java....maybe the comment from Ullmann`s is helpful for you:
Production from Nitro Compounds
Whereas the reduction of nitro compounds is one of the most important methods for the synthesis of aromatic amines, this route has not become important for the production of aliphatic amines. Because the availability of appropriate nitroalkanes is restricted, this method is used only in a few special cases, e.g., the production of 2-amino-1-butanol, the precursor for the antituberculotic ethambutol.
The reduction proceeds via the nitroso or hydroxylamine intermediate, in some cases even at room temperature, and gives the amine in yields of 90 % or more. Platinum, palladium, rhodium, nickel, or copper is used as the hydrogenation catalyst [7]. The reaction is highly exothermic (ca. 500 kJ/mol per nitro group), and therefore heat must be removed rapidly to control the process. Nitroparaffins are more difficult to hydrogenate than their aromatic counterparts [21].
Functionalization of alkenes with NO or NO2 has been described; the reaction follows a radical path and affords a mixture of products, among them nitroalkenes. Reduction of the latter also leads to amines, but has found no industrial application so far. Likewise, primary amines were obtained from paraffins by nitration with HNO3 or liquid NO2 and hydrogenation of the resulting nitroparaffin/ketone mixture in the presence of ammonia [22]. The preparation of 1,2-diamines from nitroolefins and O-alkylhydroxylamines has been described [23].
[7] J. Falbe, U. Hasserodt (eds.): Katalysatoren, Tenside und Mineralöladditive, Thieme Verlag, Stuttgart 1978.
[21] Engelhard Industries, GB 925 458, 1960.
[22] Gulf Research & Development Co., US 3 366 686, 1964 (R. W. Rosenthal, R. Seekircher); Texaco, US 3 739 027, 1971 (W. C. Gates, Jr.).
[23] Mitsui Petrochemical Ind., JP 10 095 753, 1996.
