JP4335692B2 - 担持された銀触媒およびその触媒を用いるエポキシ化方法 - Google Patents
担持された銀触媒およびその触媒を用いるエポキシ化方法 Download PDFInfo
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- JP4335692B2 JP4335692B2 JP2003570981A JP2003570981A JP4335692B2 JP 4335692 B2 JP4335692 B2 JP 4335692B2 JP 2003570981 A JP2003570981 A JP 2003570981A JP 2003570981 A JP2003570981 A JP 2003570981A JP 4335692 B2 JP4335692 B2 JP 4335692B2
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- 239000003054 catalyst Substances 0.000 title claims abstract description 92
- 238000000034 method Methods 0.000 title claims abstract description 64
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 37
- 239000004332 silver Substances 0.000 title claims abstract description 37
- 238000006735 epoxidation reaction Methods 0.000 title claims abstract description 23
- 239000011148 porous material Substances 0.000 claims abstract description 102
- 239000000203 mixture Substances 0.000 claims abstract description 74
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 68
- 150000001336 alkenes Chemical class 0.000 claims abstract description 62
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000002245 particle Substances 0.000 claims abstract description 31
- 230000008569 process Effects 0.000 claims abstract description 30
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000009826 distribution Methods 0.000 claims abstract description 19
- 239000001301 oxygen Substances 0.000 claims abstract description 19
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- 238000000151 deposition Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 239000000463 material Substances 0.000 claims description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- 150000000180 1,2-diols Chemical class 0.000 claims description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 21
- -1 clays Substances 0.000 claims description 21
- 229910052702 rhenium Inorganic materials 0.000 claims description 21
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 238000010521 absorption reaction Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 12
- 229910052721 tungsten Inorganic materials 0.000 claims description 12
- 239000010937 tungsten Substances 0.000 claims description 12
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 11
- 229910052750 molybdenum Inorganic materials 0.000 claims description 11
- 239000011733 molybdenum Substances 0.000 claims description 11
- 229910052792 caesium Inorganic materials 0.000 claims description 10
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- 150000002826 nitrites Chemical class 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 8
- 150000002823 nitrates Chemical class 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 238000001354 calcination Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000002739 metals Chemical class 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 239000011819 refractory material Substances 0.000 claims description 4
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052776 Thorium Inorganic materials 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 239000003610 charcoal Substances 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- 229910002026 crystalline silica Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052733 gallium Inorganic materials 0.000 claims description 3
