thegratefuldead
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doubt about a reaction (alkyl nitrites)
Hi ! this is my first post, im venturing in this wonderful universe of the chemistry...
Id been making Isopropyl Nitrite succesfully, doing the reaction between IPA-HCL 37% and the NaNO2-H2O about 0° celsius, and i noticed there is
practically no reaction ( no bubbles, no fumes) but its works well and gives good yield...
Now i try to make it with Butyl Alcohol, doing the same procedure and ratios, i only change the alcohol quantity respecting the molarity of the
reaction...
This reacts very bad at the 0° and doesn´t works... i wonder why its happens...
Id watched a video doing the same procedure, and it works well, and its works me well with the other alcohol...
Can be the alcohol ? maybe its old ?, its have a little solids residuals...(how it should smell?)
What could be happening ?
Thanks, sorry for my bad english
[Edited on 20-1-2017 by thegratefuldead]
[Edited on 20-1-2017 by thegratefuldead]
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Maroboduus
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SN?
You're using nitrogen monosulfide???
Most folks round these parts use sodium nitrite.
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thegratefuldead
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Hi Maroboduus!
No, you are right, Sodium Nitrite...im gonna correct it 
I think that the alcohol is mislabeled maybe
[Edited on 20-1-2017 by thegratefuldead]
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woelen
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I can confirm that n-butylalcohol works like a charm in making the nitrite ester. So, there must be something wrong with your alcohol.
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Melgar
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Yep, no problems with adding a nitrite to butyl alcohol here. I made quite a bit of it, since I wanted to try doing a variant of this reaction:
http://orgsyn.org/demo.aspx?prep=cv2p0363
It helps to use a pipette to add a saturated sodium nitrite solution to the bottom of your acidic alcohol solution. Nitrite will collect in a yellow
layer at the top, and can be stored almost indefinitely by just reacting it with sodium carbonate until it stops bubbling, then storing it over more
sodium carbonate. Nitrites decompose into acids, and acids accelerate nitrite decomposition, so you need to store it over a carbonate or bicarbonate
alkali salt if you intend to store it for any length of time.
As for the above reaction, it seems that the ether can be replaced by methanol, but what about the HCl gas? I'd really rather not have an HCl bubbler
going as part of my apparatus. They can't be used indoors unless you don't mind everything metal rusting over, and I have a tenuous enough
relationship with law enforcement that I'd rather not have to try and explain having a makeshift HCl bubbler outdoors. Could say, phosphoric acid be
used instead?
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thegratefuldead
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Thanks a lot, Woelen and Melgar.
I will try to return the bottle, or find another shop 
Now im gonna try the way that Melgar says, i was adding the acidic over the alcohol solution in the nitrite solution...
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