JP5889528B2 - エポキシ化触媒、触媒を調製するための方法および酸化オレフィン、1,2−ジオール、1,2−ジオールエーテル、1,2−カーボネートまたはアルカノールアミンを製造する方法。 - Google Patents
エポキシ化触媒、触媒を調製するための方法および酸化オレフィン、1,2−ジオール、1,2−ジオールエーテル、1,2−カーボネートまたはアルカノールアミンを製造する方法。 Download PDFInfo
- Publication number
- JP5889528B2 JP5889528B2 JP2010507616A JP2010507616A JP5889528B2 JP 5889528 B2 JP5889528 B2 JP 5889528B2 JP 2010507616 A JP2010507616 A JP 2010507616A JP 2010507616 A JP2010507616 A JP 2010507616A JP 5889528 B2 JP5889528 B2 JP 5889528B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- promoter
- mmol
- weight
- amount
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000003054 catalyst Substances 0.000 title claims description 202
- 150000001336 alkenes Chemical class 0.000 title claims description 69
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 65
- 238000000034 method Methods 0.000 title claims description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 35
- 150000000180 1,2-diols Chemical class 0.000 title claims description 33
- 238000006735 epoxidation reaction Methods 0.000 title claims description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 50
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 45
- 229910052709 silver Inorganic materials 0.000 claims description 45
- 239000004332 silver Substances 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 239000001301 oxygen Substances 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 20
- 229910052700 potassium Inorganic materials 0.000 claims description 20
- 239000011591 potassium Substances 0.000 claims description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 12
- 239000005977 Ethylene 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical group [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 11
- 229910052721 tungsten Inorganic materials 0.000 claims description 11
- 239000010937 tungsten Substances 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910052792 caesium Inorganic materials 0.000 claims description 6
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 238000000151 deposition Methods 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052776 Thorium Inorganic materials 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052758 niobium Inorganic materials 0.000 claims description 2
- 239000010955 niobium Substances 0.000 claims description 2
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052715 tantalum Inorganic materials 0.000 claims description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052716 thallium Inorganic materials 0.000 claims description 2
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 30
- 238000005470 impregnation Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 19
- 239000011148 porous material Substances 0.000 description 17
- 239000001569 carbon dioxide Substances 0.000 description 15
- 229910002092 carbon dioxide Inorganic materials 0.000 description 15
- 239000007789 gas Substances 0.000 description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000003607 modifier Substances 0.000 description 10
- -1 1,2-diol ethers Chemical class 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 7
- 229910052804 chromium Inorganic materials 0.000 description 7
- 239000011651 chromium Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 6
