Process for producing amines from olefins on zeolites of types S

Details Process for producing amines from olefins on zeolites of types S Process for producing amines from olefins on zeolites of types S

1998-01-29

1999-03-23

Burn, Brian M.

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

Organic compounds

Amino nitrogen containing

C07C20960

Patent

active

058862269

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to a process for preparing amines by reacting ammonia or primary or secondary amines with olefins at elevated temperatures and pressures in the presence of zeolites of the type SSZ-26, SSZ-33, CIT-1 or mixtures thereof.
Methods for aminating olefins are reviewed in Functionalisation of Alkenes: Catalytic Amination of Monoolefins, J. J. Brunet et al. J. Mol. Catal., 49 (1989), 235-259.
There are basically two mechanisms of catalysis. The olefin is coordinated by a metal complex. This activated species can be attacked by nucleophilic amines to form a more highly aminated product. The amine can be chemisorbed on acid centers or on metal centers (via metal amides) and reacted with the olefin in this activated state.
Zeolites are very useful catalysts. They have a large number of catalytically active centers combined with a large surface area. The zeolites which have been described differ in type and in the aftertreatment (eg. thermal treatment, dealumination, acid treatment, metal ion exchange, etc.). Examples may be found in U.S. Pat. No. 4,375,002, U.S. Pat. No. 4,536,602, EP-A-305 564, EP-A-101 921, DE-A-42 06 992.
EP-A-133 938, EP-A-431 451 and EP-A-132 736 disclose processes wherein borosilicate, gallium silicate, aluminosilicate and iron silicate zeolites are used for preparing amines from olefins and mention the possibility of doping these zeolites with alkali, alkaline earth and transition metals.
CA-A-2 092 964 discloses a process for preparing amines from olefins using BETA zeolites, which are defined as crystalline aluminosilicates of a certain composition with a pore size of greater than 5 .ANG.. Preference is given to using metal- or halogen-modified beta zeolites.
All processes for synthesizing amines from olefins over these catalysts have a low amine yield or a low space-time yield or lead to a rapid deactivation of the catalysts.
It is an object of the present invention to overcome these disadvantages.
We have found that this object is achieved by a novel and improved process for preparing amines of the general formula I ##STR4## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.2 -C.sub.20 -alkynyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, aryl, C.sub.7 -C.sub.20 -alkylaryl or C.sub.7 -C.sub.20 -aralkyl, -C.sub.9 -alkylene dichain, and -C.sub.200 -alkenyl or together a C.sub.2 -C.sub.12 -alkylene dichain by reacting olefins of the general formula II ##STR5## where R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each as defined above, with ammonia or primary or secondary amines of the general formula III ##STR6## where R.sup.1 and R.sup.2 are each as defined above, at temperatures from 200.degree. to 350.degree. C. and pressures from 100 to 300 bar in the presence of a heterogeneous catalyst, which comprises using a heterogeneous catalyst comprising zeolites of the type SSZ-26, SSZ-33, CIT-1 or mixtures thereof.
The process of the present invention can be carried out as follows:
The olefin II and ammonia or the primary or secondary amine III can be reacted at temperatures from 200.degree. to 350.degree. C., preferably from 220.degree. to 330.degree. C., particularly preferably from 230.degree. to 320.degree. C., and pressures from 100 to 300 bar, preferably from 120 to 300 bar, particularly preferably from 140 to 290 bar, in the presence of zeolites of the type SSZ-26, SSZ-33, CIT-1 or mixtures thereof as catalysts, for example in a pressure reactor, and preferably the amine obtained is separated off and the unconverted feed materials are recycled.
The present process gives a very good yield combined with a high selectivity and a high space-time yield. In addition, the deactivation of the catalyst has been suppressed.
Even with a small excess of ammonia or amine, the process of the present invention achieves a high selectivity to desired reaction product and dimerization and/or oligomerization of the olefin used is avoid

REFERENCES:
patent: 4375002 (1983-02-01), Peterson et al.
patent: 4536602 (1985-08-01), Deeba
patent: 4929758 (1990-05-01), Taglieber et al.
J. Molecular Catalysis, 49 (1989) 235-259.

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