WO2024105087A1 - Procédé de séparation d'un flux d'hydrocarbures mixtes comprenant des n-butènes à l'aide d'une colonne de distillation à paroi de séparation produisant des n-butènes et séparation de ceux-ci - Google Patents
Procédé de séparation d'un flux d'hydrocarbures mixtes comprenant des n-butènes à l'aide d'une colonne de distillation à paroi de séparation produisant des n-butènes et séparation de ceux-ci Download PDFInfo
- Publication number
- WO2024105087A1 WO2024105087A1 PCT/EP2023/081864 EP2023081864W WO2024105087A1 WO 2024105087 A1 WO2024105087 A1 WO 2024105087A1 EP 2023081864 W EP2023081864 W EP 2023081864W WO 2024105087 A1 WO2024105087 A1 WO 2024105087A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- vapor
- contacting area
- dividing wall
- liquid contacting
- distillation column
- Prior art date
Links
- 238000004821 distillation Methods 0.000 title claims abstract description 103
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 title claims abstract description 90
- 238000000034 method Methods 0.000 title claims abstract description 39
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 26
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 26
- 239000004215 Carbon black (E152) Substances 0.000 title claims abstract description 22
- 238000000926 separation method Methods 0.000 title description 13
- 239000007788 liquid Substances 0.000 claims abstract description 149
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims abstract description 48
- 150000001336 alkenes Chemical class 0.000 claims abstract description 29
- 238000001704 evaporation Methods 0.000 claims abstract description 14
- 238000005192 partition Methods 0.000 claims abstract description 12
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 238000006471 dimerization reaction Methods 0.000 claims description 32
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 30
- 239000005977 Ethylene Substances 0.000 claims description 29
- 238000004891 communication Methods 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 12
- 238000012546 transfer Methods 0.000 claims description 7
- -1 organo aluminum compound Chemical class 0.000 claims description 6
- 150000002816 nickel compounds Chemical class 0.000 claims description 4
- 230000000630 rising effect Effects 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 239000003518 caustics Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000011552 falling film Substances 0.000 claims description 2
- 239000010408 film Substances 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- 230000008569 process Effects 0.000 abstract description 14
- 230000009467 reduction Effects 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000008901 benefit Effects 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005649 metathesis reaction Methods 0.000 description 4
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 150000002815 nickel Chemical class 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 239000002918 waste heat Substances 0.000 description 3
- SMYHHAIBKWZVKX-UHFFFAOYSA-L [Ni+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [Ni+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 SMYHHAIBKWZVKX-UHFFFAOYSA-L 0.000 description 2
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 238000003466 welding Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- RZHIALGQQJESEK-UHFFFAOYSA-L dichloronickel;triethylphosphane Chemical compound Cl[Ni]Cl.CCP(CC)CC.CCP(CC)CC RZHIALGQQJESEK-UHFFFAOYSA-L 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- JOSJZPLSVYWPAG-UHFFFAOYSA-L dodecanoate;nickel(2+) Chemical compound [Ni+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O JOSJZPLSVYWPAG-UHFFFAOYSA-L 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- LVBIMKHYBUACBU-CVBJKYQLSA-L nickel(2+);(z)-octadec-9-enoate Chemical compound [Ni+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LVBIMKHYBUACBU-CVBJKYQLSA-L 0.000 description 1
- DVTHIMLUHWEZOM-UHFFFAOYSA-L nickel(2+);octanoate Chemical compound [Ni+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O DVTHIMLUHWEZOM-UHFFFAOYSA-L 0.000 description 1
- YOCBOYPGZVFUCQ-UHFFFAOYSA-L nickel(2+);tricyclohexylphosphane;dichloride Chemical compound Cl[Ni]Cl.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 YOCBOYPGZVFUCQ-UHFFFAOYSA-L 0.000 description 1
- ZBRJXVVKPBZPAN-UHFFFAOYSA-L nickel(2+);triphenylphosphane;dichloride Chemical compound [Cl-].[Cl-].[Ni+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZBRJXVVKPBZPAN-UHFFFAOYSA-L 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/141—Fractional distillation or use of a fractionation or rectification column where at least one distillation column contains at least one dividing wall
