DE60126266T2 - Verfahren zur oligomerisierung von alkenen - Google Patents
Verfahren zur oligomerisierung von alkenen Download PDFInfo
- Publication number
- DE60126266T2 DE60126266T2 DE60126266T DE60126266T DE60126266T2 DE 60126266 T2 DE60126266 T2 DE 60126266T2 DE 60126266 T DE60126266 T DE 60126266T DE 60126266 T DE60126266 T DE 60126266T DE 60126266 T2 DE60126266 T2 DE 60126266T2
- Authority
- DE
- Germany
- Prior art keywords
- alkenes
- carbon atoms
- feedstock
- weight
- alkene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 54
- 230000008569 process Effects 0.000 title claims abstract description 21
- 150000001336 alkenes Chemical class 0.000 title claims description 83
- 230000003606 oligomerizing effect Effects 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 45
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 239000010457 zeolite Substances 0.000 claims description 34
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 32
- 238000006384 oligomerization reaction Methods 0.000 claims description 32
- 229910021536 Zeolite Inorganic materials 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 24
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 23
- 238000005984 hydrogenation reaction Methods 0.000 claims description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims description 15
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims description 14
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 12
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000036571 hydration Effects 0.000 claims description 6
- 238000006703 hydration reaction Methods 0.000 claims description 6
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 6
- KZJIOVQKSAOPOP-UHFFFAOYSA-N 5,5-dimethylhex-1-ene Chemical class CC(C)(C)CCC=C KZJIOVQKSAOPOP-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 238000007037 hydroformylation reaction Methods 0.000 claims description 5
- 230000006315 carbonylation Effects 0.000 claims description 2
- 238000005810 carbonylation reaction Methods 0.000 claims description 2
- 238000006735 epoxidation reaction Methods 0.000 claims description 2
- 238000006266 etherification reaction Methods 0.000 claims description 2
- 238000005194 fractionation Methods 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 48
- 238000004817 gas chromatography Methods 0.000 description 18
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 18
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 16
- 239000013078 crystal Substances 0.000 description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 13
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 10
- 239000001282 iso-butane Substances 0.000 description 8
- 239000002808 molecular sieve Substances 0.000 description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- -1 C 4 olefin Chemical class 0.000 description 6
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000013638 trimer Substances 0.000 description 4
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 3
- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,4-dimethylpentane Chemical compound CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012159 carrier gas Substances 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- 229940069096 dodecene Drugs 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 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 2
- 239000003921 oil Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000012690 zeolite precursor Substances 0.000 description 2
- WGECXQBGLLYSFP-UHFFFAOYSA-N (+-)-2,3-dimethyl-pentane Natural products CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 1
