JP6676063B2 - オレフィンメタセシスのための触媒系 - Google Patents
オレフィンメタセシスのための触媒系 Download PDFInfo
- Publication number
- JP6676063B2 JP6676063B2 JP2017545707A JP2017545707A JP6676063B2 JP 6676063 B2 JP6676063 B2 JP 6676063B2 JP 2017545707 A JP2017545707 A JP 2017545707A JP 2017545707 A JP2017545707 A JP 2017545707A JP 6676063 B2 JP6676063 B2 JP 6676063B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- metathesis
- catalyst system
- zone
- weight
- 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.)
- Active
Links
- 239000003054 catalyst Substances 0.000 title claims description 131
- 238000005865 alkene metathesis reaction Methods 0.000 title claims description 16
- 238000005649 metathesis reaction Methods 0.000 claims description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 31
- 150000001336 alkenes Chemical class 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 25
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 24
- 229910021536 Zeolite Inorganic materials 0.000 claims description 23
- 239000010457 zeolite Substances 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 238000011144 upstream manufacturing Methods 0.000 claims description 12
- 239000011230 binding agent Substances 0.000 claims description 11
- 229910052723 transition metal Inorganic materials 0.000 claims description 10
- 230000003197 catalytic effect Effects 0.000 claims description 9
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052748 manganese Inorganic materials 0.000 claims description 9
- 239000000377 silicon dioxide Substances 0.000 claims description 9
- 150000003624 transition metals Chemical class 0.000 claims description 9
- 150000001450 anions Chemical class 0.000 claims description 8
- 229910052791 calcium Inorganic materials 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 8
- 229910052725 zinc Inorganic materials 0.000 claims description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 6
- 229910001657 ferrierite group Inorganic materials 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 4
- 229910052733 gallium Inorganic materials 0.000 claims description 4
- 229910052738 indium Inorganic materials 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 229910052702 rhenium Inorganic materials 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 3
- 239000010937 tungsten Substances 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 9
- 239000011777 magnesium Substances 0.000 description 7
- 239000011572 manganese Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000395 magnesium oxide Substances 0.000 description 5
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011651 chromium Substances 0.000 description 4
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 4
- 150000004679 hydroxides Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 150000002823 nitrates Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 150000004673 fluoride salts Chemical class 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229910001930 tungsten oxide Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005686 cross metathesis reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 229910021476 group 6 element Inorganic materials 0.000 description 1
- 229910021474 group 7 element Inorganic materials 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
Classifications
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/19—Catalysts containing parts with different compositions
-
- 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
- B01J23/007—Mixed salts
-
- 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
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/20—Carbon compounds
- B01J27/232—Carbonates
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
- B01J27/25—Nitrates
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/076—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/16—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J29/166—Y-type faujasite
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
- B01J29/48—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively containing arsenic, antimony, bismuth, vanadium, niobium tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/7038—MWW-type, e.g. MCM-22, ERB-1, ITQ-1, PSH-3 or SSZ-25
