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Author: Subject: Hydroxylamine NH2OH Uses (and Production)
chemoleo
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[*] posted on 21-2-2006 at 10:07


That's surprising really, because of the high cost of nitromethane. Isn't the bisulfite/nitrite method for hydroxylamine production way more economical?



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[*] posted on 21-2-2006 at 12:52


Well, in Ullmann's Encyclopedia of Industrial Chemistry it says that "This process has been used only to a limited
extent because of its cost and the limited availability
of raw materials." about the NM/acid process.
The Raschig process is more important as is the catalytic hydrogenation of NO or nitrates.
But since I can buy NM and not nitrite, the acid/NM method is the one I'm giong with.
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[*] posted on 25-2-2006 at 13:24


Thanks for translation, alternatives, experiances!

Quote:
Originally posted by chemoleo
Also, it mentions that the hydroxylamine HCl can be reacted with cyanamide to form oxyguanidin hydrochloride, CN3H5O:HCl. What precisely is this? Anyone knows?


H2N-C(=NH)-O-NH2 . HCl?

There is mention of (NH2O)2C=NH here,
http://ww1.ft100.net/~64671/xfiles.ft100.net/images/oxylamin...
forget what the actual journal ref this come from, I have so much of this crap on my computer, in german ... again :(

Quote:
Originally posted by Microtek
diamino furazan can be made from condensation of glyoxal and hydroxylamine to diaminoglyoxime


Were you able to do that in good yield in one step? See pg 377 of preceedings <a href="http://www.sciencemadness.org/talk/viewthread.php?tid=5393">here</a>, supposedly you can go all the way to diaminofurazan in one step from glyoxal/NH2OH.HCl/NaOH + "other", but specifics arn't mentioned.

I've isolated glyoxime, then diaminoglyoxime from that, but only in ~20% from glyoxal -> DAG.

[Edited on 25-2-2006 by Axt]
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[*] posted on 26-2-2006 at 05:55


No, I haven't actually tried that yet as I've only just gotten the hydroxylamine production in place. I plan to follow the modification proposed in "Furazan-based Energetic Ingredients" which I think I got from you at the Crucible.
The modification involves heating an excess of free hydroxylamine to 90 C and then dripping in glyoxal soln while maintaining the mix at 90 C. According to the article I mentioned, yield suffers if temp rises above 90 C which can be difficult to control if mixing the ingredients first and then heating. This should give diaminoglyoxime directly in 64 % yield ( at the 1000 g scale ).
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[*] posted on 27-2-2006 at 16:39
More uses of hydroxylamine


I had a look at Axt's article from above. It contains some interesting chemistry, some that even seems doable!

For instance, potassium hydroxylamine disulphate (KO-N(SO3K)2), which is made as described above from sulfite and nitrite, is a useful reagent for the reaction with alkylating agents, for instance dimethylsulphate or, more realistically, halogeno-alkanes.

Alpha-methyl hydroxylamine, CH3-O-NH2
Basic potassium hydroxylamine disulphonate (dissolved in 6% KOH) is mixed with the same molar quantity of dimethylsulphate or methyliodide. The latter disappears within one day, while DMS reacts much faster while heating up. This can be boiled down, and alpha methyl hydroxylamine dipotassium disulphonate CH3-O-N(SO3K)2 crystallised in good yields, which can be recrystallised in slightly ammonia-containing H2O.
To split the N-SO3 bonds, the above salt is boiled in H2SO4, under reflux. I'm not sure if reflux is necessary, but probably topping up with H2O now and then would be good. The end of the reaction is achieved after several hours. (The end is recognised by taking a small aliquot of the solution, adding BaCl2/OH2 to remove extra H2SO4, and nitrite is added, which will react with the hydroxylamine. If H2SO4 is released, then addition of further BaCl2/OH2 will result in further precipitation, which indicates unreacted sulphonic acid. Thus more boiling is required).
Once the reaction is finished, the CH3ONH2:H2SO4 salts are extracted with ethanol, seemingly recrystallisation in ethanol can separate the less soluble neutral salt ((CH3ONH2)2:H2SO4) from the more soluble acidic salt (CH3ONH2:H2SO4).

