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How to separate imine from reaction mixture?
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+ Inorganic chemistry
+ Column chromatography
+ Imines
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Luis Becerra
How to separate imine from reaction mixture?
The answer depends on the entire molecule. Imine is only one part of the molecule. TLC plates are a good guide to purification. A variety of solvents could be run, you want the Rf to be between 0.2 and 0.5. You may need a modifier such as TEA. I'd start with hexane/ethyl acetate and dichloromethane/methanol solvent systems.
The answer depends on the entire molecule. Imine is only one part of the molecule. TLC plates are a good guide to purification. A variety of solvents could be run, you want the Rf to be between 0.2 and 0.5. You may need a modifier such as TEA. I'd start with hexane/ethyl acetate and dichloromethane/methanol solvent systems.
As you must be knowing that Imine bond is prone to hydrolysis. The rate of hydrolysis gets speeded up in presence of acid or base. The stationary phase used in column like silica or alumina have acidic sites which prompt the acid hydrolysis of the imine leading to the loss of product imine (in general case) so column chromatography is not sometimes a good choice in case of schiff bases or imines. This may or may not be true in your case as i donot know the exact nature of your compounds. I can recommend purification through solvent washing's. That is say for a hypothetical case we have an un -reacted aldehyde and unreacted amine along with the product imine. Choose a dried solvent in which the product imine is most soluble than the reactant aldehyde and ammine do multiple washings with solvent/ solvent system( work out such system over TLC for your case) and remove the solvent to get the pure imine product. in another case use multiple solvents first the one in which aldeyde or amine is soluble to remove one of the reactants selectively then use another dried solvent to remove the second reactant selectively. You may have to optimize the work up protocol for your system Selective Distillation separation can also be used if the boiling points of the components of mixture are different. If the product imine is totally insoluble in some solvent, then best method would be purification by product crystallization. i have tried to give general approaches, hope any of these works for your system good luck.
As you must be knowing that Imine bond is prone to hydrolysis. The rate of hydrolysis gets speeded up in presence of acid or base. The stationary phase used in column like silica or alumina have acidic sites which prompt the acid hydrolysis of the imine leading to the loss of product imine (in general case) so column chromatography is not sometimes a good choice in case of schiff bases or imines. This may or may not be true in your case as i donot know the exact nature of your compounds. I can recommend purification through solvent washing's. That is say for a hypothetical case we have an un -reacted aldehyde and unreacted amine along with the product imine. Choose a dried solvent in which the product imine is most soluble than the reactant aldehyde and ammine do multiple washings with solvent/ solvent system( work out such system over TLC for your case) and remove the solvent to get the pure imine product. in another case use multiple solvents first the one in which aldeyde or amine is soluble to remove one of the reactants selectively then use another dried solvent to remove the second reactant selectively. You may have to optimize the work up protocol for your system Selective Distillation separation can also be used if the boiling points of the components of mixture are different. If the product imine is totally insoluble in some solvent, then best method would be purification by product crystallization. i have tried to give general approaches, hope any of these works for your system good luck.
It is tricky to separate imine using column chromatography. While using eluant like mixture of hexane and ethyl acetate or any solvent use some percentage of triethyl amine with eluent during column purification. Otherwise, If you confirm by tlc that your starting amine is totally consume during the reaction, you make it to salt with etherial HCl and then wash with organic solvent, you will get salt form of your compound. Better to separate using recrystallization technique.
It is tricky to separate imine using column chromatography. While using eluant like mixture of hexane and ethyl acetate or any solvent use some percentage of triethyl amine with eluent during column purification. Otherwise, If you confirm by tlc that your starting amine is totally consume during the reaction, you make it to salt with etherial HCl and then wash with organic solvent, you will get salt form of your compound. Better to separate using recrystallization technique.
Thank you for your suggestion. But if in the solvent washing purification method both the imine and aldehyde are soluble in same solvent then what we will do?
Thank you for your suggestion. But if in the solvent washing purification method both the imine and aldehyde are soluble in same solvent then what we will do?
