nitorxides only !!!!)

The first procedure can be - the alcohols are stirred into concntrated H2SO4 and
treated with concentrated HNO3 to make the simple nitrate.
The nitration of the -OH ion should be finished when some little blows will heat the
mix and you dump it into a smal portion of ice water. The milky liquids which will placed
are easy cleaned when they stirred with 10% soda for an hour (ratio 1:5 )
let sit and suck off the viscous layer of the f.i ethyl nitrate.

Easy Step one:
I mean the nitration to the f.i. 1-nitromethylethanol (exuse me for my thought, 1-nitroethane-2-nitroxide)
should walk after 0,5 mol of 95 to 98 % sulfuric acid is
mixed with 0,1 mol of EtOH, the stuff is stirred and over an half hour 0,3 mol of 70 to
80% HON3 is stirred into the mix that nor fumes of nitrogen oxides will form. The mix
should be chilled with a dish of cracked ice. Stirr it until it begin to bubble, the ice will
be melt and dump it into 500 ml of ice water. Let sit, add a little soda, stirr it for
an half hour, let sit and suck the little layer of ethylnitrate inot a small dish.

Easy Step Two:
Pour around 200 ml of fresh distilled acetic acid anhydride into an beaker, let sit it in a
water bad of crisehd ice, add the ethylnitrate and slowly 3 mol of 96 to 98 % HNO3 is dropped
into the solution with rapidly srirring. Stirr the mix for two hours or mor and
add more ice when it heated to much. Let sit it until the ice is molten, suck off the
nitromethylethanol (I hope it will have still a liquid, stirr it into 500 ml water with a
dissolved soon of soda, make it free of acid while stirring and let sit it that you can
separate it from the soda water.

CH3-OH ---> methylnitrate --> CH3-ONO2
CH3-CH2-OH ---> ethylnitrate --> CH3-CH2-ONO2
CH3-CH2-CH3-OH ---> nitropropanol --> CH3-(CH2)2-ONO2
CH3-(CH-OH)-CH3 ---> isopropylnitrate --> CH3-CHONO2-CH3
isopropyl-2,2-dininitromethanol ---> CH3-(C(CH-OH)2)2-CH3 ---> isopropyl(dimethanoldinitrate )
or
nitrobuthanol ---> CH3-(CH2)3-CH2ONO2 (propylnitroethanol , CH2(NO2)-(CH2)3-CH2-ONO2, pentanitrobuthanol CH2(NO2)-(CHNO2)3-ONO2)

Exucuse me for the somewhat long description. When you will make some
methylnitrate you can buy some methanolic acid from sigma, the mix is
more than good for minimum MeONO2.

Supelco - Methanolic H2SO4
10% in methanol, pkg of 6 × 5 mL
Sulfuric acid solution
CAS Number 7664-93-9

I`ve locked around at roguesci at the last two days but the forum is down.
Someone can told me why ?
The forum gives some "little " motivations to make a good stuff in the explosives section.

[Edited on 11-1-2008 by Mason_Grand_ANNdrews]
quicksilver
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 Quote: Originally posted by Zinc Did anyone had an accident while making ethyl nitrate?

During the latter part of the 2nd World War the Nazis were running short on just about everything. Slave labour was routed to the production of explosives for uniquely inexpensive land mines. Due to production techniques utilizing slave labour and economics of nitric esters instead of nitro benzenes, the common light alcohols were used. Methyl nitrate was perhaps the least expensive production ester to manufacture a "dynamite" filler. The loss of life and limb were so extensive that often the production facilities were cordoned off and many escaped due to the isolated facilities needed....

The problems in production with methyl or ethyl nitrate is that temp control is tough as the material is thin. If you study the "run-a-way" reaction mechanism in nitric esters, the thinner the material the more controls are needed to stabilize & maintain consistency in the estrification, bla, bla, bla... temp, addition speed, whatever, ...becomes a headache (pun intended)!
gnitseretni
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Could Nitromethane in ANNM mixtures be substituted with Methyl Nitrate or would it be too dangerous,as in the AN pellets 'grinding' the liquid?
AndersHoveland
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Interestingly, ethyl nitrate can be prepared with only moderately concentrated nitric acid, without the need for concentrated sulfuric acid.

