Succinic acid

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Succinic acid
Bernsteinsäure2.svg
Succinic-acid-3D-balls.png
Sample of succinic acid.jpg
Names
Preferred IUPAC name
Butanedioic acid[1]
Other names
Succinic acid[1]
Ethane-1,2-dicarboxylic acid
Identifiers
110-15-6 YesY
ChEBI CHEBI:15741 YesY
ChEMBL ChEMBL576 YesY
ChemSpider 1078 YesY
DrugBank DB00139 YesY
3637
Jmol 3D model Interactive image
PubChem 1110
UNII AB6MNQ6J6L YesY
Properties
C4H6O4
Molar mass 118.09 g·mol−1
Density 1.56 g/cm3[2]
Melting point 184 °C (363 °F; 457 K)[2]
Boiling point 235 °C (455 °F; 508 K)[2]
58 g/L (20 °C)[2] or 100 mg/mL[3]
Solubility in Methanol 158 mg/mL[3]
Solubility in Ethanol 54 mg/mL[3]
Solubility in Acetone 27 mg/mL[3]
Solubility in Glycerol 50 mg/mL[3]
Solubility in Ether 8.8 mg/mL[3]
Acidity (pKa) pKa1 = 4.2
pKa2 = 5.6
Hazards
Flash point 206 °C (403 °F; 479 K)[2]
Related compounds
Other anions
sodium succinate
propionic acid
malonic acid
butyric acid
malic acid
tartaric acid
fumaric acid
valeric acid
glutaric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Succinic acid (/səkˈsɪnk/) is a dicarboxylic acid with chemical formula (CH2)2(CO2H)2. It is a white, odorless solid. In an aqueous solution, it ionizes to anions (that is, conjugates to a conjugate base) called succinate (/ˈsʌksnt/), which plays a role in the citric acid cycle, an energy-yielding process in all living organisms. As a radical group it is called a succinyl (/ˈsʌksnəl/) group. The name derives from Latin succinum, meaning amber, from which the acid may be obtained.

Production[edit]

Common industrial routes include partial hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol.[4]

In a 2004 report, the United States Department of Energy identified bio-succinic acid as one of the renewable building block chemicals with the greatest technical feasibility and commercial potential.[5] Indeed, succinic acid is produced commercially through the fermentation of glucose from renewable feedstock.[6]

Historically known as spirit of amber,[7] succinic acid was originally obtained from amber by distillation.[7]

Reactions[edit]

Succinates[edit]

Salts formed by neutralizing succinic acid are called succinates. As a diprotic acid, succinic acid undergoes two successive reactions:

(CH2)2(CO2H)2 → (CH2)2(CO2H)(CO2) + H+
(CH2)2(CO2H)(CO2) → CH2)2(CO2)22− + H+

These anions, collectively called succinates, are also colorless, and can be isolated as the salts, e.g., Na(CH2)2(CO2H)(CO2) and Na2(CH2)2(CO2)22−.

Succinic acid also converts to diesters such are also referred to as succinates. One example is diethylsuccinate, (CH2CO2CH2CH3)2.

Other reactions[edit]

Succinic acid can be converted into fumaric acid by oxidation. The diethyl ester is a substrate in the Stobbe condensation. Dehydration of succinic acid gives succinic anhydride.[8]

Applications[edit]

Precursor to polymers, resins, and solvents[edit]

Succinic acid is a precursor to some polyesters. It is also a component of some alkyd resins.[4][9] Global 1,4-butanediol (BDO), derived from succinic acid, market size was estimated at USD 4.72 billion in 2013. BDO is a precursor to THF, a solvent and monomer. BDO is also a precursor to polybutylene terephthalate (PBT), an engineering-grade thermoplastic.[10] The automotive and electronics industries heavily rely on PBT to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams.[11]

Food and dietary supplement[edit]

As a food additive and dietary supplement, succinic acid is generally recognized as safe for those uses by the U.S. Food and Drug Administration.[12] As an excipient in pharmaceutical products it is used to control acidity[13] and, more rarely, in effervescent tablets.[14]

Succinic acid is used in the food and beverage industry, primarily as an acidity regulator.[15] Global production is estimated at 16,000 to 30,000 tonnes a year, with an annual growth rate of 10%.[16]

Biochemistry[edit]

Succinate is an intermediate in the citric acid cycle. It serves as an electron donor to the electron transport chain:

succinate + FADfumarate + FADH2.

