Process of generating a renewable biofuel from a hydrotreated stream of condensed oxygenates
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07C-001/24
C10G-003/00
출원번호
US-0681145
(2012-11-19)
등록번호
US-9290423
(2016-03-22)
발명자
/ 주소
Trewella, Jeffrey C
Smith, Edward J
Sanchez, Vicente
Moore, Brent
McGovern, Stephen J.
출원인 / 주소
KiOR, LLC
대리인 / 주소
Jones, John Wilson
인용정보
피인용 횟수 :
1인용 특허 :
8
초록▼
A renewable fuel may be obtained from a bio-oil containing C3-C5 oxygenates. In a first step, the bio-oil is subjected to a condensation reaction in which the oxygenates undergo a carbon-carbon bond forming reaction to produce a stream containing C6+ oxygenates. In a second step, the stream is hydro
A renewable fuel may be obtained from a bio-oil containing C3-C5 oxygenates. In a first step, the bio-oil is subjected to a condensation reaction in which the oxygenates undergo a carbon-carbon bond forming reaction to produce a stream containing C6+ oxygenates. In a second step, the stream is hydrotreated to produce C6+ hydrocarbons.
대표청구항▼
1. A process for producing a renewable biofuel from a liquid bio-oil or liquid pyrolysis oil, the process comprising: (a) introducing effluent from a biomass conversion unit into a separator and separating from the effluent a liquid bio-oil or pyrolysis oil;(b) subjecting carbonyl containing oxygena
1. A process for producing a renewable biofuel from a liquid bio-oil or liquid pyrolysis oil, the process comprising: (a) introducing effluent from a biomass conversion unit into a separator and separating from the effluent a liquid bio-oil or pyrolysis oil;(b) subjecting carbonyl containing oxygenates within the separated liquid bio-oil or pyrolysis oil to a carbon-carbon bond forming condensation reaction in a condensation reactor to form C6+ enriched condensates, wherein the carbonyl containing oxygenates are selected from the group consisting of C3 oxygenates, C4 oxygenates and C5 oxygenates and mixtures thereof and further wherein the C3, C4 and C5 oxygenates are selected from the group consisting of carboxylic acids, carboxylic acid esters, ketones and aldehydes;(c) contacting the bio-oil or pyrolysis oil containing condensates of step (b) with hydrogen and hydrotreating the C6+ condensates to form a hydrotreated bio-oil or pyrolysis oil comprising C6+ enriched hydrocarbons; and(d) removing the hydrotreated bio-oil or pyrolysis oil comprising C6+ enriched hydrocarbons from the hydrotreater and fractionating the hydrotreated bio-oil or pyrolysis oil comprising C6+ enriched hydrocarbons to obtain a C6+ renewable biofuel. 2. The process of claim 1, wherein the condensation reactor in step (b) is a distillation column. 3. The process of claim 2, wherein condensation in the distillation column occurs in the presence of a heterogeneous acid catalyst. 4. The process of claim 3, wherein the heterogeneous acid catalyst is selected from the group consisting of organic sulfonic acids; perfluoroalkylsulfonic acids; zeolites; sulfated transition metal oxides, and perfluorinated ion exchange polymers containing pendant sulfonic acid, carboxylic acid, or sulfonic acid groups; sulfonated copolymers of styrene and divinylbenzene; sulfated silicas, aluminas, titania and/or zirconia; and amorphous SiAl and mixtures thereof. 5. The process of claim 4, wherein the heterogeneous acid catalyst is selected from the group consisting of ZSM-type zeolites, zeolite beta, sulfonated fluoropolymers or copolymers, sulfated zirconia and amorphous SiAl. 6. The process of claim 5, wherein the heterogeneous catalyst is a zeolite beta. 7. The process of claim 3, wherein the heterogeneous acid catalyst is located in the distillation column at a pre-determined location within the distillation column. 8. The process of claim 1, wherein the carbon-carbon bond forming condensation reaction is a Diels-Alder reaction. 9. The process of claim 8, wherein the condensation reactor is a distillation column. 10. The process of claim 1, wherein the C6+ enriched condensates are prepared in step (b) by an aldol condensation reaction. 11. The process of claim 1, wherein the C6+ enriched condensates are prepared in step (b) by a Michael addition reaction. 12. The process of claim 1, wherein the C6+ enriched condensates are prepared in step (b) by a Robinson annulation reaction. 13. The process of claim 1, wherein the ketones are methyl vinyl ketone and ethyl vinyl ketone. 14. The process of claim 1, wherein the C6+ enriched hydrocarbons of step (c) are separated into a naphtha fraction containing predominately C5 through C10 hydrocarbons and a hydrocarbon fraction containing C10+ hydrocarbons. 