SG175770A1 - Simplified method for producing alkylene oxides with a high efficiency catalyst as it ages - Google Patents
Simplified method for producing alkylene oxides with a high efficiency catalyst as it ages Download PDFInfo
- Publication number
- SG175770A1 SG175770A1 SG2011077575A SG2011077575A SG175770A1 SG 175770 A1 SG175770 A1 SG 175770A1 SG 2011077575 A SG2011077575 A SG 2011077575A SG 2011077575 A SG2011077575 A SG 2011077575A SG 175770 A1 SG175770 A1 SG 175770A1
- Authority
- SG
- Singapore
- Prior art keywords
- catalyst
- alkylene oxide
- reaction temperature
- concentration
- effectiveness
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 305
- 125000002947 alkylene group Chemical group 0.000 title claims abstract description 120
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 55
- 238000006243 chemical reaction Methods 0.000 claims abstract description 188
- 238000000034 method Methods 0.000 claims abstract description 106
- 229910052709 silver Inorganic materials 0.000 claims abstract description 46
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 45
- 239000004332 silver Substances 0.000 claims abstract description 45
- 239000007789 gas Substances 0.000 claims description 96
- 230000008569 process Effects 0.000 claims description 81
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 80
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 56
- 229960003750 ethyl chloride Drugs 0.000 claims description 56
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 52
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 45
- 239000005977 Ethylene Substances 0.000 claims description 45
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 39
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 32
- 230000007423 decrease Effects 0.000 claims description 32
- 239000001301 oxygen Substances 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 31
- 230000001965 increasing effect Effects 0.000 claims description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 23
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 19
- 239000002826 coolant Substances 0.000 claims description 19
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 18
- 229910052702 rhenium Inorganic materials 0.000 claims description 17
- 150000002430 hydrocarbons Chemical class 0.000 claims description 16
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- 230000001737 promoting effect Effects 0.000 claims description 10
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- 239000007795 chemical reaction product Substances 0.000 claims description 6
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- 229910052753 mercury Inorganic materials 0.000 claims description 3
- 230000004044 response Effects 0.000 claims description 3
- 235000008331 Pinus X rigitaeda Nutrition 0.000 claims description 2
- 235000011613 Pinus brutia Nutrition 0.000 claims description 2
- 241000018646 Pinus brutia Species 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 52
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 24
- 150000001336 alkenes Chemical class 0.000 description 22
- -1 glycol ethers Chemical class 0.000 description 22
- 238000006735 epoxidation reaction Methods 0.000 description 20
- 239000000463 material Substances 0.000 description 19
- 150000003839 salts Chemical class 0.000 description 19
- 230000032683 aging Effects 0.000 description 18
- 150000001768 cations Chemical class 0.000 description 17
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 17
- 241000894007 species Species 0.000 description 17
- 150000001450 anions Chemical class 0.000 description 16
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
- 229910002092 carbon dioxide Inorganic materials 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229910052783 alkali metal Inorganic materials 0.000 description 12
- 150000001340 alkali metals Chemical class 0.000 description 12
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- 230000003197 catalytic effect Effects 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
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- 229910052801 chlorine Inorganic materials 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 229910052792 caesium Inorganic materials 0.000 description 8
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 8
