Introduction: How to Make TCPO (for Making Glow Sticks)

How to make TCPO or bis(2,4,6-trichlorophenyl) oxalate, used in glow stick reactions.

WARNING: This procedure should only be performed by, or under the direct supervision of, an experienced chemist. Please refer to the material safety data sheets of all chemicals for their hazards. Synthesis must be performed in a fumehood.

1. Start with 2,4,6-trichlorophenol and dissolve it in dry toluene (15-20mL of toluene per gram of TCP). Azeotropic distillation may be used to obtain a dry solution.

2. Chill solution in an ice bath to zero Celsius

3. Add one molar equivalent of triethylamine or similar suitable organic base. A dried base, usually over molecular sieves, is preferred.

4. Keep chilled with stirring and add 0.5 mol equivalents drop wise of oxalyl chloride. Extensive evolution of heat will occur as well as formation of a thick off-white precipitate.

5. Once all oxalyl chloride as been added, mixture is allowed to warm to room temperature. It was found that purity increases if stirring is allowed to continue overnight.

6. Suction filter the mixture on a fritted funnel. Discard the filtrate. The TCPO is a fine white powder mixed with triethylammonium chloride at this point.

7. The mixture is washed with methanol or ethanol to remove the triethylammonium chloride and then thoroughly dried, preferably under vacuum.

To perform glow stiick reaction mix these chemicals:

3mg of 9,10-bis(phenyethynyl) anthracene
300mg of sodium acetate or sodium salicylate
10mL of ethyl acetate or diethyl phthalate
All the TCPO in the video.
3mL of hydrogen peroxide added last to initiate the reaction.

The exact same process is used in glow sticks. This is NOT mountain dew. Mountain dew cannot glow like this, it does not have the crucial TCPO chemical or any chemical like that.

The reaction will glow in the dark for several minutes if you use ethyl acetate as the solvent. It will glow for several hours if you use diethyl phthalate as the solvent.

Thanks for watching!

Please subscribe, rate and comment!

We make most of our chemicals or buy them from Alfa Aesar.

For other interesting videos like this, visit our youtube channel at


MarthaM15 (author)2015-11-03

Would doing this be more or less expensive then just buying TCPO?

shubhams51 (author)2015-09-07

nurd rage i need help i am doing chemical diploma last year and i am doing project on glow stick need can you give me some help with other simple process n details....?

blank.cain.1 (author)2015-01-07

hey Rage do you still check these comments? If so, then I was wondering what that "temp one coated ??? Bar" was? You said at about 1:17 into the video. I'm not a chemistry major or anything so some of this stuff is Unkown to me Please help if you are still checking these. Thank you!

AndrewK19 (author)blank.cain.12015-07-08

That's Teflon... (PTFE)

Sir Deadless (author)2013-11-24

I'm doing a fluorescence experiment at school but the head of science says I cant use any carcinogenic chemicals, are any used here carcinogenic? if so how can I replace them? thanks.

rszabó (author)2011-03-20

haha im in the 8th grade and i don't know where to get these or i don't know a chemist and im pretty advanced in science next year im skipping 9th grade physical science and going straight into honors 10th grade biology

frodobot (author)rszabó2011-03-20

So? I'm advanced too and a google search usually brings up a list of the chemicals and where to get them

JK452 (author)2009-05-16

Dude that was awesome but uhh can u buy those chemicals somewgere because im in 8th grade and i dont think i could get any of those

NurdRage (author)JK4522009-05-16

ask whatever experienced chemist is supervising you to get the chemicals for you. (author)NurdRage2009-05-21

hmmm, somthing tells me that there isnt an experienced chemist supervising him... or me for that matter

QwertyuioLP (author)mr.space2009-12-25

I think I made may "experienced chemist" retire!! Either that or it was my teacher I made retire 'cause I kept showing him up in class and I'm in 8th grade!! LOL!

rszabó (author)QwertyuioLP2011-03-20

haha im in the 8th grade and i don't know where to get these or i don't know a chemist and im pretty advanced in science next year im skipping 9th grade physical science and going straight into honors 10th grade biology

rhu (author)2011-03-02

If i do not have an aspirator...what's the best way for me to dry out the mixture and get all the TCPO?

