[특허]Synthesis of liquid fuels from biomass

Virent, Inc.

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내보내기 페이스북 공유 트위터 공유 카카오톡 공유

Synthesis of liquid fuels from biomass

특허상세정보
국가/구분	United States(US) Patent 등록
국제특허분류(IPC7판)	C07C-002/54 C07C-001/24
미국특허분류(USC)	585/331; 585/332; 585/638; 585/709; 585/721
출원번호	US-0548963 (2009-08-27)
등록번호	US-8350108 (2013-01-08)
발명자 / 주소	Cortright, Randy D. Blommel, Paul G. Werner, Michael J. Vanstraten, Matthew R.
출원인 / 주소	Virent, Inc.
대리인 / 주소	Quarles & Brady LLP
인용정보	피인용 횟수 : 10 인용 특허 : 111

초록

Processes and reactor systems are provided for the conversion of oxygenated hydrocarbons to paraffins useful as liquid fuels. The process involves the conversion of water soluble oxygenated hydrocarbons to oxygenates, such as alcohols, furans, ketones, aldehydes, carboxylic acids, diols, triols, and/or other polyols, followed by the subsequent conversion of the oxygenates to paraffins by dehydration and alkylation. The oxygenated hydrocarbons may originate from any source, but are preferably derived from biomass.

