JP2013523741A - 非環式対称オレフィンの高炭素数オレフィンおよび低炭素数オレフィン生成物への変換 - Google Patents
非環式対称オレフィンの高炭素数オレフィンおよび低炭素数オレフィン生成物への変換 Download PDFInfo
- Publication number
- JP2013523741A JP2013523741A JP2013502692A JP2013502692A JP2013523741A JP 2013523741 A JP2013523741 A JP 2013523741A JP 2013502692 A JP2013502692 A JP 2013502692A JP 2013502692 A JP2013502692 A JP 2013502692A JP 2013523741 A JP2013523741 A JP 2013523741A
- Authority
- JP
- Japan
- Prior art keywords
- olefin
- acyclic
- alumina
- tungsten
- catalyst
- 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.)
- Granted
Links
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 155
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 87
- 125000002015 acyclic group Chemical group 0.000 title claims abstract description 73
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 65
- 229910052799 carbon Inorganic materials 0.000 title claims abstract description 61
- -1 carbon olefin Chemical class 0.000 title description 36
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 111
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 105
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims abstract description 99
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 90
- 239000003054 catalyst Substances 0.000 claims abstract description 84
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 76
- 238000000034 method Methods 0.000 claims abstract description 57
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 52
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 52
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 47
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims abstract description 44
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims abstract description 43
- 230000008569 process Effects 0.000 claims abstract description 38
- 239000007787 solid Substances 0.000 claims abstract description 17
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052721 tungsten Inorganic materials 0.000 claims description 41
- 239000010937 tungsten Substances 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 24
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 238000005865 alkene metathesis reaction Methods 0.000 abstract description 25
- 230000007246 mechanism Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 50
- 239000002243 precursor Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 23
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 22
- 239000005977 Ethylene Substances 0.000 description 22
- 150000001721 carbon Chemical group 0.000 description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 15
- 239000003446 ligand Substances 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 12
- 230000003647 oxidation Effects 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 12
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 10
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 238000005649 metathesis reaction Methods 0.000 description 9
- 238000004230 steam cracking Methods 0.000 description 9
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 238000006317 isomerization reaction Methods 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 238000004566 IR spectroscopy Methods 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 125000001118 alkylidene group Chemical group 0.000 description 6
- 238000003776 cleavage reaction Methods 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 238000004231 fluid catalytic cracking Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000005470 impregnation Methods 0.000 description 6
- 229910003480 inorganic solid Inorganic materials 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 230000007017 scission Effects 0.000 description 6