15. A process for enhancing the yield of either hydrotreated bio-oil from a liquid bio-oil stream or hydrotreated pyrolysis oil from a liquid pyrolysis stream, the liquid bio-oil stream or liquid pyrolysis stream containing oxygenates selected from the group consisting of C3 oxygenates, C4 oxygenates and C5 oxygenates and mixtures thereof wherein the C3, C4 and C5 oxygenates are selected from the group consisting of carboxylic acids, carboxylic acid esters, ketones and aldehydes, the process comprising: (a) subjecting the C3, C4 and C5 oxygenates within the liquid bio-oil stream or liquid pyrolysis stream to a carbon-carbon bond forming condensation reaction in a condensation reactor to produce C6+ oxygenates;(b) removing the C6+ oxygenates from the condensation reactor and introducing them to a hydrotreater; and(c) hydrotreating the C6+ oxygenates to render C6+ enriched hydrocarbons, wherein the amount of oxygen removed from the C6+ oxygenates in the hydrotreater is from 90 to about 99.99%. 16. A process for producing a renewable biofuel from a hydrotreated bio-oil, the process comprising: (a) feeding a liquid bio-oil stream to a distillation column;(b) subjecting lower carbon oxygenates in the liquid bio-oil stream to a carbon-carbon bond forming condensation reaction in the distillation column and forming C6+ oxygenates from the lower carbon oxygenates, wherein the lower carbon oxygenates are selected from the group consisting of C3 oxygenates, C4 oxygenates and C5 oxygenates and mixtures thereof and further wherein the C3, C4 and C5 oxygenates are selected from the group consisting of carboxylic acids, carboxylic acid esters, ketones and aldehydes;(c) removing the C6+ oxygenates from the distillation column and introducing them into a hydrotreater;(d) hydrotreating the C6+ oxygenates in the hydrotreater to render C6+ enriched hydrocarbons; and(e) subjecting the C6+ enriched hydrocarbons to fractionation to render a 180° F.-420° F. naphtha and at least one hydrocarbon fraction having a boiling point less than 180° F. 17. A process for producing a renewable biofuel from biomass, the process comprising: (a) separating a predominately organic liquid bio-oil phase from treated biomass, wherein the organic liquid bio-oil phase comprises oxygenates selected from the group consisting of C3 oxygenates, C4 oxygenates and C5 oxygenates and further wherein the C3, C4 and C5 oxygenates are selected from the group consisting of carboxylic acids, carboxylic acid esters, ketones and aldehydes;(b) forming C6+ oxygenates through a carbon-carbon bond forming reaction from the C3 oxygenates, C4 oxygenates and C5 oxygenates in the organic liquid bio-oil phase;(c) introducing the C6+ oxygenates into a hydrotreater and hydrotreating the C6+ oxygenates in the hydrotreater to produce C6+ enriched hydrocarbons; and(d) subjecting the C6+ enriched hydrocarbons to fractionation to render separate hydrocarbon fractions containing (i) C5 to C10 hydrocarbons and (ii) C10+ hydrocarbons. 18. The process of claim 17, wherein the hydrotreater has a catalytic bed. 19. The process of claim 17, wherein transportation fuels are prepared from the separated hydrocarbon fractions of step (d). 20. The process of claim 17, wherein the C3 oxygenates, C4 oxygenates and C5 oxygenates include methyl vinyl ketone and ethyl vinyl ketone. 21. The process of claim 17, wherein the C6+ oxygenates of step (b) are prepared through an aldol condensation reaction, a Diels-Alder reaction, a Michael addition, or a Robinson annulations reaction or a mixture thereof. 22. The process of claim 17, wherein the C6+ oxygenates of step (b) are prepared through a Diels-Alder reaction. 23. The process of claim 1, further comprising recovering solids from the effluent in step (a), regenerating the recovered solids and then introducing the regenerated solids into the biomass conversion unit. 24. The process of claim 1, further comprising recovering solids from the effluent in step (a), regenerating the recovered solids, introducing the regenerated solids to a biomass feedstream and then introducing the biomass feedstream into the biomass conversion unit.
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이 특허에 인용된 특허 (8)
Dessau, Ralph M., Diels-Alder Cyclization over low acidity large-pore zeolites.
Dumesic, James A.; Huber, George W.; Chheda, Juben N.; Barrett, Christopher J., Method to make alkanes and saturated polyhydroxy compounds from carbonyl compounds.
Diebold James P. (Lakewood CO) Scahill John W. (Evergreen CO) Chum Helena L. (Arvada CO) Evans Robert J. (Lakewood CO) Rejai Bahman (Lakewood CO) Bain Richard L. (Golden CO) Overend Ralph P. (Lakewoo, Process to convert biomass and refuse derived fuel to ethers and/or alcohols.
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