They summarise this to make this reaction as fast as possible:
1) methylate the potassium hydroxylamine disulphonate in basic solution, as described above.
2) Boil this with H2SO4 or HCl to dryness, while the former is prob better (no HCl fumes), and test for completion of the reaction.
3) Add NaOH to a stoichiometric excess (cooling), and boil and distill. Free methyl hydroxylamine base comes over with the water, and is directely either collected in acid, or simply in a cooled container. Yields, wrt the starting compound, is 80%

Interestingly, the methyl hydroxylamine nitrate, explodes with great force when heated to 300 deg C. The nitrate is well-soluble in absolute ethanol, which may provide a purification technique. Maybe, Axt, that's something you want to try!!!! :)

Alpha, alpha ethylene dihydroxylamine, H2N-O-CH2-CH2-O-NH2)

Again, energetic compounds of this hydroxylamine can be easily seen :)
Here, 1,2 dibromo ethane is required, Br-CH2-CH2-Br. The sulphonate salt from above is reacted with it, in a 2:1 proportion, as described with the methyliodide above. This forms the tetrasulphonate, similar to the reaction above, which precipitates/crystallises from solution due to its low solubility:

(KSO3)2N-O-CH2-CH2-O-N(SO3K)2

This is digested with H2SO4, under boiling and testing for the end of the reaction as described above. The free based distills at 203 deg C.

Next to making the nitrate salts, I wonder how good a substrate these hydroxylamines are for peroxidation...? Similar to the 'amine peroxide' thread.


Other than alkylhalides, the initial hydroxylamine sulphonate also reacts with cyanogene bromide or iodide. Sadly this is not an easy substnace, nor safe. This then forms the imine sulphonate, (KSO3-N-O)2C=NH. However, this does not form the (NH2O)2C=NH, which Axt mentioned, even though boiling this with acid should theoretically get this.


Altogether, I think this may open up potential for a whole series of compounds, given the right starting compounds (alkylhalides).

Who's going to make some methyl-hydroxylamine nitrate? :P

[Edited on 28-2-2006 by chemoleo]




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[*] posted on 1-3-2006 at 08:30


Quote:
Originally posted by Axt
I'm attaching an article which supposedly gives the synthesis of NH2OH.HCl by refluxing HCl with nitromethane.
<a href="http://xfiles.ft100.net/images/nm-hcl-hydroxylamine.pdf">Journal f. prak. Chemie, Vol 21, 1880, page 129</a>

Can a german speaker please look at that and give the specifics of the reaction (quantities, reflux time, extraction etc.). If its in there ... somewhere.

More random NH2OH articles I have:
http://scibooks.ft100.net/images/hydroxylamine.zip


Those links are broken.
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[*] posted on 1-3-2006 at 09:48


Try to secure them here........solo

http://rapidshare.de/files/14438117/nm-hcl-hydroxylamine.pdf...

http://rapidshare.de/files/14438496/hydroxylamine.zip.html




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[*] posted on 1-3-2006 at 10:22


No. The links are alright.

I could download both files.
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[*] posted on 3-3-2006 at 17:08


Thanks for the renewed links, Solo.
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[*] posted on 3-3-2006 at 22:45


For some reason the links seem to work for some but not others.

I remember where that "oxylamine" article come from, it was referenced to in PATR2700 under the entry ethylenedioxyamine. Making it Ber 53, 1489 (1920).

PATR2700 gives no actual figues but a few properties, the dinitrate detonates when heated over its melting point, and the diperchlorate is responsible for killing the two chemists working with it :) they refer to it as a "sensitive material".

Apart from the salts and possible peroxides, complexes are likely and chloramines may be possible as well. It would be interesting to try the same peroxide/complex/salts/chloramine with diaminofurazan as is possible with the alkyl amines.

The O-methylhydroxylamine or methyloxyamine is patented as rocket fuel as replacement for hydrazine US3117415, though the only sythesis reported is that translated by Chemoleo.
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[*] posted on 11-12-2006 at 01:03


i have a question. do you know anything about role of pyruvic acid in biosynthesis of l-PAC?
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[*] posted on 11-12-2006 at 03:51


Yes, I know it's not clearly on-topic.
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[*] posted on 26-2-2007 at 13:09


Wikipedia says nitrATE and bisulfite will form hydroxylamine. Im pretty sure NO3- will reduce to NO2- and then will form hydroxylamido-N,N-disulfate anion. Heat for 1 hr at 100oC in acid to get hydroxylamine salt.