- 150000001805 chlorine compounds Chemical class 0.000 description 8
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- 102100031162 Collagen alpha-1(XVIII) chain Human genes 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 101000940068 Homo sapiens Collagen alpha-1(XVIII) chain Proteins 0.000 description 7
- 230000001186 cumulative effect Effects 0.000 description 7
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- 239000011572 manganese Substances 0.000 description 7
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- 239000000126 substance Substances 0.000 description 7
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 6
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- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
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- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
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- 239000000377 silicon dioxide Substances 0.000 description 5
- 229940100890 silver compound Drugs 0.000 description 5
- 150000003379 silver compounds Chemical class 0.000 description 5
- 239000011949 solid catalyst Substances 0.000 description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
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- 150000002500 ions Chemical class 0.000 description 4
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- 229940050176 methyl chloride Drugs 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- 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
- 229910002651 NO3 Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 3
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- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 239000010937 tungsten Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
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- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
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- 239000000654 additive Substances 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- KOPBYBDAPCDYFK-UHFFFAOYSA-N caesium oxide Chemical compound [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 2
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- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
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- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
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- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
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- NCMHKCKGHRPLCM-UHFFFAOYSA-N caesium(1+) Chemical compound [Cs+] NCMHKCKGHRPLCM-UHFFFAOYSA-N 0.000 description 1
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- 238000004364 calculation method Methods 0.000 description 1
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- VODGJKZAAVKBAL-UHFFFAOYSA-L diazanium;manganese(2+);disulfate Chemical compound [NH4+].[NH4+].[Mn+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VODGJKZAAVKBAL-UHFFFAOYSA-L 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000003837 high-temperature calcination Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000003116 impacting effect Effects 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids 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
- 229940071125 manganese acetate Drugs 0.000 description 1
- 239000011564 manganese citrate Substances 0.000 description 1
- 229940097206 manganese citrate Drugs 0.000 description 1
- 235000014872 manganese citrate Nutrition 0.000 description 1
- OKVGBKABWITJQA-UHFFFAOYSA-L manganese dithionate Chemical compound [Mn+2].[O-]S(=O)(=O)S([O-])(=O)=O OKVGBKABWITJQA-UHFFFAOYSA-L 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- RGVLTEMOWXGQOS-UHFFFAOYSA-L manganese(2+);oxalate Chemical compound [Mn+2].[O-]C(=O)C([O-])=O RGVLTEMOWXGQOS-UHFFFAOYSA-L 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- ALTWGIIQPLQAAM-UHFFFAOYSA-N metavanadate Chemical compound [O-][V](=O)=O ALTWGIIQPLQAAM-UHFFFAOYSA-N 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 229910052863 mullite Inorganic materials 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000024977 response to activity Effects 0.000 description 1
- 150000003281 rhenium Chemical class 0.000 description 1
- 150000003282 rhenium compounds Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000004760 silicates Chemical class 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