The Chem Guy (author)2011-01-25

I know exactly what you mean. I was looking at a rocket candy video the other day ( the KNO3/Sucrose rockets...) and people were asking why it's called rocket "candy"...that's ridiculous! Anyways, I to am a candian citizen chemist with absolutely no luck in finding local chemicals. I am assuming that you have all the licenses for the concentrated acids, and oxidizers you know of anyway to obtain anything not labelled green in Canada? Thanks for your reply

Roxy 143 (author)2010-09-05

Very Nice !!!!!!

Rye_wrux (author)2010-02-17

Im a college student but it is a small school with limited chemical and im trying to show this reaction for a demonstration to my class. is there a way to synthesize 2,4,6-trichlorophenol and 9,10-bis(phenyethynyl) anthracene or would i need to purchase these? I have access to all other necessary chemicals and equipment.

NurdRage (author)Rye_wrux2010-02-17

Both are cheap enough that they should be purchased, making them is more expensive than buying them.

Rye_wrux (author)NurdRage2010-02-18

Thanks for all the help

frodobot (author)2010-01-19

On the "Nurdrage Lab's" bottle of TCPO, it says that this is a Carcinogenic. Is it safe to use in small amounts?

NurdRage (author)frodobot2010-01-19

like all chemicals, tcpo should be treated with respect,  its about as dangerous as benzene, so not very, but not zero.

terminator_chem (author)2009-05-31

and dude i found another reaction to make a glow liquid can you verify if this procedure is copy pastin the requirements and procedure...i think if u can tell u will help a lot of ppl;-If you don't have luminol than you are in a big problem if you want to make glowsticks. I made a glowing liquid half year ago it was glowing with a red color, the recipe is here: 1. Mix a solution of: a. 40mL distilled water b. 0.8g hydroxide c. 25g K2CO3 d. 1g pyrogallol e. 10 mL standard 37% methanal ("formaldehyde") all in a beaker too large for overflow 2. Darken the room 3. Add 30 mL standard 30% hydrogen peroxide Notes : The red glow is due to the oxidation of pyrogallol and methanal in alkaline peroxide. Either on its own should work but it works better if you use both. Pyrogallol is highly toxic. And if you add the H2O2 too fast it will boil and a lot of formaldehyde will get in to the air what is not so good. This thing is glowing until you add H2O2 to the mix. If you add it fast than it will have a strong light, if you add slow, than it will have a weak light. //I know that tis is not an easy recipe, but is is cheaper and easier than the other ones. You won't make glowstick easier. sum1 posted this recepie....can u tell every1 on instructables if it is safe or not....cause he isnt even using luminol....!!!!!

terminator_chem (author)2009-05-31

hola dude....that was awesome and incredibly kool experiment........but senor can u tell me if we have to dry it with the vaccum or can we use it wet!....and this sure breaks the mountain dew hoax though......muchos gracias amigo!

jack_swallows (author)2009-05-31

what i meant to say was that do i have to vaccum dry the TCPO or can i use it directly??

im seriously sorry if i irritated you...but pls reply when u can ...!!! :D:D:D

jack_swallows (author)2009-05-31

and do we have to dry the mixture under vaccum?

jack_swallows (author)2009-05-31

hey dude......awesome experiment liked it alot and i want to make it for my science exhibit which is coming up in 5 days time......can you please tell me an easier way to make the TCPO................please!!!!!!!!

NurdRage (author)jack_swallows2009-05-31

you can use dichloromethane instead of toluene and the ice bath is optional. You can also stir for just ten minutes and wash with water instead of alcohol. yield will be decreased, but its easier

jack_swallows (author)NurdRage2009-05-31

thanks a lot....and are there anymore experiments like this that can help me to win the prize?

