How to make TCPO (for making glow sticks)

Uploaded by NurdRage on 10.05.2009

Greetings fellow nerds.
So far we've made a lot of videos on glow sticks
and have always used the key ingredient of TCPO,
or bis(2,4,6-trichlorophenyl) oxalate.
As promised, in this video we're finally going to show you how to make it.
Now we like to work on large scale for dramatic effect,
but since most of you attempting this will be doing it as part of a college or university course
you won't have access to that much chemical.
So we'll do this on small scale for you.
If you want to make larger amounts just scale it up.
To get a sense of the size of this scale, guess how big that flask is.
OK, now let me show you,
that is my hand, and this other flask is only 10 mL in volume, less than a tablespoon.
Working at this size is cheap but requires a steady hand and attention to detail.
Ok let's get started.
Weigh out 700mg of 2,4,6-Trichlorophenol.
Then add a tiny Teflon coated magnetic stir bar and turn on the stirring.
Now add 10mL of dry toluene and stir until the trichlorophenol is dissolved.
We used toluene dried by the sodium benzophenone method
but you can use toluene dried by molecular sieves or azeotropic distillation.
At this point, I like to install a rubber septum onto the flask
to prevent moisture from getting in during the cooling step.
But this is optional.
Ok now get a syringe and inject one mole equivalent of triethylamine.
I'll leave the exact calculation to you as an exercise.
If this trichlorophenol were perfectly pure, it wouldn't change color, but mine isn't.
Some samples of trichlorophenol will even change to this reddish color.
In anycase, this is not a problem for this reaction and you shouldn't be alarmed if it occurs.
Ok now place the flask into an ice bath and give it five minutes or so to cool down.
If you're doing this larger scale you should give it more time.
Let me wipe off the fog here...
Ok now inject 0.5 mole equivalents of oxalyl chloride.
I'm using a 2 molar solution because that's what I have on hand
but you may use pure oxalyl chloride or any other dilution as long as you have the right stoichiometry.
This step should be performed slowly as it produces considerable heat.
I time lapsed this video but actually I spent five minutes injecting it.
If you're doing this on a large scale, add the oxalyl chloride drop wise
and take however long is needed to keep the temperature down.
Once everything is injected and still cold, take it out of the ice bath.
Hmm, doesn't seem to be fully mixed so give it a good shake.
Let it warm back to room temperature on its own.
Ok, the mixture is ready and first thing we need to do is filter off the unreacted chemicals.
Use a vacuum flask and a glass fritted buchner funnel and filter by the vacuum filtration technique.
Ok here is our crude TCPO product and a byproduct of triethylamine hydrochloride.
To separate the two we simply add 25mL of methanol,
which will dissolve all the triethylamine hydrochloride but very little of the valuable TCPO.
Give it a good stir to thoroughly dissolve all the by-products.
Uh, hold on a second here I need to get rid of this waste.
Ok, vacuum filter it...
Get rid of the waste....
Now with an empty vacuum flask put the vacuum on the TCPO powder for several minutes to thoroughly dry out all the methanol.
Alright, carefully scrape it out...
oh yeah, remember to retrieve the stir bar we put in earlier.
And there we have it, pure bis(2,4,6-trichlorophenyl) oxalate, better known as TCPO.
Ok, let's test our product.
Get a 20mL vial and add about
3mg of 9,10-bis(phenylethynyl)anthracene
300mg of sodium acetate or sodium salicylate,
Then add ten milliliters of ethyl acetate or diethyl phthalate.
Finally add your TCPO.
Give the whole thing a good shake.
Then add in a few milliliters of 30% hydrogen peroxide.
Let me get the lights.
There you go, a successful glow stick reaction using TCPO.