Glutaric acid
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{{Chembox new
| Name = Glutaric acid
| ImageFile = glutaric acid.png
<!-- | ImageSize = 200px -->
| ImageName = Glutaric acid
| IUPACName = pentanedioic acid
| OtherNames = Propane-1,3-dicarboxylic acid; 1,3-propanedicarboxylic acid; pentanedioic acid; n-Pyrotartaric acid
| Section1 = {{Chembox Identifiers
| CASNo = 110-94-1
| EINECS = 203-817-2
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>5</sub>H<sub>8</sub>O<sub>4</sub>
| MolarMass = 132.12 g/mol
| MeltingPt = 95 to 98 °C
| BoilingPt = 200 °C
}}
}}
'''Glutaric acid''' is the [[organic compound]] with the [[chemical formula|formula]] HO<sub>2</sub>C(CH<sub>2</sub>)<sub>3</sub>CO<sub>2</sub>H. Although the related "linear" dicarboxylic acids [[adipic acid|adipic]] and [[succinic acid]]s 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 carboxylic acid-[[nitrile]] that is hydrolyzed to the diacaid.<ref>{{OrgSynth | author = G. Paris, L. Berlinguet, R. Gaudry, J. English, Jr. and J. E. Dayan | title = Glutaric Acid and Glutaramide | collvol = 4 | collvolpages = 496 | year = 1963 | prep = cv4p0496}}</ref> Alternatively hydrolysis, followed by oxidation of [[dihydropyran]] gives glutaric acid. It can also be prepared from reacting [[1,3-dibromopropane]] with [[sodium cyanide|sodium]] or [[potassium cyanide]] to obtain the dinitrile, followed by hydrolysis.
==Uses==
[[1,5-Pentanediol]], a common [[plasticizer]] and precursor to [[polyester]]s is manufactored by [[hydrogenation]] of glutaric acid and its derivatives.<ref>Peter Werle and Marcus Morawietz "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry: 2002, Wiley-VCH: Weinheim. DOI 10.1002/14356007.a01_305</ref>
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==
<references/>
{{organic-compound-stub}}
[[Category:Dicarboxylic acids]]
[[de:Glutarsäure]]
[[lv:Glutārskābe]]
[[ja:グルタル酸]]
[[pl:Kwas glutarowy]]
[[pt:Ácido glutárico]]
[[ru:Глутаровая кислота]]
[[fi:Glutaarihappo]]