NurdRage (author)jack_swallows2009-05-31

check out my videos and my youtube channel (link in the video description) i have plenty more

lemonie (author)2009-05-11

When you refer to aezeotropic distillation, do you mean reflux with a Dean-Stark or similar?

In my experience there's a significant difference between ethanol & methanol as solvents: I would expect TCPO to dissolve in methanol to some extent?
Recrystallisation appropriate, TLC analysis?


The Journal of Unpublished Chemistry

NurdRage (author)lemonie2009-05-11

Whatever way gets you clean dry toluene you may used. Like i said i only used sodium-benzophenone dried toluene. Heck even wet toluene still works, just the yields are terrible. (tried it myself)

As said in the video, some TCPO does dissolve in the methanol, but i've found the amount negligible. In fact, when cleaning TCPO from the walls of the flask methanol doesn't even soften the TCPO residue caked on, you have to use acetone or DCM.

I selected methanol for the video because it just happen to be what i had on hand. But i have tried ethanol in the past and found no difference. Up here in Canada methanol is the cheaper of the two solvents so i try to use that when i can.

Product can be used directly without recrystallization as seen in the video. For storage, it should be vacuum dried first.

If you really want:
The TCPO can be recrystallized from hot toluene. If you want large (~1cm) crystals of ultra-pure TCPO then you can crystallize from sodium-dried tetrahydrofuran by evaporation. Alot of the product will decompose while this is happening so you'll get large crystals of TCPO covered in decomposition products. Wash off the residues with water, methanol and acetone and dry under vacuum. Excessive loss of the product will occur here but you'll get GIANT crystals of TCPO that are SO worth it. :)

I started with 100g of crude TCPO and crystallized 40g of ultra-pure TCPO but that same original sample has lasted me 2 years until this day. It's still viable and as potent as the day i made it.

BTW, tcpo must be stored in an air-tight container.

croutonicus (author)NurdRage2009-05-13

I can think of a much better use for that toluene :) However, just before you vaccum dry the mixture you pour in a clear liquid, not too sure what it is from the instructions (ethanol or methanol?)

NurdRage (author)croutonicus2009-05-13

either one, i've tried both and they work fine. In the video i used methanol because that's what i had on hand. Toluene is used extensively in paint thinner if that's what you want.

croutonicus (author)NurdRage2009-05-14

Thanks. Although why did you have methanol "to hand" :P

NurdRage (author)croutonicus2009-05-14

"to hand"? when did i say that?

croutonicus (author)NurdRage2009-05-14

Ah my main problem was that i wasn't watching with the sound on. Just don't want to get these things wrong

lemonie (author)NurdRage2009-05-11

(I should have watched the video, did you click my link?) Thanks for the info, number of times I've "done" a THF still... L

NurdRage (author)lemonie2009-05-11

I checked the link... uhh... maybe it's just a joke... but i have to ask: Are you implying i got crap chemistry going on in this instructable?

jeff-o (author)2009-05-11

Well that's not very hard at all! :-/ I was never much for chemistry - I think I'll continue using commercial glow sticks.

NurdRage (author)jeff-o2009-05-11

At least it's real, unlike "glowing mountain dew" hoaxes.

jeff-o (author)NurdRage2009-05-12

LOL. The stuff that people will fall for has ceased to amaze me. Now I just shake my head and weep for the human race.

lemonie (author)NurdRage2009-05-11

It glows like Tonic Water? (or it doesn't?) L

NurdRage (author)lemonie2009-05-11

type "mountain dew glow" in youtube. Be sure to remove all breakables from the room before you watch so you don't damage anything when you go on a homicidal rampage at how people can post, and even fall for, such crap.

About This Instructable




Bio: NurdRage is a dedicate group of science nerds trying to further amateur science with direct how-to instructions in video format. We saw what was already ... More »
More by NurdRage:Make a Tritium Nuclear Battery or Radioisotope Photovoltaic GeneratorRecover Copper and Fully Recycle Spent Copper Chloride PCB Etchant$50 Vacuum Pump That Can Boil Water at Room Temperature
Add instructable to: