Glutaric acid is the organic compound with the chemical formula C3H6(COOH)2. Although the related "linear" dicarboxylic acids adipic acid and are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50% (w/w).
Biochemistry
Glutaric acid is naturally produced in the body during the
metabolism of some
amino acids, including
lysine and
tryptophan. Defects in this metabolic pathway can lead to a disorder called glutaric aciduria, where toxic byproducts build up and can cause severe
encephalopathy.
Production
Glutaric acid can be prepared by the ring-opening of butyrolactone with potassium cyanide to give the potassium salt of the carboxylate-
nitrile that is hydrolyzed to the diacid.
Alternatively hydrolysis, followed by oxidation of dihydropyran gives glutaric acid. It can also be prepared from reacting 1,3-dibromopropane with
sodium cyanide or potassium cyanide to obtain the dinitrile, followed by hydrolysis. Using
periodate, it is obtained from oxidation of 1,3-cyclohexanedione, which proceeds with decarboxylation.
Uses
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1,5-Pentanediol, a common plasticizer and precursor to is manufactured by hydrogenation of glutaric acid and its derivatives.
[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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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.
-
Pyrogallol can be produced from glutaric diester.
Safety
Glutaric acid may cause irritation to the skin and eyes.
[ Glutaric acid, cameochemicals.com] Acute hazards include the fact that this compound may be harmful by ingestion, inhalation or skin absorption.
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