Since I have a LOT of free time I decided to search for some interesting synthesis, as im getting tired of RDX variaions. After about 5 minutes of searching, I came across the interesting acronym: MEAN(Think of the pun potential!). It stands for Monoethanolamine Nitrate, and would be almost completely OTC.

The only problem is that during an almost 4 HOUR search, I came up with NOTHING even hinting at a synthesis for this compound. It is mentioned at literally HUNDREDS of sites, and is included on the BATF's explosive compounds list.
:confused:
In additon there is not a single mention of the compound of the entire forum, which really had me stumped. I have decided that since it is a primary amine, a nitric-sulfuric nitration would probably work.

I have recently "aquired" 500 ml of Ethanolamine(2-Aminoethanol) from the chemical supply room and will attempt a standard acid-catalyzed nitration this weekend.

I am expecting success, as it is just a simple primary amine nitration, but I have no safety info for either the nitration temp range, or the stability of MEAN. I will thus be performing the nitration outdoors at 3-10C with 10 ml 0f Ethanolamine.

I will provide a detailed account of the synthesis, and if it is safe I will provide pics of the reaction once I find the optimal temp.

If anyone has ANY info on this mysterious compund, either relating to synthesis, safety, reactivity, or explosive properties it would be GREATLY appreciated. You may either post it or e-mail it to me at maddkow247@hotmail.com with the title "MEAN info"

From KIFE:

Originally developed by Dr. Hans Walter as one of the substitute explosives and designated "Formit". It is a faintly yellow explosive formulation. Developed in the late part of WWII, as the Axis powers chemical industries were being bombed to dust.

The actual composition of this explosive is Methylamine Nitrate ("MAN") 25-30%, Ammonium nitrate 67-74% and trimetnyl ammonium nitrate 1-3%.

MAN is the major sensitizer in E.I. DuPont’s "Tovex" series explosives. This is the only dynamite DuPont makes now. This is a cast explosive with a setting point of 90 degrees C. The only drawbacks of this explosive are the tendencies to extrude from the loaded munitions and the lower detonation velocity as opposed to T.N.T.. This would be a simple explosive to make.

The 37% formaldehyde solution is added to the ammonium nitrate.

CAUTION: Avoid Breathing Formaldehyde! Use with GOOD ventilation!

The resulting solution is heated to boiling in a pyrex or stainless steel pan with a lid for 1 hour ("Reflux"). This liquid is then placed in a "filtering” flask hooked to a vacuum source. A vacuum pump will work and so will a vacuum aspirator, but the latter will do so at a much cheaper cost. The vacuum will cause the solution to boil at a much lower temperature.

The flask should be placed in an electric frying pan that has been filled with cooking oil. The oil should be kept at 90 degrees C.. The solution will boil away. End point of this is at 470 ml. liquid remaining in the flask at a temperature of 90-100 degrees. A vacuum gage in line will give a drastic change when the end point is reached as the vacuum is increased.

The water will have completely boiled out of the solution. This liquid remaining in the flask is poured directly into the mold and allowed to cool, as the remaining liquid in the flask is the melted explosive munition desired.

When casting explosive, care should be taken to leave a "well" or hole for the booster and/or detonator.

37% Formaldehyde solution . . . . . . . . . . . . . . . . . . . . . . 450 ml.
AN Prills . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 480 G.

The 37% formaldehyde can have paraformaldehyde substituted for it as in the following:

Paraformaldehyde . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 180 G.
AN Prills . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 480 G.
Water . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 90 ml.

The AN is mixed with the water first and heated to effect solution. With solution the Paraformaldehyde is added and the solution heated as in the first composition and boiled for one hour as above and vacuum dehydrated as above.

The addition of 15% total explosive weight of R.D.X. or P.E.T.N. (from det. cord) will give this explosive the same amount of power as T.N.T., but the bristance or fragmentation effectiveness will be greater than T.N.T.. I also believe that the addition of 20% bullseye smokeless powder will do nearly the same thing. The undehydrated liquid could also be used as a sensitizer for slurries.

Nightstalker: that's MMAN (monomethylamine nitrate) not MEAN (monoethanolamine nitrate).

