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Maja
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Isobutyl Nitrite
Hi,
Making Isobutyl Nitrite is just like with other alcohols ?
R-OH =NaNO2/H2SO4=> R-ONO + NaSO4 + H2O
Would This work ? From MSDS : Stability
Stable. Incompatible with acids, alcohols, strong bases. Decomposes slowly in Water. Flammable - incompatible with
strong oxidizing agents. Note wide explosion limits. May be light and moisture sensitive. Oxidizer. May explode if heated.
If you have some refs on this...Or some other information on Isobutyl Nitrite. It would be great. Thank you.
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chemoleo
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May I ask what your interest is in this? Possibly because its similarity to amylnitrite?
Regardless, it's a very easy prep - simple stoichiometric titration of HNO2 (from NaNO2 and HCl) into the alcohol, or rather, a mix of ROH/NaNO2 where
HCl is titrated into. Yes it works fine with all primary alcohols, just beware some are quite volatile, particulalrly methylnitrite (gas) and
ethylnitrite.
They start to stink of NOx upon storage at RT - even after washing with NaHCO3 and the like. Not the most stable of all things.
Never Stop to Begin, and Never Begin to Stop...
Tolerance is good. But not with the intolerant! (Wilhelm Busch)
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BromicAcid
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Wow, that sounds considerably more simple then I would have imagined, I thought NaNO<sub>2</sub> was more sensitive to acid then that and
that such a reaction would not be allowed (I thought it decomposed readily in acid, then again I've never had the pleasure of working with sodium
nitrite). I did use Isopropyl nitrite though some time ago for a diazotization reaction for which it is particularly useful, though it really doesn't
matter what you want it for, I might want this chemical some day because I like the combination of letters that make up its name.
[Edited on 4/5/2006 by BromicAcid]
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Maja
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| Quote: | Originally posted by chemoleo
May I ask what your interest is in this? Possibly because its similarity to amylnitrite?
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I was interested to Amyl/Isobutyl/... other nitrites because they are so expensive (10ml for 10EU). And i thought that isobutyl nitrite synthese is
very hard... But I can see it's quite simple. Isobutyl Nitrite boils at 67C. So it wouldn't be released as a gas... Thanks.
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Douchermann
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I have done this synthesis once, along with amyl nitrite. Make a solution of NaNO2, using 95mls of water and 24 grams of NaNO2. Cool this in a
salt/ice bath to about 0C. Make another solution by first mixing 7ml water, 9ml H2SO4, then add about 29ml of your butyl alcohol. Just add these two
solutions together very slowly. Use a seperatory funnel or burette to drip a small ammount in at a time. I have gotten about 27ml (never measured
it, just eyeballed it) using these ammounts. You have to keep the temperatures really low though. Dry it with MgSO4 once you've seperated it. Its
insoluble and less dense than water by the way. Also, don't sniff the reaction vessel while you are making it. We all know what butyl nitrite is
used for, and you'll get plenty of that just from making it. Butyl nitrite will slightly decompose during distilation if you choose to distil it, so
use reduced pressure.
[Edited on 6-4-2006 by Douchermann]
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Maja
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Thanks Douchermann !
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Maja
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I have one more question... There is some stabilizer for R-Nitrites ? I have googled a little bit ,but did not find anything. Please share your
knowledge.
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chemoleo
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It's a good question, I was wondering the same. Testing some amylnitrite, even prolonged shaking in NaHCO3 did not prevent decomposition, as evidenced
by a strong smell of nitric/ous oxides after a few days. Since base doesn't seem to help I was wondering whether a tiny amount of i.e. H2SO4 would
help, although I'd doubt that very much (from a mechanistic perspective).
Maybe distillation really is the clue to this, making sure to use a non-volatile acid (i.e. H2SO4) for the synthesis, rather than HCl.
Never Stop to Begin, and Never Begin to Stop...
Tolerance is good. But not with the intolerant! (Wilhelm Busch)
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Maja
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Actually I have used a few times H2SO4 and HCl. With H2SO4 you will get a lot of precipicate(Na2SO4) and it's hard to stir with magnetic stirrer. So I
have used over head. It solved problem. Did not tried to distill isobutyl nitrite ,but shaked a few times with Soda in separatory funnel, then with
water, add a few more times with dH2O. Tested for pH.... Almost neutral. But noticed a strange thing. When a drop of R-Nitrite is dropped onto water
you can see it DECOMPOSING ! It's bubbling and then pH decreases <7... But this happens only with a few drops. I think it happens all the time when
nitrite isn't dry, but I cant see it at higher amounts. So then I dried it with MgSO4 for a few hours and filtered. Now after three days it's still
fresh and no pH change noticed and no smell/red fumes. I keep it in a brown glass bottle away from light/sunlight. And also I'm getting pretty good
yield from H2SO4. From 116ml of isobutyl alcohol I was able to get 110ml of Nitrite ! I will try adding a drop of H2SO4. Chemoleo, I think we need to
search what stabilizers used in commercial Nitrites ,but I didn't found anything named.