- RGYAVZGBAJFMIZ-UHFFFAOYSA-N 2,3-dimethylhex-2-ene Chemical compound CCCC(C)=C(C)C RGYAVZGBAJFMIZ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- AMVQGJHFDJVOOB-UHFFFAOYSA-H aluminium sulfate octadecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O AMVQGJHFDJVOOB-UHFFFAOYSA-H 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- LTPBRCUWZOMYOC-UHFFFAOYSA-N beryllium oxide Inorganic materials O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- KOYGZROXUOTUEE-UHFFFAOYSA-N butane;but-1-ene Chemical compound CCCC.CCC=C KOYGZROXUOTUEE-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052675 erionite Inorganic materials 0.000 description 1
- 238000004858 feed analysis Methods 0.000 description 1
- 229910001657 ferrierite group Inorganic materials 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical compound CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0010433 | 2000-04-28 | ||
| GBGB0010433.1A GB0010433D0 (en) | 2000-04-28 | 2000-04-28 | Alkene oligomerization process |
| PCT/US2001/012891 WO2001083407A1 (en) | 2000-04-28 | 2001-04-20 | Alkene oligomerization process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60126266D1 DE60126266D1 (de) | 2007-03-15 |
| DE60126266T2 true DE60126266T2 (de) | 2007-10-31 |
Family
ID=9890724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60126266T Expired - Lifetime DE60126266T2 (de) | 2000-04-28 | 2001-04-20 | Verfahren zur oligomerisierung von alkenen |
Country Status (13)
| Country | Link |
|---|---|
| EP (2) | EP1280747B1 (enExample) |
| JP (2) | JP5108194B2 (enExample) |
| KR (1) | KR100822318B1 (enExample) |
| CN (1) | CN1220658C (enExample) |
| AT (2) | ATE526300T1 (enExample) |
| AU (1) | AU2001255533A1 (enExample) |
| CA (1) | CA2405574C (enExample) |
| DE (1) | DE60126266T2 (enExample) |
| GB (1) | GB0010433D0 (enExample) |
| MY (1) | MY128446A (enExample) |
| TW (1) | TW527337B (enExample) |
| WO (1) | WO2001083407A1 (enExample) |
| ZA (1) | ZA200208524B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6875899B2 (en) | 2001-02-01 | 2005-04-05 | Exxonmobil Chemical Patents Inc. | Production of higher olefins |
| US7183450B2 (en) | 2002-07-22 | 2007-02-27 | Exxonmobil Chemical Patents Inc. | Olefin oligomerization |
| US7145049B2 (en) * | 2003-07-25 | 2006-12-05 | Catalytic Distillation Technologies | Oligomerization process |
| KR20070029127A (ko) * | 2003-12-18 | 2007-03-13 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 촉매화된 반응의 개선 방법 |
| US7588738B2 (en) | 2005-08-23 | 2009-09-15 | Exxonmobil Chemical Patents Inc. | Series catalyst beds |
| EP1948578B1 (en) * | 2005-09-30 | 2011-06-22 | ExxonMobil Chemical Patents Inc. | Oligomerization reaction |
| US7501548B2 (en) * | 2006-03-10 | 2009-03-10 | Exxonmobil Chemical Patents Inc. | Oligomerization of isobutene-containing feedstocks |
| CN101460428B (zh) * | 2006-06-07 | 2013-08-28 | 巴斯夫欧洲公司 | 共二聚烯烃的方法 |
| CN102482107B (zh) | 2009-08-28 | 2014-03-26 | 埃克森美孚化学专利公司 | 具有受控平均尺寸的mfs骨架类型分子筛的制备方法和应用 |
| US9394212B2 (en) | 2010-06-15 | 2016-07-19 | Basf Se | Process for the cooligomerization of olefins |
| WO2011157674A1 (de) | 2010-06-15 | 2011-12-22 | Basf Se | Verfahren zur co-oligomerisierung von olefinen |
| US9644159B2 (en) * | 2012-11-12 | 2017-05-09 | Uop Llc | Composition of oligomerate |
| CN109824802A (zh) * | 2012-12-21 | 2019-05-31 | 埃克森美孚化学专利公司 | 桥联的金属茂化合物、催化剂体系和使用它们的聚合方法 |
| SG11201702271VA (en) * | 2014-10-09 | 2017-04-27 | Basf Se | A process for the production of oligomerized olefins |
| KR102368268B1 (ko) | 2014-10-09 | 2022-02-28 | 바스프 에스이 | 흡착기 재생을 위한 생성물 회수 방법 |
| KR102368267B1 (ko) | 2014-10-09 | 2022-02-28 | 바스프 에스이 | 흡착기 재생을 위한 재순환 방법 |
| EA033601B1 (ru) | 2014-10-09 | 2019-11-08 | Basf Se | Способ регенерации адсорбера |
| EA033611B1 (ru) | 2014-10-09 | 2019-11-08 | Basf Se | Способ очистки органической композиции |
| ES2733399T3 (es) | 2014-10-09 | 2019-11-28 | Basf Se | Procedimiento de intercambio de calor para la regeneración de un adsorbedor |
| JP2018508557A (ja) * | 2015-03-20 | 2018-03-29 | エクソンモービル ケミカル パテンツ インコーポレイテッド | オレフィン含有炭化水素供給物をオリゴマー化生成物または水素化オリゴマー化生成物に変換する方法 |
| US11312669B2 (en) * | 2018-10-17 | 2022-04-26 | Exxonmobil Chemical Patents Inc. | Oligomerization of olefins |
