maxidastier - 10-3-2011 at 04:57
Can 2-(2-Ethoxyethoxy)ethanol be nitrated to yield an explosive compound?
Didn't find anything by using the search engine.
Don't blame me if this is discussed already.
12332123 - 10-3-2011 at 07:26
Only one nitrate group on a molecule that large - what exactly gave you the idea that anything fruitful could come of that.
maxidastier - 10-3-2011 at 12:33
Well, how can you make out, how many nitrate groups there will be? Is it only the OH-groups?
stygian - 10-3-2011 at 13:15
Esters are derived from allcohols, so yes.
AndersHoveland - 10-3-2011 at 17:46
2-(2-Ethoxyethoxy)ethanol has the structure CH3CH2--O--CH2CH2--O--CH2CH2OH.
Ethers are known to hydrolyze under strongly acidic conditions. It may be possible that ethers could behave as superconcentrated alcohols under
nitration conditions, potentially requiring less sulfuric acid for the nitration.
I was unable to find anything relating to nitration of esters or ethers, suggesting the reaction might be very problematic.
A good place to look for chemistry relating to possible nitration of ethers may be articles about glycol ether dinitrate (DEGDN), which was once used
as an energetic plasticizer. It has the structure
O2NO--CH2CH2--O--CH2CH2--ONO2
Perhaps ethyl nitrate could be made with concentrations as low as 60% nitric acid (0degC) if ethyl acetate was used instead of ethanol. (Ethyl acetate
would be preferable since esters are much less resistant to hydrolysis than ethers).