The Vespiary

The Hive => Chemistry Discourse => Topic started by: acx01b on October 26, 2004, 11:06:00 PM

Title: Benzyl chloride from Toluene/trichloroisocyanuric
Post by: acx01b on October 26, 2004, 11:06:00 PM
Hi,

Preparation of Benzyl Chloride (44% yield?) by refluxing Toluene and trichloroisocyanuric acid, with Benzoyl Peroxide as catalyst looks interesting...

other catalyst known ?
Title: Yes.
Post by: Organikum on October 27, 2004, 12:28:00 PM

other catalyst known ?


Yes! There are other catalysts!

regards
ORG



Title: It's not a catalyst, it's a radical initiator.
Post by: moo on October 27, 2004, 04:59:00 PM
It's not a catalyst, it's a radical initiator.

Title: "Benzoyl peroxide" is not a catalyst
Post by: Nicodem on October 27, 2004, 05:04:00 PM
There are many radical initiators that can substitute it, practicaly any compound with the -CO-OO-CO- group will do, probably AIBN or other aza compounds would work as well. And quite probably a mercury lamp would suffice too. But as far as I know, peroxybenzoic acid anhydride (aka "benzoyl peroxide") is the only one that you can easily get OTC, so I can see no point in your question. Or are you perhaps interested in other radical initiators that might increase the yields?

Title: ok ty very much Does peroxyacetic acid ...
Post by: acx01b on October 28, 2004, 08:24:00 PM
ok ty very much
Does peroxyacetic acid anhydride work ?
can it be formed from H2S2O8 NaOH and acetic acid ?
Title: preparation of diacetyl peroxide
Post by: psyloxy on October 29, 2004, 01:45:00 AM

Patent US2439399 (http://l2.espacenet.com/dips/viewer?PN=US2439399&CY=gb&LG=en&DB=EPD)


Patent US2458207 (http://l2.espacenet.com/dips/viewer?PN=US2458207&CY=gb&LG=en&DB=EPD)



...dangerous stuff !

--psyloxy--
Title: what about using 2-acetoxybenzoic acid to...
Post by: acx01b on November 05, 2004, 11:55:00 AM
what about using 2-acetoxybenzoic acid to obtain di(2-hydroxybenzoyl)peroxide ?

Aspirin + NaOH  --> Na-acetate + 2-hydroxybenzoic acid
(advices for separation?)
Title: ?
Post by: Nicodem on November 05, 2004, 01:17:00 PM
Besides of being impossible to prevent the self oxydation of such a peroxyde, WHY?

What the hell is wrong with peroxybenzoic anhydride? It is OTC all over the world and it gives acceptable yields, so why do you insist on these ideas? Could you share your secret reasons with us!

Title: no secret reasons, the reason is that the...
Post by: acx01b on November 05, 2004, 03:49:00 PM
no secret reasons, the reason is that the route throw aspirin to Ph-CH2Cl is funny !


sory i didn't understand your 1st match, you say di(2-hydroxybenzoyl)peroxide won't be obtained ? what will be obtained that way ?
Title: sunlight
Post by: yei on November 06, 2004, 05:10:00 AM
sunlight works nicely, apparently.

In a similar benzylic chlorination (with t-butyl peroxide), it was greatly superior to chemical radiacal initiators.