Selective hydrogenation of dinitrile to omega-aminonitrile catalyzed by rhodium organonitrogen complex catalyst
AssigneeAllied Corporation
InventorsSteven E. Diamond, Frank Mares, Andrew Szalkiewicz
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Abstract
A dinitrile is reacted with hydrogen in the presence of a solvent and a catalyst to form an omega-aminonitrile such as epsilon-aminocapronitrile at high selectivity. The catalyst is a rhodium complex of the formula (RR'Rh)A reacted with a strong base such as sodium hydroxide. R is derived from a diene such as 1,5-hexadiene. R' is a heterocyclic containing an aromatic ring nitrogen. A is a complex monovalent anion such as hexafluorophosphate.
Claims11
A process for selectively producing an omega-aminonitrile which comprises reacting at a temperature of between about 20.degree. C. and about 200.degree. C. a dinitrile of the formula N.tbd.C--(CH.sub.2).sub.n --C.tbd.N with n being an integer from 1 to 10 with hydrogen at a partial pressure of at least about one atmosphere in the presence of:
- (a) a solvent, and
- (b) a rhodium-containing catalyst prepared by reacting with a strong hydroxide base and then hydrogenating a rhodium complex of the formula (RR'Rh)A wherein R is derived from a non-allenic hydrocarbon diene of at least 4 carbons, R' is an aromatic heterocyclic with at least one aromatic ring nitrogen and only C, N and H and A is a complex monovalent anion which serves as a counteranion for the cation RR'Rh with rhodium being at valence +1;
- and recovering the omega-aminonitrile of the formula N.tbd.C-(CH.sub.2).sub.n --CH.sub.2 --NH.sub.2 as the major product.
Dependencies are inferred from the claim text.