Stabilization and hydrogenation methods for microbial-derived olefins

Patent metadata

Field	Value
Publication number	US-10894754-B2
Application number	US-201816228567-A
Country	US
Kind code	B2
Filing date	Dec 20, 2018
Priority date	Apr 2, 2009
Publication date	Jan 19, 2021
Grant date	Jan 19, 2021

Abstract

Processes and systems for stabilization and subsequent hydrogenation of an immiscible olefin are described. In certain embodiments, the hydrogenation is conducted in a fixed bed reactor in presence of a hydrogenation catalyst.

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 fixed bed reactor wherein the feed stream comprises an immiscible olefin and a diluent composition;
b) contacting the feed stream with hydrogen in the presence of a hydrogenation catalyst at a temperature of about 20° C. or greater thereby producing an effluent;
c) separating the effluent which comprises a hydrogenated immiscible olefin into a product stream comprising a hydrogenated immiscible olefin and a recycle stream comprising a hydrogenated immiscible olefin;
d) adding the recycle stream as part of the diluent composition to a stream comprising the immiscible olefin to form a feed stream comprising recycled hydrogenated immiscible olefin; and
e) providing the feed stream comprising recycled hydrogenated immiscible olefin to the inlet of the fixed bed reactor.

2. The method of claim 1 , wherein the feed stream comprising recycled hydrogenated immiscible olefin of steps d) and e) is combined with the feed stream comprising the immiscible olefin of step a).

3. The method of claim 1 , further comprising repeating steps b)-e) at least once.

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

5. The method of claim 1 , wherein the immiscible olefin comprises farnesene.

6. The method of claim 1 , wherein the fixed bed reactor is a one-stage, two-stage or multi-stage reactor.

7. The method of claim 5 , wherein the reactor is a cocurrent downflow reactor, a cocurrent upflow reactor or a countercurrent reactor.

8. The method of claim 5 , wherein the reactor is a cocurrent downflow reactor.

9. The method of claim 5 , wherein the reactor is maintained at a pressure between about 300 psig to about 700 psig.

10. The method of claim 5 , wherein the reactor is maintained at an axial temperature rise of about 10 to 100° C.

11. The method of claim 5 , wherein the hydrogenation reaction occurs at a temperature of about 100 to about 200° C.

12. 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.

13. 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 .

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

15. The method of claim 1 , wherein hydrogen is used in about 100% stoichiometric excess relative to the immiscible olefin.

16. The method of claim 1 , wherein the feed stream comprises about 50 to 95% diluent based on total weight of the immiscible olefin.

17. The method of claim 16 , wherein the diluent composition comprises a hydrogenated immiscible olefin.

18. The method of claim 16 , wherein the diluent composition comprises a saturated immiscible olefin.

19. The method of claim 16 , wherein the diluent composition comprises the recycled hydrogenated immiscible olefin in combination with one or more other diluents.

20. The method of claim 16 , wherein the diluent comprises n-pentane, n-hexane, n-heptane, n-octane, n-decane, farnesane or a combination thereof.

21. A method for hydrogenating an immiscible olefin comprising:
a) providing a feed stream to the inlet of a fixed bed reactor wherein the feed stream comprises an immiscible olefin and a diluent composition;
b) contacting the feed stream with hydrogen in the presence of a hydrogenation catalyst at a temperature of about 20° C. or greater thereby producing an effluent;
c) separating the effluent which comprises a hydrogenated immiscible olefin into a product stream comprising a hydrogenated immiscible olefin and a recycle stream comprising a hydrogenated immiscible olefin;
d) recycling the recycle stream into the feed stream provided to the inlet of the fixed bed reactor in step a).

Assignees

• Amyris Inc

Inventors

• Ohler Nicholas L
• Vazquez Roberto

Classifications

• Y02P30/20

  using bio-feedstock · CPC title

• C10G2300/802

  Diluents · CPC title

• C10G2300/1055

  Diesel having a boiling range of about 230 - 330 °C · CPC title

• C10G2300/1011

  Biomass · CPC title

• C10G67/04

  including solvent extraction as the refining step in the absence of hydrogen · CPC title