Homebrewing hydroxylamine
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- Опубліковано 15 вер 2024
- A.k.a. another fun usage of sodium nitrite, and one of the few reactions where nitrite acts as an oxidiser.
Also, I've now realised I called the intermediate product a bisulphonate instead of a disulphonate several times, both in the text and in the voiceover. Oops.
Thank you Yorkshire Chemist for that wonderful video and preparation.
Somehow it reminds me a bit the preparation of hydrazine hydrogenosulfate precipitate from urea-bleach, from ammonia solution and bleach as halogenator; in a sense there is here the less soluble hydrogenosulfite and hydrogenosulfate of NH2-OH (what is about equally interesting and unstable or powerful "fuel-reducer" as its sister hydrazine (H2N-NH2).
The analogy is not only into the molecule two electronegative elements linked together...see HO-OH (water peroxide), H2N-NH2 (hydrazine) and H2N-OH (hydroxylamine)... all 3 quite unstable, autocatalytically decomposable (or under the influence of tiny amounts of catalytic micro-pollutants), heat sensitive and decomposing relatively energetically.
A second analogy is the formation of cristallization product for isolation in organic chemistry with aldehydes and ketons:
R-CH=O + H2N-OH --> R-CH=N-OH + H2O (aldoxime)
Ar-CH=O + H2N-OH --> Ar-CH=N-OH + H2O (aldoxime)
(R-)2C=O + H2N-OH --> (R-)2C=N-OH + H2O (ketoxime)
(Ar-)2C=O + H2N-OH --> (Ar-)2C=N-OH + H2O (ketoxime)
R-CH=O + H2N-NH2 --> R-CH=N-NH2 + H2O
R-CH=N-NH2 + O=CH-R --> R-CH=N-N=CH-R + H2O
(R-)2C=O + H2N-NH2 --> (R-)2C=N-NH2 + H2O
(R-)2C=N-NH2 + O=C(-R )2--> (R-)2C=N-N=C(-R)2 + H2O
Ar-CH=O + H2N-NH2 --> Ar-CH=N-NH2 + H2O
Ar-CH=N-NH2 + O=CH-Ar --> Ar-CH=N-N=CH-Ar + H2O
(Ar-)2C=O + H2N-NH2 --> (Ar-)2C=N-NH2 + H2O
(Ar-)2C=N-NH2 + O=C(-Ar)2 --> (Ar-)2C=N-N=C(-Ar)2 + H2O
Finely and nonetheless; while ammonium reacts witch forms a nitrate salt (AN or NH4NO3 ) relatively unsensitive on its own that can be used as an energetic low order material (3-3,5 km/s for its velocity of detonation VOD) and oxydizer, or boostant in some compositions to generate more power exhaust from burning gases (more CO2, H2O and less C-graphite or C-diamond (energy loss and waste) as into the case of TNT) and equilibration of oxygen-balance (O.B. usually negative and ideal if = 0) of oxydation by going to the maximum exhaust of energy and maximum complete burning of the energetic mix composition... but when you consider hydrazine nitrate (HN or NH2-NH3NO3), hydrazine dinitrate (HDN or O3NH3N-NH3NO3) or hydroxylaminium nitrate (HAN or HO-NH3NO3 (NH4NO5); you look at an upper level because those are playing into the higher ground of the HEM (high energetic materials) with increased sensitivities (to heat and shock) , higher VOD, higher volume of detonation gases (VoDG); higher heat of decomposition... for understanding the max of VOD of HEM is in the range 9-11 km/s (yeah Mach 27-33 (1 Mach is speed of sound into air and this is about 27 times faster).
AN VOD = 3000-3500 m/s
HN VOD = 8900 m/s
HDN VOD = 7800m/s (denser but also a bit over-oxygenated thus energy loss by positive OB)
HAN VOD = 8000 m/s
For the rest energetic materials of the hydroxylamine family exists out of vicinal - (C=O)-(C=O) - and dehydrated like furoxans, furazans cyclic energetic rings but some of the "hydrated" poly-hydroxylamine as salts of cations are quite energetic too.
The energetic properties are also possible from salts from oxydizing anions (nitrate, perchlorate, bromate, periodate, nitrite, nitronate, dinitronate, nitroformiate, ...) of organic hydroxylamines of the type O-hydroxylamine or N-nydroxylamine, and this brings the usuals HEM salts of amines to a higher lever because of higher performances (density, sensitivity, VOD).
Anyway very interesting.
PHZ
(PHILOU Zrealone from the Science Madness forum)
o_O
Semicarbazide is another classic derivatisation reagent for aldehydes and ketones. It can be prepared from urea and hydrazine. Perhaps another idea for a project.
Might be a fun project to make the Oxime of Salicyladehyde (Salicylaldoxime) which apparently forms colourful coordination complexes with transition metals.
Thorough documentation, great instructions, and awesome video work.
Fantastic stuff, keep it up!
Thank you for this video! I really need someone to film this process so that I can learn how to successfully make hydroxylamine.