Sounds easy and I might try it. Any suggestions on what I should expect? For example, how will I know when the potassium hydroxylamido-N,N-disulfate has formed?
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[*] posted on 2-3-2007 at 19:33


Does bisulfite reduce potassium nitrate to nitrite?

I mixed some nitrate with Iron Out(sodium dithionite and sodium bisulfite) and some HCl in ice water. And nothing seemed to happen except SO2 gas coming off. I thought the nitrate would oxidize the the SO2 quickly.
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[*] posted on 3-3-2007 at 00:54


Don't trust Wikipedia on such things. Bisulphites are in my opinion unable to reduce the nitrate anion. In acidic enough conditions HNO3 should oxidize H2SO3 (or SO2). However this would produce NO2 and ultimately NO, but not hydroxylamine.
I think some Wiki author made a very common mistake of translating the old term "hydrosulfite" to bisulphite when it actually means dithionite. I assume this since sodium dithionite might perhaps be an appropriate reagent for the nitrate->hydroxylamine reduction in basic enough media, but I'm not familiar with inorganic chemistry so rather check Gmelin for the reference by yourself.




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[*] posted on 3-3-2007 at 13:21


I actually wrote down the equation for the reaction of nitrate with bisulfite and it turnes out that H+ does not play any role! So it would only react extremely slow in aqueous but it would work when the two are heated together (as I just read in the ionic nitrites thread).
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[*] posted on 26-1-2010 at 00:04
Hydroxylamine HCL synthesis from nitromethane+acetic acid+HCL


I found this description somewhere :

Quote:

400 mls nitromethane, 600 mls Acetic acid and 600 mls HCL are heated to just below reflux and held there for 2 hours then refluxed for 12 hours. The solution is reduced to half gone the cooled in fridge overnight and filtered.


I don't understand the mechanism behind the reaction, can anyone explain it? Yields are reported to be 100%+ somehow. What can the resulting product be washed/recrystallized with to increase purity? I assume this reaction utilizes glacial acetic acid and muratic acid, anyone have insight?
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[*] posted on 26-1-2010 at 08:10


"I found this description somewhere" does not say where you found it! :mad:

The only way to know more about the mechanism would be to check the original paper where the reaction was described. Sometimes the authors propose the mechanism and give supporting evidence or further reference. So why don't you check the literature? Two references where already given in our hydroxylamine thread, so half of the work is already done. All there is for you is a trip to the library.

The interpretation of the reaction by using the "likely mechanism" approach as though to students would give a tautomerization-elimination-hydrolysis route. The mechanism for the tautomerization of nitromethane is described in many schoolbooks, the mechanism of the elimination might or might not first involve the protonation of aci-nitromethane, while the hydrolysis of fulminic acid is rapid at such conditions and is well known since the year 1882 (J. Chem. Educ., 77, 851-857). I'm not going to waste time drawing such a mechanism proposal, but in short version and skipping a whole lot of intermediates and all the arrow pushing:

MeNO2_HONH2.gif - 3kB




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[*] posted on 26-1-2010 at 18:00


I wrote about this in another thread because I couldn't find this one. I found a method somewhere else but I could not find literature or any other type of reference.

(double post removed)

Edit by Nicodem: I merged your thread with this one. Next time do not double post, particularly not if you have already been receiving answers to your original post! And it is "HCl" as for hydrochloric acid, and not "HCL" as you keep mistaking.

[Edited on 27/1/2010 by Nicodem]
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[*] posted on 21-5-2010 at 06:35


Hydroxylamine has been considered as a monopropellant a possibility is the
borane salt , 3 HONH2•BH3 => B2O3 + BN + N2 + 9 H2

Related threads _
This reference on Hydroxylamine produced by reduction of HNO3 by electrolysis
http://www.sciencemadness.org/talk/viewthread.php?tid=1716#p...
is complimented by the detailed mention in the lower image posted below specifically
citing the method outlined on page 32 of The Manufacture of Chemicals by Electrolysis
from here _ http://www.sciencemadness.org/talk/viewthread.php?tid=13871#...

Hydroxylamine from primary nitroalkanes.gif - 11kB Hydroxylamine from HNO3 by electrolysisi.gif - 123kB
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[*] posted on 13-1-2011 at 23:56


Many thanks to kmno4 for alerting that Journal of Energetic Materials is for now freely accessible.
http://www.sciencemadness.org/talk/viewthread.php?tid=3724&a...