 Quote: Ethyl alcohol is nitrated continuously by adding a mixture of 61% nitric acid with 95% ethyl alcohol, saturated with urea (as much as can dissolve), into a flask set up for distillation containing boiling 50% nitric acid. The nitrate ester and water formed are continuously distilled off at about 98 °C from the reaction mixture. The volume of the reaction mixture is held constant by drainage of nitric acid and unstable by-products from it as the reactants are added. Unless you have a special flask with a stopcock on the bottom, you will have to periodically disconnect the flask from the condenser and dump out some of the used nitric acid. You will also have to momentarily disconnect the flask to add more acid/alcohol mix if you do not have an addition funnel. Be very careful doing this as you will subject yourself to a blast of acid fumes. A small quantity of gas, such as air, nitrogen, or carbon dioxide is blown through the reaction mixture to improve mixing and to facilitate the elimination of the volatile byproducts. The optimum ratio of nitric acid to ethanol is about 2:1. The yield is 78%.
Pulverulescent
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 Quote: Interestingly, ethyl nitrate can be prepared with only moderately concentrated nitric acid

 Quote: Many moons ago, I had a runaway distilling methyl nitrate from 70% HNO3 ─ 2litre RBF ~half full . . . The NO2 was like some crazy, fucking live thing, writhing, and uncoiling itself out the flask! I mean, this stuff looked like it was solid!!!

The trick is to get the adapter out of the flask real fucking quick!

P
franklyn
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Can the electrolysis of ammonium nitrate in acetic acid yield methyl nitrate ?
There is some evidence to suggest this might work.

Some New Anode Reactions Involving Nitrate Ions & Aromatic Compounds
http://actachemscand.org/pdf/acta_vol_25_p3246-3254.pdf

On the electrolysis of ammonium nitrate in acetic acid.

Kolbe electrolysis of acetic acid yields hydrogen , carbon dioxide and ethane.
The half cell reaction of the carboxyl anion is decomposed thus :
2 CH3COOH => 2 CH3COO => 2 CO2 + 2 CH3• => ( 2 CH3• => CH3CH3 )

Electrolysis of ammonium nitrate yields hydrogen , ammonia ,
and oxygen with nitrogen dioxide.
The half cell reaction of the nitrate anion is decomposed thus :
2 NH4NO3 => 2 NO3 => 2 •NO3 => O2 + 2 •NO2 => N2O4

The nitrogen trioxide radical has a fleeting existence only.

The mol weight of acetic acid is 60 , the mol weight of ammonium nitrate 80
a stoichiometric proportion of 3 to 4 , CH3COOH + NH4NO3.

The cathode would expel hydrogen and ammonia. The anode would expel
CO2 with the recombination of CH3• and •NO3 into CH3NO3

Ammonium nitrate and acetic acid ignites when warmed , it's an explosive.
This should serve to caution any intrepid investigator.
Addition of a non participating non aqeous cosolvent will provide safe operation.
Question is what ?

.
497
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Very interesting concept!
They say nitroglycol is produced from ethylene, so it seems possible to combine with a kolbe reaction. No mention of yields unfortunately.

If other options failed, you could always just hook two cells in series, so that the ethylene produced from acetate ran directly in to the next cell where it is nitrated. Nitroglycol is good stuff too, and then you'd have less oxidizer+fuel mixture risks...

A word to the wise: NEUROFEEDBACK

http://citizenworks.org/corp/dg/s2r1.pdf
http://www.newscientist.com/mobile/article/mg21228354.500-re...

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AJKOER

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I have an interesting idea to somewhat safely prepare and promptly detonate a small amount of Methyl nitrate. Place Cl2 and CH4 gas (the latter in excess) in a plastic (or glass) container (that is not dissolved by chloromethane as is ordinary rubber) . Some KNO3 (or NaNO3) has been placed on the bottom (with possibly some H2SO4). The vessel is surrounded by Aluminum foil to create a solar heat source and/or initiate a photo-chemical reaction (see http://www.youtube.com/watch?v=ukxOtG7d3OA ). Intended reactions, first:

CH4 (g) + Cl2 (g) --> HCl (g) + CH3Cl (g)

Source: Wikipedia ( http://en.wikipedia.org/wiki/CH3Cl ) which states that chloromethane is produced by heating a mixture of methane and chlorine to over 400 °C. This, however, may be a tough for a solar setup, and hopefully the photo-chemical induced chain reaction will create an effective yield. Wiki describes this reaction as moderate to fast (see: http://en.wikipedia.org/wiki/Free-radical_halogenation and also http://www.stanford.edu/group/Zarelab/publinks/zarepub525.pd... ). Otherwise, a metal container and a more conventional heating source can be employed.

Final required reaction, the nitration of the chloromethane:

KNO3 + CH3Cl --> KCl + CH3NO3 or

HNO3 + CH3Cl --> HCl + CH3NO3

Note, Gmelin, vol. 8, p. 468, for example, notes the historic use of Sulphuric acid, alcohol and saltpeter in the preparation of related Ethyl salts, although I would prefer to avoid the use of H2SO4 as the reaction vessel is intended for immediate ignition.

