TW201127785A - Process for the oxidative coupling of hydrocarbons - Google Patents
Process for the oxidative coupling of hydrocarbons Download PDFInfo
- Publication number
- TW201127785A TW201127785A TW099120468A TW99120468A TW201127785A TW 201127785 A TW201127785 A TW 201127785A TW 099120468 A TW099120468 A TW 099120468A TW 99120468 A TW99120468 A TW 99120468A TW 201127785 A TW201127785 A TW 201127785A
- Authority
- TW
- Taiwan
- Prior art keywords
- catalyst
- group
- methane
- elements
- reactor
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 57
- 238000005691 oxidative coupling reaction Methods 0.000 title claims abstract description 33
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 31
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 171
- 239000003054 catalyst Substances 0.000 claims abstract description 137
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 93
- 238000006243 chemical reaction Methods 0.000 claims abstract description 67
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000001301 oxygen Substances 0.000 claims abstract description 44
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 44
- 230000001590 oxidative effect Effects 0.000 claims abstract description 29
- 230000000737 periodic effect Effects 0.000 claims abstract description 17
- 229910052792 caesium Inorganic materials 0.000 claims abstract description 14
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 14
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 13
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 13
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 13
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 12
- 229910052746 lanthanum Inorganic materials 0.000 claims abstract description 9
- 229910052712 strontium Inorganic materials 0.000 claims abstract description 7
- 229910052788 barium Inorganic materials 0.000 claims abstract description 6
- 229910052735 hafnium Inorganic materials 0.000 claims abstract description 6
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 6
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 6
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 6
- 150000002602 lanthanoids Chemical group 0.000 claims abstract description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 61
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 22
- 239000004215 Carbon black (E152) Substances 0.000 claims description 15
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 11
- 239000005977 Ethylene Substances 0.000 claims description 11
- 238000001354 calcination Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- -1 methane oxime Chemical class 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 66
- 239000000047 product Substances 0.000 description 47
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 44
- 239000000395 magnesium oxide Substances 0.000 description 22
- 239000000758 substrate Substances 0.000 description 22
- 238000012360 testing method Methods 0.000 description 21
- 239000010453 quartz Substances 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000007789 gas Substances 0.000 description 13
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000011575 calcium Substances 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 238000009826 distribution Methods 0.000 description 9
- 238000005470 impregnation Methods 0.000 description 9
- 239000001307 helium Substances 0.000 description 7
- 229910052734 helium Inorganic materials 0.000 description 7
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 230000011987 methylation Effects 0.000 description 6
- 238000007069 methylation reaction Methods 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 238000006356 dehydrogenation reaction Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000356 contaminant Substances 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000012494 Quartz wool Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910000420 cerium oxide Inorganic materials 0.000 description 2
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229920005669 high impact polystyrene Polymers 0.000 description 2