- 229910052732 germanium Inorganic materials 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052735 hafnium Inorganic materials 0.000 claims description 3
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 229910052758 niobium Inorganic materials 0.000 claims description 3
- 239000010955 niobium Substances 0.000 claims description 3
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 3
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 3
- 235000012239 silicon dioxide Nutrition 0.000 claims description 3
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 3
- 229910052715 tantalum Inorganic materials 0.000 claims description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052716 thallium Inorganic materials 0.000 claims description 3
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 2
- 150000003282 rhenium compounds Chemical class 0.000 claims 2
- 229910021536 Zeolite Inorganic materials 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 229910052570 clay Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 9
- 238000010304 firing Methods 0.000 abstract description 5
- 238000007493 shaping process Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 238000001125 extrusion Methods 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 239000003607 modifier Substances 0.000 description 9
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 9
- 150000001340 alkali metals Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000003570 air Substances 0.000 description 7
- 238000005470 impregnation Methods 0.000 description 7
- 229910002651 NO3 Inorganic materials 0.000 description 6
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- 239000001569 carbon dioxide Substances 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
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- 229910052753 mercury Inorganic materials 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
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- 238000000465 moulding Methods 0.000 description 5
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- 238000005245 sintering Methods 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229960003750 ethyl chloride Drugs 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 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 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
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- 239000003292 glue Substances 0.000 description 3
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 3
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- 150000002897 organic nitrogen compounds Chemical class 0.000 description 3
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- 150000003839 salts Chemical class 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
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- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000000527 sonication Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
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- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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- 239000002253 acid Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