- 238000000859 sublimation Methods 0.000 description 6
- 230000008022 sublimation Effects 0.000 description 6
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 5
- 238000001994 activation Methods 0.000 description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000002524 organometallic group Chemical group 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000001354 calcination Methods 0.000 description 4
- 238000004517 catalytic hydrocracking Methods 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- 238000007580 dry-mixing Methods 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 150000001282 organosilanes Chemical group 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- 238000011144 upstream manufacturing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001345 alkine derivatives Chemical class 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 229910001593 boehmite Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000004523 catalytic cracking Methods 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 229910001679 gibbsite Inorganic materials 0.000 description 3
- 239000001307 helium Substances 0.000 description 3
- 229910052734 helium Inorganic materials 0.000 description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000002344 surface layer Substances 0.000 description 3
- 230000007306 turnover Effects 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- MEOSMFUUJVIIKB-UHFFFAOYSA-N [W].[C] Chemical compound [W].[C] MEOSMFUUJVIIKB-UHFFFAOYSA-N 0.000 description 2
- 229910052768 actinide Inorganic materials 0.000 description 2
- 150000001255 actinides Chemical class 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000004645 aluminates Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- 239000003915 liquefied petroleum gas Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentylidene Natural products CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 239000003870 refractory metal Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 238000005872 self-metathesis reaction Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000005245 sintering Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 150000003658 tungsten compounds Chemical class 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- 229910018516 Al—O Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- 241000145794 Parathesis Species 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000002820 allylidene group Chemical group [H]C(=[*])C([H])=C([H])[H] 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000004646 arylidenes Chemical group 0.000 description 1
- 229910001570 bauxite Inorganic materials 0.000 description 1
- 229910001680 bayerite Inorganic materials 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001723 carbon free-radicals Chemical class 0.000 description 1
- 229910052800 carbon group element Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 239000010431 corundum Substances 0.000 description 1
- 238000005686 cross metathesis reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- WMWXXXSCZVGQAR-UHFFFAOYSA-N dialuminum;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3] WMWXXXSCZVGQAR-UHFFFAOYSA-N 0.000 description 1
- 229910001648 diaspore Inorganic materials 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910021482 group 13 metal Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 238000010335 hydrothermal treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000002352 steam pyrolysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 150000003657 tungsten Chemical class 0.000 description 1