- 239000004797 high-impact polystyrene Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000001997 phenyl group Polymers [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 238000004227 thermal cracking Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 229910052689 Holmium Inorganic materials 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 229910052765 Lutetium Inorganic materials 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000004951 benzene Polymers 0.000 description 1
- 150000001555 benzenes Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- VNSUUHSVDYHVDK-UHFFFAOYSA-N cyclohexa-2,5-diene-1,4-dione;ethene Chemical group C=C.O=C1C=CC(=O)C=C1 VNSUUHSVDYHVDK-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011026 diafiltration Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- DHEQXMRUPNDRPG-UHFFFAOYSA-N strontium nitrate Inorganic materials [Sr+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O DHEQXMRUPNDRPG-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009736 wetting Methods 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
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
-
- 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
- C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
- C07C2/82—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen oxidative coupling
- C07C2/84—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen oxidative coupling catalytic
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/63—Platinum group metals with rare earths or actinides
-
- 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
- B01J6/00—Heat treatments such as Calcining; Fusing ; Pyrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/067—C8H10 hydrocarbons
- C07C15/073—Ethylbenzene
-
- 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
-
- 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
- C07C2521/10—Magnesium; Oxides or hydroxides thereof
-
- 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
-
- 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
- C07C2523/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the alkali- or alkaline earth metals or beryllium
-
- 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
- C07C2523/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of rare earths
-
- 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
- C07C2523/32—Manganese, technetium or rhenium
- C07C2523/36—Rhenium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/494,138 US8450546B2 (en) | 2009-06-29 | 2009-06-29 | Process for the oxidative coupling of hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201127785A true TW201127785A (en) | 2011-08-16 |
Family
ID=43381464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099120468A TW201127785A (en) | 2009-06-29 | 2010-06-23 | Process for the oxidative coupling of hydrocarbons |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US8450546B2 (enExample) |
| EP (1) | EP2448887A4 (enExample) |
| JP (1) | JP2012532105A (enExample) |
| KR (1) | KR20120115081A (enExample) |
| CN (1) | CN102471183A (enExample) |
| AU (1) | AU2010266506A1 (enExample) |
| EA (1) | EA201270080A1 (enExample) |
| TW (1) | TW201127785A (enExample) |
| WO (1) | WO2011002665A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8912381B2 (en) * | 2009-06-29 | 2014-12-16 | Fina Technology, Inc. | Process for the oxidative coupling of methane |
| US8399726B2 (en) | 2010-04-20 | 2013-03-19 | Fina Technology Inc | Reactors and processes for the oxidative coupling of hydrocarbons |
| CA2800142C (en) | 2010-05-24 | 2018-06-05 | Siluria Technologies, Inc. | Nanowire catalysts |
| US8921256B2 (en) | 2011-05-24 | 2014-12-30 | Siluria Technologies, Inc. | Catalysts for petrochemical catalysis |
| HK1202275A1 (en) | 2011-11-29 | 2015-09-25 | Siluria Technologies, Inc. | Nanowire catalysts and methods for their use and preparation |
| WO2013106771A2 (en) | 2012-01-13 | 2013-07-18 | Siluria Technologies, Inc. | Process for separating hydrocarbon compounds |
| US9446397B2 (en) | 2012-02-03 | 2016-09-20 | Siluria Technologies, Inc. | Method for isolation of nanomaterials |
| WO2013177433A2 (en) | 2012-05-24 | 2013-11-28 | Siluria Technologies, Inc. | Oxidative coupling of methane systems and methods |
| AU2013266189B2 (en) | 2012-05-24 | 2018-01-04 | Lummus Technology Llc | Catalysts comprising catalytic nanowires and their use |
