Diethyl succinate

Diethyl succinate
Names
Preferred IUPAC name
Diethyl butanedioate
Other names
Diethyl succinate
Butanedioic acid diethyl ester
Clorius
Identifiers
123-25-1
3D model (Jmol) Interactive image
907645
ChemSpider 13865630
ECHA InfoCard 100.004.194
PubChem 31249
RTECS number WM7400000
Properties
C8H14O4
Molar mass 174.194 g/mol
Appearance Colorless liquid
Density 1.047 g/mL
Melting point −20 °C (−4 °F; 253 K)
Boiling point 218 °C (424 °F; 491 K)
Slightly soluble
Vapor pressure 0.13 mmHg
Thermochemistry
24.22 kJ/g
Hazards
Main hazards Primary irritant
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
1
0
Flash point 90.56 °C (195.01 °F; 363.71 K)
Explosive limits 1.1-6.5%
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Diethyl succinate is the diethyl ester of 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.[1]

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.[2] 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. [3]

RCOOH + R'OH ↔ RCOOR' + water

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.[4] 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.[5]

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.[6]

References

  1. ↑ Loudon, Marc (2009). Organic Chemistry. Colorado: Roberts. pp. A–4. ISBN 978-0-9815194-3-2.
  2. ↑ Lehman, John (2009). Operational Organic Chemistry. New Jersey: Pearson Education. p. 856. ISBN 0-13-600092-4.
  3. ↑ Cox, Douna, O'Donnell, Michael, Jennifer, Michael (2012). Molecular Biology. New York: W.H. Freeman. p. 633. ISBN 978-0-7167-7998-8.
  4. ↑ "Chemical Book". Chemical Book. Retrieved 2012-10-19.
  5. ↑ Orjuela, Kolah, Hong, Lira, Miller, Alvaro, Aspi, Xi, Carl, Dennis (2012). "Diethyl succinate synthesis by reactive distillation". Separation and Purification Technology. 88: 218. doi:10.1016/j.seppur.2011.11.033. Retrieved 2012-10-19.
  6. ↑ "Diethyl succinate". Sigma Aldrch. Retrieved 2012-10-19.
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