Sciencemadness Discussion Board - Azide Production

Azide Production

HgDinis25 - 20-4-2014 at 06:56

I've been studying some ways to produce Azides. One method that I'm interested on is the one represented by this video:
http://www.youtube.com/watch?v=FOgKM7RvLKw

It's one of the most common ways to obtain Potassium Azide, AFAIK, with available chemicals for the home chemist.

Can this reaction work to produce Sodium Azide, if the KOH is substituted by NaOH? I ask this because I don't know the reaction mechanisms nor what's happening. Can someone share some information about the mechanisms?

Also, can Lead Azide be produced by the direct reaction between Lead Nitrite and Hydrazine Hydrate?

hissingnoise - 20-4-2014 at 07:18

Quote:

It's one of the most common ways to obtain Potassium Azide, AFAIK, with available chemicals for the home chemist.

And there's this way?

HgDinis25 - 20-4-2014 at 07:31

Quote: Originally posted by hissingnoise

Quote:

It's one of the most common ways to obtain Potassium Azide, AFAIK, with available chemicals for the home chemist.

And there's this way?

Of course, you can also buy it. But, where's the fun of it? And what happens when you can't no longer buy it?
Also, imagine that the mechanisms happening in this reaction lead you to get used to them and perhaps create a new synthesis, using the same mechanisms, on a completrly different unavailable chemical?

Zyklon-A - 20-4-2014 at 07:49

Make hydrazoic acid:

Attachment: Hydrazoic acid.pdf (86kB)
This file has been downloaded 423 times
Of course you need sodium azide for this, but you can make any azide from hydrazoic acid - which makes this very useful. Be VERY careful if you do this. It is not for a beginner.

[Edited on 20-4-2014 by Zyklonb]

HgDinis25 - 20-4-2014 at 07:55

Zyklonb, the paper you suplied, although having good information about HN3, starts off with Sodium Azide. My topic IS a bout Sodium Azide production, so assume I don't have any.
Also, I'm really interested on the reaction mechanisms of the reaction I refered to in my original post. Thanks anyway for the paper.

Zyklon-A - 20-4-2014 at 08:06

Yes, I think it would be much better to simply buy it. If you have the reagents to make sodium or potassium azide as seen in that video, go right ahead! But it will absolutely not be cost efficient.

HgDinis25 - 20-4-2014 at 08:17

Zyklonb, Yes I have the reagents. But you misundestand my intent. I want to understand the reaction mechanisms, and the multiple reactions happening. That way, I can acess if Sodium Azide can also be produced, by using NaOH instead of KOH.

hissingnoise - 20-4-2014 at 08:33

Quote:

That way, I can acess[sic] if Sodium Azide can also be produced, by using NaOH instead of KOH.

OK, don't take this the wrong way, but if your understanding of inorganics is so lacking, you probably shouldn't attempt any but the simplest procedures until you, at least, get a feeling of how they proceed?

HgDinis25 - 20-4-2014 at 08:37

Quote: Originally posted by hissingnoise

Quote:

That way, I can acess[sic] if Sodium Azide can also be produced, by using NaOH instead of KOH.

Of course, if someone is lacking inorganic understandig so bad, they shouldn't try it. I completrly agree.

Now tell me, where is my lack of knowledge? Or is it you that isn't understanding my question? Perhaps you could state why you thin I lack the proper inorganic knowledge. That way I can see why I'm wrong or why you're wrong. Just making empty assumptuions won't help me...

hissingnoise - 20-4-2014 at 08:41

Quote:

Now tell me, where is my lack of knowledge?

You're serious? FTW!

HgDinis25 - 20-4-2014 at 08:51

Ok, I see this is getting me nowhere. I'll try to give more details about where I'm stuck.

I know that IPN reacts with Hydrazine Hydrate, Potassium Hydroxide and Ethanol, yelding IPA, Potassium Azide and water. Now, is the KOH there to react with any HN3 produced to form the KN3 or does the potassium ion plays an important role in the reaction?

