Glutaric acid 2014339 170957866 2007-11-12T13:46:38Z Smokefoot 698909 oops and tidy {{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]]