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical class [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 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
- 239000007790 solid phase Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/22—Synthesis of the oxirane ring by oxidation of saturated compounds with air or molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
- C07D301/26—Y being hydrogen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epoxy Compounds (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17124809P | 2009-04-21 | 2009-04-21 | |
| PCT/US2010/031668 WO2010123842A1 (en) | 2009-04-21 | 2010-04-20 | Simplified method for producing alkylene oxides with a high efficiency catalyst as it ages |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG175770A1 true SG175770A1 (en) | 2011-12-29 |
Family
ID=42307796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG2011077575A SG175770A1 (en) | 2009-04-21 | 2010-04-20 | Simplified method for producing alkylene oxides with a high efficiency catalyst as it ages |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8389751B2 (enExample) |
| EP (1) | EP2421840B1 (enExample) |
| JP (1) | JP2012524785A (enExample) |
| KR (1) | KR101745737B1 (enExample) |
| CN (1) | CN102414187B (enExample) |
| CA (1) | CA2758818C (enExample) |
| SG (1) | SG175770A1 (enExample) |
| TW (1) | TWI508955B (enExample) |
| WO (1) | WO2010123842A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5756087B2 (ja) * | 2009-04-21 | 2015-07-29 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 高効率触媒による特定のアルキレンオキサイド製造パラメーターを達成かつ維持する改良方法 |
| US8742147B2 (en) | 2010-12-08 | 2014-06-03 | Shell Oil Company | Process for improving the selectivity of an EO catalyst |
| EP2649059B1 (en) | 2010-12-10 | 2016-02-24 | Dow Technology Investments LLC | Method of reducing the value of an alkylene oxide production parameter in a process of making an alkylene oxide using a high efficiency catalyst |
| WO2012082389A1 (en) * | 2010-12-15 | 2012-06-21 | Dow Technology Investments Llc | Method of starting-up a process of producing an alkylene oxide using a high-efficiency catalyst |
| EP2714670B2 (en) | 2011-04-29 | 2022-03-02 | Shell Internationale Research Maatschappij B.V. | Process for improving the selectivity of an eo catalyst |
| CN108707125A (zh) * | 2011-10-18 | 2018-10-26 | 哈桑·伊萨·阿拉哈迈迪 | 具有添加缓和剂的环氧化方法 |
| SG11201403042SA (en) * | 2011-12-09 | 2014-10-30 | Dow Technology Investments Llc | Method of maintaining the value of an alkylene oxide production parameter in a process of making an alkylene oxide using a high efficiency catalyst |
| SG11201507353RA (en) * | 2013-03-15 | 2015-10-29 | Dow Technology Investments Llc | Method for the production of ethylene oxide |
| JP6340895B2 (ja) * | 2014-04-24 | 2018-06-13 | 東ソー株式会社 | 触媒性能の経時変化解析方法および触媒性能の経時変化解析装置 |
| CN105330617B (zh) * | 2014-07-18 | 2018-12-28 | 中国石油化工股份有限公司 | 一种生产环氧乙烷的方法 |
| CA2972690C (en) * | 2014-12-30 | 2023-08-22 | Dow Technology Investments Llc | Process for manufacturing ethylene oxide using scaled selectivity values |
| CN109312215B (zh) | 2016-08-05 | 2021-03-26 | 神岛化学工业株式会社 | 稀土类硫氧化物蓄冷材料 |
| CN111450778B (zh) * | 2019-01-22 | 2023-04-07 | 中国石化工程建设有限公司 | 一种用于制备聚α-烯烃的聚合反应系统和方法 |
| CN111939846B (zh) * | 2019-05-17 | 2023-01-03 | 中国石化工程建设有限公司 | 一种合成聚α-烯烃的装置及方法 |
| US11249446B2 (en) | 2019-10-25 | 2022-02-15 | Dow Global Technologies Llc | Nonlinear model predictive control of a process |
| TW202239752A (zh) | 2020-12-29 | 2022-10-16 | 荷蘭商蜆殼國際研究所 | 用於生產環氧乙烷之製程 |
| WO2022214539A1 (en) | 2021-04-08 | 2022-10-13 | Shell Internationale Research Maatschappij B.V. | Moderator and catalyst performance optimization for epoxidation of ethylene |
| CN118019732A (zh) * | 2021-09-23 | 2024-05-10 | 陶氏环球技术有限责任公司 | 用于降低高选择性环氧乙烷催化剂的老化相关失活的方法 |
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| BE752859R (fr) | 1969-07-10 | 1971-01-04 | Halcon International Inc | Oxydation controlee de l'oxyde |
| US5387751A (en) * | 1978-02-10 | 1995-02-07 | Imperial Chemical Industries Plc | Production of olefine oxides |
| 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 |
| CA1286687C (en) * | 1985-08-13 | 1991-07-23 | Michael Paul Habenschuss | Process for manufacture of alkene oxide |
| IL84232A (en) | 1986-10-31 | 1992-06-21 | Shell Int Research | Catalyst and process for the catalytic production of ethylene oxide |