| US9969660B2 (en) | 2012-07-09 | 2018-05-15 | Siluria Technologies, Inc. | Natural gas processing and systems |
| AU2013355038B2 (en) | 2012-12-07 | 2017-11-02 | Lummus Technology Llc | Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products |
| US20140274671A1 (en) | 2013-03-15 | 2014-09-18 | Siluria Technologies, Inc. | Catalysts for petrochemical catalysis |
| WO2015081122A2 (en) | 2013-11-27 | 2015-06-04 | Siluria Technologies, Inc. | Reactors and systems for oxidative coupling of methane |
| CA3123783A1 (en) | 2014-01-08 | 2015-07-16 | Lummus Technology Llc | Ethylene-to-liquids systems and methods |
| US10377682B2 (en) | 2014-01-09 | 2019-08-13 | Siluria Technologies, Inc. | Reactors and systems for oxidative coupling of methane |
| US9701597B2 (en) | 2014-01-09 | 2017-07-11 | Siluria Technologies, Inc. | Oxidative coupling of methane implementations for olefin production |
| CA2947483C (en) | 2014-05-02 | 2023-08-01 | Siluria Technologies, Inc. | Heterogeneous catalysts |
| PL3194070T3 (pl) | 2014-09-17 | 2021-06-14 | Lummus Technology Llc | Katalizatory do utleniającego sprzęgania metanu i utleniającego odwodornienia etanu |
| US10793490B2 (en) | 2015-03-17 | 2020-10-06 | Lummus Technology Llc | Oxidative coupling of methane methods and systems |
| US9334204B1 (en) | 2015-03-17 | 2016-05-10 | Siluria Technologies, Inc. | Efficient oxidative coupling of methane processes and systems |
| US20160289143A1 (en) | 2015-04-01 | 2016-10-06 | Siluria Technologies, Inc. | Advanced oxidative coupling of methane |
| DE112016002573T5 (de) | 2015-06-08 | 2018-03-22 | Sabic Global Technologies B.V. | Oxidative Methankupplung mit La-Ce Katalysatoren |
| US9328297B1 (en) | 2015-06-16 | 2016-05-03 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
| US20170107162A1 (en) | 2015-10-16 | 2017-04-20 | Siluria Technologies, Inc. | Separation methods and systems for oxidative coupling of methane |
| CA3019396A1 (en) | 2016-04-13 | 2017-10-19 | Siluria Technologies, Inc. | Oxidative coupling of methane for olefin production |
| WO2018118105A1 (en) | 2016-12-19 | 2018-06-28 | Siluria Technologies, Inc. | Methods and systems for performing chemical separations |
| JP2020521811A (ja) | 2017-05-23 | 2020-07-27 | ラマス テクノロジー リミテッド ライアビリティ カンパニー | メタン酸化カップリングプロセスの統合 |
| RU2020102298A (ru) | 2017-07-07 | 2021-08-10 | Люммус Текнолоджи Ллс | Системы и способы окислительного сочетания метана |
| AU2020215051A1 (en) | 2019-01-30 | 2021-07-22 | Lummus Technology Llc | Catalysts for oxidative coupling of methane |
| EP4396156A4 (en) | 2021-08-31 | 2025-08-27 | Lummus Technology Inc | METHODS AND SYSTEMS FOR OXIDATIVE COUPLING OF METHANE |
Family Cites Families (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4239658A (en) * | 1979-04-05 | 1980-12-16 | Exxon Research & Engineering Co. | Catalysts for the conversion of relatively low molecular weight hydrocarbons to higher molecular weight hydrocarbons and the regeneration of the catalysts |
| EP0054249B2 (en) * | 1980-12-09 | 1993-04-21 | Toray Industries, Inc. | Immunoparticles and process for preparing the same |
| US4523049A (en) * | 1984-04-16 | 1985-06-11 | Atlantic Richfield Company | Methane conversion process |
| US4704493A (en) * | 1983-10-31 | 1987-11-03 | Chevron Corporation | Conversions of low molecular weight hydrocarbons to higher molecular weight hydrocarbons using a metal compound-containing catalyst (II-A) |
| US4704487A (en) * | 1983-10-31 | 1987-11-03 | Chevron Research Company | Conversions of low molecular weight hydrocarbons to higher molecular weight hydrocarbons using a metal compound-containing catalyst (IV-B) |
| US4547610A (en) * | 1984-04-16 | 1985-10-15 | Atlantic Richfield Company | Methane conversion |
| ATE81606T1 (de) * | 1984-04-16 | 1992-11-15 | Atlantic Richfield Co | Traegerkatalysatoren und ihre verwendung zur umwandlung von methan und zur dehydrogenierung von kohlenwasserstoffen. |
| US4968655A (en) * | 1985-02-28 | 1990-11-06 | Amoco Corporation | Catalysts for conversion of a lower alkane |
| US5157188A (en) * | 1985-03-19 | 1992-10-20 | Phillips Petroleum Company | Methane conversion |
| US4672145A (en) * | 1985-03-19 | 1987-06-09 | Phillips Petroleum Company | Composition of matter and method of oxidative conversion of organic compounds therewith |
