Capronitrile

Place 29 g. of n-caproamide (Section 111,109) into a 200 ml. distilling flask, and assemble the apparatus shown in Fig. Ill, 28, 1. Remove the trap momentarily and introduce 45 g. (27-5 ml.) of redistilled thionyl chloride no apparent reaction takes place in the cold. Warm the mixture on a water bath or by means of a small flame for 1 hour. Arrange the apparatus for distillation and distil oflF the excess of thionyl chloride (t.c., until the temperature reaches about 90°) and allow to cool. When cold, transfer the residue to a 100 ml. distilling flask (1). Distil from an air bath (Fig. II, 5, 3) the n-capronitrile passes over at 161-163° (2). The yield is 21 g. 

The n-capronitrile is sometimes slightly turbid the turbidity is readily removed by shaldng with a little anhydrous calcium sulphate. 

For practice, the student should carry out both alkaUne (compare Section 111,83) and acid hydrolysis of acetonitrile, n-valeronitrile (n-butyl cyanide) and n-capronitrile (n-amyl cyanide). 

Ethyl M-butylcyanoacetate has been prepared by alkylation of the sodium enolate of ethyl cyanoacetate with butyl bromide and by condensation of capronitrile with ethyl carbonate, in addition to the method given above. ... 

Calcium carbide, 32, 70 Calcium carbonate, 32, 81 Calcium formate, 31,102 CAPROIC ACID, e-AMINO, 32, 13 e-Caprolactam, 31, 72 32, 15 e-CAPROLACTIM, O-METHYL-, 31, 72 CAPRONITRILE, a-ETHYL, 32, 6S Caproyl chloride, 31, 71 CARBANILINONITRILE, O-CHLORO, 31, 19... 

Capronitrile [124-12-9] M 125.2, b 163.7°, n 1.4069, n25 1.4048. Washed twice with half volumes of cone HC1. then with saturated aqueous NaHCC>3, dried with MgS04, and distilled. 

Concerning 2-(aminomethyl)-cyclopentylamine formation, some dehydrogenation reaction of amino capronitrile can occur on the catalytic surface. Stereoselectivity can be interpreted in terms of chelating effect leading to the cis isomer. 

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