Succinic acid

Succinic acid

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Names
IUPAC name Butanedioic acid
Other names ethane-1,2-dicarboxylic acid
Identifiers
CAS Number	110-15-6 Y
ChEBI	CHEBI:15741 Y
ChEMBL	ChEMBL576 Y
ChemSpider	1078 Y
DrugBank	DB00139 Y
IUPHAR/BPS	3637
Jmol 3D model	Interactive image
PubChem	1110
UNII	AB6MNQ6J6L Y
InChI InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8) Y Key: KDYFGRWQOYBRFD-UHFFFAOYSA-N Y InChI=1/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8) Key: KDYFGRWQOYBRFD-UHFFFAOYAC
SMILES C(CC(=O)O)C(=O)O
Properties
Chemical formula	C4H6O4
Molar mass	118.09 g·mol−1
Density	1.56 g/cm3
Melting point	184 °C (363 °F; 457 K)
Boiling point	235 °C (455 °F; 508 K)
Solubility in water	58 g/L (20 °C) or 100 mg/mL
Solubility in Methanol	158 mg/mL
Solubility in Ethanol	54 mg/mL
Solubility in Acetone	27 mg/mL
Solubility in Glycerol	50 mg/mL
Solubility in Ether	8.8 mg/mL
Acidity (pKa)	pKa1 = 4.2 pKa2 = 5.6
Vapor pressure	{{{value}}}
Related compounds
Other anions	sodium succinate
Related carboxylic acids	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).
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Infobox references

Succinic acid (/səkˈsɪnᵻk/ is a dicarboxylic acid with chemical formula (CH₂)₂(CO₂H)₂. It is a white, odorless solid. as an aqueous solution, it ionizes to anions called succinate, which plays a role in the citric acid cycle, an energy-yielding process in all living organisms. The name derives from Latin succinum, meaning amber, from which the acid may be obtained.

Production

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

Petrochemical routes

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

Bio-derived succinic acid

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. Indeed, succinic acid is produced commercially through the fermentation of glucose from renewable feedstock.

Reactions

Succinates

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)₂^2- + 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)₂^2-.

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

Other reactions

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.

Applications

Precursor to polymers, resins, and solvents

Succinic acid is a precursor to some polyesters. It is also a component of some alkyd resins. 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. The automotive and electronics industries heavily rely on PBT to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams.

Food and dietary supplement

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. As an excipient in pharmaceutical products it is used to control acidity and, more rarely, in effervescent tablets.

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

Biochemistry

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

succinate + FAD → fumarate + FADH₂.

Click on genes, proteins and metabolites below to link to respective articles.

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|{{{bSize}}}px|alt=TCA Cycle edit]]

File:TCACycle WP78.png

TCA Cycle edit

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

See also: Acids in wine

See also: Succinic acid fermentation

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.

Safety

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.

See also

• Oil of amber, procured by heating succinic acid.

References

•  This article incorporates text from a publication now in the public domain: 

External links

• FDA
• Succinic Acid
• Calculator: Water and solute activities in aqueous succinic acid