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1. A method of making C6+ paraffins comprising: catalytically reacting hydrogen, water and water soluble oxygenated hydrocarbons comprising C2+O2+ hydrocarbons in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce an oxygenate comprising C2+O1-3 hydrocarbons, wherein the C2+O2+ hydrocarbon comprises a member selected from the group consisting of a sugar alcohol, a sugar, a monosaccharide, a disaccharide, a polysaccharide, a cellulosic derivative, a lignocellulosic derivative, or a mixture of any two or more of the foregoing;catalytically reacting the C2+O1-3 hydrocarbons in the presence of a dehydration catalyst at a dehydration temperature and dehydration pressure to produce a reaction stream comprising C2+ olefins; andreacting the C2+ olefins with a stream of C4+ isoparaffins in the presence of an alkylation catalyst at an alkylation temperature and alkylation pressure to produce a product stream comprising C6+ paraffins. 2. The method of claim 1, wherein the C2+O2+ hydrocarbon comprises a member selected from the group consisting of a cellulose derivative, a lignin derivative, a hemicelluloses derivative, glucose, fructose, sucrose, maltose, lactose, mannose, xylose, arabitol, erythritol, glycerol, isomalt, lactitol, malitol, mannitol, sorbitol, xylitol, and a mixture of any two or more of the foregoing. 3. The method of claim 1, wherein the C2+O1-3 hydrocarbon comprises a member selected from the group consisting of an alcohol, ketone, aldehyde, furan, diol, triol, hydroxy carboxylic acid, carboxylic acid, and a mixture of any two or more of the foregoing. 4. The method of claim 1, wherein the C6+ paraffin comprises a member selected from the group consisting of branched C6-10 alkane, a branched C6 alkane, a branched C7 alkane, a branched C8 alkane, a branched C9 alkane, a branched C10 alkane, or a mixture of any two or more of the foregoing. 5. The method of claim 1, wherein the deoxygenation catalyst comprises a support and a member selected from the group consisting of Re, Cu, Fe, Ru, Ir, Co, Rh, Pt, Pd, Ni, W, Os, Mo, Ag, Au, an alloy of any two or more of the foregoing, or a combination of any two or more of the foregoing. 6. The method of claim 5, wherein the deoxygenation catalyst further comprises a member selected from the group consisting of Mn, Cr, Mo, W, V, Nb, Ta, Ti, Zr, Y, La, Sc, Zn, Cd, Ag, Au, Sn, Ge, P, Al, Ga, In, Tl, and a combination of any two or more of the foregoing. 7. The method of claim 5, wherein the support comprises a member selected from group consisting of a nitride, carbon, silica, alumina, zirconia, titania, vanadia, ceria, boron nitride, heteropolyacid, kieselguhr, hydroxyapatite, zinc oxide, chromia, and mixtures of any two or more of the foregoing. 8. The method of claim 7, wherein the support comprises a member selected from the group consisting of carbon nanotubes, carbon fullerenes, and zeolites. 9. The method of claim 1, wherein the dehydration catalyst comprises a member selected from the group consisting of an acidic alumina, aluminum phosphate, silica- alumina phosphate, amorphous silica-alumina, aluminosilicate, zirconia, sulfated zirconia, tungstated zirconia, tungsten carbide, molybdenum carbide, titania, sulfated carbon, phosphated carbon, phosphated silica, phosphated alumina, acidic resin, heteropolyacid, inorganic acid, and a combination of any two or more of the foregoing. 10. The method of claim 9, wherein the dehydration catalyst further comprises a modifier selected from the group consisting of Ce, Y, Sc, La, Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, P, B, Bi, and a combination of any two or more of the foregoing. 11. The method of claim 9, wherein the dehydration catalyst further comprises an oxide of an element, the element selected from the group consisting of Ti, Zr, V, Nb, Ta, Mo, Cr, W, Mn, Re, Al, Ga, In, Fe, Co, Ir, Ni, Si, Cu, Zn, Sn, Cd, P, and a combination of any two or more of the foregoing. 12. The method of claim 9, wherein the dehydration catalyst further comprises a metal selected from the group consisting of Cu, Ag, Au, Pt, Ni, Fe, Co, Ru, Zn, Cd, Ga, In, Rh, Pd, Ir, Re, Mn, Cr, Mo, W, Sn, Os, an alloy of any two or more of the foregoing, and a combination of any two or more of the foregoing. 13. The method of claim 9, wherein the dehydration catalyst comprises an aluminosilicate zeolite. 14. The method of claim 13, wherein the dehydration catalyst further comprises a modifier selected from the group consisting of Ga, In, Zn, Fe, Mo, Ag, Au, Ni, P, Sc, Y, Ta, a lanthanide, and a combination of any two or more of the foregoing. 15. The method of claim 13, wherein the dehydration catalyst further comprises a metal selected from the group consisting of Cu, Ag, Au, Pt, Ni, Fe, Co, Ru, Zn, Cd, Ga, In, Rh, Pd, Ir, Re, Mn, Cr, Mo, W, Sn, Os, an alloy of any two or more of the foregoing, and a combination of any two or more of the foregoing. 