Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles
Patent
1999-02-01
2000-09-19
Lambkin, Deborah C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitriles
C07C25300
Patent
active
061214817
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
The present application relates to a process for the preparation of 6-aminocapronitrile or 6-aminocapronitrile/hexamethylene diamine mixtures starting from 5-formylvaleronitrile.
EP-A 11,401 describes the reductive amination of .delta.-cyanovaleraldehyde to produce hexamethylene diamine. According to Example 4 of the cited application a mixture containing 60% of .delta.-cyanovaleraldehyde was caused to react with ammonia and hydrogen at a temperature of 100.degree. C. and a hydrogen pressure of 140 bar in the presence of Raney nickel over a period of two hours, the conversion (based on the .delta.-compound) being only 25%. The low degree of conversion demonstrates that the aminating hydrogenation of an aldehyde group and the hydrogenation of a nitrile group in the same molecule to form a diamine represent a difficult hydrogenation problem. Furthermore the formation of 6-aminocapronitrile is not described. Furthermore the on-stream time of the catalyst used is unsatisfactory for economic exploitation.
U.S. Pat. No. 2,777,873 reveals that it is possible to perform aminating hydrogenation on 5-formyl valerate using ammonia and hydrogen in the presence of nickel, cobalt, iron, platinum, or palladium catalysts at from 100.degree. to 160.degree. C. and under pressures ranging from 1 to 1000 atmospheres to produce 6-aminocaproates. EP-A 376,121 describes this reaction also for ruthenium catatysts, the process being carried out at temperatures ranging from 80.degree. to 140.degree. C. and under pressures ranging from 40 to 1000 bar.
Cobalt, copper, and rhenium catalysts are suitable for the hydrogenation of adipodinitrile to hexamethylene diamine in the presence of ammonia, as stated in U.S. Pat. No. 3,461,167, column 3, lines 66 to 74. The process is preferably operated at from 70.degree. to 170.degree. C. and from 300 to 7000 psi. According to U.S. Pat. No. 3,471,563 ruthenium catalysts can also be used for this reaction.
Thus Group VIIIb elements hydrogenate both nitrile and aldehyde groups to produce amino groups.
It is thus an object of the present inventionto provide a process which makes it possible to prepare, starting from 5-formylvaleraldehyde, either 6-aminocapronitrile or a mixture of 6-aminocapronitrile and hexamethylene diamine at a very high conversion rate. A particular object of the invention is to find a process which guarantees long on-stream times of the catalysts. 6-aminocapronitrile or a mixture of 6-aminocapronitrile and hexamethylene diamine, in which the presence of hydrogenation catalysts selected from the group consisting of metals or metal compounds of rhenium, copper and Group VIIIb elements, giving a hydrogenation effluent, and from the hydrogenation effluent, or copper and nickel as sole components.
The starting compound used in the process of the invention is 5-formylvaleraldehyde. The patent literature reveals a number of possibilities for the preparation of 5-formylvaleronitrile:
WO 94/26688 describes a process, in which the internal olefins,
In claim 3 of the cited WO 94/26688 there are claimed nitrile-containing olefins. The hydroformylation catalysts used are rhodium/triphenylphosphine systems, in which the triphenylphosphine is rendered soluble in water by suitable functional groups.
WO 95/18783 describes the hydroformylation of internal nitrile-containing olefins using water-soluble platinum catalysts.
EP-A 11,401 also reveals that it is possible to cause 3-pentenenitrile to react with carbon monoxide and hydrogen under pressure in the presence of a cobalt catalyst. During this procedure there is formed a mixture of isomeric formylvaleronitriles and the alcohols corresponding to the aldehyde group.
5-Formylvaleronitrile is caused, in the process of the invention, to react at temperatures ranging from 40.degree. to 150.degree. C., advantageously from 50.degree. to 140.degree. C. and more advantageously from 60.degree. to 130.degree. C., and pressures ranging from 2 to 350 bar, advantageously from 20 to 300 bar and more advantageously from 40 to 250 bar, with ammon
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Fischer Rolf
Paciello Rocco
Roper Michael
Schnurr Werner
BASF - Aktiengesellschaft
Lambkin Deborah C.
Murray Joseph
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