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Author: Subject: Hydroxylamine NH2OH Uses (and Production)
Ephoton
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[*] posted on 17-2-2012 at 23:38
Nitroalkanes


another use for hydroxylamine would be making nitroalkanes
from aldehydes.



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Waffles SS
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[*] posted on 18-2-2012 at 08:24


I have BASF Hydroxyl Ammonium Sulfate and i want to convert it to Chloride salt.I want to use barium chloride solution for this purpose
Unfortunately i cant evaporate solution to get dry Hydroxylammonium chloride by heat, because it will decompose during boiling.I am looking for another simple and safer method.someone can help me?

[Edited on 18-2-2012 by Waffles SS]
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bahamuth
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[*] posted on 18-2-2012 at 09:10


Quote: Originally posted by Waffles SS  
I have BASF Hydroxyl Ammonium Sulfate and i want to convert it to Chloride salt.I want to use barium chloride solution for this purpose
Unfortunately i cant evaporate solution to get dry Hydroxylammonium chloride by heat, because it will decompose during boiling.I am looking for another simple and safer method.someone can help me?

[Edited on 18-2-2012 by Waffles SS]


Evaporate under vacuum or in a desiccator (or in a vacuum desiccator), or even crystallize it in a beaker covered with a filterpaper to keep out dust, on top of a shelf. Though the latter might not do if the hydroxylamine has a very high affinity for moisture.

Hope this helps:)




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[*] posted on 18-2-2012 at 14:39


Quote: Originally posted by AndersHoveland  
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.

Why do you have this urge to clutter the forum with such nonsense? You were already told several times to limit yourself to referenced ideas. What you wrote above is such a flight of fancy that it deserves no comment, except that you are again trying to endanger the unaware people who might be ignorant enough to follow your advice. At least have the decency to try your bad advices on yourself first.
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AJKOER
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[*] posted on 9-11-2012 at 10:58


Actually, here is a better route to the poisonous NH2Cl per Wikipedia and my personal experience. To quote (see http://en.wikipedia.org/wiki/NH2Cl ):

"NH2Cl is prepared by the chemical reaction between ammonia and hypochlorous acid[3] under mildly alkaline conditions:

NH3 + HOCl → NH2Cl + H2O

In this reaction HOCl undergoes attack by the nucleophile NH3. At a lower pH, further chlorination occurs."

Note, 'further chlorination' mentioned above by Wiki does not stress the need to avoid the formation of the highly explosive and unstable Nitrogen trichloride, a thick oily yellow chlorine smelling compound, which is sensitive to organic substances, direct sunlight, shock and heat resulting in a deadly detonation. Historically, NCl3's explosions have costs limbs, eyes and more from even experienced chemists.

Wiki also provides an alternate preparation:

"Laboratory methods
The above syntheses are useful but do not deliver NH2Cl in pure form. For research purposes, the pure compound can be prepared by contacting fluoroamine with calcium chloride:

NH2F + CaCl2 → NH2Cl + CaClF "

Now, here is a new untried and simple synthesis to NH2OH (translation: big ?). If someone is willing to undertake it, I think the results would be interesting, although I would ascribe a low chance of success. Basis, per Watt's Volume 4, page 471 (link http://books.google.com/books?id=FyzPAAAAMAAJ&pg=PA471&a... on the reaction of moist Silver oxide to quote:

"—7. The moist oxide removes halogens from many halogen containing organic compounds, replacing the halogen by OH (e.g. 2NMe4I + Ag2O.H20 = 2NMe4OH + 2AgI)"

Here is another more recent reference (see http://www.bajpaigroup.com/study%20matrial/IC25.PDF ) using moist Ag2O or AgOH to form alcohols. Cited reaction:

R-CH2-X + AgOH (aq) --> R-CH2-OH + AgX

So the proposed reaction would be to add moist Ag2O to a small volume of dilute ethereal chloramine solution (as per this synthesis http://www.orgsyn.org/orgsyn/prep.asp?prep=cv5p0408 ) or an aqueous chloramine solution.

Ag2O.H2O + 2 NH2Cl --?--> 2 NH2OH + 2 AgCl (s)

One concern is that the Ether (Et2O) and a Ag2O.H2O suspension may not produce a reaction as water and Silver oxide do not dissolve in ether. The aqueous synthesis would have to be treated with HCl to form a stable salt.