[Edited on 13-5-2006 by Maja]
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dobka
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Maybe you know the literature, where I could read the full infirmation about synthesis of isobutyl nitrite?
Would be very nice.
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Nicodem
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The general procedure for the esterification of alcohols with HNO2 is described in the most obvious place to check out before asking questions like
that, in the "Vogel's textbook of Practical Organic Chemistry, 5th edition", pages 413-414.
[Edited on 26-5-2006 by Nicodem]
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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SHOT
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Isobutyl nitrite
So I was on this trip to London, England and I was walking on the street with two more "guys". So we were walking and then we entered this creepy
looking store. They sell opiums in there, so the "guys" with me bought something called "Poppers" which was actually isobutyl nitrite. When inhalated
isobutyl nitrite decreases blood pressure which lately makes you laugh a lot. Its not compleatly non-toxic. I would like to know how can I make this
stuff. I will really be greatfull if you guys help me. Thanks
[Edited on 30-7-2006 by SHOT]
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Vitus_Verdegast
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Most of us are in the know that London is the capital of England. Opium is illegal there. "Poppers", which is either isoamyl or isobutyl nitrite, is
mainly used by "the guys" to relax the rectum sphincter as to easily allow penetration. It is certainly not completely non-toxic. Furthermore is it
easily made from the corresponding alcohol, an slight molar excess of NaNO2 and a mineral acid. You better not try this because you'll easily end up
harming yourself, due to the volatility of the substance.
R-OH + NaNO2 + H2SO4 ==> R-ONO + NaHSO4 + H2O
Better study some chemistry first before attempting this...
http://en.wikipedia.org/wiki/Nitrite_inhalants
[Edited on 30-7-2006 by Vitus_Verdegast]
Sic transit gloria mundi
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Nicodem
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I wander why new members post questions that were already answered thoroughly in other threads? And why do they like to open new threads so much?
Can't you, dear new members, use the forum's search function before posting? (it is the first damn link on the top left side of every page!)
I miss those beautiful times from another forum when we could just reply with "UTFSE!" so much!
Nostalgia, I guess, but I feel better now.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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SHOT
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| Quote: | Originally posted by Vitus_Verdegast
Most of us are in the know that London is the capital of England. Opium is illegal there. "Poppers", which is either isoamyl or isobutyl nitrite, is
mainly used by "the guys" to relax the rectum sphincter as to easily allow penetration. It is certainly not completely non-toxic. Furthermore is it
easily made from the corresponding alcohol, an slight molar excess of NaNO2 and a mineral acid. You better not try this because you'll easily end up
harming yourself, due to the volatility of the substance.
R-OH + NaNO2 + H2SO4 ==> R-ONO + NaHSO4 + H2O
Better study some chemistry first before attempting this...
http://en.wikipedia.org/wiki/Nitrite_inhalants
[Edited on 30-7-2006 by Vitus_Verdegast] |
Oh. Ive studied chemistry enough. I just wanted to know another way of making this. Those guys with me told me that they inhale this gas which
evaporates from the liquid nitrite. And this makes 'em laugh.
EDIT: I am not so dumb! I know that London is the capital of England WTF?
[Edited on 30-7-2006 by SHOT]
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Vitus_Verdegast
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I feel exceptionally kind today, so I thought what the heck I'll spoonfeed our Bulgarian friend here by using the f#&!king search engine in
his place.
After searching for 1.2 sec, look what I came up with:
https://sciencemadness.org/talk/viewthread.php?tid=5598#pid6...
But I'm all for installing the UTFSE rule ! 
(Btw, dear SHOT, you've stated "So I was on this trip to London, England" --> What I meant is, if you had stated "So I was on this trip to London,"
most of us would know that you mean the capital of England instead of the backward hick town of London, Alabama.)
[Edited on 30-7-2006 by Vitus_Verdegast]
Sic transit gloria mundi
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hvinh
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dry?
