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 separating immiscible olefin from a mixture comprising an aqueous solution, microbial cells and immiscible olefin thereby forming a crude olefin composition; purifying the crude olefin composition thereby forming a purified olefin composition; and adding a phenolic antioxidant to the purified olefin composition wherein the phenolic antioxidant is a phenol derivative containing an unfused phenyl ring with one or more hydroxyl substituents. The methods further comprise reacting the purified olefin composition with hydrogen in the presence of a hydrogen catalyst such that hydrogen saturates at least one double bond in the olefin. Hydrogenated compositions produced by the methods are further provided.
1. A hydrogenated composition derived from a microbial derived olefin composition, the hydrogenated composition produced by a method comprising:
(a) separating immiscible olefin from a mixture comprising an aqueous solution, microbial cells and immiscible olefin, thereby forming a crude olefin composition;
(b) purifying the crude olefin composition thereby forming a purified olefin composition;
(c) adding a phenolic antioxidant to the purified olefin composition to form a stabilized purified microbial-derived olefin composition, wherein the phenolic antioxidant is a phenol derivative containing an unfused phenyl ring with one or more hydroxyl substituents, and is present in an amount that is at least 0.0001% by weight of stabilized purified microbial-derived olefin composition; and
(d) reacting the stabilized purified microbial-derived olefin composition with hydrogen in the presence of a hydrogenation catalyst at a temperature at or greater than about 20° C. such that hydrogen saturates at least one double bond in the olefin, thereby producing the hydrogenated composition.
2. The hydrogenated composition of claim 1 , wherein the method further comprises adding a phenolic antioxidant to the crude olefin composition.
3. The hydrogenated composition of claim 1 , wherein the purification step comprises removing or reducing monoglycerides, diglycerides, ergosterol, squalene, or any combination thereof from the crude olefin composition.
4. The hydrogenated composition of claim 1 , wherein the phenolic antioxidant is selected from the group consisting of 3-tert-butyl-4-hydroxyanisole; 2-tert-butyl-4-hydroxyanisole; 2,4,-dimethyl-6-tert-butylphenol; and 2,6-di-tert-butyl-4-methylphenol.
5. The hydrogenated composition of claim 1 , wherein the phenolic antioxidant is a catechol.
6. The hydrogenated composition of claim 1 , wherein the phenolic antioxidant is 4-tert-butyl catechol.
7. The hydrogenated composition of claim 1 , wherein the phenolic antioxidant is present in at least about 0.001% by weight of the stabilized purified microbial-derived olefin composition.
8. The hydrogenated composition of claim 1 , wherein the phenolic antioxidant is present in at least about 0.005% by weight of the stabilized purified microbial-derived olefin composition.
9. The hydrogenated composition of claim 1 , wherein the phenolic antioxidant is present in at least about 0.01% by weight of the stabilized purified microbial-derived olefin composition.
10. The hydrogenated composition of claim 1 , wherein the hydrogenation reaction occurs at a temperature that is greater than about 100° C.
11. The hydrogenated composition of claim 1 , wherein the hydrogenated composition comprises a partially hydrogenated immiscible olefin.
12. The hydrogenated composition of claim 1 , wherein the microbial-derived olefin is a C 5 -C 20 isoprenoid.
13. The hydrogenated composition of claim 1 , wherein the microbial-derived olefin is a C 10 -C 15 isoprenoid.
14. The hydrogenated composition of claim 1 , wherein the stabilized purified microbial-derived olefin comprises farnesene in at least about 50%, 60%, 70%, 80%, 90%, 93%, 95%, 97%, 99% or greater by weight of the immiscible olefin.
15. The hydrogenated composition of claim 14 , wherein the hydrogenation reaction comprises selective hydrogenation of farnesene to reduce one, two, three, or four double bonds in farnesene.
16. The hydrogenated composition of claim 15 , wherein farnesene is selectively hydrogenated to reduce one double bond.
17. The hydrogenated composition of claim 15 , further comprising bisabolane in an amount that is equal to or greater than 0.1% by weight of the hydrogenated composition.
18. A hydrogenated composition derived from a microbial-derived olefin composition, the hydrogenated composition produced by a method comprising:
reacting a stabilized purified microbial-derived olefin composition with hydrogen in the presence of a hydrogenation catalyst, wherein the stabilized purified microbial-derived olefin composition comprises:
(a) farnesene in an amount that is at least equal to or greater than about 90% by weight of the stabilized purified microbial-derived olefin composition;
(b) bisabolene in an amount that is equal to or greater than about 0.1% by weight of the stabilized purified microbial-derived olefin composition;
(c) zingibrene in an amount that is equal to or greater than about 0.1% by weight of the stabilized purified microbial-derived olefin composition; and
(d) a phenolic antioxidant, wherein the phenolic antioxidant is a phenol derivative containing an unfused phenyl ring with one or more hydroxyl substituents in an amount that is at least about 0.005% by weight of the stabilized purified microbial-derived olefin composition,
wherein the hydrogenation reaction saturates at least one double bond in farnesene.
19. The hydrogenated composition of claim 18 , wherein the hydrogenated composition further comprises at least about 0.1% bisabolane by the weight of the hydrogenated composition.
20. The hydrogenated composition of claim 18 , wherein the hydrogenated composition comprises a partially hydrogenated farnesene.