Process for the hydrogenation of a lactone or of a carboxylic acid or an ester having a gamma-carbonyl group

• US 20060162239A1
• Filed: 12/21/2005
• Published: 07/27/2006
• Est. Priority Date: 12/23/2004
• Status: Active Grant

• Current Assignee: Shell Oil Company (Shell Plc)
• Original Assignee: Shell Oil Company (Shell Plc)
• Inventors: Lange, Jean-Paul, Van Den Brink, Peter John, Petrus, Leonardus, Von Hebel, Klaas Lambertus
• Granted Patent: US 8,003,818 B2
• Time in Patent Office: Days
• US Class Current: 44/385
• CPC Class Codes: C07C 51/377 by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups C07C51/36 - C07C51/373 take precedence
• CPC Class Codes: C07C 53/126 Acids containing more than four carbon atoms

Abstract

The invention provides a process for the hydrogenation of a reactant selected from the group consisting of: (a) a 5- or 6-membered lactone that is substituted at the ring-closing carbon atom and has a proton at a carbon atom adjacent to the ring-closing carbon atom; (b) an ester of a carboxylic acid having a gamma-carbonyl group and a proton at a carbon atom adjacent to the carbon atom of the carbonyl group; and (c) a carboxylic acid having a gamma-carbonyl group and a proton at a carbon atom adjacent to the carbon atom of the carbonyl group, wherein the reactant is contacted with a strongly acidic heterogeneous catalyst comprising a hydrogenating metal, in the presence of hydrogen, at a temperature in the range of from 100 to 350° C. and a pressure in the range of from 1 to 150 bar (absolute). The invention further provides a fuel composition, preferably a diesel composition, comprising di-alkyl 4-methylnonanedioate or di-alkyl 3-ethyl-4-methylheptanedioate.

Claims

1. A process for the hydrogenation of a reactant selected from the group consisting of:

(a) a 5- or 6-membered lactone that is substituted at the ring-closing carbon atom and has a proton at a carbon atom adjacent to the ring-closing carbon atom;

(b) an ester of a carboxylic acid having a gamma-carbonyl group and a proton at a carbon atom adjacent to the carbon atom of the carbonyl group; and

(c) a carboxylic acid having a gamma-carbonyl group and a proton at a carbon atom adjacent to the carbon atom of the carbonyl group,

wherein the reactant is contacted with a strongly acidic heterogeneous catalyst comprising a hydrogenating metal, in the presence of hydrogen, at a temperature in the range of from 100 to 350°

C. and a pressure in the range of from 1 to 150 bar (absolute).

2. The process according to claim 1, wherein the reactant is a 5-membered lactone with an alkyl group on the ring-closing carbon atom.

3. The process according to claim 1, wherein the reactant is an ester of levulinic acid, a di-ester of 4-methyl-6-oxononanedioic acid or 3-acetyl-4-methylheptanedioic acid, or a combination of two or more thereof.

4. The process according to claim 1, wherein the reactant is an alkyl ester.

5. The process according to claim 1, wherein the reactant is levulinic acid, 4-methyl-6-oxononanedioic acid, 3-acetyl-4-methylheptanedioic acid, or a combination of two or more thereof.

6. The process according to claim 1, wherein the reactant is contacted with the catalyst at a temperature in the range of from 150 to 250°

C.

7. The process according to claim 1, wherein the reactant is contacted with the catalyst at a pressure in the range of from 20 to 100 bar (absolute).

8. The process according to claim 1, wherein the hydrogenating metal is a metal of any one of groups 7 to 11 of the Periodic Table of Elements.

9. The process according to claim 1, wherein the catalyst comprises an acidic zeolite.

11. The process according to claim 1, wherein the reactant is gamma valerolactone.

12. The process according to claim 1, wherein the reactant is an alkyl ester with at most 10 carbon atoms in the alcohol fragment.

13. The process according to claim 1, wherein the reactant is ethyl ester.

14. The process according to claim 3, wherein the reactant is an alkyl ester.

15. The process according to claim 3, wherein the reactant is an alkyl ester with at most 10 carbon atoms in the alcohol fragment.

16. The process according to claim 3, wherein the reactant is an ethyl ester.

17. The process according to claim 1, wherein the reactant is contacted with the catalyst at a pressure in the range of from 50 to 80 bar (absolute).

18. The process according to claim 1, wherein the hydrogenating metal is Ni, Rh, Pd, Pt, Re or Ru.

19. The process according to claim 1, wherein the hydrogenating metal is Ni, Ru or Rh.

10. A fuel composition comprising di-alkyl 4-methylnonanedioate or di-alkyl 3-ethyl-4-methylheptanedioate.

20. A diesel composition comprising di-alkyl 4-methylnonanedioate or di-alkyl 3-ethyl-4-methylheptanedioate.