Los ésteres son compuestos orgánicos producidos por la reacción de los alcoholes con los ácidos. Al reaccionar un ácido orgánico o inorgánico, con un alcohol o fenol, se elimina agua y se forma un éster en el que el hidrógeno ácido ha sido reemplazado por un radical orgánico.
La fórmula general de los ésteres es: R-CO-O-R’
Ácido + Alcohol / Fenol ↔ éster + agua
CH3-CH2-COOH + CH3-OH ⇔ CH3-CH2-COO-CH3 + H2O
ácido propiónico + metanol ⇔ propianato de metilo + agua
Cuando la reacción se da en sentido directo se le conoce como esterificación y cuando se da en sentido inverso se le llama saponificación. Cuando se realiza con un ácido orgánico, es conveniente utilizar ácido sulfúrico o ácido clorhídrico como catalizadores.
Propiedades físicas
- Son líquidos volátiles que poseen olores agradables a frutas. Son más volátiles que los alcoholes y ácidos de igual masa molar.
- Son poderosos disolventes
- Poseen puntos de ebullición muchísimo más bajos que los ácidos carboxílicos de igual masa molar.
Aplicaciones y usos
Como se señaló anteriormente, los ésteres poseen olores agradables a frutas; por tal razón, son utilizados para la preparación de esencias y perfumes artificiales. Al ser poderosos disolventes, son empleados en la elaboración de barnices y en la extracción de antibióticos a partir de licores fermentados.
Los ésteres se encuentran distribuidos ampliamente en los reinos vegetal y animal. Su mayor fuente natural es seguramente las grasas y los aceites, que son ésteres derivados de ácidos grasos de largas cadenas (16 a 18 átomos de carbono) y de la glicerina. Debido a esto se utilizan en la elaboración de jabones mediante el proceso de saponificación.
Tabla. 1. Olores de los ésteres más comunes
Nombre |
Olor |
Acetato de n-amilo |
Banana |
Acetato de n-octilo |
Naranja |
butirato de metilo |
Piña |
Butirato de n-amilo |
Albaricoque |
Butirato de isoamilo |
Pera |
Isovalerato de isoamilo |
Manzana |
Formiato de isobutilo |
Frambuesa |
Fuente: Dr.H.Moreno González. Química Orgánica Moderna.
Nomenclatura para Ésteres
Nomenclatura IUPAC: Alcanoato de alquilo
Nomenclatura Común: Carboxilato de alquilo
Como sustituyente:
-CO-O-R’ Carboalquiloxi (se omite il de 1 a 4 átomos de carbonos) Por ejemplo:
1 átomo de carbono: carbometoxi
5 átomos de carbono: carbopentiloxi
Orden de prioridad. Estos tienen prioridad frente a los alcoholes, aldehídos, cetonas y demás grupos funcionales que están por debajo, sin embargo, los ácidos presentan mayor prioridad sobre los ésteres.
Ejercicios Resueltos
IUPAC: Etanoato de etilo
Común: Acetato de etilo
2.
IUPAC: Metanoato de propilo
Común: Formiato de n-propilo
3.
IUPAC: Hexanoato de 3,3-dimetilbutilo
Común: Caproato de neohexilo
4.
IUPAC: ácido- 3- carbo-2-butoxipropanoico
Común: ácido-3- carbo-secbutoxipropiónico
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