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/78—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J29/7815—Zeolite Beta
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/78—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J29/7876—MWW-type, e.g. MCM-22, ERB-1, ITQ-1, PSH-3 or SSZ-25
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/04—Mixing
-
- 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
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
- B01J38/50—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using organic liquids
- B01J38/52—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using organic liquids oxygen-containing
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
- C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
-
- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
-
- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/32—Manganese, technetium or rhenium
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/16—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J29/163—X-type faujasite
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/65—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the ferrierite type, e.g. types ZSM-21, ZSM-35 or ZSM-38, as exemplified by patent documents US4046859, US4016245 and US4046859, respectively
- B01J29/69—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the ferrierite type, e.g. types ZSM-21, ZSM-35 or ZSM-38, as exemplified by patent documents US4046859, US4016245 and US4046859, respectively containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- C07C2521/08—Silica
-
- 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
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- 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
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/24—Chromium, molybdenum or tungsten
- C07C2523/30—Tungsten
-
- 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
- C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
-
- 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
- C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- C07C2529/16—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
[My+ 1−xM’z+ x(OH)2]a+(Ar−)n・b(H2O)
式中
Mは第1の金属であり;
M’は第2の金属であり;
Aはアニオンであり;
xは、好ましくは0.1〜0.9の範囲の数値であり;
yは、好ましくは1又は2に等しい第1の金属の電荷数であり;
zは、好ましくは3又は4に等しい第2の金属の電荷数であり;
aは、x、y及びzによって決まり、好ましくはa=(1−x)y+xz−2であり;
rは、アニオンの電荷数であり;
nは、a及びrによって決まり、好ましくはn=a/rであり;
bは、好ましくは0〜10の範囲の水分子の数である。
メタセシス触媒粉末は、95重量%のシリカ及び5重量%のY−ゼオライトを含む担体上に9重量%のWO3を堆積させ、次いで、Mg−Al−CO3層状複水酸化物と重量で10:1の比で物理的に混合することによって得られる。触媒粉末を管反応器に充填し、次いで、エテン及び2−ブテンを含む供給流を供給して触媒上で350℃、22bar(ゲージ)で反応させ、プロペンを製造した。得られたプロペンの収率は61重量%であった。
95重量%のシリカ及び5重量%のY−ゼオライトを含む担体上の9重量% WO3とMg−Al−CO3層状複水酸化物とを重量で10:1の比で物理的に混合することによってメタセシス触媒を得た。2.2gの白土(バインダー)及び110mLの脱塩水を110gのメタセシス触媒に加えた。粉末と水は、すぐにスレッシュして(threshed)バインダーを活性化し、均質で湿った予備押出触媒を得る。次に、湿った触媒を押出機に供給する。次に、押出機から得られる触媒押出物をオーブン内で150℃で3〜4時間乾燥させる。得られた触媒で反応試験を行った。この試験では、エテンと2−ブテンを触媒上で、350℃、22bar(ゲージ)で反応させてプロペンを生成し、比較のための以下の上流系ゾーンの3つの選択肢がある。
さまざまな触媒系を表2に示す通り調製した。
本願発明には以下の態様が含まれる。
項1.
a)層状複水酸化物を実質的に含む第1系ゾーン;及び
b)メタセシス触媒を含む第2系ゾーン
を含む、オレフィンメタセシスのための触媒系。
項2.
前記第1系ゾーンが、前記第2系ゾーンに対して上流に配置される、項1に記載の触媒系。
項3.
前記メタセシス触媒が、無機担体上に担持された元素周期表の第VIA族及び第VIIA族から選択される遷移金属を含む、項1又は2に記載の触媒系。
項4.
前記メタセシス触媒が、0.1〜60重量部、好ましくは0.5〜30重量部、より好ましくは1〜20重量部のゼオライトをさらに含む、項1から3のいずれかに記載の触媒系。
項5.
前記メタセシス触媒が、0.1〜80重量部、好ましくは0.5〜50重量部、より好ましくは1〜30重量部の層状複水酸化物をさらに含む、項1から4のいずれかに記載の触媒系。
項6.
前記メタセシス触媒が、バインダーをさらに含む、項1から5のいずれかに記載の触媒系。
項7.
前記第1系ゾーン内に含まれる前記層状複水酸化物と、前記第2系ゾーン内に含まれる前記メタセシス触媒との重量比(層状複水酸化物 対 メタセシス触媒の比)が、重量で0.5:1〜10:1、好ましくは1:1〜5:1、さらに好ましくは2:1〜4:1である、項1から6のいずれかに記載の触媒系。
項8.
前記メタセシス触媒の前記遷移金属が、モリブデン、タングステン及びレニウム並びにこれらの混合物からなる群から選択される、項3から7のいずれかに記載の触媒系。
項9.
前記メタセシス触媒の前記無機担体が、シリカ、アルミナ、チタニア、ジルコニア及びこれらの混合物からなる群から選択され、好ましくはシリカである、項3から8のいずれかに記載の触媒系。
項10.
前記メタセシス触媒の前記ゼオライトが、ZSM−5、X−ゼオライト、Y−ゼオライト、β−ゼオライト、MCM−22、フェリエライト及びこれらの混合物、好ましくはZSM−5、Y−ゼオライト及びフェリエライトからなる群から選択される、項4から9のいずれかに記載の触媒系。
項11.
前記第1系ゾーン内に含まれる前記層状複水酸化物及び/又は前記メタセシス触媒の前記層状複水酸化物が、Li、Ca、Mg、Mn、Fe、Co、Ni、Cu、Zn及びこれらの混合物、好ましくはCa、Mg、Zn及びこれらの混合物からなる群から選択される第1の金属を含む、項1から10のいずれかに記載の触媒系。
項12.
前記第1系ゾーン内に含まれる前記層状複水酸化物及び/又は前記メタセシス触媒の前記層状複水酸化物が、Al、Ga、In、Mn、Fe、Co、Cr、Ni、V、Ti、Zr、Y及びこれらの混合物からなる群から選択される、好ましくはAlである、第2の金属を含む、項1から11のいずれかに記載の触媒系。
項13.
