(1) Add a little Et2O, cool to 0-5degC, the Ph3PO will often precipitate.

(2) Sometimes Ph3PO can be reduced in the presence of your product back to Ph3P (oftentimes this is easily done), and Ph3P is much less polar than Ph3PO, it easily separates from your product on a column.

TPPO also crystallises out of benzene/cyclohexane.

http://pubs.acs.org/doi/abs/10.1021/ol0002222

is apparently a good scavenger for TPPO

I have also heard Acetone/DCM as a solvent system for chromatographic separation.

Often the solution to this problem is not using free triphenylphosphine. The resin bound equivalent can work well and is easily removed.

Yes.. The compounds which we cannot separate using Ethylacetate/hexane.. Sometime can be easily separated by Acetone/DCM solvent system.. Again it vary..case by case

I use Ph2PPy instead of PPh3, see Steroids 2014 n°86 p1-4.

Article Easy stereoselective synthesis of 5α-estrane-3β,17α-diol, th...

thanks to all for your valuable suggestions :)

You can use Tri-n-butyl phosphine (n-Bu)3P as a substitute of TPP or you can remove the TPPO by crystallizing it in n-hexane.

If you want to purify your compound by column chromatography using EA:Hexane generally TPPO elutes at 60% EA make sure that your product must elute before 60% EA i.e. non polar than TPPO. 

Hi,

What solvent are you using now?

I know that triphenylphosphine oxide crystallized spontaneously in dioxane.

Also, addition of magnesium choride in toluene forms a complex with triphenylphosphine oxide, effectively removing >95% of this. 

Check out Org. Process. Res. Dev, 2013, 17, 666-671 where they discuss this issue.

Hope this helps. Let me know.

Best regards

Alejandro Trejos

If it is only removal of phosphine oxide you are looking for then crystallization out using CCl4 or dioxane is your best chance.

Dr. Mirza Arshad Alii Beg

Karachi

Some news in the area:

Article Removal of Triphenylphosphine Oxide by Precipitation with Zi...

Yes. In addition, instead of precipitating (which not always works...) one could try extraction between a solution in a water immiscible solvent and aqueous ZnCl2, with Ph3PO entering the aqueous phase.

Agree with suggestions above

Recrystallization from diethyl ether or dioxane is an option

Also zinc chloride in polar solvents csn complex TPPO:

https://www.google.si/url?sa=t&source=web&rct=j&url=https://pubs.acs.org/doi/pdf/10.1021/acs.joc.7b00459&ved=2ahUKEwjliq6v4PrbAhVCqaQKHTEADjEQFjAAegQIBBAB&usg=AOvVaw2Xp_RCr9SYhgB_tmJuHHch

Regards

I had this trouble, if your organic compound is having a free Nitrogen or like an amine group...you can protonate using 1-2 N HCl, and extract out the TPPO and then add base into the aqueous layer and extracting your compound using DCM/EA perfectly worked out for me...