- NXHILIPIEUBEPD-UHFFFAOYSA-H tungsten hexafluoride Chemical group F[W](F)(F)(F)(F)F NXHILIPIEUBEPD-UHFFFAOYSA-H 0.000 description 1
- ZQGWFFCFIGSXEL-UHFFFAOYSA-N tungsten tetrahydride Chemical class [WH4] ZQGWFFCFIGSXEL-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Classifications
-
- 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
-
- 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
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
-
- 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
-
- 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
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
-
- 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
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/40—Ethylene production
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
【選択図】図1
Description
本出願は、2010年3月30日出願の米国特許出願第12/750,005号の優先権を主張するものである。
R1R2C=CR1R2
の非環式対称オレフィンの変換から新規の生成物を効果的に生成するメタセシス触媒系は期待されない。
上記で考察したように、本発明は、炭化水素供給原料がメタセシス反応器または反応ゾーンで接触される、オレフィンメタセシス(または不均化)プロセスのための触媒系に関する。重要なことには、ここで、水素化タングステンが触媒担体中に存在するアルミナと結合したそのような触媒系が、非環式対称オレフィンを含有する炭化水素供給原料を、炭素数の異なる所望の生成物(すなわち、非環式対称オレフィンと比較して低および高炭素数を有するオレフィン生成物)へ効果的に変換することが見出された。
実施例1
W−H/Al2O3触媒によるブテン−2のプロピレンおよびその他の生成物への変換
アルミナへグラフト(結合)した水素化タングステンを含む固体触媒を、米国特許第2007/0129584号の実施例3に記載のように調製した。この場合に用いたアルミナは、表面積が125m2/gであるAeroxide(登録商標)Alu C(エボニックデグッサ社(Evonik Degussa GmbH)、エッセン,ドイツ)であった。触媒のタングステン含有量は、触媒の総重量に対して3.0重量%であった。一般的にオレフィンメタセシスに有利である条件下、マイクロ反応器スケールでの実験プロトコルに従い、純粋ブテン−2の供給原料からのプロピレンおよびその他の生成物の生成についてこの触媒を評価した。詳細には、ブテン−2を、150℃(302°F)の温度、および7時間−1の単位時間あたり重量空間速度(WHSV)に相当する7.6Nml/分の流速にて、150mgのサンプル充填量である触媒上に通した。これらの条件および1バールg(15psig)を、45時間の実験時間全体を通して維持した。
Claims (10)
- オレフィンを生成するための方法であって、前記方法は:
炭化水素供給原料を、固体担体および前記担体中に存在するアルミナと結合した水素化タングステンを含有する触媒と接触させて、前記非環式対称オレフィンと比較して、それぞれ低い炭素数および高い炭素数を有する第一および第二のオレフィン生成物を生成させることを含み、
ここで、前記炭化水素供給原料は非環式対称オレフィンを含有し、前記非環式対称オレフィンは前記炭化水素供給原料中の全オレフィンの少なくとも80重量%の量で存在する、方法。 - 前記触媒が、1重量%から10重量%の量のタングステンを含有する、請求項1に記載の方法。
- 前記非環式対称オレフィンが、前記炭化水素供給原料に対して少なくとも85重量%の量で存在する、請求項1または2に記載の方法。
- 前記炭化水素供給原料が、75℃(167°F)から250℃(482°F)の温度、0.5バール(7.3psi)から35バール(508psi)の圧力、および1時間−1から100時間−1の単位時間あたり重量空間速度にて、前記触媒と接触される、請求項1から3のいずれか一項に記載の方法。
- 前記非環式対称オレフィンがブテン−2であり、前記第一のオレフィン生成物がプロピレンであり、および、前記第二のオレフィン生成物がペンテンである、請求項1から4のいずれか一項に記載の方法。
- ブテン−2が、1パスあたり少なくとも15%の変換率で変換される、請求項5に記載の方法。
- 1パスあたりの変換率が15%から50%である、請求項6に記載の方法。
- ブテン−2が、少なくとも45%の選択性でプロピレンへ変換される、請求項6または7に記載の方法。
- ブテン−2が、少なくとも30%の選択性でペンテンへ変換される、請求項5から8のいずれか一項に記載の方法。
- プロピレンを生成するための方法であって、前記プロセスは、主としてブテン‐2を含有する炭化水素供給原料を、固体担体および前記担体中に存在するアルミナと結合した水素化タングステンを含有する触媒と接触させることを含み、
ここで、ブテン−2の1パスあたりの変換率は15%から50%であり、および、ここで、前記ブテン−2は少なくとも45%の選択性でプロピレンへ変換される、方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/750,005 US8704028B2 (en) | 2010-03-30 | 2010-03-30 | Conversion of acyclic symmetrical olefins to higher and lower carbon number olefin products |
US12/750,005 | 2010-03-30 | ||
PCT/US2011/030155 WO2011126796A2 (en) | 2010-03-30 | 2011-03-28 | Conversion of acyclic symmetrical olefins to higher and lower carbon number olefin products |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2013523741A true JP2013523741A (ja) | 2013-06-17 |
JP5739518B2 JP5739518B2 (ja) | 2015-06-24 |
Family
ID=44710416
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013502692A Active JP5739518B2 (ja) | 2010-03-30 | 2011-03-28 | 非環式対称オレフィンの高炭素数オレフィンおよび低炭素数オレフィン生成物への変換 |
Country Status (7)
Country | Link |
---|---|
US (1) | US8704028B2 (ja) |
EP (1) | EP2552870A4 (ja) |
JP (1) | JP5739518B2 (ja) |
CN (1) | CN102811987B (ja) |
BR (1) | BR112012024185A2 (ja) |
CA (1) | CA2794109C (ja) |
WO (1) | WO2011126796A2 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58219128A (ja) * | 1982-05-27 | 1983-12-20 | スナムプロゲツチ・エス・ペ−・ア− | オレフインの異性化法 |