[Edited on 9-11-2012 by AJKOER]
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[*] posted on 9-11-2012 at 21:55


I have had this thought also. One would naturally wonder whether the chlorine atom in chloramine could be substituted with a hydroxyl group. I think this would be theoretically possible, but the reaction is very problematic because there are other competing reactions, and any resulting hydroxylamine (being a reactive reducing agent) would tend to get immediately oxidized.

NH2Cl + H2O <==> NH3 + HOCl

NH2Cl + OH[-] <==> NH3 + OCl[-]

I am not entirely sure exactly how the N-Cl bond behave in nucleophilic substitution reactions. Usually with the hydrolysis of the N-Cl bond with water, it is the nitrogen atom takes the hydrogen atom, not the chlorine atom. But the other way may also be possible.

I believe this may be analogous to the reactions of haloalkanes with bases. Chloroalkanes generally do not react, while bromoalkanes are much more reactive, and iodoalkanes being even slightly more reactive. (DMSO is a good solvent for this reaction)

One investigation mentions that nucleophilic substitution on chloramine to form chloride ions proceeds at a rate more than 100 times that of chloromethane, which may still be rather slow. Consider for example that the hydrolysis of chloromethane with water takes around a whole year!
"Gas phase reactions of NH2Cl with anionic nucleophiles: nucleophilic substitution at neutral nitrogen", Roustam Gareyeva, Shuji Katoa, Veronica M. Bierbauma


Quote:

Anhydrous chloramine is an extremely hazardous (toxic and explosive) and unstable (decomposes at −50 °C) compound. Therefore, it was prepared in situ in an aqueous solution according to the modified Raschig method: Aqueous ammonia (30%) and a solution of sodium hypochlorite (11%–13% available chlorine), both chilled to −18 °C, were mixed in a 1:4 ratio by volume (a slight excess of hypochlorite) in an ice/NaCl bath. The resulting fresh solution of chloramine (10 mL, ≈3 M; kept in an ice/water bath at 0 °C) was immediately used for experiments.





The intermediate formation of hydroxylamine could potentially explain how some of the ammonia gets oxidized to nitrogen by alkaline solutions of hypochlorite.

NH3 + OCl[-] <==> NH2Cl + OH[-] --> NH2OH + Cl[-]

(2) NH2OH + OCl[-] --> H2O + N2 + Cl[-]

Again, chloramine itself acts as an oxidizing agent, and in fact aqueous solutions of chloramine are not entirely chemically stable, especially at higher concentrations. This should not really be surprising if we consider the equilibrium.

Unless there was some sort of protecting group on the hydroxylamine, it will get oxidized as quick as it forms. I am not sure, perhaps some sort of Raschig synthesis with gelatin would work, analogous to that for preparing hydrazine. Using something like (CH3)2C=N-Cl would probably not work either, because the resulting oxime could tautomerise to a nitroso group, which would then be first oxidized and then chlorinated to (CH3)2C(NO2)Cl

If you look at my previous post in this thread, you can see an idea for protecting groups that might work.
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[*] posted on 5-2-2015 at 06:42


how to produce hydroxylamine in lab??
;)


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king9491
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[*] posted on 5-2-2015 at 06:43
how to produce NH2OH


I need the process and how to synthesis NH2OH in lab.
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[*] posted on 5-2-2015 at 07:01


You can buy it on eBay for cheap. I found a listing from ChemSavers that is pretty well priced, in my opinion. Then again, I have little use for it, and would only purchase around 100g, so it depends on how much you need.

Org. Synth. 1923, 3, 61
DOI: 10.15227/orgsyn.003.0061
HYDROXYLAMINE HYDROCHLORIDE and ACETOXIME

http://www.orgsyn.org/demo.aspx?prep=cv1p0318

You could always attempt to get it from overseas, but in general, it helps if you are associated with a legitimate business entity.

[Edited on 5-2-2015 by Loptr]

[Edited on 5-2-2015 by Loptr]

I did not notice the discussion above reagarding this topic. You need to at least attempt to do your own book work before making a request like this. I have easily found several procedures in under ten minutes, and I do not have any academic affiliations at this time.

[Edited on 5-2-2015 by Loptr]
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Shivachemist
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[*] posted on 5-2-2015 at 07:05


I'm going to take a video about hydroxylamine soon ( Sodium carbonate, Sodium nitrite and sulfur dioxide as starting materials)
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[*] posted on 5-2-2015 at 07:12


@ king9491 there are numerous references to the preparation of hydroxylamine and its salts on this site, in Bauer in the forum library and elsewhere, try UTFSE

Also are you looking for the salts or the free base in a suitable solvent or the anhydrous hydroxylamine? The latter is highly unstable.
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