As you must be knowing that Imine bond is prone to hydrolysis. The rate of hydrolysis gets speeded up in presence of acid or base. The stationary phase used in column like silica or alumina have acidic sites which prompt the acid hydrolysis of the imine leading to the loss of product imine (in general case) so column chromatography is not sometimes a good choice in case of schiff bases or imines. This may or may not be true in your case as i donot know the exact nature of your compounds. I can recommend purification through solvent washing's. That is say for a hypothetical case we have an un -reacted aldehyde and unreacted amine along with the product imine. Choose a dried solvent in which the product imine is most soluble than the reactant aldehyde and ammine do multiple washings with solvent/ solvent system( work out such system over TLC for your case) and remove the solvent to get the pure imine product. in another case use multiple solvents first the one in which aldeyde or amine is soluble to remove one of the reactants selectively then use another dried solvent to remove the second reactant selectively. You may have to optimize the work up protocol for your system Selective Distillation separation can also be used if the boiling points of the components of mixture are different. If the product imine is totally insoluble in some solvent, then best method would be purification by product crystallization. i have tried to give general approaches, hope any of these works for your system good luck.
As you must be knowing that Imine bond is prone to hydrolysis. The rate of hydrolysis gets speeded up in presence of acid or base. The stationary phase used in column like silica or alumina have acidic sites which prompt the acid hydrolysis of the imine leading to the loss of product imine (in general case) so column chromatography is not sometimes a good choice in case of schiff bases or imines. This may or may not be true in your case as i donot know the exact nature of your compounds. I can recommend purification through solvent washing's. That is say for a hypothetical case we have an un -reacted aldehyde and unreacted amine along with the product imine. Choose a dried solvent in which the product imine is most soluble than the reactant aldehyde and ammine do multiple washings with solvent/ solvent system( work out such system over TLC for your case) and remove the solvent to get the pure imine product. in another case use multiple solvents first the one in which aldeyde or amine is soluble to remove one of the reactants selectively then use another dried solvent to remove the second reactant selectively. You may have to optimize the work up protocol for your system Selective Distillation separation can also be used if the boiling points of the components of mixture are different. If the product imine is totally insoluble in some solvent, then best method would be purification by product crystallization. i have tried to give general approaches, hope any of these works for your system good luck.
The answer depends on the entire molecule. Imine is only one part of the molecule.
TLC plates are a good guide to purification. A variety of solvents could be run, you want the Rf to be between 0.2 and 0.5. You may need a modifier such as TEA. I'd start with hexane/ethyl acetate and dichloromethane/methanol solvent systems.
The answer depends on the entire molecule. Imine is only one part of the molecule.
TLC plates are a good guide to purification. A variety of solvents could be run, you want the Rf to be between 0.2 and 0.5. You may need a modifier such as TEA. I'd start with hexane/ethyl acetate and dichloromethane/methanol solvent systems.
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Imine separate from reaction mixture as solid compd. You can carry out partial crystallization , other wise go to column chromatography.
Imine separate from reaction mixture as solid compd. You can carry out partial crystallization , other wise go to column chromatography.
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try crystallization method in ethanol or methanol.
try crystallization method in ethanol or methanol.
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I'm having a similar problem with unreacted benzaldehyde and aniline, which i cannot remove from my sample to get out pure imine.
I'm having a similar problem with unreacted benzaldehyde and aniline, which i cannot remove from my sample to get out pure imine.
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As you must be knowing that Imine bond is prone to hydrolysis. The rate of hydrolysis gets speeded up in presence of acid or base. The stationary phase used in column like silica or alumina have acidic sites which prompt the acid hydrolysis of the imine leading to the loss of product imine (in general case) so column chromatography is not sometimes a good choice in case of schiff bases or imines.
This may or may not be true in your case as i donot know the exact nature of your compounds. I can recommend purification through solvent washing's. That is say for a hypothetical case we have an un -reacted aldehyde and unreacted amine along with the product imine. Choose a dried solvent in which the product imine is most soluble than the reactant aldehyde and ammine do multiple washings with solvent/ solvent system( work out such system over TLC for your case) and remove the solvent to get the pure imine product.
in another case use multiple solvents first the one in which aldeyde or amine is soluble to remove one of the reactants selectively then use another dried solvent to remove the second reactant selectively.
You may have to optimize the work up protocol for your system
Selective Distillation separation can also be used if the boiling points of the components of mixture are different.
If the product imine is totally insoluble in some solvent, then best method would be purification by product crystallization.
i have tried to give general approaches, hope any of these works for your system
good luck.
As you must be knowing that Imine bond is prone to hydrolysis. The rate of hydrolysis gets speeded up in presence of acid or base. The stationary phase used in column like silica or alumina have acidic sites which prompt the acid hydrolysis of the imine leading to the loss of product imine (in general case) so column chromatography is not sometimes a good choice in case of schiff bases or imines.
