Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles
Patent
1999-02-01
2000-04-11
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitriles
C07C25500
Patent
active
060489979
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a process for preparing 6-aminocapronitrile or 6-aminocapronitrile-hexamethylenediamine mixtures.
EP-A 11401 describes the reaction of 3-pentenenitrile with carbon monoxide and hydrogen under superatmospheric pressure in the presence of a cobalt catalyst to obtain a mixture of isomeric formylvaleronitriles and the corresponding alcohols obtained from the aldehydes. The cited reference further describes the reductive amination of .delta.-cyanovaleraldehyde to hexamethylenediamine. According to Example 4 of the cited reference, a 60% .delta.-cyanovaleraldehyde mixture was reacted with ammonia and hydrogen at 100.degree. C. and a hydrogen pressure of 140 bar in the presence of Raney nickel for two hours, but the conversion (based on the .delta.compound) was only 25%. The low conversion shows that the reductive amination of an aldehyde group and the hydrogenation of a nitrile group in one and the same molecule, to a diamine, constitutes a difficult hydrogenation problem. Furthermore, the formation of 6-aminocapronitrile is not described. Moreover, the stream factor of the catalyst used is unsatisfactory for industrial utilization.
U.S. Pat. No. 2,777,873 discloses reductively aminating 5-formylvaleric esters with ammonia and hydrogen in the presence of nickel, cobalt, iron, platinum or palladium catalysts at from 100 to 160.degree. C. and pressures from 1 bis 1000 atmospheres to obtain 6-aminocaproic esters. EP-A 376 121 also describes this reaction for ruthenium catalysts, at temperatures within the range from 80 to 140.degree. C. and pressures within the range from 40 to 1000 bar.
According to U.S. Pat. No. 3,461,167 (column 3, lines 66 to 74), cobalt, copper and rhenium catalysts are suitable for hydrogenation of adiponitrile to hexamethylenediamine in the presence of ammonia. The preferred conditions are 70-170.degree. C. and 300-7000 psi. According to U.S. Pat. No. 3,471,563, this reaction can also be carried out with ruthenium catalysts.
EP-A 214 622 mentions the hydroformylation of 3-butenenitrile in the presence of rhodium/chelate phosphite catalysts in the description.
WO 94/26688 describes a process comprising the internal olefins,
Claim 3 of WO 94/26688 is directed to nitrilic 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 nitrilic olefins with water-soluble platinum catalysts.
It is an object of the present invention to make available a process for preparing either 6-aminocapronitrile or a mixture of 6-aminocapronitrile and hexamethylenediamine with a very high conversion starting from 2- and/or 3- and/or 4-pentenenitrile. More particularly, the process shall ensure long catalyst on-stream times.
We have found that this object is achieved by a process for preparing 6-aminocapronitrile or 6-aminocapronitrile/hexamethylenediamine mixture, which comprises of 2-pentenenitrile, 3-pentenenitrile and 4-pentenenitrile with carbon monoxide and hydrogen in the presence of a catalyst containing at least one element of subgroup eight as active component to obtain a hydroformylation effluent I, hydroformylation effluent I to obtain a hydroformylation effluent II, II, the presence of a hydrogenation catalyst selected from the group consisting of rhenium, copper and compounds thereof, and also metals and metal compounds of subgroup eight to obtain a hydrogenation effluent, and the hydrogenation effluent.
According to this invention, at least one pentenenitrile selected from the group consisting of 2-pentenenitrile, 3-pentenenitrile or 4-pentenenitrile is used, preferably 3- or 4-pentenenitrile.
3-Pentenenitrile, the most important starting material for the process, can be prepared for example by addition of hydrocyanic acid to butadiene in the presence of nickel(0)/phosphite complexes as catalysts (K. Weissermel, H.-J. Arpe, Industrielle organische Chemie, 4th edition, VCH Verlag Weinheim, 1994, page
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Fischer Rolf
Paciello Rocco
Roper Michael
Schnurr Werner
BASF - Aktiengesellschaft
Murray Joseph
Richter Johann
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