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Acetylanthranilic acid and a (failed) test for triboluminescence - Video Tutorial

We were intrigued by a compound which exhibits the interesting phenomenon of .

triboluminescence so we decided to have a go at making it and seeing if we could capture it .

on camera. We start with 10 grams of anthranilic acid which we oven dried for several hours before .

use. You can find out how to make this in our other video linked here. We transferred the .

anthranilic acid into a 100 milliliters flat bottomed flask. The flask needs to be big enough .

to allow some internal reflux so a 250 ml flask or conical flask would also work well. Next measure .

out 25 ml of acetic anhydride. You can find out how to make this in another of our videos linked .

here. Add the acetic anhydride to the flask containing the anthranilic acid. You will start .

doing this to make sure that the acid is absorbed by an anthranilic acid. Now condensed winners, .

to see the anthranilic acid dissolve. Then with swirling, the contents will suddenly .

turn solid. The mixture heats up and the solids dissolve .

again forming a red solution. Swirl the flask and you should see everything .

dissolve back into solution. The flask at this point is quite warm.

Place the flask on a hot plate and heat it. You want to get to a very low boil where the .

refluxing on the inside of the flask. Here we go.

Keep this going for 10 minutes and then switch off the heat and allow the flask to cool.

As you can see, we got quite a good reflux going, but with no vapor escaping from the .

flask because the anhydride has a high boiling point.

Now measure out 8 mls of water.

When you're done with the refluxing process, you should see the flask at this point. You .

40 to 50 degrees C add the water to the flask swirl the flask and you can see .

that the contents heat up again with a little bit of reflux starting up on the .

sides now put the flask back on the hot plate and heat it until it reaches a .

boil then remove the flask and place it somewhere undisturbed for a few hours in .

and for crystals to form soon you should get some very nice white crystals .

growing out of the solution this is our product and acetyl anthranilic acid .

beautiful we chilled the mixture for another few hours to see if we could get .

more crystals then it's filter time and we need to be as delicate as possible so .

as not to damage our crystals .

we left these on the pump for a good 20 minutes in order to get all the liquid .

off in the meantime we prepared 20 mils of ice-cold methanol .

we use this to rinse out their reaction flask and then gently wash the crystals .

on the filter we did notice that a small amount of product dissolved in the .

methanol .

even though it was ice cold we're not sure if any other solvents are suitable .

here though but be careful at this stage again we left the product on the pump .

until it was completely dry .

here's our product 11.7 grams of crystalline and acetyl anthranilic acid .

this is a ninety percent yield on starting and morbid acid which is great .

we place the sample .

these crystals between two glass plates and crushed them in a dark room but we .

couldn't see any flashes of light we figured that maybe they needed to be .

drier so we placed them into an oven at 100 degrees C for an hour .

here's our perfectly dry crystals again we placed some on a glass dish and .

prepared another dish that we could use to crush the crystals .

nothing either for the camera or for the naked eye .

so we're not too sure about this one we'll have a go at recrystallizing the .

product and seeing if we can get it to work with a very large single crystal if .

anyone knows how to get this to work then please let us know .

you .

stay tuned .