Process for simultaneously preparing 6-aminocapronitrile and hex

Details Process for simultaneously preparing 6-aminocapronitrile and hex Process for simultaneously preparing 6-aminocapronitrile and hex

1999-03-10

2000-11-14

McKane, Joseph K.

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitriles

564463, 564511, C07C25503

Patent

active

061472476

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

The present invention relates to a process for coproduction of 6-aminocapronitrile and hexamethylenediamine starting from a mixture comprising a phosphorus-containing compound and essentially adiponitrile and obtained by reaction of butadiene or pentenenitriles with hydrocyanic acid in the presence of a catalyst comprising a phosphorus-containing compound.
The production of adiponitrile by reaction of butadiene or pentenenitriles with hydrocyanic acid in the presence of a catalyst comprising a phosphorus-containing compound is generally known, for example from: K. Weissermel, H.-J. Arpe, Industrielle Organische Chemie, 3rd Edition, VCH Verlagsgesellschaft mbH, Weinheim, 1988, pages 263-264, Verfahren 3.
DE-A 19 500 222 and German Application 19 548 289.1 disclose a process for coproduction of 6-aminocapronitrile and hexamethylenediamine by partial hydrogenation of adiponitrile in the presence of a catalyst, removal of hexamethylenediamine and 6-aminocapronitrile from the mixture, conversion of 6-aminocapronitrile into caprolactam and recycling into the process of a portion of the residue which consists essentially of adiponitrile.
The disadvantage with the use in the aforementioned partial hydrogenation of adiponitrile obtained by reaction of butadiene or pentenenitriles with hydrocyanic acid in the presence of a catalyst comprising a phosphorus-containing compound is that the hydrogenation catalyst exhibits rapid deactivation and poor 6-aminocapronitrile yields and selectivities.
It is an object of the present invention to provide a technically simple and economical process for coproduction of 6-aminocapronitrile and hexamethylenediamine starting from a mixture comprising a phosphorus-containing compound and essentially adiponitrile and obtained by reaction of butadiene with hydrocyanic acid in the presence of a catalyst comprising a phosphorus-containing compound without the abovementioned disadvantages.
We have found that this object is achieved by a process for coproduction of 6-aminocapronitrile and hexamethylenediamine starting from a mixture comprising a phosphorus-containing compound and essentially adiponitrile and obtained by reaction of butadiene with hydrocyanic acid in the presence of a catalyst comprising a phosphorus-containing compound, which comprises calculated as phosphorus, in the mixture, catalyst to form an .alpha.,.omega.-aminonitrile, and
The production of adiponitrile from butadiene and hydrocyanic acid can be effected according to any of the known processes, for example according to any of the aforementioned processes described in: K. Weissermel, H.-J. Arpe, Industrielle Organische Chemie, 3rd Edition, VCH Verlagsgesellschaft mbH, Weinheim, 1988, pages 263-264, Verfahren 3 by, in general, performing the reaction, preferably in the liquid phase, over catalysts comprising an active component comprising a complex of a metal such as nickel with phosphorus-containing ligands such as the phosphine or phosphite compounds, for example [(C.sub.6 H.sub.5).sub.3 PO].sub.4 Ni. In general, the reaction is conducted in a plurality of steps, the first step affording a mixture of isomeric pentenenitriles and methylbutenenitriles which is then isomerized to predominantly 3- and 4-pentenenitriles. In a second step, adiponitrile is formed by renewed addition of hydrocyanic acid in the presence of the aforementioned catalysts.
The adiponitrile produced by this process comprises at least one phosphorus-containing compound, generally in weight proportions of from 1 to 50 ppm, calculated as phosphorus, based on adiponitrile. In what follows, the term "phosphorus-containing compound" shall designate both a single phosphorus-containing compound and, if there are a plurality of such compounds, the sum total of phosphorus-containing compounds.
The weight proportion of phosphorus-containing compound is subsequently reduced according to the invention, advantageously to weight proportions of phosphorus-containing compound, calculated as phosphorus, based on adiponitrile, of less than 5 ppm, prefer

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Design and Prep. Supp. Catal., Acres et al., Jan. 30 (1979).

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