These interesting amine bases and their salts related by chemoleo here
http://www.sciencemadness.org/talk/viewthread.php?tid=1928&a...
methyl hydroxylamine nitrate, and ethylene dihydroxylamine, are not " hydroxyl " amines
once that has been replaced by an organic functional group. The nomenclature is then
Oxyamine. These analogs of methylene diamine and ethylene diamine contain oxygen bridging
the carbon and nitrogen. The adduct of Methylene (bis)Oxyamine CH2(-O-NH2)2 with
Nitramine or Dinitrourea is unresearched.
CH2(-O-NH2)2 •2 H2NNO2 => CO + 5 H2O + 3 N2
CH2(-O-NH2)2 • (HNNO2)2CO => CO2 + CO + 4 H2O + 3 N2

Synthesis and characterization of Methylene (bis)Oxyamine CH2(-O-NH2)2 salts
http://www.informaworld.com/smpp/ftinterface~content=a752776...

Synthesis and Characterization of Energetic 1,2-(bis)Oxyamino Ethane Salts
http://onlinelibrary.wiley.com/doi/10.1002/prep.200600027/ab...

High Density Energetic Mono- or (bis)Oxy-5-Nitro imino tetrazoles.pdf ( copy both lines below together )
http://www.chtf.stuba.sk/~szolcsanyi/education/files/Chemia%20heterocyklickych%20zlucenin/Predn%E1%9Aka%203/Doplnkov%E9%20%9Atudijn%E9%20materi %E1ly/High-Density%20Energetic%20Mono-%20or%20Bis(Oxy)-5-Nitroiminotetrazoles.pdf
References from the bibliograpphy 15, 16 , 17
[15]
a) C. S. McDowell, M.W. Barnes, U. S. Patent 3709920, 1973;
b) C. S. McDowell, C. Merrill, U. S. Patent 3714200, 1973;
c) C. S. McDowell, C. Merrill, U. S. Patent 3714199, 1973;
d) Russ. J. Org. Chem. 2004, 40, 124 – 126
D. V. Davydov, I. P. Beletskaya,
http://www.springerlink.com/content/r260w7181k546243
Available from Madhatter's archive

[16] ( these are the first 2 links cited above )
a) J. Energ. Mater. 2001, 19, 277 – 303;
K. Tollison, G. Drake, T. Hawkins, A. Brand, M. McKay, I.Ismail, C. Merrill,
b) Propellants Explos. Pyrotech. 2006, 31, 196 – 204.
T. Hawkins, L. Hall, K. Tollison, A. Brand, M. McKay,
( had been posted as a download from rapidshare )

[17] Synthesis of 12: ( 1,2-(bis)Oxyamino Ethane )
J. Org. Chem. 1984, 49, 4487 – 4494.
D.W. Dixon, R. H. Weiss,

related thread
http://www.sciencemadness.org/talk/viewthread.php?tid=13174

.
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[*] posted on 14-1-2011 at 01:09


http://www.erowid.org/archive/rhodium/chemistry/hydroxylamin...

Check this method, maybe it works. I think I saw that method on illumina-chemie.de also, but it gave very low yield, maybe they did not do it right.

I could try this method on test tube scale, just I need to substitute potassium salts for sodium. Would that work then? I only have potassium metabisulfite.

By the way, I read on wikipedia that it is explosive, is it? I dont want to prepare compounds that will blow up me.
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[*] posted on 12-8-2011 at 19:16


Quote: Originally posted by Organikum  


Even more funny is that phenylacetylcarbinol is WRONG as this describes an isomer - but as Neuberg and Hirsch who discovered the stuff made this mistake in their first publications (corrected it lateron) the name is still used.



weird

[Edited on 13-8-2011 by MeSynth]
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[*] posted on 2-9-2011 at 04:01


Thought i would chime in!

Reagents
150 ml 36% HCL
150 ml Glacial Acetic Acid (LG)
100 ml Nitromethane (Hobby Grade, apparently 99%)

Method
HCL, GAA and NM added to 1L flask and manually mixed. Mixture was heated, without mixing, to 60C and held for 30 minutes and then gradually increased to 90C and held there for 2 hours. Mixture took on yellow translucent appearance. Gentle reflux was achieved within 1L flask, no vapor was entering condenser. After 2 hours temperature was increased to 103C to achieve reflux and held for a 12 hour period. Mixture was cooled and left to stand for 24 hours. A white crystalline mass was achieved, flask was subsequently decanted, crystals agitated, removed and dried with a weight of 25 g. Decanted liquid was then reduced to half it volume, cooled and again decanted another 48g of crystalline material was recovered.



