Difference between revisions of "Fischer esterification"
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| − | Fisher esterification is an organic chemical reaction in which an [[ | + | '''Fisher esterification''' (complete name '''Fischer–Speier esterification''') is an organic chemical reaction in which an [[alcohol]] reacts with a [[carboxylic acid]] in the presence of a strong acid to create an [[ester]] and [[water]]. This is a coupling reaction. It was first described by the chemists Hermann Emil Fischer and Arthur Speier. This is a dynamic reaction which exists in equilibrium. The chemists object is to manipulate concentration and conditions to drive the reaction towards the desired product before they die of old age. Fisher esterification is slow. It helps not a bit that in reverse, water hydrolyzes an ester to return the alcohol and the carboxylic acid. Both processes coexist, so the task is not easy. |
| − | == | + | ==Tips== |
* Remove one of the products as the reaction proceeds to force the equilibrium in that direction. | * Remove one of the products as the reaction proceeds to force the equilibrium in that direction. | ||
* Start with as little water as possible. | * Start with as little water as possible. | ||
* Start with an excess of the alcohol and let Le Chatelier do the driving. | * Start with an excess of the alcohol and let Le Chatelier do the driving. | ||
| + | * Wear comfortable shoes. | ||
| − | == | + | ==Examples== |
| − | + | A classic example is to distill glacial [[acetic acid]], anhydrous [[ethanol]] with a catalytic amount of concentrated [[sulfuric acid]] to give [[ethyl acetate]]. The resulting distillate can be then be further purified and re-distilled as described by [https://www.erowid.org/archive/rhodium/chemistry/ethyl.acetate.html Erowid]. | |
| − | A classic example is to distill glacial [[ | + | |
| − | + | ||
| − | + | ||
| + | ==Mechanism== | ||
Read about the mechanism [[http://chemwiki.ucdavis.edu/Core/Organic_Chemistry/Carboxylic_Acids/Reactivity_of_Carboxylic_Acids/Fischer_esterification here]] | Read about the mechanism [[http://chemwiki.ucdavis.edu/Core/Organic_Chemistry/Carboxylic_Acids/Reactivity_of_Carboxylic_Acids/Fischer_esterification here]] | ||
| − | == | + | ==Projects== |
| − | + | * [[Methyl salicylate]] (Oil of Wintergreen) | |
| − | * [[Methyl salicylate]] Oil of Wintergreen | + | * [[Dimethyl oxalate]] |
| − | * [[Dimethyl | + | |
==References== | ==References== | ||
| + | <references/> | ||
| + | ===Relevant Sciencemadness threads=== | ||
| + | *[http://www.sciencemadness.org/talk/viewthread.php?tid=62134 Fischer esterification equilibrium] | ||
| + | *[http://www.sciencemadness.org/talk/viewthread.php?tid=21045 Catalysts for Fischer Esterification] | ||
| + | *[http://www.sciencemadness.org/talk/viewthread.php?tid=14680 Making esters without sulfuric acid] | ||
| + | *[http://www.sciencemadness.org/talk/viewthread.php?tid=11063 Esterification of Malonic Acid to DiEthyl Malonate] | ||
| + | *[http://www.sciencemadness.org/talk/viewthread.php?tid=64203 Thought from "Fisher esterificatioon of ethylene glycol"] | ||
| + | *[http://www.sciencemadness.org/talk/viewthread.php?tid=61954 Fisher esterification of citric acid and acetic acid to make this?] | ||
| + | *[http://www.sciencemadness.org/talk/viewthread.php?tid=72016 Fisher-Esterification] | ||
| + | *[http://www.sciencemadness.org/talk/viewthread.php?tid=29079 Fisher Esterification - Flavoring Chemicals] | ||
[[Category:Reactions]] | [[Category:Reactions]] | ||
Latest revision as of 18:32, 10 June 2019
Fisher esterification (complete name Fischer–Speier esterification) is an organic chemical reaction in which an alcohol reacts with a carboxylic acid in the presence of a strong acid to create an ester and water. This is a coupling reaction. It was first described by the chemists Hermann Emil Fischer and Arthur Speier. This is a dynamic reaction which exists in equilibrium. The chemists object is to manipulate concentration and conditions to drive the reaction towards the desired product before they die of old age. Fisher esterification is slow. It helps not a bit that in reverse, water hydrolyzes an ester to return the alcohol and the carboxylic acid. Both processes coexist, so the task is not easy.
Tips
- Remove one of the products as the reaction proceeds to force the equilibrium in that direction.
- Start with as little water as possible.
- Start with an excess of the alcohol and let Le Chatelier do the driving.
- Wear comfortable shoes.
Examples
A classic example is to distill glacial acetic acid, anhydrous ethanol with a catalytic amount of concentrated sulfuric acid to give ethyl acetate. The resulting distillate can be then be further purified and re-distilled as described by Erowid.
Mechanism
Read about the mechanism [here]
Projects
- Methyl salicylate (Oil of Wintergreen)
- Dimethyl oxalate
References
Relevant Sciencemadness threads
- Fischer esterification equilibrium
- Catalysts for Fischer Esterification
- Making esters without sulfuric acid
- Esterification of Malonic Acid to DiEthyl Malonate
- Thought from "Fisher esterificatioon of ethylene glycol"
- Fisher esterification of citric acid and acetic acid to make this?
- Fisher-Esterification
- Fisher Esterification - Flavoring Chemicals