I could assume that IPN is Hydrolised by KOH to produce the corresponding alcohol (IPA) and KNO2. The KNO2, produced in situ could then react with Hydrazine to make the azide. Is this plausible? If so, why is Ethanol used? As a reaction medium? But the Hydrazine is in the form of the Hydrate so water will be present as well.

hissingnoise - 20-4-2014 at 09:19

Quote:

If so, why is Ethanol used?

Again, a question you really shoudn't need to ask ─ it's to precipitate the salt which is near-insoluble in that solvent . . . ?

HgDinis25 - 20-4-2014 at 09:25

Quote: Originally posted by hissingnoise

Quote:

If so, why is Ethanol used?

Again, a question you really shoudn't need to ask ─ it's to precipitate the salt which is near-insoluble in that solvent . . . ?

Could be because of end product solubility. Could also be because it acts as a catalyst. Couled also be because of the low solubility of contaminants formed. That's why I'm, asking. I am not sure.
Neither are you, it seems. Can we try reaching a conclusion, by discussing it, instead of you droping useless coments?

Anyway, this book helps a lot:
http://books.google.pt/books?id=VqosZeMjNjEC&pg=PA119&am...

It also explains the mechanisms, so I guess I'm done here. I hope it helps anyone out there. If I had found it earlier it would have saved me a lot of trouble.

Anyway, it seems you were wrong about the ethanol use my friend

Next time don't assume you simply know it all. And if you do, explain why. Because your participation in this thread could have been avoided at the expense of making everyone else happier.

Thanks anyway.

hyfalcon - 20-4-2014 at 09:26

Have you at least read this whole thread yet? http://www.sciencemadness.org/talk/viewthread.php?tid=1987

That's good for a start and read any and all references posted in that tread. THEN ask your questions in that tread instead of starting a new tread on azides.

HgDinis25 - 20-4-2014 at 09:28

Yes Hyfalcon, I read that ALL THREAD. It's a sticky one about my question, it's obvious I would read it. Why do you even ask? I, however, must admit I didn't read through all the references, some were about other methods or about Hydrazine production. Anyway, the answer I wanted wasn't there, was on the book I referenced on my earlier post.

hissingnoise - 20-4-2014 at 09:34

Riiight! I'm done with this total idiocy from our top "Darwin Award contestant" . . .

HgDinis25 - 20-4-2014 at 09:40

Quote: Originally posted by hissingnoise

Riiight! I'm done with this total idiocy from our top "Darwin Award contestant" . . .

Look, I don't understand why so much irony towards a question made in the beginnings topic that no one could answer. That post was unnecessary as is the one I'm writing. I'm only writing to tell that I know not all users here are as close minded as you, to disrespect a fellow user of this community like what you are doing now. If you really think yourself so good as to not answer a scientific question, not SHARE information about a scientific topic, then you shouldn't be here in the first place.

You were also wrong about the ethanol use, so you didn't know the full answer about what I was asking.

Again I ask, Why all this irony and nonsense?

BromicAcid - 20-4-2014 at 10:25

Please HgDinis25, it's one thing to post a YouTube video as a reference but please explain what is in the video. Threads are already accumulating with YouTube links and no additional information where the video's have been taken down which renders the post useless. Also, although the video was only 2 minutes in length, it would have only taken me 10 seconds to read the two sentences describing the video.

As for your question on KOH vs NaOH, hissingnoise was on you because most chemists lean early on that the two are pretty much interchangeable, being that they are strong bases and dissociate 'fully' in water. There are a few compounds stabilized more by the larger potassium cation but for the most part you can swap the two with impunity.

I don't know why you said hissingnoise was wrong about the ethanol, note that in the supplied reaction scheme nowhere does ethanol show up as a reactant. It is simply the right solvent for this reaction, starting materials are soluble, final product is insoluble (note the ethanol washes), that's the ideal situation.

hyfalcon - 20-4-2014 at 12:36

I still say it would have been better for you to ask your question, which is obviously about azides, in the azide thread, that's all.

