Sciencemadness Discussion Board

Tetraethyl lead synthysis with lithium lead alloy?

bmays - 9-8-2013 at 16:07

4NaPb + 4CH3CH2Cl → (CH3CH2)4Pb + 4NaCl + 3Pb

I see no reason the reaction will not proceed with LiPb substituted for NaPb. Am i right? I am thinking the alloy should be 1:1 by molarity.

Metacelsus - 9-8-2013 at 16:57

Why not 4:1?

Na4Pb + 4 EtCl -> Pb(Et)4 + 4 NaCl

http://pubs.acs.org/doi/full/10.1021/om030621b
(It contains a procedure for Pb(Et)4 using 4:1 Na-Pb. This is with EtBr; with EtCl it says 1:1 is best)

Anyway, Wikipedia says that it is possible with Li:
https://en.wikipedia.org/wiki/Tetraethyllead#Synthesis_and_p...
"A process with lithium was developed, but never put into practice."

You probably want to use EtBr instead of EtCl, which is a gas at STP.
https://en.wikipedia.org/wiki/Chloroethane
https://en.wikipedia.org/wiki/Bromoethane

UnintentionalChaos - 9-8-2013 at 17:59

I would strongly advise against this synthesis. TEL is volatile, highly lipophilic, and neurotoxic with a frighteningly low boiling point of only 84C. It's hardly a surprise that it killed something like 17 workers shortly after it began being manufactured on a large scale as an antiknock agent and likely poisoned quite a few more.

If you are dead set on making a stable organometallic, consider something like tetraphenyltin. While toxic and lipophilic, it is a much more easily manipulated solid with a high boiling point. The synthesis does not require a bucket of sodium alloy and alkyl halides. SnI4 can be prepared in a flask from the elements (synthesis detailed elsewhere). A solution of this is added to PhMgBr solution (prepared like any standard grignard reagent) in the right ratio and the product is worked up.