Quote: Originally posted by Douchermann  | I have done this synthesis once, along with amyl nitrite. Make a solution of NaNO2, using 95mls of water and 24 grams of NaNO2. Cool this in a
salt/ice bath to about 0C. Make another solution by first mixing 7ml water, 9ml H2SO4, then add about 29ml of your butyl alcohol. Just add these two
solutions together very slowly. Use a seperatory funnel or burette to drip a small ammount in at a time. I have gotten about 27ml (never measured
it, just eyeballed it) using these ammounts. You have to keep the temperatures really low though. Dry it with MgSO4 once you've seperated it. Its
insoluble and less dense than water by the way. Also, don't sniff the reaction vessel while you are making it. We all know what butyl nitrite is
used for, and you'll get plenty of that just from making it. Butyl nitrite will slightly decompose during distilation if you choose to distil it, so
use reduced pressure.
[Edited on 6-4-2006 by Douchermann] |
hi Douchermann:
I have a question.. amylnitrate are so expensive nowsaday.. i like to make them myself..
1. Is there a website that you recommend me to buy the ingredients?
Thanks for help!
Vincent H.
[Edited on 3-8-2011 by hvinh]
[Edited on 3-8-2011 by hvinh]
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redox
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I hate to spoonfeed, but:
All the reactants can be found on Ebay.
Sodium Nitrite: $15-20 for one pound
Sulfuric Acid: $20-25 for 500 mL
Isobutyl (isoamyl shows on Ebay once in a while): $25 for 500 mL
I would recommend learning some chemistry before you try this synthesis.
[Edited on 3-8-2011 by redox]
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Newest video: Synthesis of Chloroform
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woelen
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Don't try this yourself if you don't have any chemistry background. You will most likely poison yourself. As you can read here it is quite difficult
to get and keep the material free of nitrogen oxides. Nitrogen oxides are VERY poisonous when inhaled!
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hvinh
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Redox and Woelen,
Thanks, guys, I will try to make a very small portion at a time, and not to inhale the nitrogen oxides during the process. I had a couple
courses of chemistry in college and aware of the danger of acid... Just i have never tried to synthesize it.. You two might have done it so in the
past...
Any more suggestions or recommendations!
I'd appreciate your valuable advice !
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redox
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When I performed the butyl nitrite synthesis, I noticed that the colder the reaction temperature, the less NOx fumes were effervesced. Keep it cold,
use a salted ice bath.
Also, its already been mentioned, but the alkyl nitrites degrade significantly over time. Wash your sample with sodium or potassium carbonate solution
once in a while. It smells a lot better when its not NOx'ed.
In addition, when you perform the synthesis, add the the acid (or alcohol) dropwise to the rest of the solution. Its much less dangerous and higher
yielding when done this way.
Best regards and good luck,
Redox
My quite small but growing Youtube Channel: http://www.youtube.com/user/RealChemLabs
Newest video: Synthesis of Chloroform
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hvinh
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Redox,
At this time, i have the acid sulfuric that I purchased at Orchard Supply Hardware. It said concentrated.. and the color is "dark". The acid that
is sold on the website is clear. I wonder if it is okay to use it.
Thanks for help!
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Bot0nist
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Probably contaminated with Fe and or carbon. There are many threads here that deal with the cleaning of sub standard
H<sub>2</sub>SO<sub>4</sub> (Drain cleaners).
Dilution and filtering, and H<sub>2</sub>O<sub>2</sub> oxidation are a few ways to purify it, short of distillation. (which I
don't recommend)
I am not sure what the contaminates are or what effect they will have on the synthesis, But if you plan on exposing your lungs to the finished product
please strive to use the cleanest reagents and the neatest procedures you can. Lungs are precious and the damage they take is cumulative.
U.T.F.S.E. and learn the joys of autodidacticism!
Don't judge each day only by the harvest you reap, but also by the seeds you sow.
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redox
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It should be all right as long as you distill your final product. Do you have a distillation apparatus?
Is the sulfuric "dark" as in pitch black? Is it colloidal? Was it marketed as drain cleaner?
Details!
Also, a new lot on ebay for isopentyl alcohol just popped up, you might want to utilize this rare occurrence.
http://cgi.ebay.com/Isoamyl-alcohol-1-Liter-/390336380379?pt...
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Panache
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it works fine with isopropanol also, making the secondary nitrite obviously, i adaptated it from whatever the vogel ref. was making, i think the
secondary, for a male friend of mine who was using it in the function spelt out by Vitus. I couldn't believe the prices he was paying otherwise.
Stores fine in the freezer. He seemed pleased by it, keeps nagging me for more.
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