Process for the preparation of alcohols or amines

• US 5,550,297 A
• Filed: 02/16/1995
• Issued: 08/27/1996
• Est. Priority Date: 03/04/1992
• Status: Expired due to Term

• Current Assignee: Johnson Matthey PLC
• Original Assignee: Hoechst Aktiengesellschaft (Sanofi )
• Inventors: Frohning, Carl D., Horn, Gerhardt
• Primary Examiner(s): BURN, BRIAN M
• Application Number:
  US08/390,375
• Time in Patent Office: 558 Days
• Field of Search: 568/885, 568/874, 568/877, 564/490, 564/493
• US Class Current: 564/493
• CPC Class Codes: B01J 23/80 with zinc, cadmium or mercury
• CPC Class Codes: B01J 23/84 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
• CPC Class Codes: B01J 35/392 Metal surface area
• CPC Class Codes: B01J 35/613 10-100 m2/g
• CPC Class Codes: B01J 35/615 100-500 m2/g
• CPC Class Codes: B01J 37/031 Precipitation
• CPC Class Codes: C07C 209/48 by reduction of nitriles
• CPC Class Codes: C07C 29/149 with hydrogen or hydrogen-containing gases
• CPC Class Codes: C07C 29/177 with simultaneous reduction of a carboxy group
• CPC Class Codes: C07C 31/125 containing five to twenty-two carbon atoms

Abstract

A process for catalytic preparation of alcohols or amines by reaction of esters, fatty acids, or nitriles with hydrogen at elevated temperature and pressure. The unreduced catalyst contains, per 100 parts by weight of CuO, 40 to 130 parts by weight of ZnO, 2 to 50 parts by weight of Al₂ O₃, and optionally 0.5 to 8 parts by weight of oxide of Mn, Mo, V, Zr, and/or alkaline earth metal. It has a BET total area of 80 to 175 m² /g of catalyst in the unreduced state, and 75% to 95% of the BET total area is formed by pores having a radius r_p ≦15 nm.

Claims

1. A process for the hydrogenation of a compound selected from the class consisting of esters, fatty acids, and nitriles to form corresponding alcohols or amines, said process comprising a reaction of said compound with hydrogen at elevated pressure and elevated temperature in the presence of a catalyst which contains CuO,

said catalyst, in its unreduced state, comprising, per 100 parts of said CuO, 40 to 130 parts by weight of ZnO, 2 to 50 parts by weight of Al₂ O₃, said catalyst having a BET total area of 80 to 175 m² /g, 75% to 95% of said total area constituting pores having radii r_p ≦

15 nm.

2. The process of claim 1 wherein said catalyst, in its reduced state, has an active copper metal surface area of 30 to 125 m² /g of said copper.

3. The process of claim 2 wherein said surface area is 40 to 85 m² /g of said copper.

4. The process of claim 1 wherein said catalyst, in said unreduced state, per 100 parts by weight of said CuO, comprises 45 to 80 parts by weight of ZnO and 4 to 11 parts by weight of Al₂ O₃.

5. The process of claim 1 wherein said total area is 90 to 155 m² /g of said catalyst in said unreduced state.

6. The process of claim 1 wherein 84% to 90% of said total area constitutes said pores having radii r_p ≧

15 nm.

7. The process of claim 1 wherein said catalyst per 100 parts by weight of CuO, contains 4 to 60 parts by weight of a water-insoluble support.

8. The process of claim 7 wherein said support is selected from the group consisting of kieselguhr, silica gel, SiO₂ /Al₂ O₃, and mixtures thereof.

9. The process of claim 8 wherein said support is SiO₂ and/or Al₂ O₃.

10. The process of claim 1 wherein said compound is selected from the group consisting of esters and fatty acids, said elevated temperature is 200°

to 350°

C., and said elevated pressure is 15 to 40 MPa.

11. The process of claim 10 wherein said elevated temperature is 230°

to 320°

C. and said elevated pressure is 20 to 32 MPa.

12. The process of claim 1 wherein said compound is a carboxylic acid ester.

13. The process of claim 12 wherein said carboxylic acid is naturally occurring.

14. The process of claim 12 wherein said carboxylic acid has 8 to 30 carbon atoms.

15. The process of claim 14 wherein said carboxylic acid has 10 to 24 carbon atoms.

16. The process of claim 15 wherein said carboxylic acid has 12 to 22 carbon atoms.