JP2003519560A5 - - Google Patents
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- JP2003519560A5 JP2003519560A5 JP2001543261A JP2001543261A JP2003519560A5 JP 2003519560 A5 JP2003519560 A5 JP 2003519560A5 JP 2001543261 A JP2001543261 A JP 2001543261A JP 2001543261 A JP2001543261 A JP 2001543261A JP 2003519560 A5 JP2003519560 A5 JP 2003519560A5
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- hydrooxidation
- titanium
- regeneration
- olefin
- 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.)
- Pending
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- 239000003054 catalyst Substances 0.000 description 173
- 238000000034 method Methods 0.000 description 151
- 150000001336 alkenes Chemical class 0.000 description 74
- 229910052751 metal Inorganic materials 0.000 description 72
- 239000002184 metal Substances 0.000 description 72
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 70
- 229910052719 titanium Inorganic materials 0.000 description 66
- 239000010936 titanium Substances 0.000 description 66
- 238000011069 regeneration method Methods 0.000 description 64
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 61
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 56
- 239000001301 oxygen Substances 0.000 description 56
- 229910052760 oxygen Inorganic materials 0.000 description 56
- 230000008929 regeneration Effects 0.000 description 54
- 238000007254 oxidation reaction Methods 0.000 description 48
- 239000010931 gold Substances 0.000 description 46
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 45
- 229910052737 gold Inorganic materials 0.000 description 45
- 239000001257 hydrogen Substances 0.000 description 40
- 229910052739 hydrogen Inorganic materials 0.000 description 40
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 35
- 229910052709 silver Inorganic materials 0.000 description 35
- 239000004332 silver Substances 0.000 description 35
- 230000004913 activation Effects 0.000 description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 29
- -1 Platinum Group Metals Chemical class 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 25
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 25
- 229910001868 water Inorganic materials 0.000 description 25
- 239000000203 mixture Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- 239000003085 diluting agent Substances 0.000 description 21
- 239000001307 helium Substances 0.000 description 20
- 229910052734 helium Inorganic materials 0.000 description 20
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 20
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 19
- 239000000377 silicon dioxide Substances 0.000 description 18
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 17
- 239000003570 air Substances 0.000 description 16
- 239000007789 gas Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229910052747 lanthanoid Inorganic materials 0.000 description 14
- 230000003647 oxidation Effects 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 150000002431 hydrogen Chemical class 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000011068 loading method Methods 0.000 description 10
- 229910052914 metal silicate Inorganic materials 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000003197 catalytic effect Effects 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 229910052768 actinide Inorganic materials 0.000 description 8
- 230000003213 activating effect Effects 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 230000001172 regenerating effect Effects 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 229910052720 vanadium Inorganic materials 0.000 description 7
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 229910052761 rare earth metal Inorganic materials 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000004408 titanium dioxide Substances 0.000 description 6