| 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 |
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| GB8626687D0 (en) * | 1986-11-07 | 1986-12-10 | Shell Int Research | Preparing silver 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 |
| US4769047A (en) * | 1987-06-29 | 1988-09-06 | Shell Oil Company | Process for the production of ethylene oxide |
| GB8716653D0 (en) * | 1987-07-15 | 1987-08-19 | Shell Int Research | Silver-containing catalyst |
| US4759313A (en) * | 1987-10-30 | 1988-07-26 | Shell Oil Company | Ethylene oxide process improvement |
| US4874879A (en) * | 1988-07-25 | 1989-10-17 | Shell Oil Company | Process for starting-up an ethylene oxide reactor |
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| EP0357293B1 (en) | 1988-08-30 | 1996-02-28 | Union Carbide Corporation | Catalysts for the production of ethylene oxide and their preparation processes |
| CA1282772C (en) * | 1989-02-17 | 1991-04-09 | Union Carbide Corporation | Carbonate-supported catalytic system for epoxidation of alkenes |
| CA1337722C (en) * | 1989-04-18 | 1995-12-12 | Madan Mohan Bhasin | Alkylene oxide catalysts having enhanced activity and/or stability |
| GB9005964D0 (en) * | 1990-03-16 | 1990-05-09 | Shell Int Research | Catalyst preparation process |
| US5102848A (en) * | 1990-09-28 | 1992-04-07 | Union Carbide Chemicals & Plastics Technology Corporation | Catalyst composition for oxidation of ethylene to ethylene oxide |
| JPH04298241A (ja) | 1990-10-12 | 1992-10-22 | Union Carbide Chem & Plast Co Inc | 向上した安定性を有する超高性能アルキレンオキシド触媒 |
| CA2053411C (en) * | 1990-10-12 | 1997-06-03 | Albert Cheng-Yu Liu | Alkylene oxide catalysts having enhanced activity and/or stability |
| US5145824A (en) * | 1991-01-22 | 1992-09-08 | Shell Oil Company | Ethylene oxide catalyst |
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| US5155242A (en) * | 1991-12-05 | 1992-10-13 | Shell Oil Company | Process for starting-up an ethylene oxide reactor |
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| US5447897A (en) * | 1993-05-17 | 1995-09-05 | Shell Oil Company | Ethylene oxide catalyst and process |
| US5380697A (en) * | 1993-09-08 | 1995-01-10 | Shell Oil Company | Ethylene oxide catalyst and process |
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| 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 |
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| KR100977098B1 (ko) | 2001-11-20 | 2010-08-23 | 셀 인터나쵸나아레 레사아치 마아츠샤피 비이부이 | 올레핀의 에폭시화 방법 및 시스템 |
| RU2005102097A (ru) | 2002-06-28 | 2005-08-27 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. (NL) | Способ введения в действие способа эпоксидирования и способ эпоксидирования олефина |
| RU2328491C2 (ru) * | 2003-04-01 | 2008-07-10 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ эпоксидирования олефинов и катализатор для применения в способе |
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| US7803957B2 (en) * | 2007-09-11 | 2010-09-28 | Sd Lizenzverwertungsgesellschaft Mbh & Co. Kg | Ethylene oxide production using fixed moderator concentration |
-
2010
- 2010-04-20 JP JP2012507296A patent/JP2012524785A/ja active Pending
- 2010-04-20 US US12/763,276 patent/US8389751B2/en not_active Expired - Fee Related
- 2010-04-20 WO PCT/US2010/031668 patent/WO2010123842A1/en not_active Ceased
- 2010-04-20 TW TW099112280A patent/TWI508955B/zh active
- 2010-04-20 CN CN201080017744.4A patent/CN102414187B/zh active Active
- 2010-04-20 KR KR1020117027498A patent/KR101745737B1/ko not_active Expired - Fee Related
- 2010-04-20 EP EP10718767.6A patent/EP2421840B1/en not_active Revoked
- 2010-04-20 SG SG2011077575A patent/SG175770A1/en unknown
- 2010-04-20 CA CA2758818A patent/CA2758818C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR20120014159A (ko) | 2012-02-16 |
| CA2758818A1 (en) | 2010-10-28 |
| WO2010123842A1 (en) | 2010-10-28 |
| CN102414187A (zh) | 2012-04-11 |
| CA2758818C (en) | 2018-05-29 |
| US8389751B2 (en) | 2013-03-05 |
| TWI508955B (zh) | 2015-11-21 |
| TW201100394A (en) | 2011-01-01 |
| JP2012524785A (ja) | 2012-10-18 |
| EP2421840B1 (en) | 2015-12-16 |
| US20100267974A1 (en) | 2010-10-21 |
| KR101745737B1 (ko) | 2017-06-09 |
| CN102414187B (zh) | 2016-06-01 |
| EP2421840A1 (en) | 2012-02-29 |
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