前記第1系ゾーン内に含まれる前記層状複水酸化物及び/又は前記メタセシス触媒の前記層状複水酸化物が、クロライド、ブロマイド、カーボネート、ビカーボネート、水素ホスフェート、二水素ホスフェート、ニトリト、ボレート、ナイトレート、サルフェート、ホスフェート、ヒドロキシド、フルオリド、ヨージド及びこれらの混合物からなる群から選択される、好ましくはカーボネート及び/又はナイトレートである、アニオンを含む、項1から12のいずれかに記載の触媒系。
項14.
オレフィンを含む供給流を、項1から13のいずれかに記載の触媒系と接触させる工程を含むオレフィンメタセシスプロセス。
項15.
前記供給流が、C2直鎖オレフィン、C3直鎖オレフィン、C4直鎖オレフィン、C5直鎖オレフィン、C6直鎖オレフィン及びこれらの混合物からなる群から選択される直鎖オレフィンを含む、項14に記載のオレフィンメタセシスプロセス。
Claims (14)
- a)層状複水酸化物を含む第1系ゾーンであって、何らかの別の触媒活性種を、含まないか、または第1系ゾーン及び触媒系の触媒特性に著しく影響しない量のみを含む、第1系ゾーン;及び
b)メタセシス触媒を含む第2系ゾーン
を含み、前記第1系ゾーンが前記第2系ゾーンに対して上流に配置される、オレフィンメタセシスのための触媒系。 - 前記メタセシス触媒が、無機担体上に担持された元素周期表の第VIA族及び第VIIA族から選択される遷移金属を含む、請求項1に記載の触媒系。
- 前記メタセシス触媒が、0.1〜60重量部、好ましくは0.5〜30重量部、より好ましくは1〜20重量部のゼオライトをさらに含む、請求項1又は2に記載の触媒系。
- 前記メタセシス触媒が、0.1〜80重量部、好ましくは0.5〜50重量部、より好ましくは1〜30重量部の層状複水酸化物をさらに含む、請求項1から3のいずれかに記載の触媒系。
- 前記メタセシス触媒が、バインダーをさらに含む、請求項1から4のいずれかに記載の触媒系。
- 前記第1系ゾーン内に含まれる前記層状複水酸化物と、前記第2系ゾーン内に含まれる前記メタセシス触媒との重量比(層状複水酸化物 対 メタセシス触媒の比)が、重量で0.5:1〜10:1、好ましくは1:1〜5:1、さらに好ましくは2:1〜4:1である、請求項1から5のいずれかに記載の触媒系。
- 前記メタセシス触媒の前記遷移金属が、モリブデン、タングステン及びレニウム並びにこれらの混合物からなる群から選択される、請求項2に記載の触媒系。
- 前記メタセシス触媒の前記無機担体が、シリカ、アルミナ、チタニア、ジルコニア及びこれらの混合物からなる群から選択され、好ましくはシリカである、請求項2に記載の触媒系。
- 前記メタセシス触媒の前記ゼオライトが、ZSM−5、X−ゼオライト、Y−ゼオライト、β−ゼオライト、MCM−22、フェリエライト及びこれらの混合物、好ましくはZSM−5、Y−ゼオライト及びフェリエライトからなる群から選択される、請求項3に記載の触媒系。
- 前記層状複水酸化物が、Li、Ca、Mg、Mn、Fe、Co、Ni、Cu、Zn及びこれらの混合物、好ましくはCa、Mg、Zn及びこれらの混合物からなる群から選択される第1の金属を含む、請求項1から9のいずれかに記載の触媒系。
- 前記層状複水酸化物が、Al、Ga、In、Mn、Fe、Co、Cr、Ni、V、Ti、Zr、Y及びこれらの混合物からなる群から選択される、好ましくはAlである、第2の金属を含む、請求項1から10のいずれかに記載の触媒系。
- 前記層状複水酸化物が、クロライド、ブロマイド、カーボネート、ビカーボネート、水素ホスフェート、二水素ホスフェート、ニトリト、ボレート、ナイトレート、サルフェート、ホスフェート、ヒドロキシド、フルオリド、ヨージド及びこれらの混合物からなる群から選択される、好ましくはカーボネート及び/又はナイトレートである、アニオンを含む、請求項1から11のいずれかに記載の触媒系。
- オレフィンを含む供給流を、請求項1から12のいずれかに記載の触媒系と接触させる工程を含むオレフィンメタセシスプロセス。
- 前記供給流が、C2直鎖オレフィン、C3直鎖オレフィン、C4直鎖オレフィン、C5直鎖オレフィン、C6直鎖オレフィン及びこれらの混合物からなる群から選択される直鎖オレフィンを含む、請求項13に記載のオレフィンメタセシスプロセス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP15160033.5 | 2015-03-20 | ||
EP15160033.5A EP3069788A1 (en) | 2015-03-20 | 2015-03-20 | Catalyst system for olefin metathesis |
PCT/EP2016/055700 WO2016150794A1 (en) | 2015-03-20 | 2016-03-16 | Catalyst system for olefin metathesis |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2018509284A JP2018509284A (ja) | 2018-04-05 |
JP6676063B2 true JP6676063B2 (ja) | 2020-04-08 |
Family
ID=52727004
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017545707A Active JP6676063B2 (ja) | 2015-03-20 | 2016-03-16 | オレフィンメタセシスのための触媒系 |
Country Status (11)
Country | Link |
---|---|
US (1) | US10350587B2 (ja) |
EP (2) | EP3069788A1 (ja) |
JP (1) | JP6676063B2 (ja) |
KR (1) | KR102510961B1 (ja) |
CN (1) | CN107206364B (ja) |
ES (1) | ES2856957T3 (ja) |
PL (1) | PL3238819T3 (ja) |
SA (1) | SA517381923B1 (ja) |
SG (2) | SG10201901234PA (ja) |
TW (1) | TWI721970B (ja) |
WO (1) | WO2016150794A1 (ja) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016068814A1 (en) | 2014-10-28 | 2016-05-06 | Terramark Markencreation Gmbh | Metathesis catalyst on mixed metal oxide-zeolite support and process for use thereof |