- 229910052726 zirconium Inorganic materials 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 239000003426 co-catalyst Substances 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000005470 impregnation Methods 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 230000000737 periodic effect Effects 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 150000002344 gold compounds Chemical class 0.000 description 4
- 150000002602 lanthanoids Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052691 Erbium Inorganic materials 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229940100890 silver compound Drugs 0.000 description 3
- 150000003379 silver compounds Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910052765 Lutetium Inorganic materials 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000001351 cycling effect Effects 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- WZHKDGJSXCTSCK-UHFFFAOYSA-N hept-3-ene Chemical compound CCCC=CCC WZHKDGJSXCTSCK-UHFFFAOYSA-N 0.000 description 2
- 238000002173 high-resolution transmission electron microscopy Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002923 metal particle Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- TYKCBTYOMAUNLH-MTOQALJVSA-J (z)-4-oxopent-2-en-2-olate;titanium(4+) Chemical compound [Ti+4].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O TYKCBTYOMAUNLH-MTOQALJVSA-J 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- RZWHKKIXMPLQEM-UHFFFAOYSA-N 1-chloropropan-1-ol Chemical compound CCC(O)Cl RZWHKKIXMPLQEM-UHFFFAOYSA-N 0.000 description 1
- LWJHSQQHGRQCKO-UHFFFAOYSA-N 1-prop-2-enoxypropane Chemical compound CCCOCC=C LWJHSQQHGRQCKO-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- IRUDSQHLKGNCGF-UHFFFAOYSA-N 2-methylhex-1-ene Chemical compound CCCCC(C)=C IRUDSQHLKGNCGF-UHFFFAOYSA-N 0.000 description 1
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- RMZIOVJHUJAAEY-UHFFFAOYSA-N Allyl butyrate Chemical compound CCCC(=O)OCC=C RMZIOVJHUJAAEY-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-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
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 229910003803 Gold(III) chloride Inorganic materials 0.000 description 1
- 229910004042 HAuCl4 Inorganic materials 0.000 description 1
- 241000264877 Hippospongia communis Species 0.000 description 1
- 229910052689 Holmium Inorganic materials 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 241000404883 Pisa Species 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 229910052773 Promethium Inorganic materials 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
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- 238000005342 ion exchange Methods 0.000 description 1
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- 230000001788 irregular Effects 0.000 description 1
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- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
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- JFZUABNDWZQLIJ-UHFFFAOYSA-N methyl 2-[(2-chloroacetyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CCl JFZUABNDWZQLIJ-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
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- 239000001294 propane Substances 0.000 description 1
- 238000001055 reflectance spectroscopy Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
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- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- XNGYKPINNDWGGF-UHFFFAOYSA-L silver oxalate Chemical compound [Ag+].[Ag+].[O-]C(=O)C([O-])=O XNGYKPINNDWGGF-UHFFFAOYSA-L 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 238000005382 thermal cycling Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
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- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- ISIHFYYBOXJLTM-UHFFFAOYSA-N vanadium;pentasilicate Chemical compound [V].[V].[V].[V].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] ISIHFYYBOXJLTM-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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| US60/169,862 | 1999-12-09 | ||