- 229960003750 ethyl chloride Drugs 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000003507 refrigerant Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Chemical group 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- IIPYXGDZVMZOAP-UHFFFAOYSA-N lithium nitrate Chemical compound [Li+].[O-][N+]([O-])=O IIPYXGDZVMZOAP-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 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
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 3
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000002823 nitrates Chemical class 0.000 description 3
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 3
- 239000004323 potassium nitrate Substances 0.000 description 3
- 235000010333 potassium nitrate Nutrition 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-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
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- NLSCHDZTHVNDCP-UHFFFAOYSA-N caesium nitrate Chemical compound [Cs+].[O-][N+]([O-])=O NLSCHDZTHVNDCP-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- RKGLUDFWIKNKMX-UHFFFAOYSA-L dilithium;sulfate;hydrate Chemical compound [Li+].[Li+].O.[O-]S([O-])(=O)=O RKGLUDFWIKNKMX-UHFFFAOYSA-L 0.000 description 2
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000012633 leachable Substances 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004251 Ammonium lactate Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910001963 alkali metal nitrate Inorganic materials 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940059265 ammonium lactate Drugs 0.000 description 1
- 235000019286 ammonium lactate Nutrition 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 description 1
- NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 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
- 235000013361 beverage Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 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
- 239000004927 clay Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- NLDGJRWPPOSWLC-UHFFFAOYSA-N deca-1,9-diene Chemical compound C=CCCCCCCC=C NLDGJRWPPOSWLC-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- YXVFQADLFFNVDS-UHFFFAOYSA-N diammonium citrate Chemical compound [NH4+].[NH4+].[O-]C(=O)CC(O)(C(=O)O)CC([O-])=O YXVFQADLFFNVDS-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 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
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 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
- 239000008262 pumice Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 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
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- YWYZEGXAUVWDED-UHFFFAOYSA-N triammonium citrate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YWYZEGXAUVWDED-UHFFFAOYSA-N 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite Substances 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/04—Sulfides
- B01J27/047—Sulfides with chromium, molybdenum, tungsten or polonium
- B01J27/049—Sulfides with chromium, molybdenum, tungsten or polonium with iron group metals or platinum group metals
-
- C—CHEMISTRY; METALLURGY
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/66—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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0213—Preparation of the impregnating solution
