NurdRage - 2023-12-16
In this video, we make isopropyl nitrite without using sodium nitrite. Typically, amateur chemists use sodium nitrite, hydrochloric acid, and isopropyl alcohol for this process, but sodium nitrite is becoming harder to obtain. This sodium nitrite-free pathway goes through nitrosylsulfuric acid which can be made using more easily obtained fuming nitric acid and sulfur dioxide. To make fuming nitric acid from you can use this video: https://youtu.be/88gbfCnrV8o How to make sulfur dioxide: https://youtu.be/2AFKlLSwUZ4 To begin, we dry 400mL of 99% isopropyl alcohol using molecular sieves 3A (that itself was previously dried at 200 Celsius). In a separate flask, we mix 63g of fuming nitric acid with 150mL of glacial acetic acid, keeping the mixture cool in an ice bath. To make glacial acetic acid, i refer you to Nile Red: https://www.youtube.com/watch?v=8iG_qnkF08Y or Amateur chemistry: https://www.youtube.com/watch?v=FOb4R5_LK-I Meanwhile, a sulfur dioxide is injected from a sulfur dioxide generator into our nitric acid mixture forming nitrosylsulfuric acid. After the reaction, the nitrosylsulfuric acid precipitates out. It's filtered and i got a Yield of 117g or 91%. Due to its instability, it must be used promptly. It's slowly combined with chilled isopropanol, creating isopropyl nitrite. Careful addition and temperature control are crucial to prevent decomposition. After the reaction, we add ice and make up the volume to 1L to separate the isopropyl nitrite. A separatory funnel is used to recover the lighter organic phase of isopropyl nitrite. The final yield is 56g or about 63% based on nitric acid, with an adjusted yield of 69% based on nitrosylsulfuric acid quantity. While this method may not match the ease of sodium nitrite-based processes, it serves as a valuable alternative for those facing sodium nitrite availability challenges. Donate to NurdRage! Through Patreon (preferred): https://www.patreon.com/NurdRage Through Youtube Memberships: https://www.youtube.com/channel/UCIgKGGJkt1MrNmhq3vRibYA/join Glassware generously provided by http://www.alchemylabsupply.com/ Use the discount code "nurdrage" for a 5% discount. Twitter: https://twitter.com/NurdRage Reddit: https://www.reddit.com/r/NurdRage/ Instagram: https://www.instagram.com/nurdrageyoutube/
"Other YouTubers better than me"
Excuse me Mr Rage, that is not true. You are one of the best chemistry YouTubers. Especially your sodium production series is absolutely amazing! Don't underestimate yourself Mr Rage, you are one of the best in chemistry. I'm a chemist myself but still learn lots of new things watching your videos!
Indeed, Nurdrage is my OG chemistry youtuber, think I saw him before the periodic table of videos even
Especially given NileRed is so obviously inspired by NurdRage that people thought they were the same person in the early days...
Sodium series is what got me started watching. I still watch again from time to time. The failures were just as interesting as the wins.
Yes, the original and best!
I watch every single video when i can!
Fully agree.
I sympathise with the person as whoever it is as it is really getting harder to acquire technical (or better) grade resources.
We‘re left with what? Nail polish remover. Cat litter.
When we move on from fossil fuels there won’t be many sources for a plethora of chemicals too.
Do I understand even half of the chemistry in these videos, NO!
Do I still get excited when a new video pops up, YES!
Something about seeing someone good at their craft makes me happy.
Amazing video, this method for making isopropyl nitrite looks really good, I might try it sometime, also thank you very much for mentioning my channel, it really is an honour :)
Thumbnail: ONO
Me: OYES
So glad you're back! Super useful process! Looking forward to running it myself!
So happy you are active again, NR!
Can't believe you're still around but I'm glad you are😊
great video as always. Nice to see a different prep.
There may be others with more experience but I think you are one of the best at explaining the processes.
Fabulous stuff Nerdy !
Man I love this stuff. I'm not sure my lease will cover a fumehood installation, so until I own a place, I'm just gonna keep living vicariously through this channel.
You mentioned "better YouTubers than me"
While I wouldn't I wouldn't say anything against them as I watch most of them myself.
I would say not to sell yourself short.
Hearing the robotic voice talking about chemistry has been WAY better for my mental health than any pill or doctor visits.
Your videos are a way for me to live vicariously. Mostly because "iv played my cards wrong" but also because some of this is beyond my understanding or safety concerns come up. But if it wasn't for videos that you put out all those years ago there's a good chance that my love of chemistry and science would have died along with many other interests...not to mention I'd probably not be around to find out about those YouTube channels and certainly wouldn't be leaving this comment.
Thank you for all your uploads ❤
You have no room to call other YouTubers better than yourself! You went the hard route good lerd!
Great upload!
1:54 you'll allways be our OG chemistry youtuber
This was fun. I was believing your deep blue solution could be n2o3 and then you said it. I don't think I could know enough about notrosylating agents and the process, or the products, but it seems very interesting organic reactions can be found in their employ. Alkyl nitrites are definitely interesting. Thank you for this. ❤
Have a great Xmas. Best wishes from Australia
Our home chemist hero strikes again!
