stygian
Hazard to Others
Posts: 242
Registered: 19-9-2004
Member Is Offline
Mood: No Mood
|
|
Solvent for benzoic acid chlorination
What would be a good solvent for the chlorination of benzoic acid with a catalytic amount of phosphorus (forming PCl5 in situ) that would not
interfere with chlorination? Would ether work?
|
|
|
BromicAcid
International Hazard
Posts: 3227
Registered: 13-7-2003
Location: Wisconsin
Member Is Offline
Mood: Rock n' Roll
|
|
Don't use ether, chlorinated ethers are wicked carcinogens, try something fairly inert. I mean, what solvents do people normally preform
chlorinations in? Carbon tetrachloride springs to mind as it wouldn't be chlorinated further but the price and avilibility are major detractants of
its usefulness. There are probably some fluorocarbon mixtures out there that they sell specifically for that purpose, there's gotta be
something that I'm overlooking. As long as you keep it in the dark would free radical chlorination really be prominate, and as such couldn't
alkanes be used? Although the solubility of benzoic acid in such a medium might be crap.
|
|
|
joe_aldehyde
Hazard to Self
Posts: 68
Registered: 26-3-2005
Member Is Offline
Mood: what is mood?
|
|
chloroform or DCM is a good solvent for that, i don't think they would be further chlorinated.
otherwise, if you use thionyl chloride for the chlorination you don't need any solvent, but a catalytic amount of DMF helps a great deal.
|
|
|
Marvin
National Hazard
Posts: 995
Registered: 13-10-2002
Member Is Offline
Mood: No Mood
|
|
I don't quite follow the original question. Arte you after a ring chlorination, or forming the acid chloride? How in this situation could the
phosphorous possibly be catalyctic?
|
|
|
stygian
Hazard to Others
Posts: 242
Registered: 19-9-2004
Member Is Offline
Mood: No Mood
|
|
Im after a COCl. I was going to say it worked by 2P + 3Cl2 = 2PCl5 which would be regenerated with more Cl2 but I now realize its going to form
POCl3. Hm.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