| US11905227B2 (en) * | 2018-10-17 | 2024-02-20 | Exxonmobil Chemical Patents Inc. | Oligomerization of olefins |
| RU2709818C1 (ru) * | 2019-02-18 | 2019-12-23 | Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук | Способ получения олигомеров пент-1-ена в присутствии иерархического цеолита н-y |
| EP3990420A4 (en) * | 2019-06-27 | 2023-07-12 | GEVO, Inc. | OLIGOMERIZATION OF BIOLOGICALLY DERIVED OLEFINS THROUGH A CHABAZITE-TYPE ZEOLITE CATALYST |
| WO2021029377A1 (ja) * | 2019-08-09 | 2021-02-18 | 出光興産株式会社 | プロピレン４量体及びプロピレン４量体の製造方法 |
| JP2021028312A (ja) * | 2019-08-09 | 2021-02-25 | 出光興産株式会社 | プロピレン３量体及びプロピレン３量体の製造方法 |
| KR20220083701A (ko) * | 2019-10-18 | 2022-06-20 | 이데미쓰 고산 가부시키가이샤 | 프로필렌 올리고머의 제조 방법 |
| CN115196652A (zh) * | 2022-08-04 | 2022-10-18 | 南京工业大学 | 一种用于烯烃氧化的含钛沸石纳米片及其制备方法 |
| EP4455114A1 (de) | 2023-04-26 | 2024-10-30 | Evonik Oxeno GmbH & Co. KG | C8-kohlenwasserstoffzusammensetzungen und ein verfahren zu deren herstellung |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3542171A1 (de) * | 1985-11-29 | 1987-06-04 | Basf Ag | Verfahren zur herstellung von diisobuten aus isobuten |
| JPH0669974B2 (ja) * | 1987-12-17 | 1994-09-07 | 三菱化成株式会社 | 可塑剤用アルコールの製造法 |
| DE69012295T2 (de) * | 1989-11-16 | 1995-01-05 | Mobil Oil Corp | Verfahren zur Qualitätserhöhung von Leichtolefinströmen. |
| GB9012725D0 (en) * | 1990-06-07 | 1990-08-01 | Exxon Chemical Patents Inc | Process for catalytic conversion of olefins |
| WO1993016020A2 (en) * | 1992-01-30 | 1993-08-19 | Exxon Chemical Patents Inc. | Alkene oligomerization |
| KR100364560B1 (ko) * | 1994-02-22 | 2003-02-17 | 엑손 케미칼 패턴츠 인코포레이티드 | 올리고머화및올리고머화를위한촉매 |
| ZA96178B (en) * | 1995-01-18 | 1997-06-30 | Exxon Chemical Patents Inc | Organic compounds and processes for their manufacture |
| GB9502342D0 (en) * | 1995-02-07 | 1995-03-29 | Exxon Chemical Patents Inc | Hydrocarbon treatment and catalyst therefor |
| JPH09268132A (ja) * | 1996-04-03 | 1997-10-14 | Mitsubishi Chem Corp | オレフィンの二量化法 |
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2001
- 2001-04-20 AU AU2001255533A patent/AU2001255533A1/en not_active Abandoned
- 2001-04-20 AT AT06077125T patent/ATE526300T1/de not_active IP Right Cessation
- 2001-04-20 KR KR1020027013815A patent/KR100822318B1/ko not_active Expired - Fee Related
- 2001-04-20 CA CA2405574A patent/CA2405574C/en not_active Expired - Fee Related
- 2001-04-20 CN CNB018086381A patent/CN1220658C/zh not_active Expired - Fee Related
- 2001-04-20 EP EP01928702A patent/EP1280747B1/en not_active Expired - Lifetime
- 2001-04-20 DE DE60126266T patent/DE60126266T2/de not_active Expired - Lifetime
- 2001-04-20 JP JP2001580842A patent/JP5108194B2/ja not_active Expired - Fee Related
- 2001-04-20 WO PCT/US2001/012891 patent/WO2001083407A1/en not_active Ceased
- 2001-04-20 EP EP06077125A patent/EP1772445B1/en not_active Revoked
- 2001-04-20 AT AT01928702T patent/ATE352533T1/de not_active IP Right Cessation
- 2001-04-26 MY MYPI20011966A patent/MY128446A/en unknown
- 2001-06-05 TW TW090113603A patent/TW527337B/zh active
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2002
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1772445A1 (en) | 2007-04-11 |
| EP1280747B1 (en) | 2007-01-24 |
| TW527337B (en) | 2003-04-11 |
| JP2012229233A (ja) | 2012-11-22 |
| DE60126266D1 (de) | 2007-03-15 |
| WO2001083407A1 (en) | 2001-11-08 |
| EP1280747A1 (en) | 2003-02-05 |
| AU2001255533A1 (en) | 2001-11-12 |
| ATE526300T1 (de) | 2011-10-15 |
| KR100822318B1 (ko) | 2008-04-16 |
| ATE352533T1 (de) | 2007-02-15 |
| ZA200208524B (en) | 2003-06-06 |
| CN1220658C (zh) | 2005-09-28 |
| MY128446A (en) | 2007-02-28 |
| CA2405574C (en) | 2010-07-06 |
| GB0010433D0 (en) | 2000-06-14 |
| JP5572182B2 (ja) | 2014-08-13 |
| KR20020089470A (ko) | 2002-11-29 |
| JP5108194B2 (ja) | 2012-12-26 |
| CN1437569A (zh) | 2003-08-20 |
| CA2405574A1 (en) | 2001-11-08 |
| EP1772445B1 (en) | 2011-09-28 |
| JP2003531877A (ja) | 2003-10-28 |
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