John paul III
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Concentrating nitric acid and peforming nitration using succinic anhydride
Succinic acid easily dehydrates upon heating forming succinic anhydride. This in theory makes it an easily recyclable (and cheap to aquire in
quantity) water scavenger. I'd like to try concentrating 68% nitric acid by adding sufficient amount of succinic anhydride to react with all the water
and distilling off the concentrated HNO3.
Another idea is to add a bunch of anhydride to concentrated nitric acid for nitration of cotton to help push the reaction forward by removing the
product (water). Is there any reason to be sceptical of success?
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woelen
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This can be quite dangerous. Nitric acid is a very strong oxidizer, especially at high concentrations. I expect it to oxidize the succinic acid or
anhydride and on heating you may get a really nasty runaway, with production of huge amounts of NO2 and I can even imagine that you get fire.
I do not expect this to be succesful. In my opinion it is a recipe for disaster.
Just for fun, try it on a test tube scale (e.g. 200 milligrams of succinic anhydride, mixed with 1 to 2 ml of 65% HNO3). Heat this mix in a test tube.
I expect a plume of NO2 and a violent reaction on heating to a temperature at which the acid could boil off.
[Edited on 4-11-19 by woelen]
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PirateDocBrown
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I know you can go to succinic acid from 1,4 butanediol using nitric acid, and that reaction is fraught with the risk of thermal runaway.
I don't know if succinic can then be further oxidized, presumably to liberate CO2, by nitric alone.
Phlogiston manufacturer/supplier.
For all your phlogiston needs.
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fusso
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What about phthalic anhydride?
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UC235
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Succinic and phthalic anhydrides are very weak dehydrating agents relative to sulfuric acid. Furthermore, the formation of nitronium ion occurs
through protonation of nitric acid. The water-scavenging is only half the equation.
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Microtek
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I agree that oxidation (and runaway) is the likely outcome. However, succinic acid can be converted to succinimide which can be chlorinated by
reaction with hypochlorite and acetic acid. This makes N-chlorosuccinimide which can by used as a mild chlorinating agent, eg. for preparing
dichloroglyoxime (which is a key intermediate in TKX-50 synthesis).
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Madchemistrystudent
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Why don't you use Sulfuric acid to dehydrate the Nitric acid?
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UICalculus
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I think it may react and maybe explode.
You can try P4O10(P2O5).
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