By David Ginsburg
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Example text
Although pressure equipment would be considered uneconomical for catalytic hydrogénation of nitrobenzene to aniline, it is economically feasible to make a capital investment in such equipment for the amination of chlorobenzene. This cost is weighed against the lower cost of chlorine used for the production of chlorobenzene as against the higher cost of nitric acid used in the other process to make nitrobenzene. ci NH 3 ,206 o Cu 2 0, 60-70 atm Studies have been made of the reduction of nitrobenzene under a variety of reaction conditions.
A substituted amide is obtained and is often the ultimate product prepared by the Ritter reaction. However, hydrolysis of the amide affords the primary amine of the type R 1 R 2 R 3 CNH 2 . The reaction may be exemplified by the following cases of the preparation of t-butylamine and of 1-methylcyclobutylamine: H .. 4 ^ » CH,CO,H 70% Methylenecyclobutane CH, KOH 46% -NH, 1 -Methylcyclobutylamine 42 CONCERNING AMINES REDUCTION OF OXIMES We have seen in one of the previous sections that amines may be obtained by reduction of Schiff bases in which there is a C = N double bond.
The reducing agent in the Leuckart reaction is formic acid. The reaction is generally carried out by heating a mixture of the aldehyde or ketone with ammonium formate: O || 150-180° R1X ^>C=0 + 2HCO-NHi > R2 Ammonium formate H >CHNHC=0 + 2H 2 0 + NH 3 + C 0 2 R2 I X h° R 1 R 2 CHNH 2 + HC0 2 H Formamide, HCONH2 and other formic acid derivatives, may often be used instead of ammonium formate. The hydrolysis of the formyl derivatives may be carried out with either hydrochloric acid or sodium hydroxide.