Diethyl succinate

Properties

Diethyl succinate is a colorless liquid with the formula C₈H₁₄O₄. The organic molecule contains two ester groups and occurs naturally in both plant and animal tissues. Diethyl succinate plays a key role in the Krebs cycle which is a component of metabolism. Since it is low in molecular weight, this ester is commonly used in fragrances.

Occurrences

Diethyl succinate is a byproduct of the fermentation of sugar. It is often present in fermented wines and beers that have aged a long time. Diethyl succinate is also present in the citric acid cycle. The ester bond acts a good electron donor due to resonance, and therefore diethyl succinate acts in the electron transport chain. Diethyl succinate is also present as an additive in foods and synthetic flavorings and aromas.

Production

Diethyl succinate is formed during an esterification reaction between a carboxylic acid and an alcohol.

Fisher esterification is a common method of synthesis in which the carboxylic acid reacts with an alcohol in the presence of a dehydrating reagent. The dehyrating reagent removes water from the reaction thus pushing the equilibrium toward producing more ester. This takes advantage of le Chatelier's principles.

For diethyl succinate, the carboxylic acid involved is succinic acid, or butanedioic acid, which is a dicarboxyllic acid. The alcohol involved is ethanol.

Reactions

Diethyl succinate is produced through the reduction of a conjugated alkene with chromium(II) sulfate.

Safety

Diethyl succinate can act as an irritant. If exposed to eyes, eyes should be flushed with water. Medical attention should be sought if symptoms occur. Upon skin contant, skin should be washed with soap and water.