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

• US 8,003,818 B2
• Filed: 12/21/2005
• Issued: 08/23/2011
• Est. Priority Date: 12/23/2004
• Status: Expired due to Fees

• Current Assignee: Shell Oil Company (Shell Plc)
• Original Assignee: Shell Oil Company (Shell Plc)
• Inventors: Petrus, Leonardus, Von Hebel, Klaas Lambertus, Lange, Jean-Paul, Van Den Brink, Peter John
• Primary Examiner(s): Sullivan; Daniel
• Assistant Examiner(s): SAWYER, JENNIFER C
• Application Number:
  US11/314,404
• Publication Number:
  US 20060162239A1
• Time in Patent Office: 2,071 Days
• Field of Search: 568/861, 560/231, 560/179, 561/1
• US Class Current: 560/190
• 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: at the ring-closing carbon atom and has a proton at a

• (a) a 5- or 6-membered lactone that is substituted 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 preparing a compound selected from the group consisting of:

dialkyl 4-methylnonanedioate;

2. The process of claim 1, wherein the alkyl alcohol is ethanol, and the compound produced is diethyl-4-methylnonanedioate, diethyl 3-ethyl-4-methylheptanedioate, or a combination thereof.

3. The process of claim 1, wherein the alkyl alcohol is a diol selected from the group consisting of ethylene glycol and butane-1,4-diol.

4. The process of claim 1, wherein the dimer of levulinic acid is selected from the group consisting of:

4-methyl-6-oxononanedioic acid;

5. The process of claim 1, wherein the catalyst comprises a physical mixture of an acidic zeolite and a supported hydrogenating metal.

6. The process of claim 1, wherein the catalyst further comprises a binder selected from the group consisting of silica, alumina, acidic clay, titania and zirconia.