Sciencemadness Discussion Board

1,3,5 - Trioxane synthesis

condennnsa - 22-11-2010 at 20:40

How can trioxane be synthesized from formaldehyde? I didn't find anything online, just one reference which says that formaldehyde is acidified, catalysing it to form trioxane.

But then i'm confused cause literature says that trioxane turns to formaldehyde when acid is added.

watson.fawkes - 22-11-2010 at 22:32

Quote: Originally posted by condennnsa  
How can trioxane be synthesized from formaldehyde? I didn't find anything online, just one reference which says that formaldehyde is acidified, catalysing it to form trioxane.

But then i'm confused cause literature says that trioxane turns to formaldehyde when acid is added.
There are several patents that came up in a search for "trioxane synthesis".

The synthesis is catalyzed by acid, which means that is breakdown is also catalyzed by acid. Manufacturing techniques work by driving the equilibrium to the desired side by manipulation of physical properties that allow separation. One of the patents, for example, is about a distillation cascade.

spong - 23-11-2010 at 02:24

I've tried working with formaldehyde before, I was trying to go the other way, trioxane to paraformaldehyde. It was unpleasant and tedious to say the least, formaldehyde gas fucking HURTS when you get it in your eyes/nose/mouth, plus it'll polymerize on it's own into paraformaldehyde coating whatever flask or tube you're trying to run it through. I hate to be one of 'those guys' but you might just have to buy/purify it (camping stove tablets).
If it helps at all, trioxane sublimes readily while paraformaldehyde does not (although it will depolymerize into formaldehyde gas and probably polymerize onto whatever you're trying to sublime it onto), that could help you separate the two if you do try to make it.

condennnsa - 23-11-2010 at 21:01

Quote: Originally posted by watson.fawkes  
There are several patents that came up in a search for "trioxane synthesis".

The synthesis is catalyzed by acid, which means that is breakdown is also catalyzed by acid. Manufacturing techniques work by driving the equilibrium to the desired side by manipulation of physical properties that allow separation. One of the patents, for example, is about a distillation cascade.


So if I add a tad of acid to formaldehyde, it will act as a catalyst to trioxane, but further addition decomposes it back to CH2O?

watson.fawkes - 23-11-2010 at 21:44

Quote: Originally posted by condennnsa  
So if I add a tad of acid to formaldehyde, it will act as a catalyst to trioxane, but further addition decomposes it back to CH2O?
You've got some basic learning ahead of you. Start with Le Chatelier's principle.