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Topic: Hydrolysis of ester (saponification)  (Read 5350 times)

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Offline dbonyad

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Hydrolysis of ester (saponification)
« on: July 05, 2007, 01:46:54 PM »
Hello,

I urgently need help finding the method for hydrolyisis of an ester using NaOH under reflux, then adding HCl to get carboxylic acid.

I really need the method with concentrations and amounts etc. can anyone help or point me in the right direction?

Even guesses will help?

Thanks!
Davood

Offline Yggdrasil

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Re: Hydrolysis of ester (saponification)
« Reply #1 on: July 05, 2007, 05:21:46 PM »
The exact details would depend on the exact ester that you're trying to saponify, but you have a good outline of the reactions that you need to perform.

Offline Custos

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Re: Hydrolysis of ester (saponification)
« Reply #2 on: July 05, 2007, 10:42:03 PM »
Broadly speaking you could take your ester and mix with 10-20 times the volume of water. The ester probably will not dissolve in the water, but that's okay. You then have to add some sodium hydroxide. Since ester hydrolysis is catalysed by base you don't need an excess but it usually convenient to add a reasonable amount, say half a gram for every gram of ester.

This mixture is then refluxed for a few hours, cooled, and neutralised to around pH 7 with HCl (you can follow this with pH paper). The carboxylic acid might precipitate out but if not you may have to extract it with an organic solvent like ether or chloroform.

As Yggdrasil said, the exact details quantities etc. would depend on the actual ester.

Offline Borek

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Re: Hydrolysis of ester (saponification)
« Reply #3 on: July 06, 2007, 02:34:54 AM »
Since ester hydrolysis is catalysed by base you don't need an excess

Resulting acid will usually neutralize base present, slowing hydrolysis. I would go for an excess ;)
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