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
- C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
- C07C29/153—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
- C07C29/156—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof
- C07C29/157—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof containing platinum group metals or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/16—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by reduction or substitution, e.g. electroless plating
- C23C18/31—Coating with metals
- C23C18/42—Coating with noble metals
- C23C18/44—Coating with noble metals using reducing agents
-
- 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
- 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
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2235/00—Indexing scheme associated with group B01J35/00, related to the analysis techniques used to determine the catalysts form or properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- 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
- B01J23/683—Silver or gold with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum or tungsten
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/31—Density
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/612—Surface area less than 10 m2/g
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
- B01J35/633—Pore volume less than 0.5 ml/g
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/20—Sulfiding
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Catalysts (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本発明は、担体ならびに、担体上に付着させられた、銀、レニウム促進剤、第1の共促進剤および第2の共促進剤を含み、第1の共促進剤対第2の共促進剤のモル比は1より大きく、第1の共促進剤はイオウ、リン、ホウ素およびこれらの混合物から選択され、第2の共促進剤はタングステン、モリブデン、クロムおよびこれらの混合物から選択される、オレフィンのエポキシ化のための触媒を提供する。
この実施例は、実施例2の触媒Aの調製において使用される銀含浸ストック溶液の調製を記載している。
5リットルのステンレス鋼ビーカー中で、試薬等級の水酸化ナトリウム415gを脱イオン水2340ml中に溶解させ、温度を50℃に調節した。
触媒A(本発明による):
触媒Aは次の手順によって調製した:比重1.549g/mlの銀ストック溶液300.4gに1:1エチレンジアミン/水1g中の過レニウム酸アンモニウム0.1361g、1:1アンモニア/水1g中に溶解させたメタタングステン酸アンモニウム0.0759g、水2g中に溶解させた硫酸リチウム水和物0.1298gおよび水に溶解させた水酸化リチウム一水和物0.3193gを加えた。溶液の比重を1.539g/mlに調節するためにさらなる水を加えた。得られた溶液75gを50重量%の水酸化セシウム溶液0.1678gと混合して最終含浸溶液を作製した。担体Aの中空円筒、下記表Iを参照のこと、30グラムを収容している容器を20mmHgまで1分間真空にし、真空下のままで最終含浸溶液を担体Aに加え、次いで真空を開放して担体を液体に3分間接触させた。次いで含浸された担体Aを500rpmにおいて2分間遠心分離して過剰の液体を除去した。含浸された担体Aを振動式振とう機に入れ、16.2Nl/hの流量で流れている250℃の空気中で7分間乾燥して触媒A(本発明による)を作製した。
触媒Bは、触媒Aと類似の仕方で調製した。触媒Bの最終組成は細孔体積含浸に基づいて計算された次のものを含んでいた:銀17.5重量%、Re1ミリモル/kg、W1ミリモル/kg、S1ミリモル/kg、Li17ミリモル/kgおよびCs4.5ミリモル/kg。これらの値は触媒の重量に対するものである。
触媒Cは触媒Aと類似の仕方で調製した。触媒Cの最終組成は細孔体積含浸に基づいて計算された次のものを含んでいた:銀17.5重量%、Re1ミリモル/kg、W2ミリモル/kg、S2ミリモル/kg、Li19ミリモル/kg、およびCs4.1ミリモル/kg。これらの値は触媒の重量に対するものである。
触媒Dは、触媒Aと類似の仕方で調製した。触媒Dの最終組成は細孔体積含浸に基づいて計算された次のものを含んでいた:銀17.2重量%、Re2ミリモル/kg、W0.6ミリモル/kg、S2ミリモル/kg、Li19ミリモル/kg、およびCs5.6ミリモル/kg。これらの値は触媒の重量に対するものである。
触媒Eは触媒Aと類似の仕方で調製した。触媒Eの最終組成は細孔体積含浸に基づいて計算された次のものを含んでいた:銀17.2重量%、Re2ミリモル/kg、W0.6ミリモル/kg、S3ミリモル/kg、Li21ミリモル/kg、およびCs6.4ミリモル/kg。これらの値は触媒の重量に対するものである。
触媒Fは担体A30グラムを使用して触媒Aと類似の仕方で調製した。比重1.551g/mlの銀ストック溶液198.4グラムに、1:1のエチレンジアミン/水2g中の過レニウム酸アンモニウム0.1833g、50:50の水酸化アンモニウム/水2g中に溶解させたモリブデン酸アンモニウム0.0362g、水2g中に溶解させた硫酸リチウム一水和物0.1312gおよび水に溶解させた水酸化リチウム一水和物0.2151gを加えた。追加の水を加えて溶液の比重を1.528g/mlに調節した。得られた溶液50gを50重量%の水酸化セシウム溶液0.1591gと混合して含浸溶液を作製した。この最後の含浸溶液を使用して、触媒F(本発明による)を調製した。