| PCT/US2000/033385 WO2001041926A1 (en) | 1999-12-09 | 2000-12-07 | Activation and regeneration of a hydro-oxidation catalyst |
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| JP2003519560A JP2003519560A (ja) | 2003-06-24 |
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| AT (1) | ATE261341T1 (enExample) |
| AU (1) | AU770334B2 (enExample) |
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| DE (1) | DE60008933T2 (enExample) |
| ES (1) | ES2213064T3 (enExample) |
| WO (1) | WO2001041926A1 (enExample) |
Families Citing this family (21)
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| US6562986B2 (en) * | 1997-06-30 | 2003-05-13 | Dow Global Technologies, Inc. | Process for the direct oxidation of olefins to olefin oxides |
| ES2190280T3 (es) | 1998-12-16 | 2003-07-16 | Dow Global Technologies Inc | Procedimiento para la oxidacion directa de olefinas a oxidos de olefina. |
| US6821923B1 (en) | 1999-04-08 | 2004-11-23 | Dow Global Technologies Inc. | Method of preparing a catalyst containing gold and titanium |
| BR0211796A (pt) | 2001-08-01 | 2004-08-03 | Dow Global Technologies Inc | Método para aumentar a vida útil de um catalisador de hidro-oxidação |
| WO2004090937A2 (en) * | 2003-04-10 | 2004-10-21 | Technion Research & Development Foundation Ltd | Copper cmp slurry composition |
| US7541012B2 (en) | 2004-07-07 | 2009-06-02 | The Hong Kong University Of Science And Technology | Catalytic material and method of production thereof |
| DE102004059375A1 (de) | 2004-12-09 | 2006-06-22 | Consortium für elektrochemische Industrie GmbH | Auf nanoskaligem Titandioxid geträgerte Platin-Katalysatoren, deren Verwendung in der Hydrosilylierung, ein Hydrosilylierungsverfahren mit solchen Katalysatoren und Zusammensetzungen enthaltend solche Katalysatoren |
| US7494610B2 (en) * | 2005-08-30 | 2009-02-24 | The Hong Kong University Of Science And Technology | Methods for fabricating zeolite micromembranes |
| US7704908B2 (en) | 2005-12-22 | 2010-04-27 | Shell Oil Company | Method for reusing rhenium from a donor spent epoxidation catalyst |
| US7459589B2 (en) | 2005-12-22 | 2008-12-02 | Shell Oil Company | Process for the preparation of an alkylene glycol |
| US8357812B2 (en) | 2005-12-22 | 2013-01-22 | Shell Oil Company | Process for preparing a rejuvenated epoxidation catalyst |
| US20090325783A1 (en) * | 2008-06-30 | 2009-12-31 | Myers Daniel N | Oto quench tower catalyst recovery system utilizing a low temperature fluidized drying chamber |
| JP5933445B2 (ja) | 2009-11-27 | 2016-06-08 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | チタンゼオライト触媒の製造方法 |
| EP2600971A4 (en) | 2010-08-03 | 2014-12-24 | Aditya Birla Science And Technology Company Ltd | PROCESS FOR REGENERATING A CATALYST OF TITANOSILICATE |
| US8742147B2 (en) * | 2010-12-08 | 2014-06-03 | Shell Oil Company | Process for improving the selectivity of an EO catalyst |
| US8742146B2 (en) * | 2010-12-08 | 2014-06-03 | Shell Oil Company | Process for improving the selectivity of an EO catalyst |
| CN102133547B (zh) * | 2011-03-02 | 2013-03-20 | 华南理工大学 | 一种钒钛基烟气脱硝催化剂的臭氧处理再生方法及装置 |
| US10598599B2 (en) | 2015-11-03 | 2020-03-24 | Savannah River Nuclear Solutions, Llc | Methods and materials for determination of distribution coefficients for separation materials |
| WO2017127728A1 (en) * | 2016-01-20 | 2017-07-27 | President And Fellows Of Harvard College | Ozone-activated nanoporous gold and methods of its use |
| US10994268B2 (en) * | 2017-05-03 | 2021-05-04 | Exxonmobil Chemical Patents Inc. | Processes for rejuvenating catalysts |
| CN109174075A (zh) * | 2018-09-04 | 2019-01-11 | 中国科学院上海硅酸盐研究所 | 一种用于光催化降解VOCs的稀土元素改性二氧化钛纳米光催化材料及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB2029719B (en) | 1978-09-01 | 1982-12-08 | Mitsubishi Rayon Co | Method of regenerating an oxidized catalyst |
| AU641571B2 (en) * | 1990-11-28 | 1993-09-23 | Sumitomo Seika Chemicals Co., Ltd. | Method for treating gas and apparatus used therefor |
| US5183789A (en) * | 1991-03-11 | 1993-02-02 | Exxon Research And Engineering Company | Ozone regeneration of platinum, and polymetallic platinum reforming catalysts |
