IP Library Granted Patent US 10,787,688
Granted Patent B2
US 10,787,688 · App. 14/400,379 · Granted Sep 29, 2020

Multi-stage synthesis method with synthesis gas

Inventors: Thomas Haas (Muenster, DE); Eva Maria Wittmann (Traunreut, DE)
Assignee: Evonik Operations GmbH
C12P7/6409C12P7/02C12P7/065C12P7/24C12P7/40C12P7/42C12P7/46C12P7/54C12P7/62C12P7/6436Y02E50/17
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Quick Facts
Patent No.
US 10,787,688
App. No.
14/400,379
Granted
Sep 29, 2020
Kind
B2
Abstract

The invention provides a process for the preparation of hydrocarbons substituted with at least one group containing at least one oxygen atom, comprising the process steps A) reaction of a carbon source comprising at least one selected from CO 2 and CO to give acetate and/or ethanol with a first microorganism, B) separating off of the acetate from the first microorganism, C) reaction of the acetate to give a hydrocarbon substituted with at least one group containing at least one oxygen atom with a second microorganism and optionally D) purification of the hydrocarbon substituted with at least one group containing at least one oxygen atom.

Claims (31)

1. A process for preparing a hydrocarbon substituted with a group comprising an oxygen atom, the process comprising:

A) reacting a carbon source consisting of at least one of CO 2 and CO with a first microorganism such that at least one of acetate and ethanol is produced from the at least one of CO 2 and CO, where the first microorganism is an acetogenic microorganism;

B) separating the at least one of acetate and ethanol from the first microorganism;

C) reacting the at least one of acetate and ethanol separated in B) with a second microorganism such that the hydrocarbon substituted with a group comprising an oxygen atom is produced from the at least one of acetate and ethanol; and optionally

D) purifying the hydrocarbon substituted with a group comprising an oxygen atom,

wherein a sugar is not used in the reacting in C), and

the hydrocarbon substituted with a group comprising an oxygen atom produced in C) is selected from the group consisting of a carboxylic acid having 8 to 32 carbon atoms, a dicarboxylic acid, a hydroxycarboxylic acid, a carboxylic acid ester, a hydroxycarboxylic acid ester, an alcohol having 8 to 32 carbon atoms, an aldehyde, and a ketone.

2. The process according to claim 1 , wherein the first microorganism is at least one selected from the group consisting of Clostridium autothenogenum DSMZ 19630, Clostridium ragsdahlei ATCC no. BAA-622, Clostridium autoethanogenum, Moorella sp HUC22-1, Moorella thermoaceticum, Moorella thermoautotrophica, Rumicoccus productus, Acetoanaerobum, Oxobacter pfennigii, Methanosarcina barkeri, Methanosarcina acetivorans, Carboxydothermus, Desulphotomaculum kutznetsovii, Pyrococcus, Peptostreptococcus, Butyribacterium methylotrophicum ATCC 33266, Clostridium formicoaceticum, Clostridium butyricum, Laktobacillus delbrukii, Propionibacterium acidoprprionici, Proprionispera arboris, Anaerobierspirillum succiniproducens, Bacterioides amylophilus, Becterioides ruminicola, Thermoanaerobacter kivui, Acetobacterium woodii, Acetoanaerobium notera, Clostridium aceticum, Butyribacterium methylotrophicum, Moorella thermoacetica, Eubacterium limosum, Peptostreptococcus productus, Clostridium ljungdahlii, Clostridium ATCC 29797 and Clostridium carboxidivorans.

3. The process according to claim 1 , wherein the separating in B) comprises removing the first microorganism from a medium comprising the at least one of acetate and ethanol by sedimentation, centrifugation or filtration.

4. The process according to claim 1 , wherein the separating in B) comprises removing the acetate by extraction, with an extractant.

5. The process according to claim 4 , wherein the extractant comprises at least one alkylamine selected from the group consisting of trihexylamine, trioctylamine, tridecylamine, tricaprylamine and tridodecylamine.

6. The process according to claim 1 , wherein the hydrocarbon substituted with a group comprising an oxygen atom produced in C) comprises a fatty acid, and the second microorganism has an increased activity of a thioesterase compared to its wild type.

7. The process according to claim 1 , wherein the hydrocarbon substituted with a group comprising an oxygen atom produced in C) comprises a hydroxycarboxylic acid.

8. The process according to claim 1 , wherein the reacting in C) yields carbon dioxide, which is returned to the reacting in A) as the carbon source.

9. The process according to claim 1 , wherein the hydrocarbon substituted with a group comprising an oxygen atom produced in C) comprises an omega-hydroxycarboxylic acid, a hydroxyisobutyric acid, or both.

10. The process according to claim 1 , wherein the hydrocarbon substituted with a group comprising an oxygen atom produced in C) has 8 to 12 carbon atoms and is selected from the group consisting of a carboxylic acid, a dicarboxylic acid, a hydroxycarboxylic acid, a carboxylic acid ester, a hydroxycarboxylic acid ester, an alcohol, an aldehyde, and a ketone.

11. The process according to claim 1 , wherein the hydrocarbon substituted with a group comprising an oxygen atom produced in C) has 8 to 12 carbon atoms and is selected from the group consisting of a carboxylic acid, a hydroxycarboxylic acid, and a carboxylic acid ester.

12. The process according to claim 1 , wherein the at least one of acetate and ethanol comprises acetate.

13. The process according to claim 1 , wherein the at least one of acetate and ethanol comprises acetate and ethanol.

14. The process according to claim 1 , wherein, in the reacting in C), a carbon source reacted with the second microorganism consists of the at least one of acetate and ethanol.

15. The process according to claim 1 , wherein the carbon source in A) comprises at least 90% by weight of CO 2 .

16. The process according to claim 1 , wherein the hydrocarbon substituted with a group comprising an oxygen atom produced in C) has 8 to 32 carbon atoms and is selected from the group consisting of a carboxylic acid, a dicarboxylic acid, a hydroxycarboxylic acid, a carboxylic acid ester, a hydroxycarboxylic acid ester, an alcohol, an aldehyde, and a ketone.

17. The process according to claim 1 , wherein the second microorganism is yeast or a bacterium.

18. The process according to claim 1 , wherein the hydrocarbon substituted with a group comprising an oxygen atom produced in C) is octanoic acid, decanoic acid, or both.

19. The process according to claim 6 , wherein the thioesterase is encoded by a fatB2 gene from Cuphea hookeriana.

20. A process for preparing octanoic acid, decanoic acid, or both, the process comprising:

A) reacting a carbon source consisting of at least one of CO 2 and CO with a first microorganism such that at least one of acetate and ethanol is produced from the at least one of CO 2 and CO;

B) separating the at least one of acetate and ethanol from the first microorganism;

C) reacting the at least one of acetate and ethanol separated in B) with a second microorganism such that octanoic acid, decanoic acid, or both is produced from the at least one of acetate and ethanol; and optionally

D) purifying the octanoic acid, decanoic acid, or both produced in C),

wherein a sugar is not used in the reacting in C).

Assignments (3)
CHANGE OF NAME Recorded Jan 31, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051765/0166 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 1, 2015
From: EVONIK INDUSTRIES AG
To: EVONIK DEGUSSA GMBH
Reel/Frame 037174/0982 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 11, 2014
From: HAAS, THOMAS; WITTMANN, EVA MARIA
To: EVONIK INDUSTRIES AG
Reel/Frame 034143/0852 →
Priority Claims (1)
DE 10 2012 207 921 · May 11, 2012 · national
Continuity (1)
Related Publication 20150125912A1 · May 7, 2015