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Author: Subject: monosaacharides

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[*] posted on 10-11-2007 at 17:51

Can glucose be nitrated? I am having an argument with a friend and need a reliable answer.
I say as glucose is a monosaacharide, it can't.
I have searched and searched and cannot find a definitive answer.
My text book says, "stronger oxidizing agents ,such as aqueous HNO3 oxidize the aldehyde group and the primary alcohol group producing di-carboxylic acids.
eg. D-glucose gives D-glucaric acid.
Though if it has an alcohol group, it can be nitrated?
I am sorry if this question is kewlish, but I know I cacn get a reliable answer here.

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[*] posted on 12-11-2007 at 08:50

It can, you get (max) the pentanitrate.

The acid has to be a stronger nitrating agent than it is an oxidizer. I.e. no hot 65% nitric but subzero 99%, and precipitated by adding pre-frozen 98% sulfuric, in a salt/ice bath to stay below 0C ideally. Don't ask for the runaway temp but you bet it's lower than when making NG. I just want to say the primary alcohol group in EtOH is so succeptible to oxidation you can have a runaway where NG still has a 30C safety margin. Just a warning.

BTW when properly neutralized (difficult, needs solvants, unlike NG or NC), it makes a good plasticiser with MHN, ETN or PETN, to plasticise RDX. The good news is you have no inert crap in the mix, more power per gram than both semtex and C-4, and the plastique can be kneeded without gloves, *without* getting a headache. Bad news is storage time, at least outside the fridge.
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[*] posted on 12-11-2007 at 10:28

Would the aldehyde undergo substitution at all? I'm amazed there are conditions where it won't be oxidized while the alcohols are nitrated!


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[*] posted on 13-11-2007 at 17:07

What Boomer said, but because of all that it really is not worth the time and effort you put into making it.

But, if its to prove a friend wrong then by all means its worth it.:D

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