Stabilization methods for microbial-derived olefins
View Patent ↗Processes and systems for stabilization and subsequent hydrogenation of an immiscible olefin are described. Methods of stabilizing a microbial-derived olefin composition are also described.
1. A method of stabilizing a microbial-derived olefin composition 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; and
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.
2. The method of claim 1 that further comprises adding a phenolic antioxidant to the crude olefin composition.
3. The method of claim 1 , wherein the purification step is selected from fractional distillation, flash distillation, adsorption, liquid chromatography, solvent extraction and a combination thereof.
4. The method of claim 1 , wherein the purification step comprises removing or reducing monoglycerides, diglycerides, and triglycerides in the crude olefin composition.
5. The method of claim 1 , wherein the purification step comprises removing or reducing ergosterol or squalene in the crude olefin composition.
6. The method of claim 1 , wherein the immiscible olefin is farnesene and it is present in at least about 50%, 60%, 70%, 80%, 90% 93%, 95%, 97%, 99% or greater by weight of the immiscible olefin.
7. The method of claim 6 , wherein the immiscible olefin further comprises zingiberene, bisabolene, 10,11-dihydro-10,11-epoxyfarnesene, farnesene dimers, farnisol or a combination thereof.
8. The method of claim 1 , wherein the phenolic antioxidant is a polyphenol.
9. The method of claim 1 , wherein the phenolic antioxidant is a monophenol.
10. The method of claim 1 , wherein the phenolic antioxidant is selected from 3-tert-butyl-4-hydroxyanisole; 2-tert-butyl-4-hydroxyanisole; 2,4-dimethyl-6-tert-butylphenol; and 2,6-di-tert-butyl-4-methylphenol.
11. The method of claim 1 , wherein the phenolic antioxidant is a catechol.
12. The method of claim 11 , wherein the phenolic antioxidant is 4-tert-butylcatechol.
13. The method of claim 1 , wherein the phenolic antioxidant is present in at least about 0.0001% by weight of the stabilized microbial-derived olefin composition.
14. The method of claim 1 , wherein the phenolic antioxidant is present in at least about 0.001% by weight of the stabilized microbial-derived olefin composition.
15. The method of claim 2 , wherein the amount of phenolic antioxidant is at least about 0.005% by weight of the resulting crude olefin composition.
16. The method of claim 1 further comprising reacting the immiscible olefin with hydrogen in the presence of a hydrogenation catalyst such that hydrogen saturates at least one double bond in the olefin.
17. The method of claim 16 , wherein the hydrogenation reaction occurs at a temperature that is greater than room temperature.
18. The method of claim 16 , wherein the hydrogenation reaction occurs at a temperature that is greater than about 100° C.
19. A stabilized microbial-derived olefin composition prepared by the method of claim 1 , wherein the stabilized microbial-derived olefin composition comprises:
a) an immiscible olefin in an amount at least about 93% by weight of the composition; and
b) 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 at least about 0.0001% by weight of the composition.
20. The stabilized microbial-derived olefin composition of claim 19 , wherein the phenolic antioxidant is at least about 0.001% by weight of the composition.
21. The stabilized microbial-derived olefin composition of claim 19 , wherein the phenolic antioxidant is at least about 0.005% by weight of the composition.
22. The stabilized microbial-derived olefin composition of claim 19 , wherein immiscible olefin comprises farnesene.
23. The stabilized microbial-derived olefin composition of claim 22 , wherein the farnesene is at least about 50%, 60%, 70%, 80%, 90% 93%, 95%, 97%, 99% or greater by weight of the composition.
24. The stabilized microbial-derived olefin composition of claim 19 , wherein the immiscible olefin comprises an impurity selected from zingiberene, bisabolene, 10,11-dihydro-10,11-epoxyfarnesene, farnesene dimers, farnisol and a combination thereof.
25. The stabilized microbial-derived olefin composition of claim 24 , wherein the impurity is present in an amount of at least about 0.05% by weight of the composition.
26. The stabilized microbial-derived olefin composition of claim 19 , wherein the phenolic antioxidant is selected from: resveratrol; 3-tert-butyl-4-hydroxyanisole; 2-tert-butyl-4-hydroxyanisole; 2,4-dimethyl-6-tert-butylphenol; 2,6-di-tert-butyl-4-methylphenol; and 4-tert-butylcatechol.
27. The stabilized microbial-derived olefin composition of claim 19 , wherein the amount of phenolic antioxidant is at least about 0.005% by weight of the composition.
28. The method of claim 16 , wherein the hydrogenation reaction occurs at a temperature that is greater than about 100° C.
29. The method of claim 16 , wherein the immiscible olefin is part of the crude olefin composition.
30. The method of claim 16 , wherein the immiscible olefin is part of the purified olefin composition.
31. The method of claim 16 , wherein the immiscible olefin is part of the stabilized purified olefin composition.
32. The method of claim 16 , wherein the immiscible olefin comprises farnesene.
33. The method of claim 16 , wherein the immiscible olefin further comprises a phenolic antioxidant.
34. The method of claim 33 , wherein the phenolic antioxidant is selected from: resveratrol; 3-tert-butyl-4-hydroxyanisole; 2-tert-butyl-4-hydroxyanisole; 2,4-dimethyl-6-tert-butylphenol; and 2,6-di-tert-butyl-4-methylphenol and 4-tert-butylcatechol.
35. A purified farnesene composition prepared by the method of claim 6 , wherein the purified farnesene composition comprises:
a) a microbial-derived mixture comprising farnesene in an amount that is equal to or greater than about 93% by weight of the composition and the following compounds each of which is present in an amount that is equal to or greater than about 0.1% by weight: bisabolene, zingiberene, farnesol, and farnesene expoxide; and,
b) 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 0.001% by weight.
36. A purified farnesane composition prepared by the method of claim 6 , wherein the purified farnesene composition comprises farnesane in an amount that is equal to or greater than about 93% by weight of the composition and the following compounds each of which is present in an amount that is equal to or greater than about 0.1% by weight: bisabolane and tetradecane.