Cyclo_Knight: if I was doing this, I would be tempted to try the following: react your ethanolamine with nitric acid (not necessarily conc) to get the nitrate salt. Purify and dry this. Then add it into the strongest, colourless nitric acid you can make at about room temp. This should be able to form both the nitrate ester and nitramine groups. Forming the salt first should make it easier to keep things cool.

I think. Maybe.

The only nitric acid that I have in my lab is 99%. I am cetrainly not going to dilute this precious acid (which would set me back US$329.00 at Fischer). Thanks for your suggestion though, but I think i'll be safe as i'm only reacting 5-10 ml, and i'll be behind a 1/4 in Lexan blast shield.

Could nitrating at too LOW a temperature adversely affect my end-product, or is the added safety worth the risk? I was thinking about nitrating at 0C in an alcohol/crushed ice slurry.

I have read about certain amines reacting with NITROUS acid to form highly unstable diazonium salts. I am not sure if small quantities will generate when reacting with nitric :eek: .

My bad. :0

Though isn't ethanolamine used to make MEDINA? Or is that diethanolamine?

Maybe I am totally confused, but xyz-nitrate sounds like a simple salt (like UN, GN, HDN), so why make the salt and THEN try to form a nitrate ester/nitramine?

Sounds more like "add to 50% NA, cool, filter and dry - ready"

Well, how is your Russian, or Japanese? I have two synthesis references for MEAN in those languages.

monoethanolamine nitrate AKA Ethanol, 2-amino-, nitrate (salt); 2-Hydroxyethylammonium nitrate; Ethanolamine nitrate (salt); Ethanolamine-nitric acid salt (1:1); Ethanolammonium nitrate

formula: C2 H7 N O . H N O3

CAS # 20748-72-5

synthesis references:
Reaction of mono-, di-, and triethanolamine with nitric acid. Communication 1. Rustamova, R. M.; Alimova, G. A.; Saibova, M. T. Inst. Khim., Tashkent, USSR. Uzb. Khim. Zh. (1982), (2), 16-18. CODEN: UZKZAC ISSN: 0042-1707. Journal written in Russian. CAN 97:79872 AN 1982:479872
Abstract
Spectrophotometric study (250-320 nm) showed formation of 1:1 and 2:1 amine:nitrate complexes. Instability consts. for 1:1 mono-, di-, and triethanolamine nitrates are 3.15  10-2, 1.04  10-1, 2.09  10-1, resp.; instability consts. for 2:1 nitrates are 2.41  10-4, 5.68  10-3, and 2.30  10-3, resp.
------------------------------------------------------------------
Preparation of pyridinecarboxamidines. Goda, Satoshi; Saito, Kenji. (Sumika Fine Chemicals Co., Ltd., Japan; Kirin Brewery Co., Ltd.). Jpn. Kokai Tokkyo Koho (2000), 6 pp. CODEN: JKXXAF JP 2000327662 A2 20001128 Patent written in Japanese. Application: JP 99-138908 19990519. CAN 134:4866 AN 2000:828896
Abstract
Title compds. I (X- = acid residue; n = 2-5), useful for vasodilator drug, antihypertensives, etc., are prepd. by reaction of cyanoimidates II (R1 = C1-4 alkyl; benzyl) with H2N(CH2)nONO2 (n = 2-5) in solvents and addn. of acids in the reaction solns. An AcOEt soln. of 2-nitroxyethylamine was treated with Pr N-cyano-3-pyridinecarboximidate at 0-5 for 4 h and reacted with MeSO3H in iso-PrOH-H2O mixt. at 0-5 for 3 h to give 80.8% N-cyano-N'-(2-nitroxyethyl)-3-pyridinecarboxamidine methanesulfonate.

I'll check Chemical Abstracts next week for these two references and see if there is a more detailed abstract.

Call me crazy, but from the info I have here in front of me it looks like MEAN is produced by neutralizing ethanol amine with nitric acid. I have a little graphic here and it shows ethanol amine and nitric acid. I can check my reaction database to make sure, but I am willing to bet this is just a simple neutralization reaction.