16. The method of claim 1, wherein the alkylation catalyst comprises a member selected from the group consisting of sulfuric acid, hydrofluoric acid, aluminum chloride, boron trifluoride, solid phosphoric acid, chlorided alumina, acidic alumina, aluminum phosphate, silica-alumina phosphate, amorphous silica-alumina, aluminosilicate, aluminosilicate zeolite, zirconia, sulfated zirconia, tungstated zirconia, tungsten carbide, molybdenum carbide, titania, sulfated carbon, phosphated carbon, phosphated silica, phosphated alumina, acidic resin, heteropolyacid, inorganic acid, a mixture of a mineral acid and a Friedel-Crafts metal halide, and a combination of any two or more of the foregoing. 17. The method of claim 16, wherein the alkylation catalyst further comprises a modifier selected from the group consisting of Ga, In, Zn, Fe, Mo, Ag, Au, Ni, P, Sc, Y, Ta, a lanthanide, and a combination of any two or more of the foregoing. 18. The method of claim 16, wherein the alkylation catalyst further comprises a metal selected from the group consisting of Cu, Ag, Au, Pt, Ni, Fe, Co, Ru, Zn, Cd, Ga, In, Rh, Pd, Ir, Re, Mn, Cr, Mo, W, Sn, Os, an alloy of any two or more of the foregoing, and a combination of any two or more of the foregoing. 19. The method of claim 1, wherein the dehydration catalyst and the alkylation catalyst are atomically identical. 20. The method of claim 1, wherein at least a portion of the hydrogen is an APR hydrogen produced by a method comprising catalytically reacting a first portion of the water and the water soluble oxygenated hydrocarbon in the presence of an APR catalyst at a reforming temperature and a reforming pressure to produce the APR hydrogen. 21. The method of claim 20, wherein the APR catalyst comprises a support and a member selected from the group consisting of Fe, Ru, Os, Ir, Co, Rh, Pt, Pd, Ni, an alloy of any two or more of the foregoing, and a combination of any two or more of the foregoing. 22. The method of claim 21, wherein the APR catalyst further comprises a member selected from the group consisting of Cu, B, Mn, Re, Cr, Mo, Bi, W, V, Nb, Ta, Ti, Zr, Y, La, Sc, Zn, Cd, Ag, Au, Sn, Ge, P, Al, Ga, In, Tl, an alloy of any two or more of the foregoing, and a combination of any two or more of the foregoing. 23. The method of claim 21, wherein the support comprises a member selected from group consisting of a nitride, carbon, silica, alumina, zirconia, titania, vanadia, ceria, boron nitride, heteropolyacid, kieselguhr, hydroxyapatite, zinc oxide, chromia, and mixtures of any two or more of the foregoing. 24. The method of claim 21, wherein the support comprises a member selected from the group consisting of carbon nanotubes, carbon fullerenes, and zeolites. 25. The method of claim 20, wherein one or more of the APR catalyst, deoxygenation catalyst, and dehydration catalyst are atomically identical. 26. The method of claim 20, wherein the APR catalyst and deoxygenation catalyst comprise Pt alloyed or admixed with a member selected from the group consisting of Ni, Ru, Cu, Fe, Rh, Re, alloys of any two or more of the foregoing, and a combination of any two or more of the foregoing. 27. The method of claim 20, wherein the APR catalyst and deoxygenation catalyst comprise Ru alloyed or admixed with a member selected from the group consisting of Ge, Bi, B, Ni, Sn, Cu, Fe, Rh, Pt, alloys of any two or more of the foregoing, and a combination of any two or more of the foregoing. 28. The method of claim 20, wherein the APR catalyst comprises Ni alloyed or admixed with a member selected from the group consisting of Sn, Ge, Bi, B, Cu, Re, Ru, Fe, alloys of any two or more of the foregoing, and a combination of any two or more of the foregoing. 29. The method of claim 1 further comprising the step of providing an aqueous solution comprising water and a polysaccharide, disaccharide, monosaccharide, sugar, furfural, carboxylic acid, ketone, furan, or a combination of any two or more of the foregoing, and catalytically reacting the polysaccharide, disaccharide, monosaccharide, sugar, furfural, carboxylic acid, ketone, furan, or combination, with hydrogen in the presence of a hydrogenation catalyst at a hydrogenation temperature and hydrogenation pressure to produce the water soluble oxygenated hydrocarbon. 30. The method of claim 29, wherein the hydrogenation catalyst comprises a support and a member selected from the group consisting of Fe, Ru, Os, Ir, Co, Rh, Pt, Pd, Ni, Re, Cu, alloys of any two or more of the foregoing, and a combination of any two or more of the foregoing. 31. The method of claim 30, wherein the hydrogenation catalyst further comprises a member selected from the group consisting of Ag, Au, Cr, Zn, Mn, Sn, Bi, Mo, W, B, P, alloys of any two or more of the foregoing, and a combination of any two or more of the foregoing. 32. The method of claim 1 further comprising the step of providing an aqueous solution comprising water and a polysaccharide, disaccharide, monosaccharide, polyhydric alcohol, sugar, sugar alcohol, or a combination of any two or more of the foregoing, and catalytically reacting the sugar, sugar alcohol, polysaccharide, disaccharide, monosaccharide, polyhydric alcohol, or combination, with hydrogen in the presence of a hydrogenolysis catalyst at a hydrogenolysis temperature and hydrogenolysis pressure to produce the water soluble oxygenated hydrocarbon. 