EP3050621A1 (en) | 2015-01-30 | 2016-08-03 | Terramark Markencreation GmbH | Metathesis catalyst and process for producing olefin |
EP3335791B1 (en) | 2016-12-13 | 2020-04-08 | SMH Co., Ltd. | Catalyst system and process utilizing the catalyst system |
EP3554688B1 (en) | 2016-12-13 | 2023-08-16 | SMH Co., Ltd. | Hydrocarbon conversion catalyst system |
EP3335792B1 (en) * | 2016-12-13 | 2020-04-01 | SMH Co., Ltd. | Catalyst system and process for the conversion of a hydrocarbon feed comprising a saturated hydrocarbon compound to olefin products |
WO2019150335A2 (en) * | 2018-02-05 | 2019-08-08 | SMH Co., Ltd | Catalysts, systems, and processes for regulating a contacting state in producing light olefins from paraffins |
CN110965076A (zh) * | 2019-12-06 | 2020-04-07 | 吉林大学 | 一种双功能三维分层核壳结构电解水电极的制备方法 |
US11027270B1 (en) * | 2021-01-12 | 2021-06-08 | King Abdulaziz University | Method of performing coupling reactions |
WO2024089042A1 (en) * | 2022-10-24 | 2024-05-02 | Basell Poliolefine Italia S.R.L. | Depolymerization catalyst system and process |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3658929A (en) | 1970-11-16 | 1972-04-25 | Phillips Petroleum Co | Conversion of olefins |
US4522936A (en) | 1983-03-21 | 1985-06-11 | Phillips Petroleum Company | Metathesis catalyst |
US4575575A (en) | 1984-04-05 | 1986-03-11 | Phillips Petroleum Company | Catalysts and process for olefin conversion |
US5120894A (en) | 1988-09-19 | 1992-06-09 | Lyondell Petrochemical Company | Olefin conversion process |
US5120896A (en) * | 1989-12-21 | 1992-06-09 | Shell Oil Company | Concurrent isomerization and disproportionation of olefins |
DE19813720A1 (de) * | 1998-03-27 | 1999-09-30 | Basf Ag | Verfahren zur Herstellung von Olefinen |
JP2002143682A (ja) * | 2000-09-04 | 2002-05-21 | Showa Denko Kk | オレフィンのメタセシス反応触媒 |
DE102005009596A1 (de) | 2005-02-28 | 2006-08-31 | Basf Ag | Verfahren zur Metathese umfassend die Reinigung der Ausgangsstoffe |
KR100912882B1 (ko) * | 2005-03-03 | 2009-08-20 | 미쓰이 가가쿠 가부시키가이샤 | 올레핀류의 제조 방법 |
WO2007055361A1 (ja) * | 2005-11-14 | 2007-05-18 | Mitsui Chemicals, Inc. | バイオマス由来の炭素を含むプロピレンの製造方法 |
JP5816088B2 (ja) * | 2008-09-04 | 2015-11-18 | ラムス テクノロジー インク | オレフィン異性化およびメタセシス触媒 |
EP2196444A1 (en) * | 2008-12-11 | 2010-06-16 | Total Petrochemicals Research Feluy | Process to make alpha olefins from ethanol |
US8722557B2 (en) | 2008-12-30 | 2014-05-13 | Lyondell Chemical Technology, L.P. | Catalyst regeneration |
WO2010113993A1 (ja) * | 2009-04-01 | 2010-10-07 | 三井化学株式会社 | オレフィンの製造方法 |
CA2786607A1 (en) * | 2010-01-08 | 2011-07-14 | Gevo, Inc. | Integrated methods of preparing renewable chemicals |
FR2977890B1 (fr) * | 2011-07-15 | 2013-07-19 | IFP Energies Nouvelles | Procede de metathese des olefines utilisant un catalyseur a base d'un materiau spherique comprenant des particules metalliques oxydes piegees dans une matrice mesostructuree |
EP2975013A1 (en) * | 2013-04-03 | 2016-01-20 | Scg Chemicals Co. Ltd. | Catalyst for converting paraffin to olefin |
WO2016068814A1 (en) | 2014-10-28 | 2016-05-06 | Terramark Markencreation Gmbh | Metathesis catalyst on mixed metal oxide-zeolite support and process for use thereof |