HgDinis25 - 20-4-2014 at 14:31

Bromic Acid, yes knowing that NaOH and KOH can be swapped is common knowledge. Yet, I nedded to ask because I didn't know if that could be done in this reaction, again because I didn't understand the mechanisms, now I do thanks to the book. And I specified that on one of my posts. We all know that solubility of those two may change depending on the solvent used or the end products may also have completrly different solubility values. We all also know that. C'mon, those are all valid doubts and questions, so hissingnoise was way out of line by saying all those, lacking a better word, idiotic things.
He was wrong because ethanol is used mostly because of Hydrazine Hydrate solubility and because of it's nitrous ester. Yes, because the reaction will produce the Nitrous Ester of the alcohol used. Therefore, if Methanol was used it would make an impossible to reflux ester (b.p. -17 IIRC). If IPA was used it would lower the solubility of Hydrazine Hydrate too much.
So yes, he was wrong and thought himself in the right of doing a useless post about the Darwin Awards (sic).

hyfalcon, Yes I could but If everyone starts making questions there just because it is related to Azides, that topic would start to became huge, and finding info would be next to impossible. Again, If that was my mistake I have no trouble admiting it. Still doesn't explain hissingnoise's suddent rage against me...

hissingnoise - 22-4-2014 at 05:37

Quote:

Still doesn't explain hissingnoise's suddent rage against me...

Rage HD? What are you on about?

If you can't take the slightest whit of criticism without this interminable whingeing, you probably shouldn't be here . . .
And I'm informed that you're barely into your teens, and here you are setting to fuck around with compounds which have maimed and killed several competent chemists in the past hundred years!!!
But, since you appear to lack even basic chemistry knowledge I can only hope you do not get your hands on azides!
If you're intent on simply making bangs, try using something that won't fuck up the entire rest of your life?

HgDinis25 - 22-4-2014 at 12:04

hissingnoise, I have no interest on producing azides. I just asked about reaction mechanisms of a particular procedure to learn them. My only goal is learning and perhaps I could use the mechanisms of this reaction in another reaction. I don't know if you know but one can learn how a reaction goes without the intent of reproducing it. The two concepts can exist absent the other. Do you understand this, or is it too much for you?
Also, I didn't get the age mention. Does it matter if I'm 5,6, 14, 20, 60 or 80? There are cases of 13/14 years old already in university because they are very intelligent. The age factor mainly interfears with the experience factor. If the only thing you want is to learn the theory, then the age factor doesn't apply at all. Again, your argument is incorrect.
If you think I lack even bacic chemistry knowledge, I would be more than eager to learn some from you

blogfast25 - 22-4-2014 at 12:05

Quote: Originally posted by hissingnoise

And I'm informed that you're barely into your teens, and here you are setting to fuck around with compounds which have maimed and killed several competent chemists in the past hundred years!!!
But, since you appear to lack even basic chemistry knowledge I can only hope you do not get your hands on azides!

It is indeed a mystery why some total beginners seem to want to start their careers with something potentially... career ending, if not worse.

I really put it down to 'a little knowledge is a dangerous thing'.

Those who aren't willing to start by doing simple, interesting and mostly safe experiments are unlikely to go very far.

But I guess anyone claiming this must be 'closed minded' (a ridiculous definition of 'closed minded' if I've ever seen one)

Quote: Originally posted by HgDinis25

If you think I lack even bacic chemistry knowledge, I would be more than eager to learn some from you

That you lack basic chemistry knowledge is something you keep demonstrating here.

The positive thing is that you have no intention of preparing azides. Good: keep it that way!

[Edited on 22-4-2014 by blogfast25]

Chemosynthesis - 22-4-2014 at 12:59

I think a lot of conflict here could be avoided. I have a rather long list of friendly suggestions, so please don't read these as if I am attempting to be negative.

