TWI851793B - 使用最佳化蒸餾低聚合烯烴之方法 - Google Patents
使用最佳化蒸餾低聚合烯烴之方法 Download PDFInfo
- Publication number
- TWI851793B TWI851793B TW109128213A TW109128213A TWI851793B TW I851793 B TWI851793 B TW I851793B TW 109128213 A TW109128213 A TW 109128213A TW 109128213 A TW109128213 A TW 109128213A TW I851793 B TWI851793 B TW I851793B
- Authority
- TW
- Taiwan
- Prior art keywords
- oligomerization
- olefins
- reaction
- distillation column
- catalyst
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 55
- 238000004821 distillation Methods 0.000 title claims abstract description 51
- 238000006384 oligomerization reaction Methods 0.000 title claims abstract description 49
- 150000001336 alkenes Chemical class 0.000 title claims description 63
- 238000006243 chemical reaction Methods 0.000 claims abstract description 94
- 239000011541 reaction mixture Substances 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 31
- 239000000376 reactant Substances 0.000 claims description 25
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 18
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 17
- 238000001816 cooling Methods 0.000 claims description 14
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000003606 oligomerizing effect Effects 0.000 claims description 7
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 150000002816 nickel compounds Chemical class 0.000 claims description 4
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004408 titanium dioxide Substances 0.000 claims description 4
- 239000012876 carrier material Substances 0.000 claims description 3
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052681 coesite Inorganic materials 0.000 claims description 2
- 229910052593 corundum Inorganic materials 0.000 claims description 2
- 229910052906 cristobalite Inorganic materials 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- 229910052682 stishovite Inorganic materials 0.000 claims description 2
- 229910052905 tridymite Inorganic materials 0.000 claims description 2
- 229910001845 yogo sapphire Inorganic materials 0.000 claims description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 6
- 235000013844 butane Nutrition 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- 238000006471 dimerization reaction Methods 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910000480 nickel oxide Inorganic materials 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WEPNJTDVIIKRIK-UHFFFAOYSA-N 2-methylhept-2-ene Chemical compound CCCCC=C(C)C WEPNJTDVIIKRIK-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 150000000475 acetylene derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- HORIEOQXBKUKGQ-UHFFFAOYSA-N bis(7-methyloctyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCC(C)C HORIEOQXBKUKGQ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 239000000567 combustion gas Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000004806 diisononylester Substances 0.000 description 1
- DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
- C07C2/12—Catalytic processes with crystalline alumino-silicates or with catalysts comprising molecular sieves
-
- 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
- B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
-
- 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
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali- or alkaline earth metals
-
- 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
- C07C2/10—Catalytic processes with metal oxides
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/755—Nickel
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
- C07C2523/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36 with alkali- or alkaline earth metals or beryllium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP19192735 | 2019-08-21 | ||
| EP19192735.9 | 2019-08-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW202112714A TW202112714A (zh) | 2021-04-01 |
| TWI851793B true TWI851793B (zh) | 2024-08-11 |
Family
ID=67659610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW109128213A TWI851793B (zh) | 2019-08-21 | 2020-08-19 | 使用最佳化蒸餾低聚合烯烴之方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US11254631B2 (https=) |
| EP (1) | EP3782970B1 (https=) |
| JP (1) | JP2021031494A (https=) |
| KR (1) | KR20210023743A (https=) |
| CN (1) | CN112409120A (https=) |
| ES (1) | ES2958707T3 (https=) |
| MY (1) | MY197580A (https=) |
| SG (1) | SG10202007882QA (https=) |
| TW (1) | TWI851793B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11299443B2 (en) * | 2020-04-03 | 2022-04-12 | Exxonmobil Research And Engineering Company | Distillate production from olefins in moving bed reactors |
| EP4029926A1 (de) | 2021-01-15 | 2022-07-20 | Evonik Operations GmbH | Zweistufige abgaswäsche |
| JP2022132817A (ja) | 2021-03-01 | 2022-09-13 | 株式会社リコー | 液体組成物 |
| US20240247199A1 (en) * | 2023-01-20 | 2024-07-25 | Uop Llc | Process for converting olefins to jet fuel with dealkanizer |
