Glutaric acid

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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]
EINECS number 203-817-2
Properties
Molecular formula C5H8O4
Molar mass 132.12 g/mol
Melting point

95 to 98 °C
Boiling point

200 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and 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%.

[edit] Preparation

Glutaric acid can be prepared by the ring-opening of butyrolactone with potassium cyanide to give the mixed carboxylic acid-nitrile that is hydrolyzed to the diacaid.[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.

[edit] 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.

[edit] References

  1. ^ G. Paris, L. Berlinguet, R. Gaudry, J. English, Jr. and J. E. Dayan (1963). "Glutaric Acid and Glutaramide". Org. Synth.; 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


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