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- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
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- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 2
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- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
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- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
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- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 229910001963 alkali metal nitrate Inorganic materials 0.000 description 1
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
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- 235000013361 beverage Nutrition 0.000 description 1
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- 150000001720 carbohydrates Chemical class 0.000 description 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940063774 carbon dioxide 5 % Drugs 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
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- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- NLDGJRWPPOSWLC-UHFFFAOYSA-N deca-1,9-diene Chemical compound C=CCCCCCCC=C NLDGJRWPPOSWLC-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229910001648 diaspore Inorganic materials 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000012489 doughnuts Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 229910001679 gibbsite Inorganic materials 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 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
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910001960 metal nitrate Inorganic materials 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 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
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011163 secondary particle Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 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
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- 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
- B01J23/48—Silver or gold
- B01J23/50—Silver
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
-
- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/12—Silica and alumina
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- 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
- B01J23/66—Silver or gold
-
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- 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
- B01J23/66—Silver or gold
- B01J23/68—Silver or gold with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/688—Silver or gold with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with manganese, technetium or rhenium
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- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0018—Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
- C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
- C07D301/10—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase with catalysts containing silver or gold
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- B01J35/612—Surface area less than 10 m2/g
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- B01J35/635—0.5-1.0 ml/g
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Description
a)少なくとも1m2/gの表面積と、0.2μmから10μmの範囲の直径を有する細孔が全細孔容積の少なくとも70%に相当し、その細孔が該担体の重量に対して合わせて少なくとも0.27ml/gの細孔容積を与えるような細孔径分布とを有する担体を選択するステップと、
b)担体上に銀を析出させるステップと
を含む方法を提供する。
担体上に銀を析出させるステップを含み、
そこにおいて、該担体が、
a)平均粒径(d50)が10μm超から100μmまでであり、第1の粒子状α−アルミナ50重量%から90重量%と;
b)d50が1μmから10μmの第2の粒子状α−アルミナ10重量%から50重量%と
を含む混合物を形成するステップであって、ここに、重量%が混合物中のα−アルミナの全重量に基づくものであるステップと、
混合物を焼成して担体を形成するステップと
を含む方法で得られたものである。なかでも、一実施形態では、この混合物から成型体を作成し、この成型体を焼成して担体を形成してもよい。成型体を押し出しによって形成する場合、この混合物に、従来の焼失する材料および/または押し出し助剤および水性液体(たとえば水)を含めることが望ましい場合もある。
担体および該担体上に析出している銀を含む触媒の存在下でオレフィンを酸素と反応させるステップを含み、
該担体が少なくとも1m2/gの表面積と、0.2μmから10μmの範囲の直径を有する細孔が細孔容積の合計の少なくとも70%に相当し、この細孔が、合わせて担体の重量に対して、少なくとも0.27ml/gの細孔容積を与えるような細孔径分布とを有する方法を提供する。
担体上に銀を析出させるステップを含む方法によって得られた触媒の存在下でオレフィンを酸素と反応させるステップであって、
該担体が
a)10μm超から100μmまでのd50を有する第1の粒子状α−アルミナの50重量%から90重量%と、
b)1μmから10μmのd50を有する第2の粒子状α−アルミナ10重量%から50重量%と
を含む混合物を生成するステップを含む方法によって得られたものであり、ここに重量%は混合物中のα−アルミナの全重量に対してであるステップと、
該混合物を焼成して該担体を形成するステップとを含む方法を提供する。なかでも、一実施形態では、この混合物から成型体を作成し、この成型体を焼成して担体を形成してもよい。成型体を押し出しによって形成する場合、この混合物に、慣用の焼失材料および/または押し出し助剤および水性液体、たとえば水を含めることが望ましい場合もある。
混合物を形成するステップであって、該混合物が
a)10μm超から100μmまで、特に11μmから60μmまで、さらに特に12μmから40μmまでのd50を有する第1の粒子状α−アルミナ50重量%から90重量%と、
b)1μmから10μmまで、特に2μmから6μmまでのd50を有する第2の粒子状α−アルミナ10重量%から50重量%と、
そして好ましくはさらに、
c)結合材料と
を含み、ここに重量%は混合物中のα−アルミナの全重量に対してであるステップと、
次いで、該混合物を成型体とし、該成型体を一般的には1250℃から1500℃の温度で焼成して、担体を形成するステップと
を含む。
a)酸化アルミニウムとして計算した場合に、α−アルミナの重量に対して、1重量%から10重量%、特に2重量%から5重量%のアルミナ水和物;
b)シリコン酸化物として計算した場合に、前条に指定したようにα−アルミナの重量に対して、0.1重量%から1重量%、特に0.2重量%から0.8重量%の非晶質シリカ化合物;
c)アルカリ金属酸化物として計算した場合に、α−アルミナの重量に対して、0.01重量%から0.5重量%、特に0.05重量%から0.3重量%のアルカリ金属化合物。
該方法は、
混合物を形成するステップであって、該混合物が、
a)混合物の中のα−アルミナの全重量に対して65重量%から75重量%まで、10μmから60μmまで、特に12μmから40μmまでのd50を有する第1の粒子状α−アルミナと、
b)混合物の中のα−アルミナの全重量に対して25重量%から35重量%までの2μmから6μmまでのd50を有する第2の粒子状α−アルミナと、
c)酸化アルミニウムとして計算した場合に、混合物の中のα−アルミナの全重量に対して2重量%から5重量%のアルミナ水和物と、
d)前条に指定したように、シリコン酸化物として計算した場合に、混合物の中のα−アルミナの全重量に対して0.2重量%から0.8重量%までの非晶質シリカ化合物と、
e)アルカリ金属酸化物として計算した場合に、混合物の中のα−アルミナの全重量に対して、0.05重量%から0.3重量%までのアルカリ金属化合物と
を含むステップと、
次いで、該混合物を成型体とし、該成型体を1250℃から1500℃の温度で焼成して、担体を形成するステップと
を含む。
−10g/kgから500g/kgまでの銀、
−存在するならば、0.01ミリモル/kgから50ミリモル/kgまでのレニウム、
−存在するならば、それぞれ0.1ミリモル/kgから500ミリモル/kgまでのさらなる1つまたは複数の元素、
−存在するならば、0.1ミリモル/kgから30ミリモル/kgまでのレニウム助触媒
である。
以下の成分を混合することにより担体(以下「担体A」とする)を作成した。
1.d50が29μmのα−アルミナ67.4重量部(pbw)。
2.d50が3μmのα−アルミナ29pbw。
3.酸化アルミニウム(ベーマイトの形態で)3pbw。
4.シリカ(アンモニア安定化シリカゾルの形態で)0.5pbw。
5.酸化ナトリウム(酢酸ナトリウムの形態で)0.1pbw。
下記工程で銀−アミン−シュウ酸塩保存溶液を調製した。
Claims (21)
- 担体と該担体上に触媒の重量に対して少なくとも10g/kgの量で析出させた銀とを含むオレフィンのエポキシ化触媒であって、該担体が、少なくとも1.4m2/gの表面積と、0.2μmから10μmまでの範囲の直径を有する細孔が細孔容積の合計の80%超に相当し、かつ該細孔が合わせて担体の重量に対して、少なくとも0.27ml/gの細孔容積を与えるような細孔径分布とを有し、該担体は、耐火材料、炭化ケイ素、粘土、ゼオライト、木炭、アルカリ土類金属炭酸塩をベースとする触媒。
- 銀に加えて、担体上に析出している窒素、硫黄、リン、ホウ素、フッ素、IA族金属、IIA族金属、レニウム、モリブデン、タングステン、クロム、チタン、ハフニウム、ジルコニウム、バナジウム、タリウム、トリウム、タンタル、ニオブ、ガリウム、ゲルマニウムおよびこれらの混合物のグループから選択された1つまたは複数のさらなる元素を含む請求項1に記載の触媒。
- 銀に加えて、担体上に析出しているレニウム、モリブデン、タングステン、IA族金属、硝酸塩もしくは亜硝酸塩を生成する化合物の1つまたは複数を含む請求項1又は2に記載の触媒。
- 前記IA族金属がリチウム、カリウム、ルビジウムおよびセシウムから選択される請求項2に記載の触媒。
- 担体と、触媒の重量に対して少なくとも10g/kgの量で担体上に析出させた銀、及び元素として計算した場合触媒の重量に対して0.01〜500mmole/kgの量で担体上に析出させたレニウム又はレニウム化合物とを含み、該担体が、少なくとも1m 2 /gの表面積と、0.2μmから10μmまでの範囲の直径を有する細孔が細孔容積の合計の80%超に相当し、かつ該細孔が合わせて担体の重量に対して、少なくとも0.27ml/gの細孔容積を与えるような細孔径分布とを有し、該担体は、耐火材料、炭化ケイ素、粘土、ゼオライト、木炭、アルカリ土類金属炭酸塩をベースとするオレフィンのエポキシ化触媒。