EP3050621A1 (en) | 2015-01-30 | 2016-08-03 | Terramark Markencreation GmbH | Metathesis catalyst and process for producing olefin |
-
2015
- 2015-03-20 PL PL17171366T patent/PL3238819T3/pl unknown
- 2015-03-20 EP EP15160033.5A patent/EP3069788A1/en not_active Withdrawn
- 2015-03-20 EP EP17171366.2A patent/EP3238819B1/en active Active
- 2015-03-20 ES ES17171366T patent/ES2856957T3/es active Active
-
2016
- 2016-03-16 JP JP2017545707A patent/JP6676063B2/ja active Active
- 2016-03-16 SG SG10201901234PA patent/SG10201901234PA/en unknown
- 2016-03-16 CN CN201680005693.0A patent/CN107206364B/zh active Active
- 2016-03-16 SG SG11201705448VA patent/SG11201705448VA/en unknown
- 2016-03-16 WO PCT/EP2016/055700 patent/WO2016150794A1/en active Application Filing
- 2016-03-16 KR KR1020177026285A patent/KR102510961B1/ko active IP Right Grant
- 2016-03-16 US US15/515,720 patent/US10350587B2/en active Active
- 2016-03-18 TW TW105108487A patent/TWI721970B/zh active
-
2017
- 2017-07-13 SA SA517381923A patent/SA517381923B1/ar unknown
Also Published As
Publication number | Publication date |
---|---|
EP3238819A1 (en) | 2017-11-01 |
JP2018509284A (ja) | 2018-04-05 |
EP3238819B1 (en) | 2020-11-04 |
SA517381923B1 (ar) | 2021-03-31 |
KR102510961B1 (ko) | 2023-03-16 |
US10350587B2 (en) | 2019-07-16 |
CN107206364B (zh) | 2021-05-25 |
TW201634431A (zh) | 2016-10-01 |
EP3069788A1 (en) | 2016-09-21 |
CN107206364A (zh) | 2017-09-26 |
KR20170128339A (ko) | 2017-11-22 |
SG11201705448VA (en) | 2017-10-30 |
PL3238819T3 (pl) | 2021-08-02 |
SG10201901234PA (en) | 2019-03-28 |
ES2856957T3 (es) | 2021-09-28 |
US20170297009A1 (en) | 2017-10-19 |
WO2016150794A1 (en) | 2016-09-29 |
TWI721970B (zh) | 2021-03-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6676063B2 (ja) | オレフィンメタセシスのための触媒系 | |
JP6595606B2 (ja) | オレフィンを製造するための触媒及びプロセス | |
JP4339681B2 (ja) | 不飽和オレフィンの選択的水素化のための選択的水素化触媒、及びその使用 | |
US9713804B2 (en) | Catalyst composition for the dehydrogenation of alkanes | |
JP2011148720A (ja) | ブタジエンの製造方法 | |
EP2184106A1 (en) | Process for reactivation of metathesis catalysts and process for production of olefins comprising the reactivation | |
US7491860B2 (en) | Dehydrogenation process | |
JP6446033B2 (ja) | 不飽和炭化水素の製造方法 | |
US9527785B2 (en) | Method of forming C5 di-olefins | |
EP4313402A1 (en) | Use of a catalyst system in the production of 1,3-butadiene from ethanol in two stages |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180919 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20190708 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190730 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20191010 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20191112 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200121 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20200212 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20200311 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6676063 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |