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Topic: Extraction of organic compound that contain S  (Read 2792 times)

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Offline Rutherford

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Extraction of organic compound that contain S
« on: August 22, 2012, 03:59:30 PM »
I need to separate diethyl-sulfide and 1-butanthiol. The best way is by extraction. I am not sure if I understand the process well, so I will write it here so someone can check this:
I dissolve both in water, then I add NaOH. The thiol will react with NaOH forming a salt soluble in water. Now, I add ether, and extract the diethyl-sulfide from the water solution. After this ends, I add HCl to the water solution (okay, this confuses me, what is done with the ether solution?) and get again the thiol.

Offline discodermolide

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Re: Extraction of organic compound that contain S
« Reply #1 on: August 22, 2012, 04:06:11 PM »
I need to separate diethyl-sulfide and 1-butanthiol. The best way is by extraction. I am not sure if I understand the process well, so I will write it here so someone can check this:
I dissolve both in water, then I add NaOH. The thiol will react with NaOH forming a salt soluble in water. Now, I add ether, and extract the diethyl-sulfide from the water solution. After this ends, I add HCl to the water solution (okay, this confuses me, what is done with the ether solution?) and get again the thiol.

This is an acid base extraction. NaOH reacts with the thiol as you said. The sulfide is in the ether phase.
Adding HCl to the water phase re-protonates the thiolate to give you back the thiol.
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Offline Rutherford

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Re: Extraction of organic compound that contain S
« Reply #2 on: August 22, 2012, 04:19:51 PM »
I have one more issue about this. Ether has a lower density than water, so it will be in the top layer. Now I have to decant it first, and then add HCl, right?

Offline fledarmus

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Re: Extraction of organic compound that contain S
« Reply #3 on: August 22, 2012, 04:37:17 PM »
Usually you use a seperatory funnel - http://en.wikipedia.org/wiki/Seperatory_funnel - and drain the lower layer. With practice you can get a very accurate separation of the two layers.

Offline Rutherford

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Re: Extraction of organic compound that contain S
« Reply #4 on: August 22, 2012, 05:00:02 PM »
I didn't know that. I always thought that I need somehow to get rid of the top layer. This reminds a little of chromatography. Thanks for the help.

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