触媒Gは触媒Fと類似の仕方で調製した。触媒Gの最終組成は細孔体積含浸に基づいて計算された次のものを含んでいた:銀17.2重量%、Re2ミリモル/kg、Mo0.6ミリモル/kg、S2ミリモル/kg、Li19ミリモル/kg、およびCs6ミリモル/kg。これらの値は触媒の重量に対するものである。
触媒Hは触媒Fと類似の仕方で調製した。触媒Hの最終組成は細孔体積含浸に基づいて計算された次のものを含んでいた:銀17.2重量%、Re2ミリモル/kg、Mo2ミリモル/kg、S2ミリモル/kg、Li19ミリモル/kg、およびCs5.6ミリモル/kg。これらの値は触媒の重量に対するものである。
触媒Iは触媒Fと類似の仕方で調製した。触媒Iの最終組成は細孔体積含浸に基づいて計算された次のものを含んでいた:銀17.2重量%、Re2ミリモル/kg、Mo0.6ミリモル/kg、Li15ミリモル/kg、およびCs4.5ミリモル/kg。これらの値は触媒の重量に対するものである。
触媒Jは触媒Aと類似の仕方で調製した。触媒Jの最終組成は細孔体積含浸に基づいて計算された次のものを含んでいた:銀17.2重量%、Re2ミリモル/kg、S3ミリモル/kg、Li21ミリモル/kg、およびCs6.8ミリモル/kg。これらの値は触媒の重量に対するものである。
触媒Kは触媒Aと類似の仕方で調製した。触媒Kの最終組成は細孔体積含浸に基づいて計算された次のものを含んでいた:銀17.2重量%、Re2ミリモル/kg、S2ミリモル/kg、Li19ミリモル/kg、およびCs5.6ミリモル/kg。これらの値は触媒の重量に対するものである。
触媒Lは触媒Aと類似の仕方で調製した。触媒Lの最終組成は細孔体積含浸に基づいて計算された次のものを含んでいた:銀17.2重量%、Re2ミリモル/kg、W0.6ミリモル/kg、Li15ミリモル/kg、およびCs5.6ミリモル/kg。これらの値は触媒の重量に対するものである。
触媒Mは触媒Aと類似の仕方で調製した。触媒Mの最終組成は細孔体積含浸に基づいて計算された次のものを含んでいた:銀17.2重量%、Re2ミリモル/kg、W2ミリモル/kg、Li15ミリモル/kg、およびCs4.1ミリモル/kg。これらの値は触媒の重量に対するものである。
触媒Nは触媒Aと類似の仕方で調製した。触媒Nの最終組成は細孔体積含浸に基づいて計算された次のものを含んでいた:銀17.5重量%、Re2ミリモル/kg、W1ミリモル/kg、S1ミリモル/kg、Li17ミリモル/kg、およびCs4.9ミリモル/kg。これらの値は触媒の重量に対するものである。
触媒Oは触媒Aと類似の仕方で調製した。触媒Oの最終組成は細孔体積含浸に基づいて計算された次のものを含んでいた:銀17.2重量%、Re2ミリモル/kg、W2ミリモル/kg、S2ミリモル/kg、Li19ミリモル/kg、およびCs5.6ミリモル/kg。これらの値は触媒の重量に対するものである。
この触媒をエチレンおよび酸素から酸化エチレンを作製するために使用した。これを行うために、破砕した触媒サンプル3から5gを別個のステンレス鋼のU形管中に装填した。それぞれの管を溶融金属浴(熱媒)中に漬け、両端をガス流通装置に接続した。使用した触媒の重量および入口ガス流量は未破砕の触媒に対して計算して3300Nl/(l・h)のガス空間速度を与えるように調節した。入口ガスの圧力は1550kPa(絶対圧)であった。
Claims (15)
- オレフィンのエポキシ化のための触媒であって、担体ならびに、担体上に付着させられた、銀、セシウム、リチウム、レニウム促進剤、第1の共促進剤および第2の共促進剤を含み、
第1の共促進剤対第2の共促進剤のモル比は少なくとも3であり、かつ、最大で5であり、
第1の共促進剤はイオウであり、
第2の共促進剤はタングステン、モリブデンおよびこれらの混合物から選択される、触媒。 - 触媒が、触媒の重量に対して1.25から10ミリモル/kgの範囲内の水抽出可能なカリウム量を有する、請求項1に記載の触媒。
- 触媒が、触媒の重量に対して1.5から7.5ミリモル/kgの範囲内の水抽出可能なカリウム量を有する、請求項1に記載の触媒。
- レニウム促進剤が、触媒の重量に対して0.1から50ミリモル/kgの範囲内の量で存在する、請求項1または2から3のいずれかに記載の触媒。
- 第1の共促進剤が、触媒の重量に対して0.2から40ミリモル/kgの範囲内の量で存在する、請求項1または2から4のいずれかに記載の触媒。
- 第1の共促進剤が、触媒の重量に対して1から10ミリモル/kgの範囲内の量で存在する、請求項1または2から4のいずれかに記載の触媒。
- レニウム促進剤対第2の共促進剤のモル比が、1より大きい、請求項1または2から6のいずれかに記載の触媒。
- レニウム促進剤対第2の共促進剤のモル比が少なくとも2である、請求項1または2から6のいずれかに記載の触媒。
- 触媒が、担体上に付着させられたカリウム促進剤を、触媒の重量に対して少なくとも0.5ミリモル/kgの量でさらに含む、請求項1または2から8のいずれかに記載の触媒。
- 触媒が、担体上に付着させられたカリウム促進剤を、触媒の重量に対して少なくとも1.5ミリモル/kgの量でさらに含む、請求項1または2から8のいずれかに記載の触媒。
- 触媒が、担体上に付着された、窒素、フッ素、アルカリ金属、アルカリ土類金属、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から選択された1種以上のさらなる元素をさらに含む、請求項1または2から10のいずれかに記載の触媒。
- オレフィンのエポキシ化のための触媒を調製する方法であって、銀、セシウム、リチウム、レニウム促進剤、第1の共促進剤および第2の共促進剤を担体上に付着させることを含み、
第1の共促進剤対第2の共促進剤のモル比は少なくとも3であり、かつ、最大で5であり、
第1の共促進剤はイオウであり、
第2の共促進剤はタングステン、モリブデンおよびこれらの混合物から選択される、方法。 - オレフィンおよび酸素を含む供給原料を請求項1または2から11のいずれかに記載の触媒の存在下で反応させることによる酸化オレフィンを調製する方法。
- オレフィンが、エチレンを含む、請求項13に記載の方法。
- 1,2−ジオール、1,2−ジオールエーテル、1,2−カーボネートまたはアルカノールアミンを調製する方法であって、酸化オレフィンを1,2−ジオール、1,2−ジオールエーテル、1,2−カーボネートまたはアルカノールアミンに転化させることを含み、この酸化オレフィンは請求項13または14に記載の酸化オレフィンを調製する方法によって調製されている、方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US91695807P | 2007-05-09 | 2007-05-09 | |
US60/916,958 | 2007-05-09 | ||