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
L'invention concerne un procédé de séparation d'un flux d'hydrocarbures mélangés comprenant du 1-butène, du 2-butène, des oléfines plus lourdes qui comprend l'introduction du flux d'hydrocarbures mélangés dans la section d'alimentation d'une colonne de distillation à paroi de séparation. La colonne de distillation à paroi de séparation a une coque définissant une zone de contact intermédiaire vapeur-liquide, une zone de contact supérieure vapeur-liquide et une zone de contact inférieure vapeur-liquide. La zone de contact intermédiaire vapeur-liquide contient au moins une cloison orientée verticalement divisant la zone de contact intermédiaire vapeur-liquide en au moins une section d'alimentation définie par la coque et la cloison et une section de soutirage latéral définie par la coque et la cloison. De l'énergie thermique est fournie à la colonne de distillation à paroi de séparation par l'intermédiaire d'un rebouilleur inférieur. De l'énergie thermique supplémentaire est fournie à la colonne de distillation à paroi de séparation par soutirage d'une fraction liquide de la colonne de distillation à paroi de séparation par l'intermédiaire d'un soutirage latéral, par chauffage et évaporation partielle de la fraction liquide dans un évaporateur à soutirage latéral, et l'acheminement de la fraction chauffée partiellement évaporée en retour vers la colonne de distillation à paroi de séparation. Le procédé augmente au maximum la proportion d'énergie thermique fournie à un niveau de température relativement inférieur tout en réduisant au minimum la demande globale en énergie du procédé. Avec toutes les autres variables constantes, le procédé permet en outre une réduction du nombre de plaques dans la section d'alimentation de la zone de contact intermédiaire vapeur-liquide.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP22207461.9 | 2022-11-15 | ||
| EP22207461 | 2022-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2024105087A1 true WO2024105087A1 (fr) | 2024-05-23 |
Family
ID=88793064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2023/081864 WO2024105087A1 (fr) | 2022-11-15 | 2023-11-15 | Procédé de séparation d'un flux d'hydrocarbures mixtes comprenant des n-butènes à l'aide d'une colonne de distillation à paroi de séparation produisant des n-butènes et séparation de ceux-ci |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2024105087A1 (fr) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3321546A (en) | 1962-11-30 | 1967-05-23 | Shell Oil Co | Olefin dimerization using aluminum alkyl halide-nickel complex catalyst |
| US4242531A (en) | 1978-08-14 | 1980-12-30 | Phillips Petroleum Company | Olefin dimerization |
| US4476341A (en) | 1982-04-06 | 1984-10-09 | Exxon Research & Engineering Co. | Butene dimerization method |
| US5260499A (en) | 1992-01-14 | 1993-11-09 | Phillips Petroleum Company | Ethylene dimerization and catalyst therefor |
| US5414178A (en) | 1992-07-17 | 1995-05-09 | Phillips Petroleum Company | Dimerization catalyst systems and processes |
| US20120095275A1 (en) | 2010-10-13 | 2012-04-19 | Lyondell Chemical Technology, L.P. | Production of 1-Butene and Propylene From Ethylene |
-
2023
- 2023-11-15 WO PCT/EP2023/081864 patent/WO2024105087A1/fr unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3321546A (en) | 1962-11-30 | 1967-05-23 | Shell Oil Co | Olefin dimerization using aluminum alkyl halide-nickel complex catalyst |
| US4242531A (en) | 1978-08-14 | 1980-12-30 | Phillips Petroleum Company | Olefin dimerization |
| US4476341A (en) | 1982-04-06 | 1984-10-09 | Exxon Research & Engineering Co. | Butene dimerization method |
| US5260499A (en) | 1992-01-14 | 1993-11-09 | Phillips Petroleum Company | Ethylene dimerization and catalyst therefor |
| US5414178A (en) | 1992-07-17 | 1995-05-09 | Phillips Petroleum Company | Dimerization catalyst systems and processes |
| US20120095275A1 (en) | 2010-10-13 | 2012-04-19 | Lyondell Chemical Technology, L.P. | Production of 1-Butene and Propylene From Ethylene |
Non-Patent Citations (1)
| Title |
|---|
| DÜNNEBIER GUIDO ET AL: "Optimal Design of Thermally Coupled Distillation Columns", INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, vol. 38, no. 1, 11 December 1998 (1998-12-11), pages 162 - 176, XP093039852, ISSN: 0888-5885, DOI: 10.1021/ie9802919 * |
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