Methods and systems of producing monoolefins by the extraction-hydrogenation of highly unsaturated hydrocarbons
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07C-005/03
C07C-005/00
출원번호
US-0712686
(2003-11-13)
발명자
/ 주소
Cheung,Tin Tack Peter
Johnson,Marvin M.
출원인 / 주소
Chevron Phillips Chemical Company LP
인용정보
피인용 횟수 :
7인용 특허 :
18
초록▼
In some embodiments, methods of producing monoolefins include contacting an olefin stream with a polar solvent to extract a highly unsaturated hydrocarbon from the olefin stream, followed by contacting the polar solvent with a hydrogenation catalyst in the presence of hydrogen at conditions effectiv
In some embodiments, methods of producing monoolefins include contacting an olefin stream with a polar solvent to extract a highly unsaturated hydrocarbon from the olefin stream, followed by contacting the polar solvent with a hydrogenation catalyst in the presence of hydrogen at conditions effective to hydrogenate the highly unsaturated hydrocarbon to a monoolefin. The monoolefin then desorbs from the polar solvent and enters the purified olefin stream, allowing the polar solvent to be recycled. In other embodiments, monoolefin production systems include an extraction-hydrogenation zone for performing the extraction and hydrogenating steps in situ. In alternative embodiments, the hydrogenation zone is disposed downstream from the extraction zone.
대표청구항▼
What is claimed is: 1. A method of producing monoolefins, comprising: (a) contacting an olefin stream with a polar solvent and a high boiling additive such that a highly unsaturated hydrocarbon in the olefin stream becomes dissolved in the polar solvent and the high boiling additive; and (b) contac
What is claimed is: 1. A method of producing monoolefins, comprising: (a) contacting an olefin stream with a polar solvent and a high boiling additive such that a highly unsaturated hydrocarbon in the olefin stream becomes dissolved in the polar solvent and the high boiling additive; and (b) contacting the polar solvent and the high boiling additive with a hydrogenation catalyst comprising palladium and silver in the presence of hydrogen at conditions effective to hydrogenate the highly unsaturated hydrocarbon to a monoolefin, wherein the polar solvent comprises a compound selected from the group consisting of N-methylpyrrolidone, formamide, N-methylformamide, N-ethylformamide, N-phenylformamide, N,N-dimethylformamide, N,N-diethylformamide, N,N-diphenylformamide, sulfolane, n-formyl morpholine, glycerol, triethylene, glycerol, tetraethylene glycerol, and combinations thereof. 2. The method of claim 1, wherein step (b) comprises feeding both the olefin stream and the polar solvent having the highly unsaturated hydrocarbon dissolved therein to a hydrogenation reactor. 3. The method of claim 1, further comprising separating the olefin stream from the polar solvent having the highly unsaturated hydrocarbon dissolved therein before performing step (b). 4. The method of claim 1, wherein a weight ratio of the polar solvent to the highly unsaturated hydrocarbon ranges from about 0.00006 to about 0.15. 5. The method of claim 1, wherein the olefin stream comprises cracked gas recovered from an ethylene cracker. 6. The method of claim 1, wherein the olefin stream primarily comprises ethylene separated from cracked gas. 7. The method of claim 1, wherein the olefin stream primarily comprises propylene separated from cracked gas. 8. The method of claim 1, wherein the highly unsaturated hydrocarbon comprises a compound selected from the group consisting of an acetylene, a diolefin, and combinations thereof. 9. The method of claim 1, wherein the highly unsaturated hydrocarbon comprises a compound selected from the group consisting of acetylene, methylacetylene, vinylacetylene, ethylacetylene, 2-butyne, propadiene, butadiene, isoprene, 1-3 pentadienes, cyclopentadiene, and combinations thereof. 10. The method of claim 1, wherein the hydrogenation catalyst further comprises fluorine. 11. The method of claim 1, wherein the high boiling additive is combined with the polar solvent before said contacting the olefin stream with the polar solvent. 12. The method of claim 11, wherein a mixture of the polar solvent and the high boiling additive comprises from about 0.0001 to about 10 wt. % of the high boiling additive based on the total weight of the mixture. 13. The method of claim 12, wherein a selectivity to the monoolefin during the hydrogenation is greater than about 30%. 14. The method of claim 12, wherein a selectivity to the monoolefin during the hydrogenation is greater than about 80%. 15. The method of claim 11, wherein a mixture of the polar solvent and the high boiling additive comprises from about 0.001 to about 1 wt. % of the high boiling additive based on the total weight of the mixture. 16. The method of claim 11, wherein a mixture of the polar solvent and the high boiling additive comprises from about 0.01 to about 0.1 wt. % of the high boiling additive based on the total weight of the mixture. 17. The method of claim 11, wherein the high boiling additive comprises a compound selected from the group consisting of triphenylphosphine, diphenyiphosphine, benzothiophene, dibenzothiophenc, substituted dibenzothiophenes, pyridine, substituted pyridines, aniline, substituted anilinea, alkali metal fluorides, and combinations thereof. 18. The method of claim 11, wherein the high boiling additive is present in the polar solvent during the hydrogenation. 