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Author: Subject: add nitro groups to acetylene (ethyne)?
physics inclination
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[*] posted on 29-6-2017 at 10:41
add nitro groups to acetylene (ethyne)?


Hi, I was wondering if it would be possible in theory to make a molecule of acetylene aka ethyne C2H2, but with one or both of the hydrogens replaced with nitro functional groups -NO2.
I wondered this because acetylene burns really hot normally, so maybe it could make a very powerful (and likely unfortunately unstable) energetic compound if it were given nitro groups. It would also theoretically have a perfect oxygen balance, and actually produce only N2 and CO2 on combustion; no water would be produced which would be interesting.

Alternatively, for a similar compound with a more oxygen-rich ratio, maybe take ethylene aka ethene C2H4 and add nitrate ester groups -ONO2 to each end, one per carbon atom.

Again, I don't intend to try and make these, I wouldn't even know where to begin, I'm just curious if these are even theoretically possible to exist (that is, without spontaneously igniting at standard temperature and pressure).
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[*] posted on 29-6-2017 at 11:35


As far as I know, no one has succeeded in preparing dinitroacetylene, though numerous attempts have been made. It does appear based on a quick lit search that novel syntheses of nitroacetylene have been found, but I'll let those who are more experienced with EM give a more in-depth answer.

EGDN on the other hand has seen quite a lot of discussion on SciMad, see here.




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[*] posted on 29-6-2017 at 13:06


One could conceivably prepare the compound by reaction of a salt containing the acetylide dianion (such as Li2C2 or CaC2) with a salt containing the nitronium cation (like nitronium tetrafluoroborate).

However, I would expect dinitroacetylene to be extremely, horrendously unstable. Even dichloroacetylene will readily and violently explode on contact with air. (Incidentally, I once had some form as a side product of a certain reaction. It was quite the surprise.) I don't think one could isolate dinitroacetylene, although it may be stable in cold, dilute solution.

[Edited on 6-29-2017 by Metacelsus]




As below, so above.
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PHILOU Zrealone
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[*] posted on 30-6-2017 at 00:40


Did you use the forum search engine with as keyword "dinitroacetylen"?
Has already been discussed a lot...all that has to be known is written into previous treads.

O2NO-CH=CH-ONO2 doesn't exist yet...as can be theoricized nitrate esters of enols aren't very stable and readily form NO2(+)...For example phenol nitrate turns immediately into nitrophenol.
******************
So more than probably
O2NO-CH=CH-ONO2 <--==> HO-C(NO2)=C(NO2)-OH (nitroenol)<--==> O2N-CHOH-CO-NO2

NO2 next to electronwithdrawing groups suffer from nitro-nitrite rearrangement and fast hydrolysis

O2N-CHOH-CO-NO2 ==> O=N-O-CHOH-CO-O-N=O =H2O=> HO-CHOH-CO2H + 2 HO-N=O

HO-CHOH-CO2H ==> O=CH-CO2H + H2O =oxydant like nitrous acid=> H2O + CO2
******************

Related compound has been synthetized by Klapote's team...(O2NO)2CH-CH(ONO2)2...glyoxal tetranitrate (or acetylen tetranitrate) itself brother of methylene dinitrate (formaldehyde dinitrate)...those are potent explosive oxydiser of moderate stability.


[Edited on 30-6-2017 by PHILOU Zrealone]




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[*] posted on 30-6-2017 at 18:56


Thanks for all the responses :)
and I now realize that the second compound I described is just an inferior cousin compound to EGDN like you said, why didnt I see that before.

(edit at 22:00 June 30):
also sorry I did not search about these compounds before, as I did not know what the exact name would be (I did search google for a few names of what I thought it would be and none turned up, not even results on pages here)

[Edited on 7-1-2017 by physics inclination]
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