Sciencemadness Discussion Board

Concentrating nitric acid and peforming nitration using succinic anhydride

John paul III - 19-9-2019 at 10:55

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?

woelen - 20-9-2019 at 00:05

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]

PirateDocBrown - 20-9-2019 at 03:13

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.

fusso - 3-11-2019 at 12:49

What about phthalic anhydride?

UC235 - 3-11-2019 at 14:25

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.

Microtek - 4-11-2019 at 00:43

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).

Madchemistrystudent - 16-11-2019 at 07:03

Why don't you use Sulfuric acid to dehydrate the Nitric acid?

UICalculus - 17-11-2019 at 03:55

I think it may react and maybe explode.
You can try P4O10(P2O5).