Click on genes, proteins and metabolites below to link to respective articles. [§ 1]

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TCACycle_WP78 go to article go to article go to article go to article go to HMDB go to article go to article go to article Go to article go to article go to article go to article go to article go to article Go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to HMDB go to article go to article go to HMDB go to article go to article go to HMDB go to article go to article go to HMDB go to article go to article go to article go to article go to article go to article go to article go to article go to article go to article go to WikiPathways go to article go to article go to article go to article
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  1. ^ The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78". 

This conversion is catalysed by the enzyme succinate dehydrogenase (or complex II of the mitochondrial ETC). The complex is a 4 subunit membrane-bound lipoprotein which couples the oxidation of succinate to the reduction of ubiquinone. Intermediate electron carriers are FAD and three 2Fe-2S clusters part of subunit B.

Fermentation[edit]

See also: Acids in wine

Succinic acid is created as a byproduct of the fermentation of sugar. It lends to fermented beverages such as wine and beer a common taste that is a combination of saltiness, bitterness and acidity.[17]

Safety[edit]

Succinic acid is an essential biosynthetic intermediate that occurs in all living creatures. Like most simple mono- and dicarboxylic acids, it is not dangerous but can be an irritant to skin and eyes.[18]

See also[edit]

References[edit]

  1. ^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 747. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. 
  2. ^ a b c d e Record in the GESTIS Substance Database of the IFA
  3. ^ a b c d e f "Product Information Sheet: Succinic Acid" (PDF). Sigma Aldrich. Retrieved 7 November 2015. 
  4. ^ a b Boy Cornils, Peter Lappe (2005), "Dicarboxylic Acids, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a08_523 
  5. ^ "Top Value Added Chemicals from Biomass, Volume 1: Results of Screening for Potential Candidates from Sugars and Synthesis Gas" (PDF). U.S. Department of Energy. November 1, 2004. Retrieved 2013-11-12. 
  6. ^ "Sustainability: Life Cycle Analysis - A Carbon Neutral Footprint". BioAmber Inc. 
  7. ^ a b Chambers, E., ed. (1728). "Spirit of Amber". Cyclopaedia. p. 75. 
  8. ^ Louis F. Fieser, E. L. Martin, R. L. Shriner, and H. C. Struck (1932). "Succinic Anhydride". Org. Synth. 12: 66.  ; Coll. Vol., 2, p. 560 .
  9. ^ "BioAmber S-1/A". Securities and Exchange Commission. May 9, 2013. Retrieved 2013-11-11. 
  10. ^ "1,4-Butanediol (BDO)". Lyondell Basell. Retrieved 2013-11-12. 
  11. ^ "1,4-Butanediol (BDO) Market Analysis By Application (Tetrahydrofuran, Polybutylene Teraphthalate, Gamma-Butyrolactone & Polyurethanes), And Segment Forecasts To 2020". Grand View Research. September 2015. Retrieved 2015-11-18. 
  12. ^ FDA GRAS Database. Succinic acid in the FDA SCOGS Database
  13. ^ "Overview of pharmaceutical excipients used in tablets and capsules". Modern Medicine Network. 24 October 2008. Retrieved 7 November 2015. 
  14. ^ Lachman, Leon; Joseph B. Schwartz (1990). Pharmaceutical Dosage Forms--tablets. p. 288. ISBN 9780824780449. 
  15. ^ Zeikus, J. G.; Jain, M. K.; Elankovan, P. (1999). "Biotechnology of succinic acid production and markets for derived industrial products". Applied Microbiology and Biotechnology. 51 (5): 545. doi:10.1007/s002530051431. 
  16. ^ NNFCC Renewable Chemicals Factsheet: Succinic Acid
  17. ^ Peynaud, Emile (1984). Knowing and Making Wine. 
  18. ^ "Safety Data Sheet Bio-Based Succinic Acid". BioAmber Inc. April 23, 2015. Retrieved 2015-12-03. 

External links[edit]