PCT/US2008/062876 WO2008141032A1 (en) | 2007-05-09 | 2008-05-07 | An epoxidation catalyst, a process for preparing the catalyst, and a process for the production of an olefin oxide, a 1,2-diol, a 1,2-diol ether, a 1,2-carbonate, or an alkanolamine |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014048422A Division JP5931106B2 (ja) | 2007-05-09 | 2014-03-12 | エポキシ化触媒、触媒を調製するための方法および酸化オレフィン、1,2−ジオール、1,2−ジオールエーテル、1,2−カーボネートまたはアルカノールアミンを製造する方法 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010526655A JP2010526655A (ja) | 2010-08-05 |
JP2010526655A5 JP2010526655A5 (ja) | 2013-06-20 |
JP5889528B2 true JP5889528B2 (ja) | 2016-03-22 |
Family
ID=39629048
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010507616A Active JP5889528B2 (ja) | 2007-05-09 | 2008-05-07 | エポキシ化触媒、触媒を調製するための方法および酸化オレフィン、1,2−ジオール、1,2−ジオールエーテル、1,2−カーボネートまたはアルカノールアミンを製造する方法。 |
JP2014048422A Active JP5931106B2 (ja) | 2007-05-09 | 2014-03-12 | エポキシ化触媒、触媒を調製するための方法および酸化オレフィン、1,2−ジオール、1,2−ジオールエーテル、1,2−カーボネートまたはアルカノールアミンを製造する方法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014048422A Active JP5931106B2 (ja) | 2007-05-09 | 2014-03-12 | エポキシ化触媒、触媒を調製するための方法および酸化オレフィン、1,2−ジオール、1,2−ジオールエーテル、1,2−カーボネートまたはアルカノールアミンを製造する方法 |
Country Status (11)
Country | Link |
---|---|
US (1) | US20110034710A1 (ja) |
EP (2) | EP3187493B1 (ja) |
JP (2) | JP5889528B2 (ja) |
KR (1) | KR20100017691A (ja) |
CN (1) | CN101715444B (ja) |
AR (1) | AR069263A1 (ja) |
BR (1) | BRPI0811311A2 (ja) |
CA (1) | CA2686825C (ja) |
TW (1) | TWI446963B (ja) |
WO (1) | WO2008141032A1 (ja) |
ZA (1) | ZA200907525B (ja) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7932408B2 (en) | 2006-09-29 | 2011-04-26 | Scientific Design Company, Inc. | Catalyst with bimodal pore size distribution and the use thereof |
US20110034710A1 (en) * | 2007-05-09 | 2011-02-10 | Marek Matusz | Epoxidation catalyst, a process for preparing the catalyst, and a process for the production of an olefin oxide, a 1,2-diol, a 1,2-diol ether, a 1,2-carbonate, or an alkanolamine |
CN102414189B (zh) | 2009-04-21 | 2014-09-17 | 陶氏技术投资有限公司 | 环氧化反应及其操作条件 |
CN103547365B (zh) | 2011-04-11 | 2016-03-16 | 陶氏技术投资有限责任公司 | 调节高效环氧乙烷催化剂的方法 |
WO2013164727A1 (de) | 2012-05-04 | 2013-11-07 | Basf Se | Katalysator zur epoxidation von alkenen |
SG11201507353RA (en) | 2013-03-15 | 2015-10-29 | Dow Technology Investments Llc | Method for the production of ethylene oxide |
JP2017501864A (ja) * | 2013-12-09 | 2017-01-19 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | アルケンのエポキシ化用触媒 |
US10450287B2 (en) | 2015-12-15 | 2019-10-22 | Shell Oil Company | Processes and systems for removing an alkyl iodide impurity from a recycle gas stream in the production of ethylene oxide |
US11000819B2 (en) | 2015-12-15 | 2021-05-11 | Shell Oil Company | Guard bed system and process |
EP3390379B1 (en) | 2015-12-15 | 2019-10-30 | Shell International Research Maatschappij B.V. | Processes and systems for removing a vinyl iodide impurity from a recycle gas stream in the production of ethylene oxide |
US10526300B2 (en) | 2015-12-15 | 2020-01-07 | Shell Oil Company | Processes and systems for removing iodide impurities from a recycle gas stream in the production of ethylene oxide |
TWI772330B (zh) | 2016-10-14 | 2022-08-01 | 荷蘭商蜆殼國際研究所 | 用於定量分析氣態製程流之方法及設備 |
WO2018128639A1 (en) | 2017-01-05 | 2018-07-12 | Scientific Design Company, Inc. | Carrier, catalyst, methods for producing them and method for producing ethylene oxide |
Family Cites Families (48)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1976677A (en) * | 1929-08-20 | 1934-10-09 | Ig Farbenindustrie Ag | Production of alkylene derivatives from alkylene oxides |
