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US 9,040,268 B2Granted
Method for controlling undesirable byproducts formation caused by contaminating organisms in the production of ethanol from syngas
AssigneeCoskata, Inc.
InventorsRathin Datta, Andrew Reeves, Laura T. Kliman
Life of this patent
Estimating the term…
Abstract
A method of operating a fermentation zone for the production of ethanol from syngas uses a crotonate-like compound to prevent or reverse the effects of butyrogen contamination. The crotonate-like compound works in continuous fermentation processes to reduce or eliminate contamination from butyrate and butanol in the syngas derived ethanol product.
Claims19
A process for the metabolic conversion of substrate to light oxygenates comprising:
- a. contacting in a fermentation liquid containing said substrate with microorganisms capable of bioconverting the substrate to light oxygenates under fermentation conditions, said fermentation liquid being susceptible to a presence of contaminating bacteria capable of producing at least one of butyrate or butanol from said substrate or from said light oxygenates through a butyryl CoA enzyme;
- and
- b. providing in said fermentation liquid a sufficient amount of a crotonate-like compound to restrict the production of said at least one of butyrate or butanol by a butyryl-CoA dehydrogenase, wherein the crotonate-like compound is represented by the structural formula:
- R2(R3)C═C(H)C(O)R1 I.
- or
- R2-A-C(O)R1 II.
- wherein:
- R1 is —OH, —OR5, or —N(R4)2, wherein R5 is hydrocarbyl and each R4 may be the same or different and is hydrogen or hydrocarbyl;
- R2 is hydrogen, —NH2, —OH or —CX3 wherein each X may be the same or different and is hydrogen or halogen;
- R3 is hydrocarbyl of 1 to 18 carbons which may be unsubstituted or substituted with —OH, alkoxyl of 1 to about 6 carbons, or halogen;
- A is an aromatic moiety having 5 or 6 ring atoms which may be all carbon atoms or may be heterocyclic with one hetero atom selected from the group consisting of oxygen and nitrogen which aromatic moiety has —R2 at the 2 position wherein —R2 is as defined above and which aromatic moiety may be unsubstituted or substituted at one or more of the higher carbon positions with (i) hydrocarbyl of 1 to 18 carbons which may be substituted with —OH, alkoxyl of 1 to about 6 carbons, or halogen, (ii) —OR6 wherein R6 is lower alkyl, (iii) —N(R7)2 wherein each R7 is the same or different and is hydrogen or hydrocarbyl or (iv) halogen;
- with the proviso that in structural formula I, at least one of R2 and R3 is or is substituted with haloalkyl and that in formula II at least the 2 or 3 carbon position of the aryl moiety is substituted with an electron withdrawing group selected from the group consisting of halogen and haloalkyl.
9 more elements
A method of restricting the production of butyrate and/or butanol in an anaerobic fermentation of a gas substrate comprising at least one of CO and a mixture of CO2 with hydrogen, the method comprising:
- a. passing the gas stream to an anaerobic fermentation zone containing at least one species of anaerobic microorganism capable of producing an liquid product comprising light oxygenates;
- b. converting at least a portion of the gas stream to the liquid product by contact of the microorganism in the fermentation zone with the gas stream;
- c. providing at least one crotonate-like compound in the fermentation liquid in an amount effective to restrict production of butyrate and/or butanol by butyryl-CoA dehydrogenase, said crotonate-like compound represented by the structural formula
- R2(R3)C═C(H)C(O)R1 I.
- or
- R2-A-C(O)R1 II.
- wherein:
- R1 is —OH, —OR5, or —N(R4)2, wherein R5 is hydrocarbyl and each R4 may be the same or different and is hydrogen or hydrocarbyl;
- R2 is hydrogen, —NH2, —OH or —CX3 wherein each X may be the same or different and is hydrogen or halogen;
- R3 is hydrocarbyl of 1 to 18 carbons which may be unsubstituted or substituted with —OH, alkoxyl of 1 to about 6 carbons, or halogen;
- A is an aromatic moiety having 5 or 6 ring atoms which may be all carbon atoms or may be heterocyclic with one hetero atom selected from the group consisting of oxygen and nitrogen which aromatic moiety has —R2 at the 2 position wherein —R2 is as defined above and which may be unsubstituted or substituted at one or more of the higher carbon positions with (i) hydrocarbyl of 1 to 18 carbons which may be substituted with —OH, alkoxyl of 1 to about 6 carbons, or halogen, (ii) —OR6 wherein R6 is lower alkyl, (iii) —N(R7)2 wherein each R7 is the same or different and is hydrogen or hydrocarbyl or (iv) halogen;
- with the proviso that in structural formula I, at least one of R2 and R3 is or is substituted with haloalkyl and that in formula II at least the 2 or 3 carbon position of the aryl moiety is substituted with an electron withdrawing group selected from the group consisting of halogen and haloalkyl;
- d. withdrawing fermentation liquid containing the liquid product from the fermentation zone;
- and
- e. recovering the liquid product from the fermentation liquid.
12 more elements
A method of producing a product comprising a C2 oxygenate by the fermentation of a gas substrate comprising at least one of CO and a mixture of CO2 with hydrogen using a homoacetogenic microorganism to convert the gas stream to the product, the method comprising:
- a. passing the gas substrate stream to a fermentation zone containing an anaerobic microorganism and a fermentation liquid;
- b. converting the gas substrate stream to the product by contact of the anaerobic microorganism in the fermentation zone with the gas substrate stream;
- c. providing at least one crotonate-like compound to the fermentation liquid in an amount sufficient to inhibit a production of butyrate and/or butanol by butyryl-CoA dehydrogenase by at least one species of microorganism in the fermentation zone, said crotonate-like compound represented by the structural formula
- R2(R3)C═C(H)C(O)R1 I.
- or
- R2-A-C(O)R1 II.
- wherein:
- R1 is —OH, —OR5, or —N(R4)2, wherein R5 is hydrocarbyl and each R4 may be the same or different and is hydrogen or hydrocarbyl;
- R2 is hydrogen, —NH2, —OH or —CX3 wherein each X may be the same or different and is hydrogen or halogen;
- R3 is hydrocarbyl of 1 to 18 carbons which may be unsubstituted or substituted with —OH, alkoxyl of 1 to about 6 carbons, or halogen;
- A is an aromatic moiety having 5 or 6 ring atoms which may be all carbon atoms or may be heterocyclic with one hetero atom selected from the group consisting of oxygen and nitrogen which aromatic moiety has —R2 at the 2 position wherein —R2 is as defined above and which aromatic moiety may be unsubstituted or substituted at one or more of the higher carbon positions with (i) hydrocarbyl of 1 to 18 carbons which may be substituted with —OH, alkoxyl of 1 to about 6 carbons, or halogen, (ii) —OR6 wherein R6 is lower alkyl, (iii) —N(R7)2 wherein each R7 is the same or different and is hydrogen or hydrocarbyl or (iv) halogen;
- with the proviso that in structural formula I, at least one of R2 and R3 is or is substituted with haloalkyl and that in formula II at least the 2 or 3 carbon position of the aryl moiety is substituted with an electron withdrawing group selected from the group consisting of halogen and haloalkyl;
- d. withdrawing the product containing fermentation liquid from the fermentation zone;
- and
- e. recovering the product from the fermentation liquid.
12 more elements
Dependencies are inferred from the claim text.