IP Library › Granted Patent US 12,187,674
Granted Patent B2
US 12,187,674 · App. 18/371,412 · Granted Jan 7, 2025

Olefins and methods for making the same

Inventors: Nicholas Ohler (Emeryville, CA); Karl Fisher (Emeryville, CA); Jin Ki Hong (Emeryville, CA)
Assignee: AMYRIS, INC.
C07C5/05C07C5/03C10L1/04C10M105/02C10M105/04C10M107/14C07C2521/04C07C2523/44C07C2523/75C10M2203/003C10M2203/0206C10M2203/022C10M2203/024C10M2205/083Y02P20/582
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,187,674
App. No.
18/371,412
Granted
Jan 7, 2025
Kind
B2
Abstract

Provided herein are olefinic feedstocks derived from conjugated hydrocarbon terpenes (e.g., C 10 -C 30 terpenes), methods for making the same, and methods for their use.

Claims (16)

1. A method comprising selectively hydrogenating, in two or more stages, a conjugated terpene comprising at least three olefinic bonds wherein two of the at least three olefinic bonds form a conjugated diene to make a composition comprising at least about 50% mono-olefinic species and about 20% or less di-olefinic species in a mixture of hydrogenated reaction products,

wherein the hydrogenating comprises catalytic hydrogenation with a catalyst, a catalyst loading, a reaction temperature, and hydrogen pressure,

wherein the catalyst, the catalyst loading, the reaction temperature, and the hydrogen pressure are selected so that less than about 10% of the molecules in an intermediate product have a conjugated diene moiety after the first hydrogenation stage.

2. The method of claim 1 , wherein the temperature of the second stage is greater than the temperature of the first stage.

3. The method of claim 1 , wherein the hydrogen pressure of the second stage is less than or equal to the hydrogen pressure of the first stage.

4. The method of claim 1 , wherein one or more stage of the selective hydrogenation occurs in the presence of a catalyst.

5. The method of claim 1 , capable of making a composition comprising at least about 50% mono-olefinic species and about 15% or less di-olefinic species.

6. The method of claim 1 , capable of making a composition comprising at least about 55% mono-olefinic species and at most about 10% di-olefinic species, at least about 60% mono-olefinic species and at most about 10% di-olefinic species, or at least about 65% mono-olefinic species and at most about 10% di-olefinic species.

7. The method of claim 1 , capable of making a composition comprising at most about 5% di-olefinic species.

8. A method comprising selectively hydrogenating, in two or more stages, a conjugated terpene comprising at least three olefinic bonds wherein two of the at least three olefinic bonds form a conjugated diene to make a composition comprising greater than 60% mono-olefinic species in a mixture of hydrogenated reaction products,

wherein the hydrogenating comprises catalytic hydrogenation with a catalyst, a catalyst loading, and a reaction temperature or hydrogen pressure,

wherein the catalyst, the catalyst loading, the reaction temperature, and the hydrogen pressure are selected so that less than about 10% of the molecules in an intermediate product have a conjugated diene moiety after the first hydrogenation stage.

9. The method of claim 8 , wherein the temperature of the second stage is greater than the temperature of the first stage.

10. The method of claim 8 , wherein the hydrogen pressure of the second stage is less than or equal to the hydrogen pressure of the first stage.

11. The method of claim 8 , wherein one or more stage of the selective hydrogenation occurs in the presence of a catalyst.

12. The method of claim 9 , capable of making a composition comprising at least about 65% mono-olefinic species, at least about 70% mono-olefinic species, or at least about 75% mono-olefinic species.

