dormouse (Member)
04-25-00 01:21
No 108856
      Hydrogenation of benzoyl peroxide -phalaris  Bookmark   


   the Hive BB
  Novel Discourse
  Hydrogenation of benzoyl peroxide
  
profile | register | preferences | faq | search
 
 next newest topic | next oldest topic 
Author  Topic:   Hydrogenation of benzoyl peroxide 
phalaris
Hive Bee   posted 02-14-2000 11:54 PM           
--------------------------------------------------------------------------------
I have an idea which I think is interesting, and I have been unable to find any information on the subject.
Benzoyl peroxide has an interesting structure - two benzene rings joined by four oxygen molecules... That long string of oxygen molecules looks surprisingly easy to attack to make...

It looks like this: http://194.196.248.66/cat/web2.disp_struct?v_id=801641 
 

Benzoyl peroxide is easily available as 10% of OTC acne medications. It could probably be extracted by a wash with water, careful dehydration, extraction with the appropriate solvents, cromatographed, and crystalized. It may only necessary to do parts of this procedure (thus saving effort), but I am quite sure that it would work.

I think it may be possible to hydrogenate it to benzaldehyde. Anybody ever heard of anyone doing this?

I think that simply bubbling hydrogen through a solution of benzoyl peroxide in methanol (with a trace of HCl), it would become benzaldehyde. A catalyst might be needed, but I doubt it. Heat or pressure might be necessary though. Is this worth trying, or is it a waste of time?

------------------
The first duty of a revolutionary is to get away with it.
-- Abbie Hoffman


 
phalaris
Hive Bee   posted 02-14-2000 11:56 PM           
--------------------------------------------------------------------------------
My apologies for typos in the previous post.
 
phalaris
Hive Bee   posted 02-15-2000 12:12 AM           
--------------------------------------------------------------------------------
Dammit! I meant two oxygen molecules.
I blame the ganja.


Osmium
PimpBee   posted 02-15-2000 05:17 AM           
--------------------------------------------------------------------------------
Benzoyl peroxide is in polyester resin hardener. Cheap, easy, everywhere.
BUT, I don't think that your idea will work. There is a variant of the ozone oxidation workup, where Zn/AcOH is used. Maybe this will work, but I'm not very confident. You will most likely end up with benzoic acid.


Wizard X
PimpBee   posted 02-15-2000 07:33 PM           
--------------------------------------------------------------------------------
phalaris: Benzoic acid + SOCl2 => C6H5COCl
Benzoic acid chloride, C6H5COCl
C6H5COCl + Pd/BaSO4/Quinine/H2=> C6H5CHO +HCl


CHEM GUY
Hive Bee   posted 02-16-2000 12:13 AM           
--------------------------------------------------------------------------------
Why would you want to synthesize benzylaldehyde? Just get almond oil... ~90% benzylaldehyde. Then separate... somehow. It seems a lot easier doesn't it
 
phalaris
Hive Bee   posted 02-18-2000 12:01 AM           
--------------------------------------------------------------------------------
CHEMGUY: It was merely an idea that I had some months ago. I have also considered the almond oil route - distillation seems like it would be the best method.
I was under the impression that almond oil was only about 10% benzaldehyde.


phalaris
Hive Bee   posted 02-18-2000 03:59 AM           
--------------------------------------------------------------------------------
I believe that is is possible to go from benzoic acid to bezaldehyde directly with lithium aluminum hydride.


Osmium
PimpBee   posted 02-18-2000 06:10 AM           
--------------------------------------------------------------------------------
No, but maybe you can do that with LAH/BuOH -----> LiAlH(BuO)3.
Jeeze guys this is really not an option. Wasting LAH to prepare benzaldehydes??
 
All times are CT (US)
 next newest topic | next oldest topic


Administrative Options: Close Topic | Archive/Move | Delete Topic
    Hop to: Select a Forum or ArchiveList of Forums:General DiscussionNewbie ForumAcquisition DiscourseChemistry DiscourseMethods DiscourseNovel DiscourseCrystal MethSerious Chemistry ForumThe Hive CouchAdmin Chill-out TentList of Archives:Couch ArchivesClassics!Law and OrderThe litter box.misc. PEAs  

Contact Us | the Hive

Powered by: Ultimate Bulletin Board, Version 5.43c
Infopop Corporation (formerly Madrona Park, Inc.), 1998 - 2000.