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Process for preparing amines by conditioning the catalyst with ammonia

A technology of catalyst and catalyst amount, applied in catalyst activation/preparation, amino compound preparation, physical/chemical process catalyst, etc., can solve problems such as reducing catalyst activity

Inactive Publication Date: 2007-08-22
DEGUSSA AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Addition of ammonia to the reaction mixture has the disadvantage of reducing the catalyst activity (see e.g. US 4375003 Example IX; C.D. Frohning: J. Falbe and U. Hasserrodt (eds.), "Katalysatoren, Tenside und Mineral® ladditive", Georg Thieme Verlag Stuttgart, 1978, pp. 44ff; Jiri Volf and Josef Pasek, "Hydrogenation of Nitriles", Studies in Surface Science and Catalysis, 27 (1986) pp. 105-144

Method used

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  • Process for preparing amines by conditioning the catalyst with ammonia
  • Process for preparing amines by conditioning the catalyst with ammonia
  • Process for preparing amines by conditioning the catalyst with ammonia

Examples

Experimental program
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Embodiment 1

[0058] Amination and hydrogenation of 3-cyano-3,5,5-trimethylcyclohexanone (isophoronenitrile) with a cobalt-supported catalyst to obtain 3-aminomethyl-3,5,5-trimethylcyclohexanone Hexylamine (isophoronediamine).

[0059] The experimental apparatus consisted of a 100 mL fixed bed reactor for the catalyzed formation of imines by IPN and ammonia filled with an ion exchanger according to EP 042119 and a downstream connected fixed bed filled with 300 mL of cobalt catalyst in the form of small flakes (diatomaceous earth support) Reactor composition. To condition the catalyst, 300 mL / h (180 g / h) of ammonia was led through the fixed bed at a temperature of 60-100°C. During conditioning, the hydrogen partial pressure was adjusted to approximately 100 bar. Conditioning ended after two hours. Immediately after conditioning, 30 mL / h (about 28 g / h) of IPN and 400 mL / h (370 g / h) of ammonia were supplied. The two source streams can be mixed with one another immediately before the ion ex...

Embodiment 2

[0066] Amination and hydrogenation of 3-cyano-3,5,5-trimethylcyclohexanone (isophoronenitrile) with a Raney-type cobalt catalyst to obtain 3-aminomethyl-3,5,5-trimethyl Cyclohexylamine (isophorone diamine).

[0067] The experimental apparatus consisted of a 100 mL fixed bed reactor for the catalytic formation of imines from IPN and ammonia filled with an ion exchanger according to EP 042119 and a downstream connected fixed bed reactor filled with a 66 mL spherical Raney type cobalt catalyst. To condition the catalyst, 100 mL / h (60 g / h) of ammonia was led through the fixed bed at a temperature of about 100°C. During conditioning, the hydrogen partial pressure was adjusted to approximately 100 bar. Conditioning ended after two hours. Immediately after conditioning, supply 100 mL / h of a 14% solution of IPN in ammonia (LHSV=1.5h -1 ). The results of gas chromatography experiments for the product are listed in Table 2 below under the column "Conditioned".

Embodiment 3

[0074] Hydrogenation of trimethylhexamethylenedinitrile to trimethylhexamethylenediamine

[0075]The experiments were carried out in a 1 L hydrogenation autoclave equipped with a catalyst basket (static basket with stirrer, "Mahoney type". The catalyst is freshly filled.

[0076] For conditioning with ammonia, the reactor was first filled with about 500 mL of ammonia and then kept under stirring at 50° C. and 250 bar for about 2 hours. Ammonia is then evolved by depressurizing the reactor.

[0077] After conditioning, 20% to 600 mL of trimethylhexamethylene dinitrile (2,4,4-isomer and mixture of 2,2,4-isomer) at 120 °C and 250 bar total pressure The solution was hydrogenated for 6 hours. The product was drawn off and then checked by gas chromatography. The results are listed in Table 3 under the "Conditioned" column.

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Abstract

The invention relates to a process for preparing amines by conditioning the catalyst with ammonia.

Description

technical field [0001] The present invention relates to a process for the preparation of amines by conditioning a catalyst with ammonia. Background technique [0002] The preparation of amines and diamines by means of catalytic hydrogenation of the corresponding nitriles or by catalytic reductive amination of aldehydes or ketones is known. Suitable are, for example, nickel, copper, iron, palladium, rhodium, ruthenium and cobalt catalysts. [0003] For many applications, cobalt and ruthenium catalysts are preferred because of their high selectivity for the formation of primary amines (see, e.g., Jiri Volf and Josef Pasek, "Hydrogenation of Nitriles", Studies in Surface Science and Catalysis, 27( 1986) pp. 105-144; Silvia Gomez et al., "The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control, Adv. Synth. Catal. 344 (2002) pp. 1037-1057). [0004] Numerous methods have been described in order to increase ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/48C07C209/16B01J37/16B01J23/75B01J25/00
CPCC07C209/48C07C209/26C07C2101/14C07C2601/14C07C211/09C07C211/12C07C211/36
Inventor C·勒特曼J·利佩
Owner DEGUSSA AG
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