DE2967112D1 (en) | 1978-02-10 | 1984-08-23 | Ici Plc | Production of olefine oxides |
US4430312A (en) * | 1982-06-23 | 1984-02-07 | Eickmeyer Allen Garland | Removal of CO2 from gas mixtures |
US4845296A (en) * | 1983-12-13 | 1989-07-04 | Union Carbide Corporation | Process for preparing alkanolamines |
JPS6110570A (ja) * | 1984-06-25 | 1986-01-18 | Mitsui Toatsu Chem Inc | エチレンオキシドの製造方法 |
GB8423044D0 (en) | 1984-09-12 | 1984-10-17 | Ici Plc | Production of ethylene oxide |
IL84232A (en) * | 1986-10-31 | 1992-06-21 | Shell Int Research | Catalyst and process for the catalytic production of ethylene oxide |
US4808738A (en) * | 1986-10-31 | 1989-02-28 | Shell Oil Company | Ethylene oxide process |
US4761394A (en) * | 1986-10-31 | 1988-08-02 | Shell Oil Company | Ethylene oxide catalyst and process for preparing the catalyst |
US4766105A (en) | 1986-10-31 | 1988-08-23 | Shell Oil Company | Ethylene oxide catalyst and process for preparing the catalyst |
US4820675A (en) * | 1986-10-31 | 1989-04-11 | Shell Oil Company | Ethylene oxide catalyst & process for preparing the catalyst |
US4908343A (en) * | 1987-02-20 | 1990-03-13 | Union Carbide Chemicals And Plastics Company Inc. | Catalyst composition for oxidation of ethylene to ethylene oxide |
US4874879A (en) * | 1988-07-25 | 1989-10-17 | Shell Oil Company | Process for starting-up an ethylene oxide reactor |
EP0357293B1 (en) | 1988-08-30 | 1996-02-28 | Union Carbide Corporation | Catalysts for the production of ethylene oxide and their preparation processes |
CA1337722C (en) * | 1989-04-18 | 1995-12-12 | Madan Mohan Bhasin | Alkylene oxide catalysts having enhanced activity and/or stability |
CN1068320C (zh) * | 1989-04-18 | 2001-07-11 | 联合碳化化学品及塑料有限公司 | 烯化氧的生产方法 |
US5187140A (en) * | 1989-10-18 | 1993-02-16 | Union Carbide Chemicals & Plastics Technology Corporation | Alkylene oxide catalysts containing high silver content |
US5102848A (en) * | 1990-09-28 | 1992-04-07 | Union Carbide Chemicals & Plastics Technology Corporation | Catalyst composition for oxidation of ethylene to ethylene oxide |
US5112795A (en) * | 1990-10-12 | 1992-05-12 | Union Carbide Chemicals & Plastics Technology Corporation | Supported silver catalyst, and processes for making and using same |
EP0480538B1 (en) * | 1990-10-12 | 1998-09-02 | UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY CORPORATION, Three Cristina Centre | Alkylene oxide catalysts having enhanced activity and/or stability |
US5145658A (en) * | 1990-11-28 | 1992-09-08 | Eickmeyer & Associates, Inc. | Reclaiming of heat of reaction energy from an alkaline scrubbing solution used in acid gas removal processes and apparatus therefor |
US5380697A (en) | 1993-09-08 | 1995-01-10 | Shell Oil Company | Ethylene oxide catalyst and process |
US5418202A (en) * | 1993-12-30 | 1995-05-23 | Shell Oil Company | Ethylene oxide catalyst and process |
US5545603A (en) | 1994-11-01 | 1996-08-13 | Shell Oil Company | Ethylene oxide catalyst and process |
US5504052A (en) * | 1994-12-02 | 1996-04-02 | Scientific Design Company, Inc. | Silver catalyst preparation |
US5705661A (en) * | 1995-09-25 | 1998-01-06 | Mitsubishi Chemical Corporation | Catalyst for production of ethylene oxide |