Assignments (3)
SECURITY INTEREST Recorded Apr 15, 2025
From: AMYRIS, INC.
To: EUAGORE, LLC
Reel/Frame 070848/0512 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2024
From: OHLER, NICHOLAS; FISHER, KARL; HONG, JIN KI
To: AMYRIS, INC.
Reel/Frame 068145/0431 →
SECURITY INTEREST Recorded May 24, 2024
From: AMYRIS, INC.
To: EUAGORE, LLC
Reel/Frame 067528/0467 →
Continuity (10)
Continuation 17518540 · Nov 3, 2021
Division 16389690 · Apr 19, 2019
Division 14112235
Provisional Application 61524143 · Aug 16, 2011
Provisional Application 61502252 · Jun 28, 2011
Provisional Application 61493316 · Jun 3, 2011
Provisional Application 61482122 · May 3, 2011
Provisional Application 61475221 · Apr 13, 2011
Provisional Application 61475217 · Apr 13, 2011
Related Publication 20240043356A1 · Feb 8, 2024
References Cited (57)
US 2417220A · Smith et al. · 1947 [cited by applicant]
US 2674634A · Greensfelder · 1954 [cited by applicant]
US 3702348A · Nehring et al. · 1972 [cited by applicant]
US 3987121A · Koppel et al. · 1976 [cited by applicant]
US 4310714A · Pavlin · 1982 [cited by applicant]
US 4546110A · Dawson et al. · 1985 [cited by applicant]
US 4590319A · Imaki et al. · 1986 [cited by applicant]
US 5118837A · Chalk et al. · 1992 [cited by applicant]
US 5151172A · Kukes et al. · 1992 [cited by applicant]
US 5208405A · Cheung et al. · 1993 [cited by applicant]
US 5378767A · Massie · 1995 [cited by applicant]
US 5475173A · Cheung et al. · 1995 [cited by applicant]
US 5723709A · Phillips, Jr. et al. · 1998 [cited by applicant]
US 6403844B1 · Zhang et al. · 2002 [cited by applicant]
US 7399323B2 · Renninger et al. · 2008 [cited by applicant]
US 7592295B1 · Fisher et al. · 2009 [cited by applicant]
US 7659097B2 · Renninger et al. · 2010 [cited by applicant]
US 8257957B2 · Keasling et al. · 2012 [cited by applicant]
US 8519204B2 · Ohler et al. · 2013 [cited by applicant]
US 20020091214A1 · Waanders et al. · 2002 [cited by applicant]
US 20080274523A1 · Renninger et al. · 2008 [cited by applicant]
US 20090137014A1 · Tsuruta et al. · 2009 [cited by applicant]
US 20100267971A1 · Ohler et al. · 2010 [cited by applicant]
US 20110287988A1 · Fisher et al. · 2011 [cited by applicant]
US 20130123379A1 · Mcphee · 2013 [cited by applicant]
US 20130252295A1 · Renninger et al. · 2013 [cited by applicant]
GB 693407A · 1953 [cited by applicant]
WO WO2007139924 · 2007 [cited by applicant]
WO WO2010027464 · 2010 [cited by applicant]
WO WO2010042208 · 2010 [cited by applicant]
WO WO2010115097 · 2010 [cited by applicant]
WO WO2012141784 · 2012 [cited by applicant]
WO WO2013028307 · 2013 [cited by applicant]
U.S. Appl. No. 61/475,217, filed Apr. 13, 2011, Ohler et al. [cited by applicant]
U.S. Appl. No. 61/475,221, filed Apr. 13, 2011, Tirmizi et al. [cited by applicant]
U.S. Appl. No. 61/482,122, filed May 3, 2011, Ohler. [cited by applicant]
U.S. Appl. No. 61/493,316, filed Jun. 3, 2011, Ohler et al. [cited by applicant]
U.S. Appl. No. 61/502,252, filed Jun. 28, 2011, Fisher et al. [cited by applicant]
U.S. Appl. No. 61/524,143, filed Aug. 16, 2011, Fisher et al. [cited by applicant]
International Search Report for PCT/US2012/024922, mailed Jul. 12, 2012, 3 pages. [cited by applicant]
Examination report dated Feb. 13, 2018 for the EP Application No. 12708189.1; 7 pages. [cited by applicant]
