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Author: Subject: Oxidation of sugars

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[*] posted on 25-5-2011 at 11:56
Oxidation of sugars

I just read that "Sugars in the presence of sufficient oxidizing
agent give degradation to 1C compounds" and then it gave a diagram that showed glucose being degraded into 5 parts formic acid and 1 part formaldehyde. Is this true? If I was to oxidise glucose with potassium permanganate would I end up with a mixture of formic acid, formaldehyde and reduced permanganate?
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International Hazard

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[*] posted on 25-5-2011 at 13:14

Oxidation of sugars... products depend heavily on the conditions. Potassium permanganate will oxidize sugars to carbonic acid (i.e. CO2) in acid solution; maybe in alkaline solution some formic acid would be fixed. If it's formic acid you're after, it's worth noting that sucrose is decomposed to (in part) formic acid by the action of strong acids, e.g. HCl, phosphoric acid and sulfuric acid all give formic acid in addition to other products (the Org Syn prep of levulinic acid is one example, though it wasn't the formic acid they were after). Oxidation is not required though it might give you more acid per molecule of sugar.
Anyway, a diagram that shows glucose turning neatly into five parts formic acid and one part formaldehyde is highly idealized. In the real world, the first step is to figure out how you're going to separate the formic acid from the soup/syrup/awful mess that you are liable to make, and work from there.
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