33. The method of claim 32, wherein the hydrogenolysis catalyst comprises a member selected from the group consisting of phosphate, Cr, Mo, W, Re, Mn, Cu, Cd, Fe, Ru, Os, Ir, Co, Rh, Pt, Pd, Ni, alloys of any two or more of the foregoing, and a combination of any two or more of the foregoing. 34. The method of claim 33, wherein the hydrogenolysis catalyst further comprises a member selected from the group consisting of Au, Ag, Zn, Sn, Bi, B, Cr, Mn, O, alloys of any two or more of the foregoing, and a combination of any two or more of the foregoing. 35. The method of claim 33, wherein the hydrogenolysis catalyst further comprises an alkaline earth metal oxide. 36. The method of claim 1 wherein the step of catalytically reacting hydrogen, water and water soluble oxygenated hydrocarbons in the presence of a deoxygenation catalyst is performed in either a liquid phase, a vapor phase, or a combination of the foregoing. 37. The method of claim 1, wherein the C2+O2+ hydrocarbon further comprises a recycled C2+O2+ hydrocarbon. 38. A method of making a C6+ paraffins comprising: catalytically reacting hydrogen, water and water soluble oxygenated hydrocarbons comprising C2+O2+ hydrocarbons in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce an oxygenate comprising C2+O1-3 hydrocarbons and one or more C4+ normal paraffins, aromatics and/or naphthenes, wherein the C2+O2+ hydrocarbon comprises a member selected from the group consisting of a sugar alcohol, a sugar, a monosaccharide, a disaccharide, a polysaccharide, a cellulosic derivative, a lignocellulosic derivative, or a mixture of any two or more of the foregoing; collecting a portion of the C4+ normal paraffins, aromatics and/or naphthenes and catalytically reacting the C4+ normal paraffins, aromatics and/or naphthenes in the presence of an isomerization catalyst to produce a stream of C4+ isoparaffins;catalytically reacting the C2+O1-3 hydrocarbons in the presence of a dehydration catalyst at a dehydration temperature and dehydration pressure to produce a reaction stream comprising C2+ olefins; andcatalytically reacting the C2+ olefins with the C4+ isoparaffins in the presence of an alkylation catalyst at an alkylation temperature and alkylation pressure to produce a product stream comprising C6+ paraffins. 39. The method of claim 38, wherein at least a portion of the hydrogen is an APR hydrogen produced by a method comprising catalytically reacting a first portion of the water and the water soluble oxygenated hydrocarbon in the presence of an APR catalyst at a reforming temperature and a reforming pressure to produce the APR hydrogen. 40. The method of claim 38 further comprising the step of providing an aqueous solution comprising water and a polysaccharide, disaccharide, monosaccharide, sugar, furfural, carboxylic acid, ketone, furan, or a combination of any two or more of the foregoing, and catalytically reacting the polysaccharide, disaccharide, monosaccharide, sugar, furfural, carboxylic acid, ketone, furan, or combination of any two or more of the foregoing, with hydrogen in the presence of a second hydrogenation catalyst at a hydrogenation temperature and hydrogenation pressure to produce the water soluble oxygenated hydrocarbon. 41. The method of claim 38 further comprising the step of providing an aqueous solution comprising water and a polysaccharide, disaccharide, monosaccharide, polyhydric alcohol, sugar, sugar alcohol, or a combination of any two or more of the foregoing, and catalytically reacting the sugar, sugar alcohol, polysaccharide, disaccharide, monosaccharide, polyhydric alcohol, or combination of any two or more of the foregoing, with hydrogen in the presence of a hydrogenolysis catalyst at a hydrogenolysis temperature and hydrogenolysis pressure to produce the water soluble oxygenated hydrocarbon. 42. The method of claim 38, wherein the isomerization catalyst comprises a member selected from the group consisting of a zeolite, zirconia, sulfated zirconia, tungstated zirconia, alumina, silica-alumina, zinc aluminate, chlorided alumina, phosphoric acid, and combinations of any two or more of the foregoing. 43. The method of claim 42, wherein the isomerization catalyst is an acidic beta, mordenite, or a ZSM-5 zeolite. 44. The method of claim 42, wherein the isomerization catalyst further comprises a metal selected from the group consisting of Y, Pt, Ru, Pd, Ni, Rh, Ir, Fe, Co, Os, Zn, a lanthanide, or an alloy or combination of any two or more of the foregoing. 45. The method of claim 42, wherein the isomerization catalyst comprises a support, the support comprising alumina, sulfated oxide, clay, silica gel, aluminum phosphate, bentonite, kaolin, magnesium silicate, magnesium carbonate, magnesium oxide, aluminum oxide, activated alumina, bauxite, silica, silica-alumina, activated carbon, pumice, zirconia, titania, zirconium, titanium, kieselguhr, or zeolites. 