JPS61207356A (ja) * | 1985-03-11 | 1986-09-13 | Babcock Hitachi Kk | メチルエチルケトン製造装置 |
US6586649B1 (en) * | 1998-09-04 | 2003-07-01 | Sasol Technology (Proprietary) Limited | Production of propylene |
JP2005298394A (ja) * | 2004-04-09 | 2005-10-27 | Idemitsu Kosan Co Ltd | 2−ブテン製造方法 |
WO2008071949A1 (en) * | 2006-12-14 | 2008-06-19 | Bp Oil International Limited | Process for manufacturing neohexene |
JP2009541478A (ja) * | 2006-06-26 | 2009-11-26 | ビーピー オイル インターナショナル リミテッド | 2,3−ジメチルブタン調製プロセスおよび得られた生成物の用途 |
US7635794B2 (en) * | 2004-07-02 | 2009-12-22 | Cpe Lyon Formation Continue Et Recherche-Cpe Lyon Fcr | Method for metathesis of compounds comprising an olefinic double bond, in particular olefins |
JP2010501495A (ja) * | 2006-08-23 | 2010-01-21 | 中国科学院大▲連▼化学物理研究所 | メタノールからの低級オレフィンの製造過程における再生熱の回収方法 |
Family Cites Families (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3691095A (en) * | 1970-09-16 | 1972-09-12 | Exxon Research Engineering Co | Catalyst for olefin reactions |
US3658929A (en) * | 1970-11-16 | 1972-04-25 | Phillips Petroleum Co | Conversion of olefins |
US3978150A (en) | 1975-03-03 | 1976-08-31 | Universal Oil Products Company | Continuous paraffin dehydrogenation process |
JPS54123100A (en) | 1978-03-17 | 1979-09-25 | Mitsubishi Heavy Ind Ltd | Toll road terminal station |
US5026935A (en) | 1989-10-02 | 1991-06-25 | Arco Chemical Technology, Inc. | Enhanced production of ethylene from higher hydrocarbons |
US5026936A (en) | 1989-10-02 | 1991-06-25 | Arco Chemical Technology, Inc. | Enhanced production of propylene from higher hydrocarbons |
DE19640026A1 (de) * | 1996-09-27 | 1998-04-02 | Basf Ag | Verfahren zur Herstellung von Propen |
US5914433A (en) | 1997-07-22 | 1999-06-22 | Uop Lll | Process for producing polymer grade olefins |
DE19746040A1 (de) | 1997-10-17 | 1999-04-22 | Basf Ag | Verfahren zur Herstellung von Propen |
EP0921179A1 (en) | 1997-12-05 | 1999-06-09 | Fina Research S.A. | Production of olefins |
DE19805716A1 (de) | 1998-02-12 | 1999-08-19 | Basf Ag | Verfahren zur Herstellung von Propen und gegebenenfalls 1-Buten |
FR2789072B1 (fr) | 1999-01-29 | 2001-04-13 | Inst Francais Du Petrole | Procede de metathese des olefines en presence d'un agent stabilisant du catalyseur |
EP1063274A1 (en) | 1999-06-17 | 2000-12-27 | Fina Research S.A. | Production of olefins |
EP1195424A1 (en) | 2000-10-05 | 2002-04-10 | ATOFINA Research | A process for cracking an olefin-rich hydrocarbon feedstock |
US20050124839A1 (en) | 2001-06-13 | 2005-06-09 | Gartside Robert J. | Catalyst and process for the metathesis of ethylene and butene to produce propylene |
US6777582B2 (en) * | 2002-03-07 | 2004-08-17 | Abb Lummus Global Inc. | Process for producing propylene and hexene from C4 olefin streams |
US6867341B1 (en) | 2002-09-17 | 2005-03-15 | Uop Llc | Catalytic naphtha cracking catalyst and process |
CN1277608C (zh) | 2002-10-16 | 2006-10-04 | 中国石油化工股份有限公司 | 用于丁烯歧化生产丙烯的固定床催化剂 |
US7214841B2 (en) * | 2003-07-15 | 2007-05-08 | Abb Lummus Global Inc. | Processing C4 olefin streams for the maximum production of propylene |
US7268265B1 (en) | 2004-06-30 | 2007-09-11 | Uop Llc | Apparatus and process for light olefin recovery |
FR2872510B1 (fr) | 2004-07-02 | 2006-09-08 | Cpe Lyon Fcr | Procede de transformation d'ethylene en propylene |
US7220886B2 (en) | 2004-10-27 | 2007-05-22 | Catalytic Distillation Technologies | Olefin metathesis |
EP1860087A1 (en) | 2006-05-22 | 2007-11-28 | Total Petrochemicals Research Feluy | Production of Propylene and Ethylene from Butane and Ethane |
CN101172925B (zh) | 2006-11-02 | 2010-05-12 | 中国石油化工股份有限公司 | 乙烯与丁烯歧化生产丙烯的方法 |