US5739075A (en) * | 1995-10-06 | 1998-04-14 | Shell Oil Company | Process for preparing ethylene oxide catalysts |
US5801259A (en) | 1996-04-30 | 1998-09-01 | Shell Oil Company | Ethylene oxide catalyst and process |
US5840932A (en) * | 1996-05-21 | 1998-11-24 | Shell Oil Company | Process for ethylene oxide production |
US6040467A (en) * | 1997-07-24 | 2000-03-21 | Praxair Technology, Inc. | High purity oxygen for ethylene oxide production |
US6080897A (en) * | 1998-03-19 | 2000-06-27 | Mitsubishi Chemical Corporation | Method for producing monoethylene glycol |
BR9913600A (pt) | 1998-09-14 | 2001-05-22 | Shell Int Research | Processos para aumentar as propriedades de um veìculo para catalisador através de um tratamento, para preparar um catalisador, e para a epoxidação catalìtica de um alceno com um gás contendo oxigênio |
US6372925B1 (en) * | 2000-06-09 | 2002-04-16 | Shell Oil Company | Process for operating the epoxidation of ethylene |
US6533843B2 (en) * | 2001-06-05 | 2003-03-18 | Scientific Design Company, Inc. | Two stage flash for hydrocarbon removal |
US6452027B1 (en) * | 2001-09-10 | 2002-09-17 | Scientific Design Company, Inc. | Heat recovery procedure |
RU2342190C2 (ru) * | 2002-02-25 | 2008-12-27 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Катализатор и способ его применения |
CN100512966C (zh) * | 2002-06-28 | 2009-07-15 | 国际壳牌研究有限公司 | 提高催化剂选择性的方法和烯烃环氧化方法 |
DE60304197T2 (de) * | 2002-06-28 | 2006-12-14 | Shell Internationale Research Maatschappij B.V. | Verfahren zum initiieren eines epoxidationsverfahrens, katalysator und verfahren zur epoxidation eines olefins |
TWI346574B (en) * | 2003-03-31 | 2011-08-11 | Shell Int Research | A catalyst composition, a process for preparing the catalyst composition and a use of the catalyst composition |
TW200507933A (en) * | 2003-04-01 | 2005-03-01 | Shell Int Research | An olefin epoxidation process and a catalyst for use in the process |
AU2004238820B2 (en) | 2003-05-07 | 2008-01-31 | Shell Internationale Research Maatschappij B.V. | Silver-containing catalysts, the manufacture of such silver containing catalysts, and the use thereof |
CN101757914A (zh) * | 2003-10-16 | 2010-06-30 | 陶氏技术投资有限责任公司 | 用于烯化氧制备的具有提高稳定性、效率和/或活性的催化剂 |
US7479565B2 (en) | 2004-06-18 | 2009-01-20 | Shell Oil Company | Process for the production of an olefin oxide, a 1,2-diol, a 1,2-diol ether, or an alkanolamine |
TW201109083A (en) * | 2005-06-07 | 2011-03-16 | Saint Gobain Ceramics & Plastics Inc | A process for preparing a catalyst carrier |
RU2008136381A (ru) | 2006-02-10 | 2010-03-20 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. (NL) | Способ получения катализатора, катализатор и способ получения олефиноксида, 1,2-диола, простого эфира 1,2,-диола или алканоламина |
JP2007277744A (ja) * | 2006-04-04 | 2007-10-25 | Nitivy Co Ltd | 耐熱性に優れたアルミナ繊維およびその前駆体繊維の製造方法 |
EP2013194A2 (de) * | 2006-04-21 | 2009-01-14 | Basf Se | Verfahren zur herstellung von ethylenoxid in einem mikrokanalreaktor |
US20110034710A1 (en) * | 2007-05-09 | 2011-02-10 | Marek Matusz | Epoxidation catalyst, a process for preparing the catalyst, and a process for the production of an olefin oxide, a 1,2-diol, a 1,2-diol ether, a 1,2-carbonate, or an alkanolamine |
-
2008
- 2008-05-07 US US12/865,021 patent/US20110034710A1/en not_active Abandoned
