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Topic: About separating funnel extraction  (Read 2587 times)

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Offline kamiyu

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About separating funnel extraction
« on: February 12, 2014, 03:46:05 PM »
Hi guys

I think it is a quite common phenomenon that when you shake the stuff in a seperatory funnel, there will be some gas coming out (but there is no NaHCO3 or Na2CO3 used).

Can anyone come up with any explanation???

Offline TheUnassuming

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Re: About separating funnel extraction
« Reply #1 on: February 12, 2014, 04:13:33 PM »
I think the pressure is due to the vapor pressure of the organic layer.   
When you shake up a lower boiling solvent in a contained vessel it will cause a rise in pressure as it attempts to equilibrate.   
When in doubt, avoid the Stille coupling.

Offline TheUnassuming

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Re: About separating funnel extraction
« Reply #2 on: February 12, 2014, 04:17:58 PM »
Just tried DCM alone in a sep funnel, seems to cause a rise in pressure when you shake it up.
When in doubt, avoid the Stille coupling.

Offline kamiyu

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Re: About separating funnel extraction
« Reply #3 on: February 12, 2014, 05:18:13 PM »
Thanks for your trial!

I quite often observe this gas formation when i am using DCM.

Shaking results in slight boiling ???
Just tried DCM alone in a sep funnel, seems to cause a rise in pressure when you shake it up.

Offline TheUnassuming

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Re: About separating funnel extraction
« Reply #4 on: February 12, 2014, 05:59:56 PM »
... wait... when you shake the reaction in DCM it starts to bubble/boil?   
I've only ever seen that with Et2O when I rushed and didn't let the reaction cool down far enough before extracting.
When in doubt, avoid the Stille coupling.

Offline kamiyu

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Re: About separating funnel extraction
« Reply #5 on: February 12, 2014, 06:35:26 PM »
Sorry, the word "boil" means sth like "more vigorous" vaporization.... not actually boiling

I would like to say, shaking may result in faster evaporization of DCM.
... wait... when you shake the reaction in DCM it starts to bubble/boil?   
I've only ever seen that with Et2O when I rushed and didn't let the reaction cool down far enough before extracting.

Offline TheUnassuming

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Re: About separating funnel extraction
« Reply #6 on: February 13, 2014, 12:16:30 PM »
Ah, that makes more sense.  I was trying to envision an exothermic reaction that might take place upon partitioning and heat up your organic layer :P.
Increasing the evaporation is another way to think about it the rise in vapor pressure, just depends on how you best visualize it.
When in doubt, avoid the Stille coupling.

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