HgDinis25, I appreciate your asking questions, even if you didn't follow protocol by posting in the established thread. Rather than minimize other peoples' expressed desires for you to post in such a thread, after having another thread on the same topic moved to Detritus, you should incorporate their suggestions on forum decorum into your behavior. That's the best way to get people to answer you.
Thread link: http://www.sciencemadness.org/talk/viewthread.php?tid=30128

Quote: Originally posted by HgDinis25

Look, I don't understand why so much irony towards a question made in the beginnings topic that no one could answer.

It's not irony, and a lack of answering isn't necessarily indicative of inability to answer; there are many questions that are left unanswered on the forums that members could easily reply to, but don't, for a multitude of reasons. Most I have encountered are either of questionable legality, or make members uncomfortable due to safety concerns. Questions on azides can fall under either.

No one here is obligated to help you. You absolutely have to realize this. We are here in our spare time and can not be compelled to answer a question or post a methodology. While love of the hobby brings us here, you usually pay for tutoring or schooling, as many of us have. My impression is that there is valid concern on younger and less experienced members being handed too much information without demonstrating a maturity or comprehension about the dangers of certain reactions or chemicals.

You found an answer to your question, which could be taken to mean you did not adequately search earlier. The reaction you were interested in is in organic chemistry textbooks, and probably the library on this forum. Generally the forum expects a poster to do their due diligence in perusing the literature before asking a question here.
That's why there are links to free texts here: http://www.sciencemadness.org/talk/viewthread.php?tid=6664

In fact, in the forum guidelines are somewhat applicable here. I would like to politely point out where I think people take issue:
3. Get acculturated: I believe this would include posting in the azide thread rather than starting your own.
9. List of things to avoid, subsection Avoid cross-posting or double-posting: I believe this would include your thread in Detritus.
And a friendly recommendation that you view the post in that thread titled "The literature searching guidelines," as they will help you foster your interest in chemistry without having to rely on youtube, and I think it will help you avoid conflicts from members who are concerned.
http://www.sciencemadness.org/talk/viewthread.php?tid=19143

If you're interested in learning more about potential mechanisms behind the ion interchangeability in this thread, you may look into J. Org. Chem., 1958, 23 (11), pp 1595–1599 (DOI: 10.1021/jo01105a001). Once you see the difference between alkyl and arylhydrazine nitrosation, and why the reaction equilibria is altered between the two cases, I believe you will be able to reach conclusions about the interchangeability of ions in the role they play here, particularly with BromicAcid's post. Note that the publication date was 1958, so I'm pretty sure plenty of members understand nitrosation well, as I know I've seen posts on similar topics before, as it's a very basic introductory undergraduate chemistry reaction. When you try to insinuate that membership here is somehow incapable of answering that, it's insulting and indicative of your presumed lack of formal education. Neither are liable to get you positive attention, in my experience.

I happen to work with azides almost daily, and you should be aware that there is no specific treatment for azide poisoning, so if you do decide to try and work with them, you should be warned.

Also, Hissingnoise was actually correct about general solvent selection, as noted above. Usually one doesn't explain why alternative solvents are inappropriate to justify why the "best" solvent is the best. Methanol is also toxic via ingestion, inhalation, and percutaneous absorption, by the way... and this is often understated in the workplace. I've seen HPLC techs get tested for various liver enzymes and notice they had undetected chronic toxic exposure. This happens to be in a medical facility, too, so they are more cognizant than others of these risks since we run biomedical tests inhouse, they use protective equipment, and many of our staff is specifically attuned to medical issues. This is important because it's a common solvent that actually has under represented potential for danger, and it's relevant to why other solvents aren't used. Cost is often also an issue.

It seems to be rather rude, at least to me, for you claim hissingnoise incorrect. That probably doesn't reflect on positively, which is unfortunate and unnecessary. Also, when scientists publish, it is considered necessary to define your abbreviations that are not standard IUPAC nomenclature. An example, when you use "IPN" to presumably abbreviate isopropyl nitrite. You are expected to use the full name first. Example: In this sentence, I will abbreviate isopropyl nitrite (IPN).
It might feel annoying, but we do this every time we publish.

[Edited on 22-4-2014 by Chemosynthesis]