- 元素として計算した場合、触媒の重量に対して0.01〜50mmole/kgのレニウム又はレニウム化合物とを含む請求項5に記載の触媒。
- タングステン、モリブデン及び/又はIA族金属から選択されるさらなる元素を更に含む請求項5又は6に記載の触媒。
- 1つ又は複数の硫黄、リン、ホウ素及びこれらの化合物から選択されるレニウム助触媒を更に含む請求項5又は6に記載の触媒。
- 前記担体が、0.2μmから10μmまでの範囲の直径を有する細孔が細孔容積の合計の80%超に相当し、かつ該細孔が合わせて担体の重量に対して少なくとも0.28ml/gの細孔容積を与え、10μm超の直径を有する細孔が細孔容積の合計の15%未満に相当し、かつ0.2μm未満の直径を有する細孔が、細孔容積の合計の10%未満に相当するような細孔径分布を有する請求項1、2及び4〜6のいずれかに記載の触媒。
- 前記担体が、0.2μmから10μmまでの範囲の直径を有する細孔が細孔容積の合計の90%超に相当し、かつ該細孔が合わせて担体の重量に対して少なくとも0.3ml/gの細孔容積を与え、10μm超の直径を有する細孔が細孔容積の合計の10%未満に相当し、かつ0.2μm未満の直径を有する細孔が、細孔容積の合計の7%未満に相当するような細孔径分布を有する請求項1、2及び4〜6のいずれかに記載の触媒。
- 前記担体が0.28ml/gから0.8ml/gまでの範囲の合計細孔容積および最大2.9m2/gの表面積を有する請求項1、2及び4〜6のいずれかに記載の触媒。
- 前記担体が少なくとも95重量%のα−アルミナを含み、該担体が0.3g/gから0.8g/gまでの範囲の吸水率、および1.4m2/gから2.6m2/gまでの範囲の表面積を有する請求項1、2及び4〜6のいずれかに記載の触媒。
- 触媒の重量に対して50g/kgから500g/kgまでの量で担体上に銀が析出している請求項1、2及び4〜6のいずれかに記載の触媒。
- 前記担体が、結晶性シリカ含有組成物の形成のための阻害剤を含むシリカ含有組成物をベースとする結合材料を含む請求項1、2及び4から6のいずれかに記載の触媒。
- 前記担体が、少なくとも95重量%のアルミナ含有量を有し、前記結合材料が、アルミナ水和物、非晶質シリカ化合物、アルカリ金属化合物をベースとする請求項14に記載の触媒。
- 請求項1から15のいずれか一項に記載の触媒を調製するための方法であって、触媒の重量に対して少なくとも10g/kgの量で担体上に少なくとも銀、及び必要により窒素、硫黄、リン、ホウ素、フッ素、IA族金属、IIA族金属、レニウム、モリブデン、タングステン、クロム、チタン、ハフニウム、ジルコニウム、バナジウム、タリウム、トリウム、タンタル、ニオブ、ガリウム、ゲルマニウムおよびこれらの混合物のグループから選択された1つまたは複数のさらなる元素を析出させることを含む方法。
- 該担体が、
a)10μm超から100μmまでの平均粒径(d50)を有する第1の粒子状α−アルミナ50重量%から90重量%と、
b)1μmから10μmまでの平均粒径(d50)を有する第2の粒子状α−アルミナ10重量%から50重量%と
を含む混合物を形成するステップであって、ここに重量%は混合物中のα−アルミナの全重量に対してであるステップと、
混合物を焼成して担体を形成するステップと
を含む方法で得られたものである請求項16に記載の方法。 - 前記担体が、少なくとも95重量%のアルミナ含有量を有し、前記混合物が、
a)混合物中のα−アルミナの全重量に対して65重量%から75重量%までの、11μmから60μmまでの平均粒径(d50)を有する第1の粒子状α−アルミナと、
b)混合物の中のα−アルミナの全重量に対して25重量%から35重量%までの、2μmから6μmまでの平均粒径(d50)を有する第2の粒子状α−アルミナと、
c)酸化アルミニウムとして計算して混合物の中のα−アルミナの全重量に対して2重量%から5重量%のアルミナ水和物と、
d)酸化ケイ素として計算して混合物の中のα−アルミナの全重量に対して0.2重量%から0.8重量%までの非晶質シリカ化合物と、
e)アルカリ金属酸化物として計算して、混合物の中のα−アルミナの全重量に対して0.05重量%から0.3重量%までのアルカリ金属化合物と
を含み、該混合物を成型体とし、該成型体を1250℃から1500℃の温度で焼成する請求項17に記載の方法。 - オレフィンのエポキシ化の方法であって、請求項1から15のいずれかに記載の触媒の存在下で、もしくは請求項16から18のいずれかに記載の方法によって得られた触媒の存在下で、オレフィンを酸素と反応させるステップを含む方法。
- 前記オレフィンがエチレンである請求項19に記載の方法。
- 1,2−ジオール、1,2−ジオールエーテルまたはアルカノールアミンを製造するためにオレフィンオキサイドを使用する方法であって、請求項19または20に記載のオレフィンのエポキシ化の方法によって得られたオレフィンオキサイドを、1,2−ジオール、1,2−ジオールエーテルまたはアルカノールアミンに変換することを含む、該方法。
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EP1511563A2 (en) | 2005-03-09 |
CN101085425A (zh) | 2007-12-12 |
CA2477069C (en) | 2012-08-21 |
RU2342190C2 (ru) | 2008-12-27 |
CA2477069A1 (en) | 2003-09-04 |
BR0307958B1 (pt) | 2013-07-09 |
AU2003217756A1 (en) | 2003-09-09 |
RU2004128458A (ru) | 2005-04-10 |
IN2004DE02399A (ja) | 2005-04-01 |
MXPA04008167A (es) | 2004-11-26 |
JP2005518276A (ja) | 2005-06-23 |
US20090177016A1 (en) | 2009-07-09 |
BR0307958A (pt) | 2004-12-21 |
CN1642637A (zh) | 2005-07-20 |
WO2003072246A2 (en) | 2003-09-04 |
AU2003217756B2 (en) | 2008-11-20 |
EP1511563B1 (en) | 2012-11-28 |
KR101001503B1 (ko) | 2010-12-14 |
US20070184973A1 (en) | 2007-08-09 |
ZA200406645B (en) | 2006-05-31 |
CN100553763C (zh) | 2009-10-28 |
US20030162984A1 (en) | 2003-08-28 |
WO2003072246A3 (en) | 2004-01-08 |
KR20040086431A (ko) | 2004-10-08 |
CN100408168C (zh) | 2008-08-06 |
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