Stabilization and hydrogenation methods for microbial-derived olefins
View Patent ↗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.
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.