Glutaric acid

Glutaric acid
IUPAC name	pentanedioic acid
Other names	Propane-1,3-dicarboxylic acid; 1,3-propanedicarboxylic acid; pentanedioic acid; n-Pyrotartaric acid
Identifiers
CAS number	110-94-1 Y
EC number	203-817-2
SMILES	C(CC(=O)O)CC(=O)O
ChemSpider ID	723
Properties
Molecular formula	C5H8O4
Molar mass	132.12 g/mol
Melting point	95 to 98 °C
Boiling point	200 °C
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Glutaric acid is the organic compound with the formula HO₂C(CH₂)₃CO₂H. Although the related "linear" dicarboxylic acids adipic and succinic acids are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50%.

Preparation

Glutaric acid can be prepared by the ring-opening of butyrolactone with potassium cyanide to give the mixed potassium carboxylate-nitrile that is hydrolyzed to the diacid.^[1] Alternatively hydrolysis, followed by oxidation of dihydropyran gives glutaric acid. It can also be prepared from reacting 1,3-dibromopropane with sodium or potassium cyanide to obtain the dinitrile, followed by hydrolysis.

Uses

1,5-Pentanediol, a common plasticizer and precursor to polyesters is manufactored by hydrogenation of glutaric acid and its derivatives.^[2]

Glutaric acid itself has been used in the production of polymers such as polyester polyols, polyamides. The odd number of carbon atoms (i.e. 5) is useful in decreasing polymer elasticity.

References

1. ^ G. Paris, L. Berlinguet, R. Gaudry, J. English, Jr. and J. E. Dayan (1963), "Glutaric Acid and Glutaramide", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0496 ; Coll. Vol. 4: 496 
2. ^ Peter Werle and Marcus Morawietz "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry: 2002, Wiley-VCH: Weinheim. DOI 10.1002/14356007.a01_305

External links

• Calculator: Water and solute activities in aqueous glutaric acid

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