Very helpful.
But I would still like to find some nitrite!
Great video
great video, thank you
Awesome sauce! I wish we could see some mechanisms, they make it so much easier to understand
hmmm.. good point! i'll see what i can do in future videos :)
@@NurdRage if glacial acetic acid is moderately flammable and fuming nitric acid is a powerful oxidizing agent why does it not result in the glacial acetic acid and fuming nitric acid mixture igniting or a violent chemical reaction when you mix the glacial acetic acid and the fuming nitric acid at the start of this video ? Is it because you put the mixture of glacial acetic acid and fuming nitric acid in an ice bath soon after mixing them that those acids didn't react violently when you mixed them ?
Adding a small aquarium pump in the water bath increases the cooling efficiency - I found this beneficial especially at scale because of the lower area-to-volume ratio. Professional labs use jacketed vessels or even countercurrent heat exchange.
Thanks for sharing
Nice one buddy.
That nitrite functional group has seen things
I feel all invounlentary smooth muscle below my waist relaxing just thinking about the scent of alkyl-nitrites.
gapes wow really?!
Thanks NurdRage🎉
Amaizing process! definitely learnt something new. 👍
"ono" the FBI-Agent said.
Are you going to make sodium azide with the IPN?
That wet chemistry is fucking insane!
as a pharma QC chemist myself i always wondered how to get a Job in a small Lab.
i actualy find it very boring over the years to do my analysis and was always interested in the synthesis side of things.
how would your search for a workplace like that and what would the jobtitle be?
now i´m a Chemical lab technician and all jobs in that field bring me be to QC for pharma.
not sure if this has been mentioned but there may be a slim chance that explosive acetyl nitrate may be formed due to the reaction of the nitric and acetic acids in the presence of trace sulfuric acid (as the FNA and GAA although "anhydrous" in reality will always have trace water) but i honestly dont think that should be an issue considering the low temperatures but im not entirely sure. neat video though, ive also been investigating different ways to make nitrosating agents (more for sandmeyer reactions) and it seems this probably beats out my idea which was the HCl/NaNO3/Cu method to generate nitrous acid in situ but ill probably still try it
also finally another person who doesnt call fuming nitric acid red fuming, this is something that has always irritated me as the stuff from a typical distillation is yellow not red and doesnt have the issue of building up pressure (at least as much/quickly)
Interesting! i think acetyl nitrate isn't made here because the conditions aren't dehydrating enough, any that is made would be a trace. I think a lot of milder nitrating reactions are done in acetic acid, so if acetyl nitrate was an issue we'd know about it. Although granted, i don't do much nitrating so maybe it is well known and i never came across it!
Yeah fuming nitric acid has been a peeve of mine as well. RFNA has different enough from fuming nitric acid that they should be viewed as different substances. Some reactions occur in RFNA that do not occur in fuming nitric acid. They are not interchangeable!
indeed the reaction conditions are not favorable but it wouldnt do harm to put some water in the filtrate. the nitrations with acetic generally are done so as the formed acetyl nitrate (in equilibrium) is more selective/efficient in some cases eg nitration of salicylic acid w/ AcOH/Ca(NO3)2, in some cases not requiring a strong acid whatsoever but generally the acetyl nitrate shouldn't pose much a hazard if it is not purposefully isolated in large amounts.
for the nitric acid i have also noted that if azeotropic or possibly even less concentrated acid is simply saturated with nitrogen dioxide (the distillate from the sodium bisulfate method is an example of this) it will still have the capability to ignite nitrile albeit a little slower and perhaps not always hypergolic, the oxidizing properties are not only from the nitric acid itself but also the NO2:N2O4 equilibrium which makes sense considering NO2/N2O4 is used in hypergolic rockets and nitric acid with NO2 has been established to cause certain reactions to fail and/or runaway
The iupac name of the isopropyl nitrite is 2-nitropropane. This chemical can be named in many ways too
assuming it works to make methyl nitrite from methanol, a primary alcohol, i assume it will also work with ethanol to produce nitroethane?
Hey there.. can you please tell me can nitric acid be made using sulfuric acid and ferric/iron nitrate...I can't find how nowhere..thanks for the great videos 😊
yep, should be able to.
I don't see why it wouldn't work. One issue might be formation of some transition metal nitrosyl complex due to inevitable decomposition of nitric acid to NOx and the subsequent absorbtion of nitric oxide by the iron(III). Another problem might be hydrolysis of iron(III) or its poor solubility.
But if you already have that salt, you can easily convert it to sodium or potassium salt with corresponding hydroxide:
Fe(NO3)3 + 3 NaOH -> Fe(OH)3 + 3 NaNO3
8:26 it is can use as an antidote for cyanide poisoning?
you know anything useful about it?
Is this for sodium azide? I definitely wouldnt inhale it
Summary
- 0:02 Safety Warning: Experiment involves fuming nitric acid; use vinyl gloves, not nitrile gloves.
