How to Make TCPO (for Making Glow Sticks)

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About: 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 online and we thought "we could do better".....

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!

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

For other interesting videos like this, visit our youtube channel at http://www.youtube.com/NurdRage

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    43 Discussions

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    MarthaM15

    3 years ago

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

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    shubhams51

    3 years ago on Introduction

    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....?

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    blank.cain.1

    4 years ago on Introduction

    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!

    1 reply
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    Sir Deadless

    5 years ago on Introduction

    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.

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    rszabó

    7 years ago on Introduction

    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

    1 reply
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    frodobotrszabó

    Reply 7 years ago on Introduction

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

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    JK452

    9 years ago on Introduction

    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

    4 replies
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    NurdRageJK452

    Reply 9 years ago on Introduction

    ask whatever experienced chemist is supervising you to get the chemicals for you.

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    mr.spaceNurdRage

    Reply 9 years ago on Introduction

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

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    QwertyuioLPmr.space

    Reply 9 years ago on Introduction

    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!

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    rszabóQwertyuioLP

    Reply 7 years ago on Introduction

    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

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    rhu

    7 years ago on Introduction

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

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    The Chem Guy

    7 years ago on Introduction

    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 etc...do you know of anyway to obtain anything not labelled green in Canada? Thanks for your reply

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    Rye_wrux

    8 years ago on Introduction

    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.

    2 replies
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    NurdRageRye_wrux

    Reply 8 years ago on Introduction

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

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    frodobot

    9 years ago on Introduction

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

    1 reply
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    NurdRagefrodobot

    Reply 9 years ago on Introduction

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