| EP4613727A1 (de) * | 2024-03-04 | 2025-09-10 | Evonik Oxeno GmbH & Co. KG | Energieeffizientes verfahren zur oligomerisierung von olefinen |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040181105A1 (en) * | 2003-03-11 | 2004-09-16 | Thomas Heidemann | Preparation of oligomers of alkenes having from 4 to 8 carbon atoms |
| US20100312031A1 (en) * | 2008-01-29 | 2010-12-09 | Basf Se | Method for oligomerizing alkenes |
| TW201518257A (zh) * | 2013-06-27 | 2015-05-16 | Evonik Industries Ag | 具有極低１－丁烯含量的ｃ物流之低聚合作用 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10335510A1 (de) | 2003-07-31 | 2005-03-10 | Stockhausen Chem Fab Gmbh | Beschichteter Katalysator-Trägerkörper |
| US20090068440A1 (en) | 2005-06-20 | 2009-03-12 | Gunther Bub | Production of acrolein, acrylic acid and water-absorbent polymer structures made from glycerine |
| DE102006039203B4 (de) | 2006-08-22 | 2014-06-18 | Evonik Degussa Gmbh | Verfahren zur Herstellung von durch Kristallisation gereinigter Acrylsäure aus Hydroxypropionsäure sowie Vorrichtung dazu |
| DE102006039205A1 (de) | 2006-08-22 | 2008-03-20 | Stockhausen Gmbh | Auf nachwachsenden Rohstoffen basierende Acrylsäure und wasserabsorbierende Polymergebilde sowie Verfahren zu deren Herstellung mittels Dehydratisierung |
| DE102008007081B4 (de) * | 2008-01-31 | 2018-12-06 | Evonik Degussa Gmbh | Verfahren zur Herstellung von n-Buten-Oligomeren und 1-Buten aus technischen Mischungen I von C4-Kohlenwasserstoffen |
| KR100977454B1 (ko) | 2008-02-26 | 2010-08-24 | 삼성전자주식회사 | 광대역 무선통신 시스템에서 하향링크 버스트 할당 장치 및방법 |
| KR101669300B1 (ko) * | 2008-11-19 | 2016-10-25 | 바스프 에스이 | 올레핀의 올리고머화 |
| CN103946187B (zh) * | 2011-11-21 | 2016-01-20 | 巴斯夫欧洲公司 | 制备丁烯低聚物的方法 |
| JP6228246B2 (ja) | 2015-03-03 | 2017-11-08 | エボニック デグサ ゲーエムベーハーＥｖｏｎｉｋ Ｄｅｇｕｓｓａ ＧｍｂＨ | エテンのオリゴマー化に使用される不均一系触媒の再生 |
| WO2017075209A1 (en) * | 2015-10-30 | 2017-05-04 | Worleyparsons Group Inc. | Methods and systems for lower olefin conversion |
| PL3255029T3 (pl) | 2016-06-10 | 2019-04-30 | Evonik Degussa Gmbh | Oligomeryzacja etenu w warunkach nadkrytycznych |
| EP3266757B1 (de) | 2016-07-08 | 2019-12-25 | Evonik Operations GmbH | Herstellung von zumindest 1-hexen und octen aus ethen |
| US10227279B2 (en) | 2016-09-12 | 2019-03-12 | Evonik Degussa Gmbh | Dehydrogenation of LPG or NGL and flexible utilization of the olefins thus obtained |
| ZA201801183B (en) * | 2017-02-27 | 2019-01-30 | Evonik Degussa Gmbh | Selective oligomerization of olefins |
| US10882028B2 (en) | 2018-03-14 | 2021-01-05 | Evonik Operations Gmbh | Ni-containing catalyst for the oligomerization of olefins |
| US11253844B2 (en) | 2018-03-14 | 2022-02-22 | Evonik Operations Gmbh | Oligomerization catalyst and process for the production thereof |
| US10850261B2 (en) | 2018-03-14 | 2020-12-01 | Evonik Operations Gmbh | Oligomerization catalyst and process for the production thereof |
| US10882027B2 (en) | 2018-03-14 | 2021-01-05 | Evonik Operations Gmbh | Process for producing an oligomerization catalyst |
| US10633302B2 (en) | 2018-07-25 | 2020-04-28 | Evonik Operations Gmbh | Process for oligomerization of butene with determination of the proportion of acidic catalysis |
| US11186782B2 (en) | 2019-01-08 | 2021-11-30 | Evonik Operations Gmbh | Catalyst and process for removing mercaptans from hydrocarbon streams |
| EP3680224B1 (de) | 2019-01-08 | 2023-05-24 | Evonik Operations GmbH | Verfahren zur entfernung mehrfach ungesättigter kohlenwasserstoffe aus c4-kohlenwasserstoffströmen in anwesenheit von mercaptanen, disulfiden und c5-kohlenwasserstoffen |
-
2020
- 2020-08-12 US US16/991,327 patent/US11254631B2/en active Active
- 2020-08-13 EP EP20190803.5A patent/EP3782970B1/de active Active
- 2020-08-13 ES ES20190803T patent/ES2958707T3/es active Active
- 2020-08-18 MY MYPI2020004232A patent/MY197580A/en unknown
- 2020-08-18 SG SG10202007882QA patent/SG10202007882QA/en unknown
- 2020-08-19 TW TW109128213A patent/TWI851793B/zh active
- 2020-08-20 JP JP2020139310A patent/JP2021031494A/ja active Pending
- 2020-08-20 KR KR1020200104333A patent/KR20210023743A/ko active Pending
- 2020-08-21 CN CN202010846513.XA patent/CN112409120A/zh active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040181105A1 (en) * | 2003-03-11 | 2004-09-16 | Thomas Heidemann | Preparation of oligomers of alkenes having from 4 to 8 carbon atoms |
| US20100312031A1 (en) * | 2008-01-29 | 2010-12-09 | Basf Se | Method for oligomerizing alkenes |
| TW201518257A (zh) * | 2013-06-27 | 2015-05-16 | Evonik Industries Ag | 具有極低１－丁烯含量的ｃ物流之低聚合作用 |
Also Published As
| Publication number | Publication date |
|---|---|
| US11254631B2 (en) | 2022-02-22 |
| CN112409120A (zh) | 2021-02-26 |
| TW202112714A (zh) | 2021-04-01 |
| MY197580A (en) | 2023-06-26 |
| KR20210023743A (ko) | 2021-03-04 |
| EP3782970A1 (de) | 2021-02-24 |
| EP3782970B1 (de) | 2023-07-12 |
| US20210053891A1 (en) | 2021-02-25 |
| ES2958707T3 (es) | 2024-02-13 |
| SG10202007882QA (en) | 2021-03-30 |
| JP2021031494A (ja) | 2021-03-01 |
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