- 0:12 Experiment Environment: Must be conducted outside or in a fume hood due to the use of sulfur dioxide and isopropyl nitrite.
- 0:21 Objective: Making isopropyl nitrite, useful for azides and azo compounds.
- 0:28 Traditional Method: Combining sodium nitrite, hydrochloric acid, and isopropyl alcohol.
- 0:46 Alternative Method (Sodium Nitrite-Free): Involves nitrosylsulfuric acid pathway.
- 0:56 Preparation Steps:
- Dry isopropyl alcohol using molecular sieves (3A) heated at 200°C.
- Mix 400mL of 99% isopropyl alcohol with 150mL of molecular sieves and leave overnight.
- 1:23 Acid Mixture: Combine 63g fuming nitric acid with 150mL glacial acetic acid, then cool in an ice bath.
- 2:13 Sulfur Dioxide Generation: Use sodium metabisulfite and hydrochloric acid to produce sulfur dioxide, which reacts with nitric acid to form nitrosylsulfuric acid.
- 3:16 Reaction Specifics: Avoid water in nitric acid to stop the production at nitrosylsulfuric acid.
- 3:55 Role of Glacial Acetic Acid: Serves as a solvent to prevent solidification of nitrosylsulfuric acid.
- 4:27 Monitoring Reaction: Solution turns blue or green as an indicator of reaction completion.
- 4:52 Handling Nitrosylsulfuric Acid: Filter and use quickly due to instability.
- 5:23 Reaction with Isopropanol: Slowly add nitrosylsulfuric acid to cooled isopropanol, maintaining low temperature to avoid decomposition.
- 7:24 Final Steps:
- Add ice to the reaction mixture, then separate isopropyl nitrite using a separatory funnel.
- Yield: 56g or 63% based on nitric acid, 69% based on nitrosylsulfuric acid.
- 8:36 Storage Tip: Add sodium carbonate for pH stabilization and extended shelf life.
- 8:55 Conclusion: Alternative method to sodium nitrite-based processes, useful when sodium nitrite is unavailable. Sodium nitrite gets harder to acquire for the amateur.
This is wonderfully done! A thorough, reader-friendly and easy to follow summary!
Will this make nitroethane?
This should work without separating the acetic acid. Since the nitrosylsulfuric acid doesn't react with the acetic by itself the added isopropyl alcohol and nitrite should not either. The acetic acid would not form esters at these low temperatures. It might hinder the separation but some bicarbonate to neutralise the acids would likely solve that.
Fuming nitric acid is almost hypergolic with isopropanol. While there should be very little leftover, for safety, filtering should be done in case something went horribly wrong during the sulfur dioxide generation and it never happened, or it leaked and never reacted. If you add fuming nitric acid to isopropanol you have a very bad day ahead. So filtering removes most of the fuming nitric acid and you can proceed safely.
@@NurdRage one more reason to shoot for that colored end point. I suspect the acetic acid would slow the reaction but I don't currently have a safe place to test potentially hypergolic reactions.
Oh boy!
I'm still convinced that it's easier to buy, make or steal NaNO2 than to go through all this (esp. including 100% HNO3 and anhydrous acetic acid)
My whole channel is that. Absolutely nothing i have ever shown is cheaper or easier than buying it directly. I do what i do to demonstrate interesting scientific principles.
And as NurdRage even says in the video, not everyone can always buy all of the different reagents depending on where they are.
Iso is known for causing eye problems but most people agree it hits the hardest
I was waiting for this lol
That's probably just because it has the lowest boiling point. Ethyl nitrite should hit even harder but it's barely a liquid
the real deets
O no, you made the ONO group
Isn't NaNO3 used in sausage making? Hard to imagine it being hard to get curing salt...
It is but its generally a small part of the whole and its been harder and harder to get.
Curing salt is only like a few percent sodium nitrite (NaNO2) mixed with regular table salt. Some even contain both sodium nitrite and sodium nitrate (NaNO3). Not terribly useful for synthesis.
#1 curing salt is 6.25% nitrite. Not exactly spectacular yield.
@@lrmackmcbride7498where I live you can't even get curing salt with > 2% nitrite. Thankfully you can buy pure NaNO2 in neighbouring countries easily
Better chemistry youtubers than you ?
No there is no such thing
Any idea why Sodium Nitrite is hard to get now? Even last year I remember seeing it online fairly regularly.
I did some more research. Apparently people were using it as an exit plan for themselves so they banned it from a lot of places sometime last year.
@@metiscus yup, this is why. It's part of one of the cocktails.
Yay
@NurdRage - 2023-12-16
I'm going to try and have one more video before Christmas.
@FaizCaliph - 2023-12-16
Thank you
@custos3249 - 2023-12-16
Let me guess - recreating the chemical reactions seen in Nightmare Before Christmas
@catfishtv411 - 2023-12-16
Dissolve a small tree in sulfuric acid
@copperchopper4626 - 2023-12-16
yay! the best christmas gift for a nerd like me
@Sniperboy5551 - 2023-12-16
@catfishtv411 Or selenic acid, like ChemicalForce 😉