“CRC Handbook of Chemistry and Physics”, 95th Edition, Internet version (http://www.hbcpnetbase.com/); Haynes, W.D., ed.; 2015: Ch.3, pp. 216 and 217. [cited by applicant]
Anet E.F.L.J., “Synthesis of (E,Z)-a-, and (Z)-β-farnesene”, Aust. J. Chem. 23(10), 1970, pp. 2101-2108. [cited by applicant]
Braun et al., “Hexahydro-farnesal and Nor hexahydro-farnesal”, Beriche Der Deutsche Chemische Gesellschaft, Jan. 1, 1929, vol. 62, No. 6, pp. 1489-1491, with English translation. [cited by applicant]
Dieguez et al., “Weakening C—O Bonds: Ti(111), a New Regent for Alcohol Deoxygenation and Carbonyl Coupling Olefination,” J. Am. Chem. Soc., vol. 132, pp. 254-259 (2010). [cited by applicant]
Frolov et al., “Highly active supported palladium catalysts for selective hydrogenation of conjugated dienes into olefins,” Reaction Kinetics and Catalysis Letters, vol. 25, Nos. 3-4, pp. 319-322 (1984) book 4 pgs attac… [cited by applicant]
Hernandez-Torres et al., “Stereocontrolled generation of the (2R) chroman core of vitamin E: total synthesis of (2R, 40RS,8′RS)-alpha-tocopherol”, Organic Letters, vol. 11, No. 21, 2009, pp. 4930-4933. [cited by applicant]
Belt et al., “A novel chemical fossil of palaeo sea ice: IP25”, Organic Geochemistry, vol. 38, issue 1, Jan. 2007, pp. 16-27. [cited by applicant]
Jong Tae Lee et al, “Regioselective hydrogenation of conjugated dienes catalyzed by hydridopentacyanocobaltate anion using β-cyclodextrin as the phase transfer agent and lanthanide halides as promoters,” J. Org. Chem. 5… [cited by applicant]
Kim, “Biosynthetic Studies of 4,8-Dimethyldecanal, the Aggregation Pheromone of the Red Flour Beetle, Tribolium castaneum”, Thesis (Ph. D. in Agricultural Science)—University of Tsukuba, (A), No. 3755, Mar. 25, 2005. [cited by applicant]
Lukasik et al., “The influence of hydrogen pressure on the heterogeneous hydrogenation of S-nnyrcene in a CO2-expanded liquid”, The Journal of Supercritical Fluids, ScienceDirect, 2010, pp. 46-52. [cited by applicant]
Moore et al., “Selective Hydrogenation of Polyolefins with Metal Sulfide Catalysts in the Liquid Phase”, Journal of the American Chemical Society, 1952, 74(2), p. 373-375. [cited by applicant]
Sharma, S. et al. “Radical co-polymerization of limonene with N-vinyl pyrrolidone: synthesis and characterization”, Designed Monomers and Polymers, Jan. 1, 2006, vol. 9, N° 5, pp. 503-516. [cited by applicant]
Smith, “Vitamin E. XLII. Long Chain Aliphatic Compounds with Recurring “Isoprene” Units”, J. Am. Chem. Soc. 65, 1943, pp. 745-750. [cited by applicant]
Speziali et al., “Selective hydrogenation of myrcene catalyzed by complexes of ruthenium, chromium, iridium and rhodium”, Journal Of Molecular Catalysis A: Chemical, Elsevier, Amsterdam, NL, Sep. 14, 2005, vol. 239, No.… [cited by applicant]
Tungler et al., “Reduction of Dienes and Polyenes,” in The Chemistry of Dienes and Polyenes, vol. 2 (ed. Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK, (2003). [cited by applicant]
Xu et al., “Occurrence of C25 highly branched isoprenoids (HBIs) in Florida Bay: Paleoenvironmental indicators of diatom-derived organic matter inputs”, Organic Geochemistry, vol. 37, Issue 7, Jul. 2006, pp. 847-859. [cited by applicant]