Home > Community > How does one remove triphenylphosphine oxide from product?
Upvote

25

Downvote
+ Inorganic chemistry
+ Phosphines
+ Solvents
+ Recrystallisation
+ Ethers
+ Benzene
Posted by
Oleg Savkin

How does one remove triphenylphosphine oxide from product?

Chukwuebuka Sunday  Follow

The synthesis of NiCl2(OPPh3)2 was among the references I've sent above.

More

Upvote

VOTE

Downvote
Atif Yousafzai  Follow

I've recently been having some luck by dissolving the crude reaction mixture in diethyl ether (as concentrated as you can), layering on pentane and leaving the sealed flask overnight - by morning the oxide has mostly crystallised out. Comparatively low effort procedure :)

More

Upvote

VOTE

Downvote
Dan Gengor  Follow

Thank you Mr. Imre Tóth, Krassimira Guerra , Elisenda Reixach and John James Hayward for your valuable suggestion and feedback. I will work on the suggested methods.

More

Upvote

VOTE

Downvote
Austin Mccormack  Follow

I have performed several reactions where the byproduct is triphenylphosphine oxide. The simplest way I have found to get rid of PPh3O is to dissolve the reaction mixture in ethanol, add 2 equivalents of zinc chloride (2 equivalents in comparison to PPh3) and stir for a couple of hours at room temperature. This forms a PPh3O-Zn complex, insoluble in ethanol, and can be filtered off. Refer to this paper for more information: Article Removal of Triphenylphosphine Oxide by Precipitation with Zi...


More

Upvote

VOTE

Downvote
Bryan Michaels-Lex  Follow

Triphenylphosphine oxide is not soluble at all in pentane. You could try chromatography the crude of the reaction with this solvent. 

More

Upvote

VOTE

Downvote
David Goodman  Follow

Triphenylphosphine oxide is poorly soluble in hexane. First I'd try to crystallize it out from your crude product mixture from or by adding hexane. Cooling down in cold diethyl ether could also lead to crystallization. (TPPO is a good iniator for crystallization.) You can also try chromatography of crude products using etheral or hexane solutions. If nothing works you could also think about selective complex formation either with TPPO or with the diolefine. There are lots of TPPO complexes known (see attachment below). Of course, selectivity should be checked first in this case.

More

Upvote

VOTE

Downvote
Donna Baker  Follow

If your compound doesn’t coordinate with Ni you can explore de the tetrahedral species NiCl2(OPPh3and try to crystallize it to remove

More

Upvote

VOTE

Downvote