Author Topic: Isopropyl nitrite  (Read 153 times)

zajcek01

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Isopropyl nitrite
« on: July 16, 2009, 11:29:31 PM »
Hi.

Today swim tried to make some isopropyl nitrite, and here it is:

Chemicals used:
Sodium nitrite [NaNO2]
Isopropyl alcohol [C3H7OH]
water[H2O]
concentrated (98%) sulfuric acid [H2SO4]
sodium hydrogen carbonate [NaHCO3]

Equipment:
A flask and a beaker


A flask was filled with 100ml of water [H2O] and 23.00g of dry sodium nitrite [NaNO2] and cooled in freezer.

A beaker was filled with 7ml of water [H2O] and to this, 8ml of concentrated sulfuric acid [H2SO4] were added slowly. When the mixture cooled, 23,5ml of isopropyl alcohol [C3H7OH] were added and cooled in freezer for 30 minutes, the same as the flask.

Solution from beaker was slowly added to flask with swirling by hand in the course of approximately  7 minutes.
When mixing the two solutions, bubbles of isopropyl nitrite and something else appeared. It looked like mineral water
with oil floating on top ;)
When a solution was left to stand for a couple of minutes, it became more clear and organic matter floating on top became lighter in color (less yellow).

This was the test run for a scaled up reaction where additional cooling with salt/ice will be used and
maybe H2SO4 will be replaced for HCl.
Isopropyl nitrite is to be used in isonitrosopropiophenone synthesis.

So here is my question: Would the product be pure enough to be used in synthesis if it is to be separated from water, washed, neutralized with NaHCO3 and dried?

and here are some pictures of the end product:
« Last Edit: July 16, 2009, 11:41:59 PM by zajcek01 »
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Vesp

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Re: Isopropyl nitrite
« Reply #1 on: July 16, 2009, 11:42:42 PM »
You'd probably want to rinse it with ice cold water to get out any remaining IPA. IPA can be salted out of solution, and might be more soluble in IPN then water.

Distillation would probably yield a more pure product, and you'd probably want to dry it with some desiccant if the reaction is water sensitive.

Nice write up by the way, did you get a headache from it? I've heard that happens with the IPN synthesis.

HCl might interfere with the reaction, since HNOx + HCl can make a bunch of nasty little things like NOCl, Cl2, etc. I'd test the HCl reaction on a smaller scale just to be safe, or just use H2SO4 for the larger scale.
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zajcek01

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Re: Isopropyl nitrite
« Reply #2 on: July 17, 2009, 12:09:34 AM »
Small scale with HCl will be tried first, then the results will be compared.

Tomorrow, the remaining of IPN will be salted out of solution and neutralized with NaHCO3 and dried over MgSO4 or something similar. MgSO4 has to be bought from the pharmacy ;)

It will have to wait until tomorrow, because it is 2 AM now.

The headache was not severe, almost negligible during the reaction, but it became more apparent while transfering IPN out of the flask with an eyedropper to another container for storage. Some cardiovascular issues were noticed.
My heart started racing, I became a bit dizzy and my veins on my arms looked like I was on bodybuilding contest. :D

I had to remove to get some fresh air. After a couple of minutes I recovered back to normal, with no headache for now.
« Last Edit: July 17, 2009, 12:14:22 AM by zajcek01 »
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Vesp

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Re: Isopropyl nitrite
« Reply #3 on: July 17, 2009, 12:21:46 AM »
Glad everything is ok, I hear with IPN, and other compounds such as nitroglycerin it can be rather dangerous when it comes to their pharmacological effects if you don't pay attention.
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zajcek01

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Re: Isopropyl nitrite
« Reply #4 on: July 17, 2009, 12:38:49 AM »
I hate working with nitroglycerin, it gives me a long lasting headache every time I work with it.

It is different for alkyl nitrites, symptoms stop much faster, if you are not exposed to high doses by intentionally inhaling it like some people do.