This may or may not be true in your case as i donot know the exact nature of your compounds. I can recommend purification through solvent washing's. That is say for a hypothetical case we have an un -reacted aldehyde and unreacted amine along with the product imine. Choose a dried solvent in which the product imine is most soluble than the reactant aldehyde and ammine do multiple washings with solvent/ solvent system( work out such system over TLC for your case) and remove the solvent to get the pure imine product.
in another case use multiple solvents first the one in which aldeyde or amine is soluble to remove one of the reactants selectively then use another dried solvent to remove the second reactant selectively.
You may have to optimize the work up protocol for your system
Selective Distillation separation can also be used if the boiling points of the components of mixture are different.
If the product imine is totally insoluble in some solvent, then best method would be purification by product crystallization.
i have tried to give general approaches, hope any of these works for your system
good luck.
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It is tricky to separate imine using column chromatography. While using eluant like mixture of hexane and ethyl acetate or any solvent use some percentage of triethyl amine with eluent during column purification. Otherwise, If you confirm by tlc that your starting amine is totally consume during the reaction, you make it to salt with etherial HCl and then wash with organic solvent, you will get salt form of your compound. Better to separate using recrystallization technique.
It is tricky to separate imine using column chromatography. While using eluant like mixture of hexane and ethyl acetate or any solvent use some percentage of triethyl amine with eluent during column purification. Otherwise, If you confirm by tlc that your starting amine is totally consume during the reaction, you make it to salt with etherial HCl and then wash with organic solvent, you will get salt form of your compound. Better to separate using recrystallization technique.
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But before you start your reaction is the amine soluble in the solvent you used.
But before you start your reaction is the amine soluble in the solvent you used.
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Thank you for your suggestion. But if in the solvent washing purification method both the imine and aldehyde are soluble in same solvent then what we will do?
Thank you for your suggestion. But if in the solvent washing purification method both the imine and aldehyde are soluble in same solvent then what we will do?
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I agree with Dr. Madhukar Baburao Deshmukh.
I agree with Dr. Madhukar Baburao Deshmukh.
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As you must be knowing that Imine bond is prone to hydrolysis. The rate of hydrolysis gets speeded up in presence of acid or base. The stationary phase used in column like silica or alumina have acidic sites which prompt the acid hydrolysis of the imine leading to the loss of product imine (in general case) so column chromatography is not sometimes a good choice in case of schiff bases or imines.
This may or may not be true in your case as i donot know the exact nature of your compounds. I can recommend purification through solvent washing's. That is say for a hypothetical case we have an un -reacted aldehyde and unreacted amine along with the product imine. Choose a dried solvent in which the product imine is most soluble than the reactant aldehyde and ammine do multiple washings with solvent/ solvent system( work out such system over TLC for your case) and remove the solvent to get the pure imine product.
in another case use multiple solvents first the one in which aldeyde or amine is soluble to remove one of the reactants selectively then use another dried solvent to remove the second reactant selectively.
You may have to optimize the work up protocol for your system
Selective Distillation separation can also be used if the boiling points of the components of mixture are different.
If the product imine is totally insoluble in some solvent, then best method would be purification by product crystallization.
i have tried to give general approaches, hope any of these works for your system
good luck.
As you must be knowing that Imine bond is prone to hydrolysis. The rate of hydrolysis gets speeded up in presence of acid or base. The stationary phase used in column like silica or alumina have acidic sites which prompt the acid hydrolysis of the imine leading to the loss of product imine (in general case) so column chromatography is not sometimes a good choice in case of schiff bases or imines.
This may or may not be true in your case as i donot know the exact nature of your compounds. I can recommend purification through solvent washing's. That is say for a hypothetical case we have an un -reacted aldehyde and unreacted amine along with the product imine. Choose a dried solvent in which the product imine is most soluble than the reactant aldehyde and ammine do multiple washings with solvent/ solvent system( work out such system over TLC for your case) and remove the solvent to get the pure imine product.
in another case use multiple solvents first the one in which aldeyde or amine is soluble to remove one of the reactants selectively then use another dried solvent to remove the second reactant selectively.
You may have to optimize the work up protocol for your system
Selective Distillation separation can also be used if the boiling points of the components of mixture are different.
If the product imine is totally insoluble in some solvent, then best method would be purification by product crystallization.
i have tried to give general approaches, hope any of these works for your system
good luck.
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www.rsc.org/suppdata/p1/b1/b102578n/b102578n.doc
www.rsc.org/suppdata/p1/b1/b102578n/b102578n.doc
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