Method and apparatus for the preparation of ketones

• US 20020193638A1
• Filed: 05/10/2002
• Published: 12/19/2002
• Est. Priority Date: 11/19/1998
• Status: Active Grant

• Current Assignee: EagleView Technologies Incorporated (Eagleview Technologies, Inc. /Wa/)
• Original Assignee: EagleView Technologies Incorporated (Eagleview Technologies, Inc. /Wa/)
• Inventors: Warren, Jack S.
• Granted Patent: US 6,495,696 B1
• Time in Patent Office: Days
• US Class Current: 568/354
• CPC Class Codes: C07C 45/00 Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
• CPC Class Codes: C07C 45/48 involving decarboxylation
• CPC Class Codes: C07C 49/293 to a three- or four-membered ring
• CPC Class Codes: C07D 261/08 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Abstract

A method and apparatus for continuously producing a ketone in a tube reactor at elevated weight hourly space velocities and in the presence of a catalyst from feed material comprised of a first carboxylic acid or aldehyde or their derivatives and a second carboxylic acid and a method for using the ketone production method to produce herbicidal or other agricultural compounds.

Claims

1. A method of preparing a desired ketone comprising the steps of:

providing a catalytic bed;

providing a raw material feed comprised of a first carboxylic acid or aldehyde or their derivatives and a second carboxylic acid in the ratio of from 1;

2 to 1;

20;

passing said raw material feed through said catalytic bed at a temperature of between about 350°

C. and 500°

C. at a weight hourly space velocity greater than two; and

separating said desired ketone.

2. The method of claim 1 including determining the optimum bed reaction temperature for said raw material feed and preheating said catalytic bed to said optimum bed reaction temperature.

3. The method of claim 1 wherein said desired ketone is an unsymmetrical ketone.

4. The method of claim 3 wherein said desired ketone is a cyclopropyl ketone and said aldehyde is cyclopropylaldehyde.

5. The method of claim 3 wherein said desired ketone is a cyclopropyl ketone and said first carboxylic acid is cyclopropanecarboxylic acid.

6. The method of claim 5 wherein said second carboxylic acid is acetic acid and said desired ketone is methyl cyclopropyl ketone.

7. The method of claim 1 wherein said catalytic bed includes a CeO₂/ZrO₂ catalyst structure in the range of about 1 to 5% CeO₂ per gram of ZrO₂.

8. The method of claim 1 including maintaining said raw material feed in said catalytic bed at a pressure in the range of 10 to 200 psi as said raw material passes through said catalytic bed.

9. The method of claim 1 wherein said weight hourly space velocity is about 5-20.

10. The method of claim 1 wherein said first carboxylic acid and said second carboxylic acid are different.

11. A method of preparing a desired ketone comprising the steps of:

providing a catalytic bed;

providing a raw material feed comprised of a first carboxylic acid or aldehyde or their derivatives and a second carboxylic acid in the ratio of from 1;

2 to 1;

20;

passing said raw material feed through said catalytic bed in a vertically upward direction at a temperature of between 350°

C. and 500°

C.; and

separating said desired ketone.

12. The method of claim 11 including determining a preferred bed reaction temperature for said raw material feed and preheating said catalytic bed to said preferred bed reaction temperature.

13. The method of claim 11 wherein said desired ketone is an unsymmetrical ketone.

14. The method of claim 13 wherein said desired ketone is methyl cyclopropyl ketone.

15. The method of claim 11 wherein said catalytic bed includes a CeO₂/ZrO₂ catalyst structure in the range of about 1 to 5% CeO₂ per gram of ZrO₂.

17. The method of claim 16 including determining a preferred bed reaction temperature for said raw material feed and preheating said catalytic bed of said one tube reactor to said preferred bed reaction temperature.

18. The method of claim 16 including selectively stopping the passage of raw material feed through the catalytic bed of said one tube reactor and passing said raw material feed through the catalytic bed of one of the other(s) of said tube reactors and passing said raw material feed through the catalytic bed of said one of the other(s) of said tube reactors.

19. The method of claim 16 including providing a single ketone recovery means selectively connectable to said one tube reactor or said one of the other(s) of said tube reactors for recovering said ketone wherein said means is connected with said one tube reactor.

20. The method of claim 19 including selectively stopping the passage of raw material feed through the catalytic bed of said one tube reactor and connecting the raw material feed through the catalytic bed of said one of the other(s) of said tube reactors and disconnecting said recovery means from said one tube reactor and connecting said recovery means to said one of the other(s) of said tube reactors.

21. The method of claim 20 including regenerating the catalytic bed of said one tube reactor.

22. The method of claim 16 wherein said catalytic bed includes a CeO₂/ZrO₂ catalyst structure in the range of about 1 to 5% CeO₂ per gram of ZrO₂.

24. The apparatus of claim 23 wherein said means for supplying includes a selection valve positioned between said feed material source and said plurality of tube reactors.

25. The apparatus of claim 23 wherein said plurality of tube reactors are mounted to facilitate vertically upward flow of said first and second feed materials through the catalytic bed of said one tube reactor.

27. The method of claim 26 wherein said pressure is in the range of about 20 psig to 100 psig.

29. The process of claim 28, wherein the second carboxylic acid is acetic acid.

16. A method of preparing a ketone comprising:

providing a plurality of tube reactors, each having a catalytic bed;

providing a raw material feed comprised of first and second raw materials which react in a ketone production reaction to produce said ketone;

selectively passing said raw material feed through the catalytic bed of one of said plurality of tube reactors and not the other(s) of said plurality of tube reactors at a temperature of between 350°

C. and 500°

C.; and

recovering said ketone.

23. An apparatus for producing a ketone from first and second feed materials via a ketone production reaction comprising:

a feed material source for providing said first and second feed materials;

a plurality of tube reactors, each having an inlet end, an outlet end and a catalytic bed therebetween;

means for selectively supplying said first and second feed materials to the inlet end of one of said plurality of tube reactors in a predetermined ratio and preventing the supply of said first and second feed materials to the inlet end of the other(s) of said plurality of tube reactors.

26. A method of preparing a desired ketone comprising the steps of:

providing a catalytic bed;

providing a raw material feed comprised of a first carboxylic acid or aldehyde or their derivatives and a second carboxylic acid in the ratio of from 1;

2 to 1;

20;

passing said raw material feed through said catalytic bed at a temperature of between about 100°

C. and 500°

C. and at a pressure in the range of about 10 psig to about 200 psig; and

separating said desired ketone.

28. A process for the preparation of a compound of formula (I)

30. A process for the preparation of a compound of formula (X)