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Encyclopedia Britannica



GLUTARIC ACID, or NORMAL PYROTARTARIC ACID

This article appears in Volume V12, Page 145 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: GEO-GNU
GLUTARIC ACID, or NORMAL PYROTARTARIC ACID , H02CCH2CH2CH2CO2H, an organic acid prepared by the reduction of a-oxyglutaric acid with hydriodic acid, by reducing glutaconic acid, HO2C CH2 CH:CH CO2H, with sodium amalgam, by conversion of trimethylene bromide into the
cyanide
  and
hydrolysis
  of this compound, or from acetoacetic ester, which, in the form of its sodium derivative, condenses with /3=iodopropionic ester to form acetoglutaric ester, CH3COCH(CO2C2H5)CH2CH2CO2C2H5, from which glutaric acid is obtained by
hydrolysis
 . It is also obtained when sebacic, stearic and oleic acids are oxidized with nitric acid. It crystallizes in large
monoclinic
  prisms which melt at 97' 5 C., and distils between 3020 and 3040 C., practically without decomposition. It is soluble in water, alcohol and ether. By
long
 
heating
  the acid is converted into its anhydride, which, however, is obtained more readily by
heating
  the silver
salt
  of the acid with acetyl chloride. By
distillation
  of the ammonium
salt
  glutarimide, CH2(CH2CP)2NH, is obtained; it forms small crystals melting at 151 to 152 C. and sublimes unchanged.
On the alkyl glutaric acids, see C.
Hell
  (Ber., 1889, 22, pp. 48, 6o), C. A. Bischoff (Ber., 1891, 24, p. 1041), K. Auwers (Ber., 1891, 24, p. 1923) and W. H.
Perkin
 , junr. Grown. Chem. Soc., x896, 69, p. 268),


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