- 2008-05-07 BR BRPI0811311-4A2A patent/BRPI0811311A2/pt active IP Right Grant
- 2008-05-07 KR KR1020097025534A patent/KR20100017691A/ko active Search and Examination
- 2008-05-07 CA CA2686825A patent/CA2686825C/en active Active
- 2008-05-07 WO PCT/US2008/062876 patent/WO2008141032A1/en active Application Filing
- 2008-05-07 EP EP17155480.1A patent/EP3187493B1/en active Active
- 2008-05-07 JP JP2010507616A patent/JP5889528B2/ja active Active
- 2008-05-07 TW TW097116878A patent/TWI446963B/zh active
- 2008-05-07 EP EP08747772.5A patent/EP2152681B1/en not_active Revoked
- 2008-05-07 CN CN2008800189069A patent/CN101715444B/zh active Active
- 2008-05-07 AR ARP080101927A patent/AR069263A1/es unknown
-
2009
- 2009-10-27 ZA ZA200907525A patent/ZA200907525B/xx unknown
-
2014
- 2014-03-12 JP JP2014048422A patent/JP5931106B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
CN101715444B (zh) | 2012-11-21 |
EP2152681A1 (en) | 2010-02-17 |
EP3187493A1 (en) | 2017-07-05 |
TW200906485A (en) | 2009-02-16 |
CA2686825A1 (en) | 2008-11-20 |
EP2152681B1 (en) | 2017-03-29 |
BRPI0811311A2 (pt) | 2015-01-27 |
EP3187493B1 (en) | 2019-07-10 |
CA2686825C (en) | 2016-09-13 |
US20110034710A1 (en) | 2011-02-10 |
JP2014159028A (ja) | 2014-09-04 |
WO2008141032A1 (en) | 2008-11-20 |
TWI446963B (zh) | 2014-08-01 |
AR069263A1 (es) | 2010-01-13 |
JP5931106B2 (ja) | 2016-06-08 |
CN101715444A (zh) | 2010-05-26 |
JP2010526655A (ja) | 2010-08-05 |
ZA200907525B (en) | 2010-05-26 |
KR20100017691A (ko) | 2010-02-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5542659B2 (ja) | エポキシ化触媒、触媒を調製する方法、および酸化オレフィン、1,2−ジオール、1,2−ジオールエーテル、1,2−カーボネートまたはアルカノールアミンの製造方法 | |
JP5931106B2 (ja) | エポキシ化触媒、触媒を調製するための方法および酸化オレフィン、1,2−ジオール、1,2−ジオールエーテル、1,2−カーボネートまたはアルカノールアミンを製造する方法 | |
JP5868703B2 (ja) | オレフィンオキシド、1,2−ジオール、1,2−ジオールエーテル、1,2−カーボネートまたはアルカノールアミンの製造方法 | |
JP5507444B2 (ja) | 酸化オレフィン、1,2−ジオール、1,2−ジオールエーテル、1,2−カーボネートまたはアルカノールアミンの製造方法 | |
WO2009029578A2 (en) | A carrier, a process for preparing the carrier, an olefin epoxidation catalyst, a process for preparing the catalyst, and a process for the production of an olefin oxide, a 1,2-diol, a 1,2-diol ether, or an alkanolamine |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110428 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20121113 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20121225 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130122 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20130128 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130418 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130425 |
|
A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20130501 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130716 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20131112 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140312 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20140418 |
|
A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20140523 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20150414 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150707 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20151201 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160217 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5889528 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 |