| US4658077A (en) * | 1985-06-07 | 1987-04-14 | Phillips Petroleum Company | Composition of matter and method of oxidative conversion of organic compounds therewith |
| US4895823A (en) * | 1985-03-19 | 1990-01-23 | Phillips Petroleum Company | Composition of matter for oxidative conversion of organic compounds |
| US4982038A (en) * | 1985-03-19 | 1991-01-01 | Phillips Petroleum Company | Oxidative methylation of organic compounds |
| US4950836A (en) * | 1985-06-07 | 1990-08-21 | Phillips Petroleum Company | Oxidative methylation of organic compounds |
| US4658076A (en) * | 1985-03-19 | 1987-04-14 | Phillips Petroleum Company | Composition of matter and method of oxidative conversion of organic compounds therewith |
| US4775654A (en) * | 1985-03-19 | 1988-10-04 | Phillips Petroleum Company | Composition of matter |
| US5210357A (en) * | 1985-06-07 | 1993-05-11 | Phillips Petroleum Company | Composition of matter and method of oxidative conversion of organic compounds therewith |
| US5146027A (en) * | 1985-05-24 | 1992-09-08 | Atlantic Richfield Co. | Methane conversion process |
| US5959170A (en) * | 1985-05-24 | 1999-09-28 | Atlantic Richfield Company | Methane conversion process |
| US4620057A (en) * | 1985-06-07 | 1986-10-28 | Phillips Petroleum Company | Methane conversion |
| US5105045A (en) * | 1985-06-07 | 1992-04-14 | Phillips Petroleum Company | Method of oxidative conversion |
| US4774216A (en) * | 1985-06-07 | 1988-09-27 | Phillips Petroleum Company | Composition of matter for oxidative conversion of organic compounds |
| US5160502A (en) * | 1986-12-22 | 1992-11-03 | Phillips Petroleum Company | Composition of matter and method of oxidative conversion of organic compounds therewith |
| US5118899A (en) * | 1986-12-22 | 1992-06-02 | Phillips Petroleum Company | Composition of matter and method of oxidative conversion of organic compounds therewith |
| US5087787A (en) * | 1986-12-29 | 1992-02-11 | Phillips Petroleum Company | Method of oxidative conversion |
| US4886931A (en) * | 1987-06-04 | 1989-12-12 | The Standard Oil Company | Upgrading low molecular weight hydrocarbons |
| JPH0674215B2 (ja) * | 1987-12-11 | 1994-09-21 | 宇部興産株式会社 | 炭化水素の製造方法 |
| GB8802731D0 (en) * | 1988-02-06 | 1988-03-09 | British Petroleum Co Plc | Chemical process |
| US4826796A (en) * | 1988-03-28 | 1989-05-02 | Institute Of Gas Technology | Mixed basic metal oxide catalyst for oxidative coupling of methane |
| US4950827A (en) * | 1988-03-28 | 1990-08-21 | Institute Of Gas Technology | Oxidative coupling of aliphatic and alicyclic hydrocarbons with aliphatic and alicyclic substituted aromatic hydrocarbons |
| US4956327A (en) * | 1989-05-31 | 1990-09-11 | Institute Of Gas Technology | Mixed basic metal oxide/sulfide catalyst |
| EP0335130A1 (en) * | 1988-03-28 | 1989-10-04 | Institute of Gas Technology | Mixed basic metal oxide catalyst |
| US4950830A (en) * | 1988-03-28 | 1990-08-21 | Institute Of Gas Technology | Dehydration of aliphatic and alicyclic hydrocarbons and aliphatic and alicyclic substituted aromatic hydrocarbons |
| FR2629451B1 (fr) * | 1988-04-05 | 1991-07-12 | Inst Francais Du Petrole | Procede de production d'olefines a partir du gaz naturel |
| US5028577A (en) * | 1989-01-11 | 1991-07-02 | Amoco Corporation | Lower alkane conversion catalysts |
| JPH0822825B2 (ja) * | 1989-01-26 | 1996-03-06 | 日本鋼管株式会社 | エチルベンゼンとスチレンの製造方法 |
| JPH02225425A (ja) * | 1989-02-28 | 1990-09-07 | Ube Ind Ltd | マグネシアを触媒の一成分とする炭化水素の製造方法 |
| US5026945A (en) * | 1989-09-19 | 1991-06-25 | Union Carbide Chemicals And Plastics Technology Corporation | Perovskite catalysts for oxidative coupling |
| CA2016675A1 (en) * | 1990-05-14 | 1991-11-14 | Kevin James Smith | Process for the oxidative coupling of methane to higher hydrocarbons |
| US5132482A (en) * | 1990-06-14 | 1992-07-21 | Alberta Research Council | Process for the oxidative coupling of methane to higher hydrocarbons |
| IT1244484B (it) * | 1990-12-21 | 1994-07-15 | Eniricerche Spa | Procedimento e catalizzatore per la trasformazione del metano in prodotti idrocarburici superiori |
| US5097086A (en) * | 1991-05-31 | 1992-03-17 | Institute Of Gas Technology | Liquid catalyst for oxidative coupling reactions |
| JPH04368342A (ja) * | 1991-06-17 | 1992-12-21 | Sekiyu Shigen Kaihatsu Kk | メタンを原料とするエタン、エチレンの製造方法 |