| US5365009A (en) * | 1993-04-14 | 1994-11-15 | Exxon Research And Engineering Company | Heterogeneous alkylation and regeneration of alkylation catalysts |
| DE4425672A1 (de) | 1994-07-20 | 1996-01-25 | Basf Ag | Oxidationskatalysator, Verfahren zu seiner Herstellung und Oxidationsverfahren unter Verwendung des Oxidationskatalysators |
| JP2615432B2 (ja) * | 1994-10-28 | 1997-05-28 | 工業技術院長 | 金−酸化チタン含有触媒による炭化水素の部分酸化方法 |
| US5753576A (en) | 1995-05-18 | 1998-05-19 | Arco Chemical Technology, L.P. | Regeneration of a titanium-containing molecular sieve |
| DE19528220C1 (de) | 1995-08-01 | 1997-01-09 | Degussa | Verfahren zur Regenerierung eines Katalysators und Verfahren zur Herstellung eines Epoxids in Gegenwart des Katalysators |
| DE19600708A1 (de) | 1996-01-11 | 1997-07-17 | Basf Ag | Oxidationskatalysator mit einem Gehalt an Lanthanoidmetallen, Verfahren zu seiner Herstellung und Oxidationsverfahren unter Verwendung des Oxidationskatalysators |
| US5681789A (en) | 1996-02-12 | 1997-10-28 | Arco Chemical Technology, L.P. | Activation of as-synthesized titanium-containing zeolites |
| JP4135818B2 (ja) * | 1997-03-03 | 2008-08-20 | 株式会社日本触媒 | 炭化水素の部分酸化用触媒および炭化水素の部分酸化方法 |
| US5932750A (en) | 1996-03-21 | 1999-08-03 | Agency Of Industrial Science And Technology | Catalysts for partial oxidation of hydrocarbons and method of partial oxidation of hydrocarbons |
| DE69708880T2 (de) | 1996-07-01 | 2002-04-11 | The Dow Chemical Co., Midland | Verfahren zur direkten oxidation von olefinen zu olefinoxiden |
| BE1010717A3 (fr) | 1996-10-25 | 1998-12-01 | Solvay | Procede de regeneration de catalyseurs. |
| US5798313A (en) | 1996-12-20 | 1998-08-25 | Arco Chemical Technology, L.P. | Heterogeneous catalyst regeneration |
| DE19723949A1 (de) * | 1997-06-06 | 1998-12-10 | Basf Ag | Verfahren zur Regenerierung eines Zeolith-Katalysators |
| DE19723950A1 (de) * | 1997-06-06 | 1998-12-10 | Basf Ag | Verfahren zur Oxidation einer mindestens eine C-C-Doppelbindung aufweisenden organischen Verbindung |
| BR9714951A (pt) | 1997-06-30 | 2000-10-17 | Dow Chemical Co | Processo para preparar um óxido de olefina, composição de catalisador e processo para regenerar um composição. |
| DE19804711A1 (de) | 1998-02-06 | 1999-08-12 | Bayer Ag | Verfahren zur Regenerierung von mit Goldteilchen belegten Trägerkatalysatoren für die Oxidation ungesättigter Kohlenwasserstoffe |
| DE19804712A1 (de) | 1998-02-06 | 1999-08-12 | Bayer Ag | Verfahren zur Standzeitverlängerung von mit Goldteilen belegten Trägerkatalysatoren für die Oxidation ungesättigter Kohlenwasserstoffe |
| US5939569A (en) | 1998-03-10 | 1999-08-17 | Jones; C. Andrew | Epoxidation process |
| ES2190280T3 (es) | 1998-12-16 | 2003-07-16 | Dow Global Technologies Inc | Procedimiento para la oxidacion directa de olefinas a oxidos de olefina. |
| JP4646409B2 (ja) | 1999-04-08 | 2011-03-09 | ダウ グローバル テクノロジーズ インコーポレイティド | 酸化された金触媒を使用してオレフィンをオレフィンオキシドにハイドロ酸化するための方法 |
| JP4395580B2 (ja) * | 1999-04-28 | 2010-01-13 | 独立行政法人産業技術総合研究所 | エポキシドの製造方法 |
-
2000
- 2000-12-07 KR KR1020027007287A patent/KR20030003219A/ko not_active Withdrawn
- 2000-12-07 US US10/148,804 patent/US7018948B2/en not_active Expired - Fee Related
- 2000-12-07 BR BR0016486-0A patent/BR0016486A/pt active Search and Examination
- 2000-12-07 AU AU22567/01A patent/AU770334B2/en not_active Ceased
- 2000-12-07 AT AT00986298T patent/ATE261341T1/de not_active IP Right Cessation
- 2000-12-07 CN CNB008181780A patent/CN1151891C/zh not_active Expired - Fee Related
- 2000-12-07 ES ES00986298T patent/ES2213064T3/es not_active Expired - Lifetime
- 2000-12-07 WO PCT/US2000/033385 patent/WO2001041926A1/en not_active Ceased
- 2000-12-07 DE DE60008933T patent/DE60008933T2/de not_active Expired - Lifetime
- 2000-12-07 JP JP2001543261A patent/JP2003519560A/ja active Pending
- 2000-12-07 EP EP00986298A patent/EP1283747B1/en not_active Expired - Lifetime
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