2- -glutaric acid, from

For conversion of aliphatic dinitriles into dicarboxylic acids it is best to use concentrated hydrochloric acid, e.g., for the preparation of glutaric acid from the dinitrile.622 Aromatic nitriles such as a-tolunitrile are hydrolysed by ca. 75% sulfuric acid. 

Borsook and co-workers arrived at the scheme of catabolism shown in Fig. 11 by isolating C -labeled a-ketoadipic acid and glutaric acid from guinea pig liver homogenates incubated with isotopic a-aminoadipic acid. These authors observed that the deamination of a-aminoadipic acid is much slower than its formation from L-lysine and that the decarboxylation of a-ketoadipic acid is faster than the deamination of the above acid. 

Y. Nishizuka, A. Ichiyama, R. K. Gholson, and O. Hayaishi, Studies on the metabolism of the benzene ring of tryptophan in mammalian tissues. I. Enzymic formation of glutaric acid from 3-hydroxyanthranilic acid, / Biol. Chem. 240, 733-739 (1965). 

Rothstein and Miller (162) isolated radioactive glutaric acid from the urine of rats injected with L-lysine-6-C and unlabeled glutarate and established its chemical and radioactive purity. 

Glutaric acid from green sugar and beet juice reacts vith xyli-tol forming polyesters. ... 

In a 2-litre round-bottomed flask, equipped with a double surface condenser, place 60 g. of triniethylene dicyanide (Section 111,114) and 900 g. of 50 per cent, sulphuric acid (by weight). Reflux the mixture for 10 hours and allow to cool. Saturate the solution with ammonium sul phate and extract wit-h four 150 ml. portions of ether dry the ethereal extracts with anhydrous sodium or magnesium sulphate. Distil off the ether on a water bath the residual glutaric acid (69 g.) crystallises on cooling and has m.p. 97-97-5°. Upon recrystalhsation from chloroform, or benzene, or benzene mixed with 10 per cent, by weight of ether, the m.p. is 97 -5-98°. 

An alternative method of separation consists in treating the dry residue several times with a warm mixture of benzene and ether. The residual solid (about 20 g.) is moderately pure succinic acid, m.p. 183-184°. Upon evaporating the benzene - ether extract, and recrystallising the residue from chloroform or from benzene, about 70 g. of glutaric acid, m.p. 95-96°, are obtained. 

In the above reaction one molecular proportion of sodium ethoxide is employed this is Michael s original method for conducting the reaction, which is reversible and particularly so under these conditions, and in certain circumstances may lead to apparently abnormal results. With smaller amounts of sodium alkoxide (1/5 mol or so the so-called catal3rtic method) or in the presence of secondary amines, the equilibrium is usually more on the side of the adduct, and good yields of adducts are frequently obtained. An example of the Michael addition of the latter type is to be found in the formation of ethyl propane-1 1 3 3 tetracarboxylate (II) from formaldehyde and ethyl malonate in the presence of diethylamine. Ethyl methylene-malonate (I) is formed intermediately by the simple Knoevenagel reaction and this Is followed by the Michael addition. Acid hydrolysis of (II) gives glutaric acid (III). 

Finally, when polyamides containing four or five carbon diacids, ie, succinic acid [110-15-6] and glutaric acid [110-94-1], respectively, are heated, they form cychc imides that cap the amine ends and prevent high molecular weights from being achieved (84). For nylon-x,4, n = 1 and for nylon-x,5, n = 2. 

One of the methods used to isolate succinic acid from the waste stream of the adipic acid process is esterification of the mixture of succinic, glutaric, and adipic acid followed by fractionation (65—69). 

Pigment retention and drainage additives made with polyamines include polyamines made from ethyleneamines, ethan olamines, and epichl orohydrin (262) ethyleneamines combined with phosphoms-modifted polyamines made by reaction of ethyleneamines with POCl [10025-87-3] (263) and a DETA—glutaric acid polyamide crosslinked with PEG-bis(3-chloro-2-hydroxypropyl) ether (264). Polyamines made from ethyleneamines and EDC are useful flocculating agents (265). 

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