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[*] posted on 16-2-2012 at 17:54


Quote:
Preparation of Hydroxylamine hydrochloride by reduction of nitrite, using sulfur dioxide
40g potassium nitrite (KNO2) and 50g potassium acetate (CH3COOK) are dissolved in 100ml ice water. 750g finely crushed ice is added. Into this solution a stream of sulfur dioxide (SO2) is bubbled until the solution smells of SO2. The temperature must be kept below 0°C through the whole reaction. The salt of K2[HON(SO3)2] separates and is filtered off and washed with ice water. The salt is dissolved in 500ml 0.5 M HCl and boiled for two hours. Still boiling a solution of Barium chloride (BaCl2) is added as long as barium sulfate (BaSO4) precipitates ( CaCl2 may possibly work instead). The BaSO4 is filtered off and the clear filtrate is evaporated to dryness. The residue consists of Potassium Chloride (KCl) and NH2OH*HCl. Anhydrous ethanol(EtOH) is used for extraction of the Hydroxylammonium chloride, the KCl remains undissolved. The EtOH is evaporated on a water bath and the product can be recrystallised from water (mp 151°C).

Mix cold saturated solutions containing one molecular proportion of sodium nitrate, and two molecular proportions of acid sodium sulphite, and then adding a saturated solution of potassium chloride to the mixture. After standing for a day, hydroxylamine potassium disulphonate crystallizes out. This is boiled for some hours with water and the solution cooled, when potassium sulphate separates first, and then hydroxylamine sulphate.



Free hydroxylamine is both unstable and very hygroscopic, and relatively volatile (melts at 33 C and boils at 58 C), which is the reason it is normally found in the form of the hydrochloride salt.

If you make separate solutions in ethanol of hydroxylamine hydrochloride and potassium hydroxide, and then mix, you precipitate KCl, which you can filter off, and end up with a fresh solution on NH2OH in ethanol which can be used straight away and is much more stable.


I also had an idea to modify the ketazine process to use make hydroxylamine instead of hydrazine. Not sure if it would work...

Preparation of Hydroxylamine using the oxime process ?
Sodium hypoclorite (bleach) and ammonium hydroxide would react to produce chloramine gas (NH2Cl). This unstable poisonous would then be bubbled into a solution of methylethylketone and sodium ethoxide* dissolved in pure alcohol. The chloramine gas reacts with the methylethylketone and sodium ethoxide to form O-ethyl-methylethyloxime, with a structure CH3CH2ON=C(CH3)CH2CH3.
The byproduct, NaCl, precipitates out at the bottom at this time, since it is not soluble in alcohol. The progress of the reaction can be estimated by the formation of the solid byproduct.

Cool the contents and allow an hour for all the NaCl to settle at the bottom, then decant out the liquid into a separate container, leaving the all solid at the bottom in the first container. The O-ethyl-methylethyloxime then hydrolyzes with a 20% solution of sulfuric acid to form hydroxylamine sulfate. This would mostly precipitate out at the bottom if only a small amount of the acid solution is added.

*(The sodium ethoxide could be prepared by adding solid NaOH pure alcohol. After several hours, the bottom will consist of solid hydrated NaOH, a small layer of water saturated with NaOH will form immediately above, and the top layer will consist of pure alcohol with the associated sodium ethoxide dissolved in it. The top layer would be decanted out. Alternatively, Na2CO3, used to regulate pH for use in pools, and CaO, used as cement lime can be used instead of solid NaOH, 90% concentrated alcohol can then be used )
http://www.sciencemadness.org/talk/viewthread.php?tid=2656&a...
http://www.sciencemadness.org/talk/viewthread.php?tid=17074


Hydroxylamine (and its compounds) may also be of interest for propellents and explosives:
hydroxylamine perchlorate, hygroscopic solid
melting point between 87.5 and 89degC.
Decomposes at 120degC.
Drop height value of only 2cm, meaning very sensitive to impact.
addition of small ammounts of hydroxylamine perchlorate to several propellents could roughly double their burning rates
US 3748199 (1965)



[Edited on 17-2-2012 by AndersHoveland]
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