| JPH059133A (ja) * | 1991-06-28 | 1993-01-19 | Sekiyu Shigen Kaihatsu Kk | メタンからエタン、エチレンの製造方法 |
| US5763722A (en) * | 1992-12-11 | 1998-06-09 | Repsol Petroleo S.A. | Method for the methane chemical conversion into C2 hydrocarbons |
| JPH1025257A (ja) * | 1996-07-12 | 1998-01-27 | Toyota Motor Corp | メチル基をビニル基に転化する方法 |
| US5780003A (en) * | 1996-08-23 | 1998-07-14 | Uop Llc | Crystalline manganese phosphate compositions |
| DE19634192A1 (de) * | 1996-08-23 | 1998-02-26 | Basf Ag | Bismut-haltige Katalysatoren |
| US6096934A (en) * | 1998-12-09 | 2000-08-01 | Uop Llc | Oxidative coupling of methane with carbon conservation |
| CA2427722C (en) * | 2003-04-29 | 2007-11-13 | Ebrahim Bagherzadeh | Preparation of catalyst and use for high yield conversion of methane to ethylene |
| RU2007119938A (ru) * | 2004-12-09 | 2009-01-20 | Хрд Корп. (Us) | Катализатор и способ преобразования парафиновых углеводородов с низким молекулярным весом в алкены |
| KR20080069211A (ko) * | 2005-10-28 | 2008-07-25 | 바스프 에스이 | Ｃ1-ｃ4-알칸으로부터 방향족 탄화수소를 합성하는 방법,및 ｃ1-ｃ4-알칸 함유 생성물 흐름의 이용법 |
| RU2478426C2 (ru) * | 2007-04-25 | 2013-04-10 | Хрд Корп. | Катализатор и способ конвертации природного газа в высокоуглеродистые соединения |
| US8912381B2 (en) * | 2009-06-29 | 2014-12-16 | Fina Technology, Inc. | Process for the oxidative coupling of methane |
| US9089832B2 (en) * | 2009-06-29 | 2015-07-28 | Fina Technology, Inc. | Catalysts for oxidative coupling of hydrocarbons |
| US8399726B2 (en) * | 2010-04-20 | 2013-03-19 | Fina Technology Inc | Reactors and processes for the oxidative coupling of hydrocarbons |
-
2009
- 2009-06-29 US US12/494,138 patent/US8450546B2/en not_active Expired - Fee Related
-
2010
- 2010-06-23 TW TW099120468A patent/TW201127785A/zh unknown
- 2010-06-25 CN CN2010800291488A patent/CN102471183A/zh active Pending
- 2010-06-25 EP EP10794571.9A patent/EP2448887A4/en not_active Withdrawn
- 2010-06-25 EA EA201270080A patent/EA201270080A1/ru unknown
- 2010-06-25 AU AU2010266506A patent/AU2010266506A1/en not_active Abandoned
- 2010-06-25 JP JP2012517753A patent/JP2012532105A/ja active Pending
- 2010-06-25 KR KR1020117030880A patent/KR20120115081A/ko not_active Withdrawn
- 2010-06-25 WO PCT/US2010/039888 patent/WO2011002665A1/en not_active Ceased
-
2013
- 2013-04-22 US US13/867,295 patent/US8729328B2/en not_active Expired - Fee Related
- 2013-11-06 US US14/072,971 patent/US8796497B2/en not_active Expired - Fee Related
-
2014
- 2014-05-21 US US14/283,529 patent/US9227887B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EA201270080A1 (ru) | 2012-08-30 |
| EP2448887A1 (en) | 2012-05-09 |
| US8796497B2 (en) | 2014-08-05 |
| US9227887B2 (en) | 2016-01-05 |
| CN102471183A (zh) | 2012-05-23 |
| AU2010266506A1 (en) | 2011-12-22 |
| US8450546B2 (en) | 2013-05-28 |
| US8729328B2 (en) | 2014-05-20 |
| US20140257005A1 (en) | 2014-09-11 |
| EP2448887A4 (en) | 2013-11-27 |
| JP2012532105A (ja) | 2012-12-13 |
| WO2011002665A1 (en) | 2011-01-06 |
| US20100331593A1 (en) | 2010-12-30 |
| KR20120115081A (ko) | 2012-10-17 |
| US20140066677A1 (en) | 2014-03-06 |
| US20130231513A1 (en) | 2013-09-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW201127785A (en) | Process for the oxidative coupling of hydrocarbons | |
| US9089832B2 (en) | Catalysts for oxidative coupling of hydrocarbons | |
| TW201119979A (en) | Process for the oxidative coupling of methane | |
| US9371257B2 (en) | Reactors and processes for the oxidative coupling of hydrocarbons | |
| CN101730586B (zh) | 用于将天然气转化为高碳化合物的催化剂和方法 | |
| TW201016641A (en) | Process for production of olefin, and production apparatus for same | |
| JP2004143373A (ja) | 炭化水素の接触分解によるオレフィンの製造方法 | |
| KR101985861B1 (ko) | 메탄 및 프로판 공동 반응물의 직접 탈수소방향족화 반응을 위한 중형기공성 hzsm-11에 담지된 금속 산화물 촉매의 제조 방법 및 상기 촉매를 이용한 btx 제조 방법 | |
| JPH01284338A (ja) | 塩基性混合金属酸化物触媒 | |
| TW202402389A (zh) | 觸媒組成物及其製造和使用方法 | |
| WO2018015828A1 (en) | Process for high-pressure hydrogenation of carbon dioxide to syngas in the presence of used chromium oxide supported catalysts | |
| CN106518604B (zh) | 乙苯的合成方法 | |
| JP2023079580A (ja) | 酸化物触媒、炭化水素の製造方法 | |
| JP2024124632A (ja) | 金属含有ゼオライトおよびそれを含む触媒 | |
| WO2017082752A1 (ru) | Катализатор, способ его приготовления и процесс обогащения смесей углеводородных газов метаном |