video 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.
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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
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!
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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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?
L
The Journal of Unpublished Chemistry
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.