Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1997-05-19
1998-05-12
Burn, Brian M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
502324, 564448, 564491, 564492, C07C20948
Patent
active
057507880
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a continuous process for preparing amines by hydrogenation of compounds having at least 3 cyano groups, prepared by addition of acrylonitrile onto ammonia or primary amines, at elevated temperatures and elevated pressure on novel cobalt catalysts.
Angew. Chem. 105 (1993) 1367 to 1372 discloses the batchwise reduction of nitrites with hydrogen on Raney cobalt in methanolic solution.
DE-A-27 39 917 discloses catalysts for the hydrogenation of cyanoethylated amines which contain cobalt or nickel as catalysts on a suitable support.
The batchwise process disclosed to date for reducing multiply cyano-containing compounds are not economically attractive for production on the industrial scale.
Accordingly, a novel and improved process for preparing amines by hydrogenation of compounds having at least 3 cyano groups, prepared by addition of acrylonitrile onto ammonia or primary amines, at from 80.degree. to 200.degree. C. under from 5 to 500 bar has been found and comprises carrying out the hydrogenation continuously on a catalyst which contains from 80 to 98% by weight of cobalt oxides, from 1 to 10% by weight of manganese oxide, from 1 to 10% by weight of phosphorus pentoxide and from 0 to 5% by weight of alkali metal oxides, and novel cobalt catalysts.
The hydrogenation according to the invention can be carried out in the following way: or primary amines and has one or more cyano groups can be reacted in the presence or absence of ammonia in the presence of hydrogen at from 80.degree. to 200.degree. C., preferably 100.degree. to 160.degree. C., particularly preferably 110.degree. to 150.degree. C., under from 5 to 500 bar, preferably 50 to 300 bar, particularly preferably 100 to 250 bar, on a catalyst which contains from 80 to 98% by weight of cobalt oxide, from 1 to 10% by weight of manganese oxide and from 1 to 10% by weight of phosphorus pentoxide and from 0 to 5% by weight of alkali metal oxide, preferably from 86 to 94% by weight of cobalt oxide, from 3 to 7% by weight of manganese oxide and from 3 to 7% by weight of phosphorus pentoxide and from 0 to 5% by weight of alkali metal oxide, particularly preferably from 88 to 92% by weight of cobalt oxide, from 4 to 6% by weight of manganese oxide, from 4 to 6% by weight of phosphorus pentoxide and from 0 to 4% by weight of alkali metal oxide, as a rule in an inert solvent.
The abovementioned cobalt catalysts, excepting Raney cobalt, can be used as catalysts on inert supports such as alumina, silica, titanium oxide, zirconium oxide or zeolites of the pentasil, faujasite, X or Y type or, preferably, as unsupported catalysts. These cobalt catalysts preferably consist only of cobalt oxide, manganese oxide, phosphorus pentoxide and alkali metal oxide, preferably Na.sub.2 O, where appropriate on inert supports. The preparation of the catalysts to be used according to the invention is described, for example, in DE-A 43 25 847 and in German Patent Applications 19516845 and 19507398.
The hydrogenation can also be carried out without ammonia. However, ammonia as a rule is preferably used in gas or liquid form, but generally not in aqueous solution, in a ratio of mol of ammonia per cyano group of the amino nitrile formed as inetrmediate of from 1:1 to 10,000:1, preferably from 1.5:1 to 3000:1, particularly preferably from 2:1 to 1000:1. The excess of ammonia can also be more than 10,000:1 without problems.
The hydrogen is generally introduced into the reaction in an amount of from 5 to 400 l(STP), preferably in an amount of from 50 to 200 l(STP) per mol of amino nitrile.
The practical procedure for the reaction is to feed the amino nitrile in an inert solvent and ammonia simultaneously to the heterogeneous catalyst, which is normally located in a fixed bed reactor which is preferably heated from outside, at the required temperature under the required pressure. The space velocity is generally from 0.001 to 5.0, preferably 0.005 to 2.0 and, particularly preferably, from 0.01 to 1.5 1 of amino nitrite per liter of cobalt catalyst and hour.
It
REFERENCES:
patent: 3565957 (1971-02-01), Mirviss et al.
patent: 5105015 (1992-04-01), Lin et al.
Haussling Lukas
Neuhauser Horst
Paulus Wolfgang
BASF - Aktiengesellschaft
Burn Brian M.
Shurtleff John H.
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