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Author: Subject: Synthesis of 2-nitro 3-acetoxy 1-propane and precursors
a nitrogen rich explosive
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[*] posted on 14-4-2016 at 02:02
Synthesis of 2-nitro 3-acetoxy 1-propane and precursors


How would I synthesise 2-nitro 3-acetoxy 1-propane? I need it for experiments with heptanitropentane. There is little mention of 2-N 3-A 1-P on the Internet or in any literature that I can find.



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[*] posted on 14-4-2016 at 02:09


Quote: Originally posted by a nitrogen rich explosive  
How would I synthesise 2-nitro 3-acetoxy 1-propane? I need it for experiments with heptanitropentane. There is little mention of 2-N 3-A 1-P on the Internet or in any literature that I can find.


2-nitro 3-acetoxy 1-propane

Something is wrong here. If it is propane, then it can't be 1-

Do you mean 1-propene?

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[*] posted on 14-4-2016 at 03:07


Sorry about that, wasn't thinking...

Any idea of synthesis (the only paper I can find costs £59.99.)




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[*] posted on 14-4-2016 at 03:17


What is the reference?
Is this what you have in mind? http://link.springer.com/article/10.1007%2FBF00912288

And BTW are you confirming that the target compound is 2-nitro 3-acetoxy 1-propene ?

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[*] posted on 14-4-2016 at 04:36


Yes that is. It isn't as expensive as I thought it was.

Yes, that is the target compound.
I will be reacting it with nitroform to form HNP, then nitrating the pyridium salt of that into octonitropentane.

My worry is that just about everything in this reaction is explosive/extremely oxidising (virtually all steps within the reaction yield alkenes in various states of nitration.)

[Edited on 14-4-2016 by a nitrogen rich explosive]




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[*] posted on 14-4-2016 at 09:15


Very easy...
CH3-NO2 + 2 CH2=O --> HO-CH2-CH(-NO2)-CH2-OH
(amongst other molecules like HO-CH2-CH2-NO2, CH2=CH-NO2, polynitrovinyle, O2N-CH2-CH2-CH2-NO2, HO-CH2-C(-NO2)=CH2 and of course (HO-CH2-)3C-NO2 depending on initial reactant ratio and reaction conditions)

The reverse reaction is also possible...
(HO-CH2-)3C-NO2 -base-> HO-CH2-CH(-NO2)-CH2-OH + CH2=O (CH3OH and HCO2H in basic media) -base-> HO-CH2-CH2-NO2 + CH2=O --> CH3-NO2 + CH2=O

Then after isolation...
HO-CH2-CH(-NO2)-CH2-OH + Acetic anhydride --> CH3-CO-O-CH2-CH(-NO2)-CH2-O-CO-CH3 + CH3-CO-O-CH2-C(-NO2)=CH2 + CH3-CO2H (equal to CH3-CO-OH)
HO-CH2-C(-NO2)=CH2 + Acetic anhydride --> CH3-CO-O-CH2-CH(-NO2)-CH2-O-CO-CH3 + CH3-CO-O-CH2-C(-NO2)=CH2 + CH3-CO2H (equal to CH3-CO-OH)




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[*] posted on 14-4-2016 at 11:00


1) How would you separate the 3-hydroxypropyl nitrate from all the other things that form?

2) How the hell would you separate the 2-nitro 3-acetoxy 1-propene from the acetic acid and the acetic acid derivatives?




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[*] posted on 15-4-2016 at 05:07


Quote: Originally posted by a nitrogen rich explosive  
1) How would you separate the 3-hydroxypropyl nitrate from all the other things that form?

2) How the hell would you separate the 2-nitro 3-acetoxy 1-propene from the acetic acid and the acetic acid derivatives?

1) Where does your HOCH2-CH2-CH2-ONO2 come from?
Not present!
2) Acetic acid is soluble in water while product should'nt be. Acetic acid is also very volatile while product should'nt be
--> Crystalization, chromatography.

Are you sure you know enough chemistry to go in that synthesis?




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[*] posted on 15-4-2016 at 05:46


1) I was reading this over in a cursory manner. I just added up the molcular formula C3H7NO4 and I worked it out as 3-hydroxypropyl nitrate (3-carbon chain, NO3 bonded at the end, 6 hydrogen atoms joined to the carbon chain, one hydroxy group bonded to the other end - 3-hydroxypropyl nitrate.) Sorry if I got that wrong.
2) Didn't think about that... Need to apply myself more before I post.

[Edited on 15-4-2016 by a nitrogen rich explosive]

[Edited on 15-4-2016 by a nitrogen rich explosive]




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