46. The method of claim 45, wherein the isomerization catalyst comprises a support of a sulfated oxide or hydroxide of a Group IVB metal, at least one Group IIIA compound, and a Group VIII metal. 47. The method of claim 46, wherein the Group IVB metal comprises, zirconium, titanium, alloys of the foregoing, or mixtures of the foregoing, and the Group IIIA compound comprises gallium, indium, or mixtures of the foregoing. 48. The method of claim 46, wherein the Group VIII metal comprises Pd, Pt, Ru, Rh, Ir, Os, allows of any two or more of the foregoing, or mixtures of any two or more of the foregoing. 49. The method of claim 42, wherein the isomerization catalyst further includes Fe, Co, Ni, Re, Y, Eu, Tm, Ho, Er, Yb, Tb, or mixtures of any two or more of the foregoing. 50. The method of claim 38, wherein the C2+O2+ hydrocarbon comprises a member selected from the group consisting of a cellulose derivative, a lignin derivative, a hemicelluloses derivative, glucose, fructose, sucrose, maltose, lactose, mannose, xylose, arabitol, erythritol, glycerol, isomalt, lactitol, malitol, mannitol, sorbitol, xylitol, and a mixture of any two or more of the foregoing. 51. The method of claim 38, wherein the C2+O2+ hydrocarbon further comprises a recycled C2+O2+ hydrocarbon. 52. A method of making a C6+ paraffins comprising: catalytically reacting hydrogen, water and water soluble oxygenated hydrocarbons comprising C2+O2+ hydrocarbons in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce an oxygenate comprising C2+O1-3 hydrocarbons, wherein the C2+O2+ hydrocarbon comprises a member selected from the group consisting of a sugar alcohol, a sugar, a monosaccharide, a disaccharide, a polysaccharide, a cellulosic derivative, a lignocellulosic derivative, or a mixture of any two or more of the foregoing;catalytically reacting the C2+O1-3 hydrocarbons in the presence of a dehydration catalyst at a dehydration temperature and dehydration pressure to produce a reaction stream comprising C2+ olefins and one or more C4+ normal paraffins, aromatics and/or naphthenes;collecting a portion of the C4+ normal paraffins, aromatics and/or naphthenes and catalytically reacting the C4+ normal paraffins, aromatics and/or naphthenes in the presence of an isomerization catalyst to produce a stream of C4+ isoparaffins; andcatalytically reacting the C2+ olefins with the C4+ isoparaffins in the presence of an alkylation catalyst at an alkylation temperature and alkylation pressure to produce a product stream comprising C6+ paraffins. 53. The method of claim 52, wherein at least a portion of the hydrogen is an APR hydrogen produced by a method comprising catalytically reacting a first portion of the water and the water soluble oxygenated hydrocarbon in the presence of an APR catalyst at a reforming temperature and a reforming pressure to produce the APR hydrogen. 54. The method of claim 52 further comprising the step of providing an aqueous solution comprising water and a polysaccharide, disaccharide, monosaccharide, sugar, furfural, carboxylic acid, ketone, furan, or a combination of any two or more of the foregoing, and catalytically reacting the polysaccharide, disaccharide, monosaccharide, sugar, furfural, carboxylic acid, ketone, furan, or combination, with hydrogen in the presence of a second hydrogenation catalyst at a hydrogenation temperature and hydrogenation pressure to produce the water soluble oxygenated hydrocarbon. 55. The method of claim 52 further comprising the step of providing an aqueous solution comprising water and a polysaccharide, disaccharide, monosaccharide, polyhydric alcohol, sugar, sugar alcohol, or a combination of any two or more of the foregoing, and catalytically reacting the sugar, sugar alcohol, polysaccharide, disaccharide, monosaccharide, polyhydric alcohol, or combination, with hydrogen in the presence of a hydrogenolysis catalyst at a hydrogenolysis temperature and hydrogenolysis pressure to produce the water soluble oxygenated hydrocarbon. 56. The method of claim 52, wherein the C2+O2+ hydrocarbon comprises a member selected from the group consisting of a cellulose derivative, a lignin derivative, a hemicelluloses derivative, glucose, fructose, sucrose, maltose, lactose, mannose, xylose, arabitol, erythritol, glycerol, isomalt, lactitol, malitol, mannitol, sorbitol, xylitol, and a mixture of any two or more of the foregoing. 57. The method of claim 52, wherein the C2+O2+ hydrocarbon further comprises a recycled C2+O2+ hydrocarbon.

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Synthesis of liquid fuels from biomass

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Synthesis of liquid fuels from biomass

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이 특허에 인용된 특허 (111)

이 특허를 인용한 특허 피인용횟수: 10

IPC 상위 출원인

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상세정보조회

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IPC 상세정보(version : 201201)

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