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Fischer-Speier Esterification: Sulfuric acid removal following creation of ester
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Louis Buff Parry
Fischer-Speier Esterification: Sulfuric acid removal following creation of ester
In a typical esterification, the sulfuric acid plays a catalytic role, so you don't need a lot, and removing it should not be a concern. Also, to drive the equilibrium reaction forward, you would want a slight excess of one of the reactants, usually the cheaper one of the acid or the alcohol (acetic acid in your particular case). The sulfuric acid is also a good dehydrating agent, so the sieves seem excessive. Finally, the ester is a bit more volatile than the other components (check a handbook for boiling points!), so distillation is standard. Otherwise, look into a Dean-Stark trap.
For other ideas on how one usually conducts an esterification, look up related syntheses in Organic Synthesis; e.g. this one or this one or this one.
In a typical esterification, the sulfuric acid plays a catalytic role, so you don't need a lot, and removing it should not be a concern. Also, to drive the equilibrium reaction forward, you would want a slight excess of one of the reactants, usually the cheaper one of the acid or the alcohol (acetic acid in your particular case). The sulfuric acid is also a good dehydrating agent, so the sieves seem excessive. Finally, the ester is a bit more volatile than the other components (check a handbook for boiling points!), so distillation is standard. Otherwise, look into a Dean-Stark trap.
For other ideas on how one usually conducts an esterification, look up related syntheses in Organic Synthesis; e.g. this one or this one or this one.
Catalytic sulfuric acid is required so just a few drops should do it.
To remove (or as it normally expressed work up) dilute the mixture with a relatively low boiling point organic solvent - ethyl acetate is good - and wash the solution with dil. sodium hydrogen carbonate solution. Separate off the organic phase (upper phase if you used EtOAc), dry it with a solid drying agent such as anhydrous magnesium sulfate, filter and remove the solvent under reduced pressure.
Catalytic sulfuric acid is required so just a few drops should do it.To remove (or as it normally expressed work up) dilute the mixture with a relatively low boiling point organic solvent - ethyl acetate is good - and wash the solution with dil. sodium hydrogen carbonate solution. Separate off the organic phase (upper phase if you used EtOAc), dry it with a solid drying agent such as anhydrous magnesium sulfate, filter and remove the solvent under reduced pressure.
In a typical esterification, the sulfuric acid plays a catalytic role, so you don't need a lot, and removing it should not be a concern. Also, to drive the equilibrium reaction forward, you would want a slight excess of one of the reactants, usually the cheaper one of the acid or the alcohol (acetic acid in your particular case). The sulfuric acid is also a good dehydrating agent, so the sieves seem excessive. Finally, the ester is a bit more volatile than the other components (check a handbook for boiling points!), so distillation is standard. Otherwise, look into a Dean-Stark trap.
For other ideas on how one usually conducts an esterification, look up related syntheses in Organic Synthesis; e.g. this one or this one or this one.
In a typical esterification, the sulfuric acid plays a catalytic role, so you don't need a lot, and removing it should not be a concern. Also, to drive the equilibrium reaction forward, you would want a slight excess of one of the reactants, usually the cheaper one of the acid or the alcohol (acetic acid in your particular case). The sulfuric acid is also a good dehydrating agent, so the sieves seem excessive. Finally, the ester is a bit more volatile than the other components (check a handbook for boiling points!), so distillation is standard. Otherwise, look into a Dean-Stark trap.
For other ideas on how one usually conducts an esterification, look up related syntheses in Organic Synthesis; e.g. this one or this one or this one.
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Catalytic sulfuric acid is required so just a few drops should do it. To remove (or as it normally expressed work up) dilute the mixture with a relatively low boiling point organic solvent - ethyl acetate is good - and wash the solution with dil. sodium hydrogen carbonate solution. Separate off the organic phase (upper phase if you used EtOAc), dry it with a solid drying agent such as anhydrous magnesium sulfate, filter and remove the solvent under reduced pressure.
Catalytic sulfuric acid is required so just a few drops should do it.To remove (or as it normally expressed work up) dilute the mixture with a relatively low boiling point organic solvent - ethyl acetate is good - and wash the solution with dil. sodium hydrogen carbonate solution. Separate off the organic phase (upper phase if you used EtOAc), dry it with a solid drying agent such as anhydrous magnesium sulfate, filter and remove the solvent under reduced pressure.
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