While working with alkyl nitrites, you can get exposed slowly, to reach higher doses and be unaware of it.
While under the influence, your judgment may get impaired and reactions may become slower leading to spills, exposure to higher doses..... spills can lead to fire, because alkyl nitrites are very flamable.

I think symptoms can be reduced with vitamin B12, vitamin C and others. I think antioxidants in general help, like from lemon and orange juice, I could be wrong...
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heisenberg

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Re: Isopropyl nitrite
« Reply #5 on: July 17, 2009, 03:53:27 AM »
Drink caffeine, lots of caffeine. It'll reconstrict your blood vessels and kill the headache. Aspirin makes it worse.
I spent all my money on booze and hookers, the rest I wasted - Charles Bukowski

Douchermann

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Re: Isopropyl nitrite
« Reply #6 on: July 17, 2009, 03:14:45 PM »
As dangerous as lots of caffeine is, heisenberg is correct.  Things that also work are Meclizine HCl (look for anti-motion sickness, it's OTC), pseudoephedrine, and pseudo's replacement - phenylephrine (OTC nasal decongestant).

This is the exact procedure I use for making other alkyl nitrites, such as butyl and amyl nitrite, just calculate moles/grams of the alcohol and use directly.  It also works for methyl and ethyl, however special accomadations must be made due to their low boiling point (perhaps bubbling in another solvent, or performing the reaction in a freezer.  What are your plans with the IpONO? NaN3?

zajcek01

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Re: Isopropyl nitrite
« Reply #7 on: July 17, 2009, 03:40:45 PM »
It will be used in the production of isonitrosopropiophenone, then it will be reduced.
Phenyl-Propanolamine is my primary goal.

I have enough of NaN3 for my uses, so currently I do not feel the need to synthesize it yet. (maybe someday)

Procedure similar to this will be used, We will see what will happen ;)
Those reactions look nice on paper, but in real world, it is not that perfect.
http://www.freepatentsonline.com/3090812.html
http://www.orgsyn.org/orgsyn/prep.asp?prep=CV2p0363

As for a headache: a black caffe or red bull (and similar) + 250mg of naproxen is enough.
Fresh air also helps, try not to lay down, it only gets worse, try to sit down and just relax until caffeine and naproxen kicks in.

To much of caffeine is not god for you.
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Sedit

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Re: Isopropyl nitrite
« Reply #8 on: July 17, 2009, 04:13:26 PM »
Can anyone elaborate in the short question threed on the production of azides from IPN please. Ill be greatful ;D.
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POSEIDON

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Re: Isopropyl nitrite
« Reply #9 on: July 19, 2009, 05:43:10 AM »
Hey sedit i still looking the synth of azides by IPN, for the moment look this link:
http://www.organic-chemistry.org/synthesis/C1N/azides/alkylazides.shtm
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Re: Isopropyl nitrite
« Reply #10 on: July 20, 2009, 01:20:35 PM »
NG headaches are WAY overrated. A cup o coffee, a smoke, and some paracetamol does away with it. And constant exposure to NG makes you immune - hell there were cases of ADDICTION.

IPN is good for many purposes, I would use it as a sensitizer in thermobarics, but thats just me.

IPN is also a recreational drug :eek:

2bfrank

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Re: Isopropyl nitrite
« Reply #11 on: July 23, 2009, 05:41:32 AM »
What about a decent mask. They come in all shapes/styles and colors. Hardly know youve got one on, and has filters that remove most things I believe. Good for headaches too.

heisenberg

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Re: Isopropyl nitrite
« Reply #12 on: July 23, 2009, 06:47:15 AM »
What about a decent mask. They come in all shapes/styles and colors. Hardly know youve got one on, and has filters that remove most things I believe. Good for headaches too.

That would certainly work, but I'd reserve them for the nastier gasses.
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2bfrank

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Re: Isopropyl nitrite
« Reply #13 on: July 23, 2009, 09:42:59 AM »
Each to their own - Headaches that is. :D