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Process to continuously prepare aqueous mixture of epsi-caprolacta and epsi caprolactam precursors

A technology of caprolactam and carrier, which is applied in the field of continuous preparation of aqueous mixture of ε-caprolactam and ε-caprolactam precursor, can solve the problems of hindering filtration operation, catalyst loss, catalyst activity reduction, etc., to achieve improved selectivity, high yield, The effect of improving the initial activity

Inactive Publication Date: 2004-03-24
INVISTA TECHNOLOG IES S A R L
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Another disadvantage of this method is that when the reductive amination reaction is carried out for a long time, it has been found that the particle size of the Raney nickel and alumina catalyst particles becomes smaller
This is undesirable as these fine particles may hinder filtration operations or cause catalyst loss due to entrainment of catalyst in the product stream
[0005] A further disadvantage of this method is the relatively low initial activity of the catalyst system
[0006] Another disadvantage of this method is that the activity of the catalyst may decrease after several hours of continuous operation.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment I

[0032] 1 gram of 5wt.% ruthenium / zirconia (BET surface area 86m 2 / g) into a 100ml autoclave, add 5.8mg Rh(CO) 2 AcAc. The catalyst was reduced in 57 g of water at 150° C. for 1 hour under a hydrogen pressure of 5.0 MPa. After adding 23.1 g of ammonia, the temperature was raised to 100° C. and the pressure was increased to 5.0 MPa. Subsequently, 2.8 g of methyl 5-formylvalerate and 1.5 g of methanol were added. The calculated first order reaction coefficient is 126×10 -4 / Second. The overall yield of ε-caprolactam and ε-caprolactam precursors was 98%.

[0033] Comparative experiment A

[0034] 1 gram of 5 wt.% ruthenium / γ-alumina was placed in a 100 ml autoclave. The catalyst was reduced in 57 g of water at 150° C. for 1 hour under a hydrogen pressure of 5.0 MPa. After adding 24.5 g of ammonia, the temperature was raised to 100° C. and the pressure was increased to 5.0 MPa. Subsequently, 2.8 g of methyl 5-formylvalerate and 1.5 g of methanol were added. The calcula...

Embodiment II

[0038] 0.16 grams of 5wt.% ruthenium / titanium dioxide (BET surface area is 55m 2 / g) was placed in a 100ml autoclave, and 0.77mg Ni(NO 3 ).6H 2 O. The catalyst was reduced in 56 g of water at 150° C. for 1 hour under a hydrogen pressure of 5.0 MPa. After adding 23.1 g of ammonia, the temperature was raised to 100° C. and the pressure was increased to 5.0 MPa. Subsequently, 2.8 g of methyl 5-formylvalerate and 1.5 g of methanol were added. The calculated first order reaction coefficient is 249×10 -4 / Second. The overall yield of ε-caprolactam and ε-caprolactam precursors was 90%.

Embodiment III

[0040] 0.16 grams of 5wt.% ruthenium / titanium dioxide (BET surface area is 55m 2 / g) was placed in a 100ml autoclave, and 7.8mg Ni(NO 3 ).6H 2 O. The catalyst was reduced in 56 g of water at 150° C. for 1 hour under a hydrogen pressure of 5.0 MPa. After adding 23.1 g of ammonia, the temperature was raised to 100° C. and the pressure was increased to 5.0 MPa. Subsequently, 2.6 g of methyl 5-formylvalerate and 1.4 g of methanol were added. The calculated first order reaction coefficient is 369×10 -4 / Second. The overall yield of ε-caprolactam and ε-caprolactam precursors was 99.8%.

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Abstract

The present invention provides a process for preparing an aqueous mixture of epsilon -caprolactam and 6-aminocaproic acid and or 6-aminocaproamide which involves, as the reductive amination step, contacting 5-formylvaleric acid and / or an alkyl 5-formylvalerate in water as solvent with hydrogen and an excess of ammonia in the presence of a ruthenium on carrier, as a catalyst, wherein the carrier is titanium oxide, zirconium oxide, graphite or carbon and the catalyst also contains at least one of the metals of group 8-11, or a compound of these metals. The aqueous mixture can be used to prepare epsilon -caprolactam.

Description

technical field [0001] The present invention relates to the preparation of ε-caprolactam with 6 by reductive amination of 5-formylvaleric acid and / or alkyl 5-formylvaleric acid in water with hydrogen and excess ammonia in the presence of a supported ruthenium catalyst Aqueous mixtures of aminocaproic acid and / or 6-aminocaproamide. Background technique [0002] A process for the preparation of ε-caprolactam is described in US Patent 4,730,040. In this method, methyl 5-formylvalerate is first hydrolyzed in the presence of water and an acidic substance to form 5-formylvaleric acid (step a). Furthermore, in this method, 5-formylvaleric acid is reductively aminated in water by contact with ammonia and hydrogen using a ruthenium / zirconium catalyst supported on alumina, a Raney nickel catalyst, or a Raney cobalt catalyst, A reaction mixture containing 6-aminocaproic acid is thus obtained. After separation of the ammonia, the reaction mixture resulting from the reductive aminatio...

Claims

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Application Information

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IPC IPC(8): C07D223/10B01J23/46C07B61/00C07C227/08C07C229/08C07C231/14C07C237/06C07D201/08
CPCC07D201/08C07C231/14C07C227/08Y02P20/52
Inventor R·佩斯特曼L·H·W·M·范利肖特
Owner INVISTA TECHNOLOG IES S A R L
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