Sciencemadness Discussion Board

Good Read: Trichloroisocyanuric Acid - A Safe and Efficient Oxidant

Mephisto - 7-11-2004 at 05:58

TCCA (Trichloroisocyanuric Acid) will play a more important role for (clandestine-) chemists as reagent for different chemical reactions. Mainly for oxidation (e.g. Benzyl Alcohol to Benzaldehyde) and chlorination. The publication "Trichloroisocyanuric Acid: A Safe and Efficient Oxidant" (Organic Process Research & Development 2002, 6, 384-393) gives a good review about the versatile use and possibilities of TCCA.

IMHO a must-read.

Attachment: Trichloroisocyanuric Acid - A Safe and Efficient Oxidant.pdf (148kB)
This file has been downloaded 3752 times

THANKS

chloric1 - 15-5-2005 at 18:42

Hey thanks alot dude! I could imagine that recycling the TCCA would be an interesting endeavor for the intrepid experimenter!:cool:

oH yea

chloric1 - 16-5-2005 at 03:56

One more thing, that article eludes to preparing acid chlorides and alkyl chlorides with TCCA and triphenylphosphine as a reducing agent. the cheapest source of triphenylphosphine is $124 for 1 KG and I am not confident this company would sell to me.:( I was wondering if anyone knew of a suitable reducing agent that could be substituted? May a sulfide?

tina_craig - 17-5-2005 at 13:57

Is the above PDF still available, I couldn't get it to download.

skippy - 17-5-2005 at 15:29

Interesting idea, chloric1. I've thought about that myself. Im guessing you could electrolyze a salt solution and bubble the chlorine into a cyanuric acid slurry. Then dry the slurry and you have alot of TCCA. If the process is easy, it might even be worth it because you could get lots of alkaline hydroxides for your trouble too. It could be fun. ;)

DMF

chloric1 - 18-5-2005 at 03:48

Tina_I downloaded the files just 2 days ago. Persistance is always the rule as for me anyways.:cool:

I realized that after further digging I found out that a imidium salt is formed from TCCA and Dimethyl formamide. THis in turn chlorinates alcohols to their respective chlorides. I will post the article when I can remember where I saved it to and what title I saved as..:o

DMF can be found with a little effort. There is a supplier in California called High Valley that specifically says they sell to hobbyist. They have a whopping 4L of DMF for $62 plus shipping!:o:o Here is the link if you want to check it out.HIgh valley Chemical

[Edited on 5/18/2005 by chloric1]

[Edited on 5/18/2005 by chloric1]

Organikum - 18-5-2005 at 05:07

I have uploaded the folder of my harddisk which contains references on TCCA and hypochlorite reactions and some ratio calculations. It´s to large for an attachment so it´s on rapidshare as .rar file.

Download here

Nicodem - 18-5-2005 at 11:41

Organikum, thanks a lot sincerely. There were a few papers I did not have and some of them are really good. The least I can do to thank you is to return the favor by adding the difference from my hard disk:

http://www.sciencemadness.org/scipics/TCICA.rar

Hmm, I hope I did not do something wrong by putting the RAR file on the pics server? But I can't make the attachement function to work anyway...

evil_lurker - 18-5-2005 at 13:44

Many thanks Organikum. :D

Lots of nifty info... Personally I like the "Clorine Gas On Demand" using TCCA and Salt coupled with vacuum.

Organikum - 18-5-2005 at 15:46

I have to thank YOU Nicodem, a convenient preparation of alpha-chloropropanoic acid is something I was after for quite some time! Mille Gracia! :)

And I would bet Polverone will like the acetic acid chlorination!

/ORG


PS: TCCA_und_hypochlorites.rar and TClCA.rar are on the ftp now.

[Edited on 19-5-2005 by Organikum]

Another striking oxidation with TCCA

chloric1 - 20-5-2005 at 03:46

Hey I came across this article on cleavage and oxidation of ethers with TCCA. Apparantly they also realized that Benzyl alcohol can be oxidized only to the aldehyde! SWEET!:cool:

By the way, I cannot seem to get *.rar files to work on my PC, what do I need to view these?

[Edited on 5/20/2005 by chloric1]

chloric1 - 20-5-2005 at 03:48

I guess it would be nice if I attached the pdf file.:P:P

Attachment: Direct conversion of ethers to esters by trichloroisocyanuric acid.pdf (95kB)
This file has been downloaded 2319 times

Organikum - 20-5-2005 at 04:57

Quote:

By the way, I cannot seem to get *.rar files to work on my PC, what do I need to view these?

Any packer which can handle .rar files will do. Like WinRar or a thousand freeware or shareware programs. Usually those which can handle .zip files can also handle .rar files.

garage chemist - 20-5-2005 at 07:12

A question: does one mol of TCCA produce 3 mol of Cl2, or only 2 mol? In your Chlorine recipe, you wrote that 500g (2 moles of the 92% OTC stuff) of TCCA with 7-8mol HCl give nearly 6 mol of Cl2.
But in your calculations here, you stated that only 2 mol Cl2 are produced per mol TCCA.

What's right now?

(My question in the "Chlorine" thread seemed to have gone unnoticed, so I'm asking it here again)

Organikum - 20-5-2005 at 07:53

1 mol TCCA + 3 mol HCl = 3 mol Cl2

My calculations in the file were actually not for publication, they may be wrong.

/ORG

Thank you

chloric1 - 21-5-2005 at 08:30

Thank you Organikum for you help. i downloaded the Wnrar and I can see everything now!:D I must confess, I never heard of rar files until I started using this forum.