I honestly don’t know why I saw this in my recommended, but I gotta admit it it’s pretty cool. How’d you make your own lab from home? Got any tips?
glad you liked it!
for making a home lab I can offer several handy tips:
* have a split-level late Victorian terraced house built on the side of a hill, which is steep enough that the street-level entrance opens onto the front room and living room, and the kitchen, back garden and former coal cellar are on the lower level
* if the cellar is large enough, get a damp course installed (this will also boost your house's value when you eventually sell it)
* acquire reagents, glassware and assorted equipment over the course of several months
* don't skimp on the glassware - decent quality glassware with ISO/ASTM standard ground-glass joints is worth its weight in gold
* if you're working with something that generates lots of toxic/corrosive/otherwise unpleasant fumes, buy a portable extraction fan (the kind used for building work) and run the ducting out of the kitchen window
@@yorkshirechemistI'm still a high schooler, you don't have to crush my hopes in dreams like that ;-;
On a serious note I greatly appreciate the glassware tips, just bought L.G. Wade's Organic chemistry so hopefully I'll do something fun however makeshift it may be. Keep up with the videos! Not quite sure I entirely understand everything but it's stimulating enough to give me encouragement to do things for myself
Ooh I live in a late Victorian terraced house, sort of on top of a hill, not split level, apparently not steep enough, and there's no cellar, just a dusty mess under the floor. My hopes of creating a home lab have been dashed! I do have a basic distillation setup in the conservatory though. BTW I found this channel via a comment on a Thy Labs video. I think this may be the first British home chemistry channel I've seen on YT. Subbed.
@@igotes I live near Barnsley, so there's no shortage of steep hills round here - but seriously, the coal cellar is huge in comparison to the general size of the house
also, Sodium Interesting is a Britbong amateur chemist with quality content; he's more focussed on inorganic chemistry, and his style of videos is very different to mine, but he's ambitious and he's well worth watching
@@yorkshirechemist Thanks, I'll check out his channel. Regular uploads and all!
There's a fair few hills around here in Devon too, I just don't live on a particularly steep one :)
Just got a new subscriber! Great video! I appreciate you doing something that other chem UA-camrs haven't done
thank you! and that is one of the fundamental reasons I make videos, to demonstrate methods that haven't been done before on camera
based Brauer aficionado, together with Vogel and Organikum the holy trinity of practical chemistry tomes
Great stuff.
Can be prepared from chloramine solution and NaOH I believe.
now there's an idea for a future video...
But NH2Cl is quite reactive (towards mucosas (eyes, nostrils, lungs and sweat wetted thin skin) and carcinogenic and most likely unstable or autocataliticaly disproportionable and because into the process from NH3 and NaOCl you also get N2H4 that is uncompatible with NO2(-) and both destructs and probably with NH2OH or NH2Cl.
NH2Cl also tends to form by oxydiredox the unstable NHCl2 and NCl3 (the terrible yellow stuf so unstable watching at it can result into a disaster ;o) ).
So the mild reductive solution depicted here si probably the only available, safe and viable to DIY chemists.
So via NaNO2 and NaHSO3, Na2SO3 or SO2.(beware toxic gas).
PHZ
(PHILOU Zrealone from the Science Madness forum.
Do you have good ventilation?
very cool video thank you for your time.
amazing ❤
Keep up the good work mate!
What exactly is "methylated spirits"? We don't use that term here I don't think.
We call it "denatured alcohol". It's Ethanol with something like 10% or so of Methanol added so that it cannot be safely drunk.
industrial methylated spirit (the stuff I used here) is 95% ethanol / 5% methanol
you can buy non-industrial methylated spirit over the counter from any good hardware/DIY shop, but that also contains petroleum spirit and pyridine, and is dyed with methyl violet
the main purpose of the dye is to make it visually distinct from white spirit, which is high-boiling petroleum ether; the two are not interchangeable
@@yorkshirechemist OK, just wasn't 100% sure what the term meant. I've got some absolute ethanol that I'll use then.
Why can you dry the product with acetone instead of forming the oxime?
because it's not at all reactive at room temperature; I made that mistake when trying to dry phenylhydrazine, which is why I recommended drying it with THF
Hydroxylamine bisulphonate? not bisulphate? first one is amide second is just salt. just asking because i am not sure with one is right
the disulphonate (which I called bisulphonate throughout the video) is the poorly soluble intermediate product, and the bisulphate salt is the much more soluble final product - hope that helps
@@yorkshirechemist thanks! i was thinking is it some mistake my mind catched or some additional chemical i never come about in readings. Now everything is clear!
How do you make iron stabilized hydroxamic acid?
the acid is formed from the reaction between hydroxylamine and a suitable ester/acid chloride; it's not something I've tried myself
@yorkshirechemist That is my understanding, too. It is a test for esters. Ester plus hydroxlamine and iron give colourful complexs. Only you need to have hydroxylamine, which is very hard to get. That chemistry book is worth its weight in gold or 700 euros for all 3 bands.
You bought your nano2 from poland?
I did - Poland is one of the few places where vendors are still willing to sell it to individuals, probably because the culture is much less litigious than in western Europe
@@yorkshirechemist yeah, the laws here are pretty chill
move your phone away from the recording device
I was going to say exact same fucken thing :D
@@ShimoriUta it's an easy mistake to make. But probably not a good idea to have a phone around any microphone and it's cables..
So , what is the purpose of this chemical ?
it's extremely versatile, it can have any purpose you want it to 😎
but seriously, you can use it to purify aldehydes and ketones, you can use it in Mannich reactions, you can use it to make nitrous oxide, and when you combine it with aldehydes or ketones, you can reduce the resultant oximes to amines and make some very interesting compounds that way
Dope.
Indeed.
here's one flor the algo-
hello fellow "possible terrorist list" people
Don't project
Nah. We're just interested in......."Capybaras" if you know what I mean.
in fairness, this stuff is not even flammable, so it would be a total failure as an explosive
with that knowledge, what kind of terrorists with an IQ above 70 would even go for it?
I enjoy your videos because you record them so well