Question Nitroethane fractional distillation

[Evilcarrot2]

Can nitroethane be fractionally distilled from ethyl acetate?

I see the boiling temps are quite far apart so sounds logical.
But do they form an azeotrope?
I put 200ml of the mixture in a RB flask and started heating but there has never been a 56 degree portion to come over but a constant 60-75 degree. I'm about half way through this attempt.
Can I break the azeotroke or is there such a way to convert either to a salt so can be filtered. Or am I just half way through and over thinking it?

 

[Evilcarrot2]

I
I apologise its ethyl formate

 

[Evilcarrot2]

So I've completed 1st distillation of this and will give my results thus far.

Msds says 30-60% nitroethane
30-60% ethyl formate

After 1st distillation of 200ml
I got 100ml 1st fraction between 60-80°c at atmospheric pressure.

Second fraction 80ml was under vacuum 85-95°c

Did not distill to dryness so possibly 10ml or so left behind.
Just got to complete this another 4 times which should roughly equate to 400ish ml nitroethane which I will re-distill under reduces pressure.

Hopefully it's a viable source of nitroethane ethane for me at 78usd per 1kg product before seperation

 

[MadHatter]

Interesting. what was your original source of nitroethane?

 

[TheShocker]

rc fuel

 

[Evilcarrot2]

Rc fuel contains nitromethane and I found out the hard way. I did reaction with the rc fuel distillation and got lots and lots of amazing yellow crystals thinking I'd cracked an easy way to p2np, to be told by g.patton it would be nitrostyrene I was not convinced and really thought I had p2np. Melting point mid 50's confirmed Mr patton was correct.

 

[G.Patton]

Hello, have you used Vigreux column?
have you checked bp at 1 atm? Nitroethane has 114 *C bp.

 

[Evilcarrot2]

No I didn't use vigreux although I do have one. I've actually used it in reaction for p2np and have the nicest looking crystals to date after 1 recrystalisation from hot ipa.
Can I ask patton a question?
Will benzaldehyde and ethyl formate produce any unwanted side products if my nitroethane was slightly diluted with ethyl formate?
I hate long distillations.
My crystals are currently air drying to find out weight.

 

[G.Patton]

I think yes, they can. Looks nice. Check mp, when it will be dried.

 

[Evilcarrot2]

Right I've done a MP TEST on my yellow crystals and the results are:
It started shrinking from sides at 62°C and was fully liquified at 65°C
My melting apparatus came with a broken thermometer and the hole where the thermometer goes is so skinny none of my other 30+ thermometers fit so I have to use a k-type thermocouple so I'd give +-1°c for accuracy.
Pics added unfortunately I couldn't get both in pic at same time due to viewing hole.

I think MP's dead on?

 

[G.Patton]

Hi, it looks like pure p2np, congrats!

 

[Evilcarrot2]

Yield from this was 400g p2np which I'm pleased with. It could probably be improve by using a vigreux column and then redistill the nitroethane again. That way less ethyl formate in the reaction which probably hurt it a lot. Say there was 30% nitroethane in the 1L mixture that's roughly 4mols of nitroethane
And yield was 2.45 mols of p2np
I think that's 61.25% so not my average 70% but a 10% loss of product to not have to distill and re-distill is a win for me.