Olefins and methods for making the same

Patent metadata

Field	Value
Publication number	US-12187674-B2
Application number	US-202318371412-A
Country	US
Kind code	B2
Filing date	Sep 21, 2023
Priority date	Apr 13, 2011
Publication date	Jan 7, 2025
Grant date	Jan 7, 2025

Abstract

Provided herein are olefinic feedstocks derived from conjugated hydrocarbon terpenes (e.g., C10-C30 terpenes), methods for making the same, and methods for their use.

First claim

The invention claimed is:

1. A method comprising selectively hydrogenating, in two or more stages, a conjugated terpene comprising at least three olefinic bonds wherein two of the at least three olefinic bonds form a conjugated diene to make a composition comprising at least about 50% mono-olefinic species and about 20% or less di-olefinic species in a mixture of hydrogenated reaction products,
wherein the hydrogenating comprises catalytic hydrogenation with a catalyst, a catalyst loading, a reaction temperature, and hydrogen pressure,
wherein the catalyst, the catalyst loading, the reaction temperature, and the hydrogen pressure are selected so that less than about 10% of the molecules in an intermediate product have a conjugated diene moiety after the first hydrogenation stage.

2. The method of claim 1 , wherein the temperature of the second stage is greater than the temperature of the first stage.

3. The method of claim 1 , wherein the hydrogen pressure of the second stage is less than or equal to the hydrogen pressure of the first stage.

4. The method of claim 1 , wherein one or more stage of the selective hydrogenation occurs in the presence of a catalyst.

5. The method of claim 1 , capable of making a composition comprising at least about 50% mono-olefinic species and about 15% or less di-olefinic species.

6. The method of claim 1 , capable of making a composition comprising at least about 55% mono-olefinic species and at most about 10% di-olefinic species, at least about 60% mono-olefinic species and at most about 10% di-olefinic species, or at least about 65% mono-olefinic species and at most about 10% di-olefinic species.

7. The method of claim 1 , capable of making a composition comprising at most about 5% di-olefinic species.

8. A method comprising selectively hydrogenating, in two or more stages, a conjugated terpene comprising at least three olefinic bonds wherein two of the at least three olefinic bonds form a conjugated diene to make a composition comprising greater than 60% mono-olefinic species in a mixture of hydrogenated reaction products,
wherein the hydrogenating comprises catalytic hydrogenation with a catalyst, a catalyst loading, and a reaction temperature or hydrogen pressure,
wherein the catalyst, the catalyst loading, the reaction temperature, and the hydrogen pressure are selected so that less than about 10% of the molecules in an intermediate product have a conjugated diene moiety after the first hydrogenation stage.

9. The method of claim 8 , wherein the temperature of the second stage is greater than the temperature of the first stage.

10. The method of claim 8 , wherein the hydrogen pressure of the second stage is less than or equal to the hydrogen pressure of the first stage.

11. The method of claim 8 , wherein one or more stage of the selective hydrogenation occurs in the presence of a catalyst.

12. The method of claim 9 , capable of making a composition comprising at least about 65% mono-olefinic species, at least about 70% mono-olefinic species, or at least about 75% mono-olefinic species.

Assignees

• Amyris Inc

Inventors

• Ohler Nicholas
• Fisher Karl
• Hong Jin Ki

Classifications

• C10M2203/003

  used as base material · CPC title

• C10M105/02

  Well-defined hydrocarbons (petroleum fractions C10M101/02) · CPC title

• C07C2523/75

  Cobalt · CPC title

• C07C5/03

  of non-aromatic carbon-to-carbon double bonds · CPC title

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title