Triethylamine was added in excess to a reaction, so how can I get rid of it from my product?
as mentioned in earlier comments..Triethyl amine is easy to remove on rota..
But if I get a chance I will alwas choose Di-isopropylethyl amine (DIPEA) over NEt3. The Hydrochloride salt of triethylamine is solid, which may cause trouble during extraction (specially for higher scales), as the solubility of this salt is not great in water. Where as DIPEA salt is quit easy to remove by water washing..
Triethyl amine can be removed on rota by co-evaporating with higher boiling solvent. And the triethylamine hydrochloride could be removed by multiple co-evaporation with hexane/heptane.
Make Triethylamine hydrochloride salt by pouring your reaction mixture into 1N HCl. Extract with Ethylacetate/DCM twice or thrice then combined organic layers to be washed with water, concentrate organic layer to get your product. Washing the organic layer with water makes difference!
what will happen if compound also forms water soluble salt .i think it should be distilled out as such/or with water under vacuum to remove excess of tri ethyl amine
Your question is not clear enough. But in proinciple you can remove TEA simply by evaporation in vacuum. To remove its traces you can co-evaporate the residue again several times with a solvent with higher boiling point. The choice may depend on your reaction, but in most cases toluene will be good.
depends on the solvent you are working in and if you want to remove the excess (so, the neutral TEA, which is volatile, then evaporation is good, if you have a distillation step somewhere to purify the product) or also the salt (charged, can not be removed by evaporation/distilaation) which was formed. In the latter case : if the salt precipitates in the solvent you use filtration. If the precipitate is not there, you can use liquid - liquid extraction. hope this helps.
as mentioned in earlier comments..Triethyl amine is easy to remove on rota..
But if I get a chance I will alwas choose Di-isopropylethyl amine (DIPEA) over NEt3. The Hydrochloride salt of triethylamine is solid, which may cause trouble during extraction (specially for higher scales), as the solubility of this salt is not great in water. Where as DIPEA salt is quit easy to remove by water washing..
Triethyl amine can be removed on rota by co-evaporating with higher boiling solvent. And the triethylamine hydrochloride could be removed by multiple co-evaporation with hexane/heptane.
The Organic solvent washed by saturated ammonium chloride solution.
What if the product is sensitive to water? Are there any other ways to remove TEA from a reaction? Because rotovap and is kind of ineffective if i'm not mistaken.
Distill of TEA under vacuum and then give stripping thrice with any of Toluene/ethyl acetate/Acetonitrile.
If you have triethylamine and its salt in mixture (which is a usual case), you can go several ways:
1) Remove triethylamine on rotor. Try and wash triethylamine salt of with tetrahydrofuran, many of them aren't soluble
2) Neutralise salt with inorganic base, like potassium carbonate solution. You can dissolve your reaction mixture in dichloromethane and add base solution, remove organic layer, extract aqueous layer to make sure none of your product's left behind, dry it and remove solvent on rotor. In this case all TEA will be converted to free base, which will be removed on rotor along with solvent.
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