19. The method of claim 11, wherein the monoolefin desorbs from the polar solvent, and further comprising recycling the polar solvent comprising the high boiling point additive for use in removing the highly unsaturated hydrocarbon from the olefin stream. 20. The method of claim 1, wherein a molar ratio of the hydrogen to the highly unsaturated hydrocarbon is in a range of from about 0.5 to about 20. 21. The method of claim 1, wherein a molar ratio of the hydrogen to the highly unsaturated hydrocarbon is in a range of from about 2 to about 5. 22. The method of claim 1, wherein the highly unsaturated hydrocarbon is acetylene and the monoolefin is ethylene. 23. The method of claim 1, wherein the monoolefin desorbs from the polar solvent. 24. The method of claim 23, further comprising introducing the monoolefin to the olefin stream from which the highly unsaturated hydrocarbon has been removed. 25. The method of claim 23, further comprising recycling the polar solvent for use in removing the highly unsaturated hydrocarbon from the olefin stream. 26. The method of claim 23, wherein the hydrogenation occurs in a liquid phase and the monoolefin desorbs from the liquid phase into a gas phase. 27. The method of claim 1, wherein the monoolefin desorbs from the polar solvent and combines with the olefin stream in situ. 28. The method of claim 1, wherein the polar solvent removes all or a portion of any oligomers formed on the hydrogenation catalyst during hydrogenation. 29. The method of claim 1, wherein the hydrocarbon stream comprises one or more streams from an ethylene cracker. 30. A method of removing a highly unsaturated hydrocarbon from a hydrocarbon stream, comprising: (a) extracting the highly unsaturated hydrocarbon from the hydrocarbon stream with a polar solvents and a high additive, wherein the polar solvent comprises a compound selected from the group consisting of N-methylpyrrolidone, formamide, N-methylformamide, N-ethylformamide, N-phenylformamide, N,N-dimethylformamide, N,N-diethylformamide, N,N-diphenylformamide, sulfolane, n-formyl morpholine, glycerol, triethylene glycerol, tetracthylene glycerol,and combinations thereof; and (b) hydrogenating the highly unsaturated hydrocarbon in the polar solvent to a monoolefin via contact wit a hydrogenation catalyst comprising palladium and silver. 31. The method of claim 30, further comprising separating the polar solvent from the hydrocarbon stream prior to hydrogenation. 32. The method of claim 31, further comprising recovering the monoolefin and adding the monoolefin to the hydrocarbon stream. 33. The method of claim 31, further comprising recycling the polar solvent for use in step (a). 34. The method of claim 30, wherein step (b) comprises feeding both the hydrocarbon stream and the polar solvent to a hydrogenation reactor. 35. The method of claim 34, wherein the monoolefin desorbs from the polar solvent and combines with the hydrocarbon stream in situ after step (b), and further comprising separating the polar solvent from the hydrocarbon stream. 36. The method of claim 35, further comprising recycling the polar solvent for use in step (a). 37. A method of producing monoolefins, comprising: (a) contacting an olefin stream with a polar solvent such that a highly unsalurated hydrocarbon in the olefin stream becomes dissolved in the polar solvent, wherein the polar solvent comprises a compound selected from the group consisting of sulfolane, glycerol, triethylene glycerol, tetraethylenc glycerol, and combinations thereof; and (b) contacting the polar solvent with a hydrogenation catalyst comprising palladium and silver in the presence of hydrogen at conditions effective to hydrogenate the highly unsaturated hydrocarbon to a monoolefin. 38. The method of claim 37, wherein step (b) comprises feeding both the olefin stream and the polar solvent having the highly unsaturated hydrocarbon dissolved therein to a hydrogenation reactor. 39. The method of claim 37, further comprising separating the olefin stream from the polar solvent having the highly unsaturated hydrocarbon dissolved therein before performing step (b). 40. The method of claim 37, wherein the hydrogenation catalyst further comprises fluorine. 41. The method of claim 37, wherein the monoolefin desorbs from the polar solvent. 42. The method of claim 41, further comprising introducing the monoolefin to the olefin stream from which the highly unsaturated hydrocarbon has been removed. 43. The method of claim 41, further comprising recycling the polar solvent for use in removing the highly unsaturated hydrocarbon from the olefin stream. 44. The method or claim 37, wherein the monoolefin desorbs from the polar solvent and combines with the olefin stream in situ. 45. The method of claim 37, wherein a weight ratio of the polar solvent to the highly unsaturated hydrocarbon ranges from about 0. 00006 to about 0.15. 46. The method of claim 37, wherein the olefin stream comprises cracked gas recovered from an ethylene cracker. 47. The method of claim 37, wherein the olefin stream primarily comprises ethylene separated from cracked gas. 48. The method of claim 37, wherein the olefin stream primarily comprises propylene separated from cracked gas. 49. The method of claim 37, wherein the highly unsaturated hydrocarbon comprises a compound selected from the group consisting of an acetylene, a diolefin, and combinations thereof.
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