US7586018B2 (en) | 2006-12-21 | 2009-09-08 | Uop Llc | Oxygenate conversion to olefins with dimerization and metathesis |
US8178737B2 (en) | 2007-06-14 | 2012-05-15 | Lyondell Chemical Technology, L.P. | Propylene production |
-
2010
- 2010-03-30 US US12/750,005 patent/US8704028B2/en active Active
-
2011
- 2011-03-28 WO PCT/US2011/030155 patent/WO2011126796A2/en active Application Filing
- 2011-03-28 JP JP2013502692A patent/JP5739518B2/ja active Active
- 2011-03-28 BR BR112012024185A patent/BR112012024185A2/pt not_active IP Right Cessation
- 2011-03-28 EP EP11766423.5A patent/EP2552870A4/en not_active Withdrawn
- 2011-03-28 CN CN201180015042.7A patent/CN102811987B/zh not_active Expired - Fee Related
- 2011-03-28 CA CA2794109A patent/CA2794109C/en not_active Expired - Fee Related
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58219128A (ja) * | 1982-05-27 | 1983-12-20 | スナムプロゲツチ・エス・ペ−・ア− | オレフインの異性化法 |
JPS61207356A (ja) * | 1985-03-11 | 1986-09-13 | Babcock Hitachi Kk | メチルエチルケトン製造装置 |
US6586649B1 (en) * | 1998-09-04 | 2003-07-01 | Sasol Technology (Proprietary) Limited | Production of propylene |
JP2005298394A (ja) * | 2004-04-09 | 2005-10-27 | Idemitsu Kosan Co Ltd | 2−ブテン製造方法 |
US7635794B2 (en) * | 2004-07-02 | 2009-12-22 | Cpe Lyon Formation Continue Et Recherche-Cpe Lyon Fcr | Method for metathesis of compounds comprising an olefinic double bond, in particular olefins |
JP2009541478A (ja) * | 2006-06-26 | 2009-11-26 | ビーピー オイル インターナショナル リミテッド | 2,3−ジメチルブタン調製プロセスおよび得られた生成物の用途 |
JP2010501495A (ja) * | 2006-08-23 | 2010-01-21 | 中国科学院大▲連▼化学物理研究所 | メタノールからの低級オレフィンの製造過程における再生熱の回収方法 |
WO2008071949A1 (en) * | 2006-12-14 | 2008-06-19 | Bp Oil International Limited | Process for manufacturing neohexene |
Also Published As
Publication number | Publication date |
---|---|
JP5739518B2 (ja) | 2015-06-24 |
CA2794109A1 (en) | 2011-10-13 |
WO2011126796A3 (en) | 2012-02-23 |
WO2011126796A2 (en) | 2011-10-13 |
BR112012024185A2 (pt) | 2016-07-05 |
EP2552870A4 (en) | 2013-09-18 |
US8704028B2 (en) | 2014-04-22 |
CN102811987A (zh) | 2012-12-05 |
EP2552870A2 (en) | 2013-02-06 |
CN102811987B (zh) | 2015-05-13 |
CA2794109C (en) | 2015-06-16 |
US20110245569A1 (en) | 2011-10-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5816261B2 (ja) | オレフィンメタセシス条件下におけるブチレンのプロピレンへの変換 | |
AU2008306668B2 (en) | Solid metal compound, preparations and uses thereof | |
US20090306441A1 (en) | Method for treatment of oil and/or gas field waste and by product materials | |
EP2099732B1 (en) | Process for manufacturing neohexene | |
KR101668504B1 (ko) | 촉매 재생 | |
EA007872B1 (ru) | Композиции молекулярных сит, их катализатор, их приготовление и применение в процессах превращения | |
JPH01284587A (ja) | 液体炭化水素の製造方法 | |
JP5739518B2 (ja) | 非環式対称オレフィンの高炭素数オレフィンおよび低炭素数オレフィン生成物への変換 | |
TWI458551B (zh) | 烯烴置換方法及包含鎢氟鍵之催化劑 | |
US8389788B2 (en) | Olefin metathesis reactant ratios used with tungsten hydride catalysts | |
JP2020100520A (ja) | 酸化亜鉛修飾mfi型ゼオライト及びそれを用いた芳香族化合物の製造方法 | |
Barger et al. | i, United States Patent (10) Patent No.: US 8.704, 029 B2 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20140124 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140206 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140415 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20141024 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150223 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20150304 |
|
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: 20150420 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150423 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5739518 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |