Home >
Community >
Failed esterification of 1-butanol and ethanoic acid
Upvote
29
Downvote
+ Synthesis
+ Esters
+ Color
Posted by
Njabulo Twala
Failed esterification of 1-butanol and ethanoic acid
I don't think the brown color necessarily means that the reaction failed. It could be due to some contaminant in your reagents but in a small quantity that wouldn't cause the reaction to fail. The fruity smell could very well be due to your product see: n-butyl acetate has a sweet banana smell. I would take the distillate you collected (or skip the distillation altogether) and try an aqueous work-up: Add very carefully aqueous $\ce{Na2CO3}$ until basic $\ce{pH}$ and then extract this mixture with ether. This way any ester product will be in the the organic layer and sulfuric/acetic acid will stay in the aqueous together with most of the alcohol.
To finish the work-up dry the ether layers over $\ce{Na2SO4}$, filter and remove the ether (unless you have access to a Buchi evaporator, the safest way is to leave it in an open flask/beaker overnight). You can further purify the final product by distillation.
You might improve the yield if you cool the reaction mixture in an ice bath before adding sulfuric acid
I don't think the brown color necessarily means that the reaction failed. It could be due to some contaminant in your reagents but in a small quantity that wouldn't cause the reaction to fail. The fruity smell could very well be due to your product see: n-butyl acetate has a sweet banana smell. I would take the distillate you collected (or skip the distillation altogether) and try an aqueous work-up: Add very carefully aqueous $\ce{Na2CO3}$ until basic $\ce{pH}$ and then extract this mixture with ether. This way any ester product will be in the the organic layer and sulfuric/acetic acid will stay in the aqueous together with most of the alcohol.
To finish the work-up dry the ether layers over $\ce{Na2SO4}$, filter and remove the ether (unless you have access to a Buchi evaporator, the safest way is to leave it in an open flask/beaker overnight). You can further purify the final product by distillation.
You might improve the yield if you cool the reaction mixture in an ice bath before adding sulfuric acid
I don't think the brown color necessarily means that the reaction failed. It could be due to some contaminant in your reagents but in a small quantity that wouldn't cause the reaction to fail. The fruity smell could very well be due to your product see: n-butyl acetate has a sweet banana smell. I would take the distillate you collected (or skip the distillation altogether) and try an aqueous work-up: Add very carefully aqueous $\ce{Na2CO3}$ until basic $\ce{pH}$ and then extract this mixture with ether. This way any ester product will be in the the organic layer and sulfuric/acetic acid will stay in the aqueous together with most of the alcohol.
To finish the work-up dry the ether layers over $\ce{Na2SO4}$, filter and remove the ether (unless you have access to a Buchi evaporator, the safest way is to leave it in an open flask/beaker overnight). You can further purify the final product by distillation.
You might improve the yield if you cool the reaction mixture in an ice bath before adding sulfuric acid
I don't think the brown color necessarily means that the reaction failed. It could be due to some contaminant in your reagents but in a small quantity that wouldn't cause the reaction to fail. The fruity smell could very well be due to your product see: n-butyl acetate has a sweet banana smell. I would take the distillate you collected (or skip the distillation altogether) and try an aqueous work-up: Add very carefully aqueous $\ce{Na2CO3}$ until basic $\ce{pH}$ and then extract this mixture with ether. This way any ester product will be in the the organic layer and sulfuric/acetic acid will stay in the aqueous together with most of the alcohol.
To finish the work-up dry the ether layers over $\ce{Na2SO4}$, filter and remove the ether (unless you have access to a Buchi evaporator, the safest way is to leave it in an open flask/beaker overnight). You can further purify the final product by distillation.
You might improve the yield if you cool the reaction mixture in an ice bath before adding sulfuric acid
More
VOTE