Author Topic: Benzyl chloride from Toluene/trichloroisocyanuric  (Read 3073 times)

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acx01b

  • Guest
Benzyl chloride from Toluene/trichloroisocyanuric
« 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 ?

Organikum

  • Guest
Yes.
« Reply #1 on: October 27, 2004, 12:28:00 PM »

other catalyst known ?


Yes! There are other catalysts!

regards
ORG




moo

  • Guest
It's not a catalyst, it's a radical initiator.
« Reply #2 on: October 27, 2004, 04:59:00 PM »
It's not a catalyst, it's a radical initiator.


Nicodem

  • Guest
"Benzoyl peroxide" is not a catalyst
« Reply #3 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?


acx01b

  • Guest
ok ty very much Does peroxyacetic acid ...
« Reply #4 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 ?

psyloxy

  • Guest
preparation of diacetyl peroxide
« Reply #5 on: October 29, 2004, 01:45:00 AM »

Patent US2439399


Patent US2458207



...dangerous stuff !

--psyloxy--

acx01b

  • Guest
what about using 2-acetoxybenzoic acid to...
« Reply #6 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?)

Nicodem

  • Guest
?
« Reply #7 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!


acx01b

  • Guest
no secret reasons, the reason is that the...
« Reply #8 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 ?

yei

  • Guest
sunlight
« Reply #9 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.