The amount of CH3NO3 formed (via the suggested gaseous reaction synthesis) would be small, but given the reputation of Methyl nitrate, this may be a good thing.

[EDIT] Note, the MSDS for CH3Cl (see http://www.airgas.com/documents/pdf/001036.pdf or http://www.mesagas.com/_Specialty%20Gas%20MSDS/Methyl%20Chlo... ) warns that chloromethane is extremely flammable in the presence of strong oxidizers (KNO3/HNO3 in this case) even without or before the formation of any CH3NO3, which per Wiki, explodes at 64.6 C. Both compounds are toxic.

[Edited on 9-9-2012 by AJKOER]
AJKOER

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OK, I may be a day early on a similar concept that was recently presented by AndersHoveland. My idea is the creation of Methyl nitrate from CH3Cl and a nitrate, and AndersHoveland's is proposing the formation of RDX from CH2Cl2 + NH4NO3 (link: http://www.sciencemadness.org/talk/viewthread.php?tid=19106 ).

Note, the related formation of these two methyl chlorides:

CH4 (g) + Cl2 (g) --> HCl (g) + CH3Cl (g)

and with added chlorine:

CH3Cl (g) + Cl2 (g) --> HCl (g) + CH2Cl (g)

Some comments by AndersHoveland that may be applicable to my suggested methyl nitrate synthesis:

 Quote: Originally posted by AndersHoveland ..... NH4NO3 and CH2Cl2 might be able to react using DMSO as the solvent, with some CuCl2 and ZnO as the catalysts. The reaction would probably take about 24 hours. Under these conditions, the ammonium ions should be able to act as a nucleophile toward the CH2Cl2, and the resulting HCl should be able to act as the dehydrating agent.

However, in the presence of Methyl chloride, CH3Cl, one MSDS notes an explosion hazard (see http://www.mesagas.com/_Specialty%20Gas%20MSDS/Methyl%20Chlo... ) in the presence of Zn (or ZnO?) and AlCl3 (or CuCl2?, may react similarly). I believe I have also seem mention of Iron (forming FeCl3) as a catalyst, but these catalysts may be unnecessary or inappropriate (precipitating a possible detonation, so exercise extreme caution).

[Edited on 10-9-2012 by AJKOER]
AJKOER

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 Quote: Originally posted by AJKOER ..... Final required reaction, the nitration of the chloromethane: KNO3 + CH3Cl --> KCl + CH3NO3 or HNO3 + CH3Cl --> HCl + CH3NO3

Some have implied a preference for an Ammonium salt (NH4NO3) in place of KNO3/HNO3 to accomplish the nitration of chloromethane. There is seemingly some support by the fact that CH3Cl is readily attacked by Ammonia. For example, the ammonolysis reaction, per one source (http://www.docstoc.com/docs/68188299/CHAPTER13 ) is given as:

CH3Cl + NH3 --> CH3NH2.HCl --> CH3NH2.HCl + NH3 --> CH3NH2 + NH4Cl

and combine this with the thermal decomposition of NH4NO3 which proceeds in two stages, with the 1st stage, at temperatures below 200 C, characterized by an endothermic dissociation into NH3 and HNO3. The second stages, at 200 C to 290 C, creating the ionic NO2(+), which leads to the formation of N2O (see http://energetics.chm.uri.edu/system/files/1989%20Thermal%20... ).

Clearly, limiting the thermal decomposition of the NH4NO3 to the 1st stage only might produce a successful reaction if:

CH3NH2 + HNO3 --?--> CH3NO3 + NH3

recycling some of the NH3 to react with more CH3Cl. However, research suggests the following reaction instead (see top of last page at: http://math-wizard.com/netionic.pdf )

H(+) (aq) + CH3NH2 (aq) --> CH3NH3(+) (aq)

implying the formation of Methylammoniun nitrate and not Methyl nitrate. In fact, per Wiki (http://en.wikipedia.org/wiki/Methylammonium_nitrate ) "Methylammonium nitrate is an explosive chemical with the molecular formula CH6N2O3, alternately CH3NH3+NO3-. It is the salt formed by the neutralization of methylamine with nitric acid. This substance is also known as methylamine nitrate and monomethylamine nitrate, not to be confused with methyl nitramine or monomethyl nitramine." And further, unlike Methyl nitrate which has no military applications, apparently methylamine nitrate was first used as an explosive ingredient by the Germans during World War II. It more recently as been combined with AN to form PR-M which is considered a low cost blasting agent (water gel explosives) to replace explosives based on nitroglycerin (dynamites).

A major assumption of this possible synthesis of methylamine nitrate is, however, that a low temperature heating of the dry NH4NO3 salt in an atmosphere of CH3Cl does not immediately precipitate an explosion.

[Edited on 23-9-2012 by AJKOER]
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