Stabilization and hydrogenation methods for microbial-derived olefins

Patent metadata

Field	Value
Publication number	US-9611189-B2
Application number	US-201313951137-A
Country	US
Kind code	B2
Filing date	Jul 25, 2013
Priority date	Apr 2, 2009
Publication date	Apr 4, 2017
Grant date	Apr 4, 2017

Abstract

Methods and compositions for stabilization and subsequent hydrogenation of a microbial-derived immiscible olefin are described. The methods comprise providing a feed stream to the inlet of a reactor, wherein the feed stream comprises a microbial-derived immiscible olefin composition stabilized with a phenolic antioxidant which is a phenol derivative containing an unfused phenyl ring with one or more hydroxyl substituents. The methods further comprise contacting the feed stream with hydrogen in the presence of a hydrogenation catalyst at a temperature of about 20° C. or greater, and generating a product stream comprising a hydrogenated immiscible olefin composition. The microbial-derived immiscible olefin composition stabilized with the phenolic antioxidant remains stable over time, and its hydrogenation reaction time and process are improved.

First claim

What is claimed is:

1. A method for hydrogenating an immiscible olefin comprising:
a) providing a feed stream to the inlet of a reactor wherein the feed stream comprises a microbial-derived immiscible olefin composition stabilized with a phenolic antioxidant which is a phenol derivative containing an unfused phenyl ring with one or more hydroxyl substituents, wherein the phenolic antioxidant is present in an amount of at least 0.005% by weight of the microbial-derived immiscible olefin composition;
b) contacting the feed stream with hydrogen in the presence of a hydrogenation catalyst at a temperature of about 20° C. or greater and
c) generating a product stream comprising a hydrogenated immiscible olefin composition.

2. The method of claim 1 , wherein the hydrogenation reaction occurs at a temperature that is greater than about 100° C.

3. The method of claim 1 , wherein the microbial-derived immiscible olefin comprises farnesene.

4. The method of claim 3 , wherein the method comprises selective hydrogenation of farnesene to reduce one, two, three, or four double bonds in farnesene.

5. The method of claim 3 , wherein the farnesene is selectively hydrogenated to reduce one double bond.

6. The method of claim 1 , wherein the reactor is a fixed bed reactor.

7. The method of claim 6 , wherein the hydrogenation reaction occurs at a temperature of about 100° C. to about 200° C.

8. The method of claim 6 , wherein the fixed bed reactor is a one stage, two stage or multi stage reactor.

9. The method of claim 8 , wherein the reactor is a cocurrent downflow reactor, a cocurrent upflow reactor or a countercurrent reactor.

10. The method of claim 9 , wherein the reactor is a cocurrent downflow reactor.

11. The method of claim 9 , wherein the reactor is maintained at a pressure between about 300 psig to about 700 psig.

12. The method of claim 9 , wherein the reactor is maintained at an axial temperature rise of about 10° C. to 100° C.

13. The method of claim 1 , wherein the catalyst comprises Ni, Pd, Ru, Pt, Rh, Ir, Cu, Fe, an alloy of a platinum group catalyst, a Raney-type porous catalyst or a hydroprocessing catalyst.

14. The method of claim 1 , wherein the catalyst is selected from 0.3% Pd/Al 2 O 3 , 5% Ni/Al 2 O 3 , 8% Ni/Al 2 O 3 , and 20% Ni/Al 2 O 3 .

15. The method of claim 1 , wherein hydrogen is in about 1-1000% stoichiometric excess relative to the microbial-derived immiscible olefin composition.

16. The method of claim 1 , wherein hydrogen is used in about 100% stoichiometric excess relative to the microbial-derived immiscible olefin composition.

Assignees

• Amyris Inc

Inventors

• Ohler Nicholas L
• Vazquez Roberto

Classifications

• C10G45/00

  Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds · CPC title

• C07C2523/755

  Nickel · CPC title

• C07C11/21

  Alkatrienes; Alkatetraenes; Other alkapolyenes · CPC title

• C10L1/04

  essentially based on blends of hydrocarbons · CPC title

• C10G2300/1011

  Biomass · CPC title