Process for isomerization and decarboxylation of unsaturated organic compounds with a metal catalyst or catalyst precursor

Patent metadata

Field	Value
Publication number	US-10457615-B2
Application number	US-201715834616-A
Country	US
Kind code	B2
Filing date	Dec 7, 2017
Priority date	Mar 15, 2013
Publication date	Oct 29, 2019
Grant date	Oct 29, 2019

Abstract

Disclosed is the use of a metal catalyst or catalyst precursor that catalyzes the isomerization of an unsaturated fatty acid, unsaturated fatty acid derivative, or an unsaturated triglyceride. Also disclosed is the use of a metal catalyst or catalyst precursor that catalyzes the decarboxylation of an unsaturated organic compound. Also disclosed is the use of a catalyst or catalyst precursor for the dual function isomerization and decarboxylation of an unsaturated fatty acid to an unsaturated organic compound.

First claim

The embodiment of the invention in which exclusive property or privilege is claimed is defined as follows:

1. A process for the isomerization and decarboxylation of an unsaturated fatty acid, the process comprising contacting an unsaturated fatty acid in the presence of a catalyst or catalyst precursor containing one or more a osmium carbonyl carboxylates at a temperature at which the isomerization and decarboxylation occurs and recovering the products which are isomerized and decarboxylated unsaturated olefins, wherein the C—C double bonds in said isomerized and decarboxylated unsaturated olefins are in different locations compared to said unsaturated fatty acid, and wherein the number of C—C double bonds in said isomerized and decarboxylated unsaturated olefins are the same as in said unsaturated fatty acid; the process comprising an additional step of contacting an additional monocarboxylic acid to said unsaturated fatty acid in the presence of a catalyst or catalyst precursor.

2. The process of claim 1 wherein the monocarboxylic acid is selected from the group consisting of benzoic acid, cinnamic acid, propanoic acid, undecanoic acid, acetic acid, stearic acid, and oleic acid.

3. The process of claim 1 wherein the isomerized and decarboxylated unsaturated organic compound product is a mixture of internal and alpha-olefins.

4. The process of claim 1 wherein the isomerized and decarboxylated unsaturated organic compound product is a conjugated internal olefin.

Assignees

• Us Agriculture

Inventors

• Murray Rex E
• Doll Kenneth M
• Liu Zengshe

Classifications

• C10G50/00

  Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation · CPC title

• C07C2527/12

  Fluorides · CPC title

• C07C2521/06

  Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof · CPC title

• C10G3/47

  containing platinum group metals or compounds thereof · CPC title

• C07C67/333

  by isomerisation; by change of size of the carbon skeleton (introduction or elimination of carboxyl groups C07C67/313, C07C67/32) · CPC title