And if funky acronymns are your deal, research the explosive SEX :) also what about BEAF (the other nitrated meat).

have read about certain amines reacting with NITROUS acid to form highly unstable diazonium salts.that's monoarylamines. monoalkylamines also react with HNO2 but the diazocompound is so unstable that immediately losses nitrogen forming an alcohol (in this case forming ethylene glycol)

from "Explosives (Rudolf Meyer)":
Ethanolamine Dinitrate Monoethanolamindinitrat; dinitrate d’ ´ethanolamine
O2NOCH2CH2NH2.HNO3
colorless crystals. empirical formula: C2H7N3O6 . molecular weight: 169.1 . oxygen balance: –14.2% . nitrogen content: 24.85% . volume of explosion gases: 927 l/kg.
heat of explosion:
(H2O liq.): 1254 kcal/kg = 5247 kJ/kg
(H2O gas): 1089 kcal/kg = 4557 kJ/kg
specific energy: 118.8 mt/kg = 1165 kJ/kg . density: 1.53 g/cm3 . melting point: 103°C = 217°F . lead block test: 410 cm3/10 g . deflagration point: 192°C = 378°F .
This compound is readily soluble in water, sparingly soluble in cold alcohol, and somewhat hygroscopic. It is prepared by dissolution of monoethanolamine in concentrated nitric acid and precipitation from alcohol or ether with cooling.

I can get ethanolamine for 20€/l.
Maybe I will try to make it another time. Because I have enough projekts and synth-misfires at the time :(.

One simple question: Is the lead salt of EADN (ethanolamine dinitrate) a explosive salt or only only a simple nitrate salt?

just a thought...I remember that there was a rocket fuel combination that involved aliphatic and aromatic amine and (fuming?) nitric acid. Russians use it in the old AAA defence system in 60's and shot down U2 with it ...f*cking huge rocket completely unusable by anyone who do not have a country as big as them as time for fueling the system was measured in hours, but on the other hand anything that can deliver 20kg of HE on 22km altitude deserve respect. I post this as an explanation/warning to those playing with this as I noticed the mentioning of diazo compounds and nitrous acid in thread...

to Mega: If it is life-or-death situation I can understand a Russian with a very little help of a dictionary...but we have a couple of guys here that are native speaker and present better option. I like the keywords mentioned:D

I just tried to produce MEAN.
1.)I mixed 12-13ml yellow (about 70% or a little bit more) HNO3 with 10ml destilled water.
2.)Than, I mixed 10ml ethanol amine, 10ml destilled water and 1 drop of a 10% phenolphtalein (as indicator).
3.)At least I dropped the first sloution (nitric acid) dropwise into the second solution until the solution turns colourless. I hold the temperature under 35°C.
After 2min the solution turns from water-clear and clourless to a light NO2-yellow
4.)I tried to precipate the MEAN by adding of EtOH and acetone but nothing precipated. :(

Now the beaker is standing on a heatener. I'm waiting now until most of the water is evaporated. Than I will dry it completely in a dessicator.

I will EDIT the post when I get the first solid results.

Questions:
-
Is it possible to get MEADN (monoethanolamine dinitrate) directly by dissolving 3mol NH4NO3 in 3mol H2SO4 and adding of about 50ml ethanol amine or 100g MEAN? I yes, how can I seperate the ammonium sulphate and the MEADN?
Does ammonium sulphate dissolve in alcohol or ether?
-
Does ethanolamine, ethanolamine nitrate and ethanolamine dinitrate dissolve in dichlormethane or chloroform?
If yes, is it possible to mix K-nitrate with H2SO4, extracting the nitric with DCM/TCM and adding ethanol amine? Will MEAN or MEADN precipated?
-
THX! :D

Ethanol amine can only form one true nitrate ester, so no, you can't have 2 nitrates. I suppose it is possible to have a nitrate salt with the amine group on there. I believe it is however possible to further nitrate the compound. It would be more like Mononitromonoethanolamine Nitrate.

Ethanol amine can only form one true nitrate ester, so no, you can't have 2 nitrates. I suppose it is possible to have a nitrate salt with the amine group on there.

Ethanolamine dinitrate is just that, a nitrate ester and a nitrate salt.

Try <a href="http://v3.espacenet.com/textdoc?DB=EPODOC&IDX=DE516284&F=0">DE516284</a>, Verfahren zur Herstellung von Monoaethanolamindinitrat. <i>(English: Procedure for production of Ethanolamine dinitrate).</i>

MeAN is highly hygroscopic, so you'll not get a solid without vacuum dessication.