JP5946772B2 - エポキシ化始動工程 - Google Patents
エポキシ化始動工程 Download PDFInfo
- Publication number
- JP5946772B2 JP5946772B2 JP2012544826A JP2012544826A JP5946772B2 JP 5946772 B2 JP5946772 B2 JP 5946772B2 JP 2012544826 A JP2012544826 A JP 2012544826A JP 2012544826 A JP2012544826 A JP 2012544826A JP 5946772 B2 JP5946772 B2 JP 5946772B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- ethylene
- temperature
- epoxidation
- moderator
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 44
- 238000006735 epoxidation reaction Methods 0.000 title claims description 32
- 230000008569 process Effects 0.000 title description 22
- 239000003054 catalyst Substances 0.000 claims description 59
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 31
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 26
- 239000005977 Ethylene Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
- 239000001301 oxygen Substances 0.000 claims description 23
- 239000007789 gas Substances 0.000 claims description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 230000008859 change Effects 0.000 claims description 6
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 3
- 229960003750 ethyl chloride Drugs 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical group [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 230000000977 initiatory effect Effects 0.000 claims description 2
- 150000002896 organic halogen compounds Chemical group 0.000 claims description 2
- 238000012423 maintenance Methods 0.000 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 34
- 229910052709 silver Inorganic materials 0.000 description 34
- 239000004332 silver Substances 0.000 description 34
- 229910052702 rhenium Inorganic materials 0.000 description 22
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 22
- 238000004519 manufacturing process Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- 150000001336 alkenes Chemical class 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000001737 promoting effect Effects 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 9
- 150000001340 alkali metals Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 238000005470 impregnation Methods 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- 229910052723 transition metal Inorganic materials 0.000 description 7
- 150000003624 transition metals Chemical class 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 238000001994 activation Methods 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 229910052792 caesium Inorganic materials 0.000 description 4
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 4
- 238000001354 calcination Methods 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 4
- 230000000536 complexating effect Effects 0.000 description 4
- 239000008139 complexing agent Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 150000003282 rhenium compounds Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- -1 silica Chemical compound 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000005909 Kieselgur Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 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
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 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
- 230000014759 maintenance of location Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 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
- 235000012239 silicon dioxide Nutrition 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
- 238000002791 soaking Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 238000005507 spraying Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 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
- 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
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/04—Ethylene
-
- 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
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28739309P | 2009-12-17 | 2009-12-17 | |
| US61/287,393 | 2009-12-17 | ||
| PCT/US2010/060769 WO2011084600A2 (en) | 2009-12-17 | 2010-12-16 | Process for epoxidation start-up |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013514387A JP2013514387A (ja) | 2013-04-25 |
| JP5946772B2 true JP5946772B2 (ja) | 2016-07-06 |
Family
ID=44152004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012544826A Expired - Fee Related JP5946772B2 (ja) | 2009-12-17 | 2010-12-16 | エポキシ化始動工程 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8530682B2 (show.php) |
| EP (2) | EP2778157A1 (show.php) |
| JP (1) | JP5946772B2 (show.php) |
| KR (1) | KR101790254B1 (show.php) |
| CN (1) | CN102666514B (show.php) |
| BR (1) | BR112012014695A2 (show.php) |
| CA (1) | CA2783604C (show.php) |
| IN (1) | IN2012DN05178A (show.php) |
| MX (1) | MX2012007043A (show.php) |
| MY (1) | MY157612A (show.php) |
| RU (1) | RU2542978C2 (show.php) |
| TW (1) | TWI485141B (show.php) |
| WO (1) | WO2011084600A2 (show.php) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI446964B (zh) | 2007-05-09 | 2014-08-01 | Shell Int Research | 環氧化催化劑，製備該催化劑之方法及製備烯烴氧化物、１，２-二醇、１，２-二醇醚、１，２-碳酸酯或烷醇胺之方法 |
| BR112012014695A2 (pt) * | 2009-12-17 | 2015-09-15 | Scient Design Co | processo para start-up de epoxidação |
| US20110152073A1 (en) | 2009-12-23 | 2011-06-23 | Scientific Design Company, Inc. | Epoxidation process and microstructure |
| WO2012141942A1 (en) | 2011-04-11 | 2012-10-18 | Dow Technology Investments Llc | Process for conditioning a high efficiency ethylene oxide catalyst |
| WO2013102177A1 (en) | 2011-12-30 | 2013-07-04 | Saint-Gobain Ceramics & Plastics, Inc. | Shaped abrasive particle and method of forming same |
| CA3056658C (en) | 2012-01-10 | 2023-07-04 | Doruk O. Yener | Abrasive particles having complex shapes and methods of forming same |
| KR101888347B1 (ko) | 2012-05-23 | 2018-08-16 | 생-고뱅 세라믹스 앤드 플라스틱스, 인코포레이티드 | 형상화 연마입자들 및 이의 형성방법 |
| CN104822494B (zh) | 2012-10-15 | 2017-11-28 | 圣戈班磨料磨具有限公司 | 具有特定形状的磨粒以及形成这种粒子的方法 |
| CN104884443B (zh) * | 2012-12-31 | 2017-07-04 | 科学设计公司 | 用于环氧乙烷催化剂的启动方法 |
| EP2943477B1 (en) * | 2013-01-11 | 2018-03-07 | Scientific Design Company Inc. | Epoxidation process with post-conditioning step |
| ES2984562T3 (es) | 2013-03-29 | 2024-10-29 | Saint Gobain Abrasives Inc | Partículas abrasivas que tienen formas particulares y métodos de formación de dichas partículas |
| EP3052270B1 (en) | 2013-09-30 | 2025-10-29 | Saint-Gobain Ceramics & Plastics, Inc. | Shaped abrasive particles and methods of forming same |
| US9221776B2 (en) | 2013-12-23 | 2015-12-29 | Scientific Design Company, Inc. | Epoxidation process |
| EP3089851B1 (en) | 2013-12-31 | 2019-02-06 | Saint-Gobain Abrasives, Inc. | Abrasive article including shaped abrasive particles |
| US9771507B2 (en) | 2014-01-31 | 2017-09-26 | Saint-Gobain Ceramics & Plastics, Inc. | Shaped abrasive particle including dopant material and method of forming same |
| EP4306610A3 (en) | 2014-04-14 | 2024-04-03 | Saint-Gobain Ceramics and Plastics, Inc. | Abrasive article including shaped abrasive particles |
| US9914864B2 (en) | 2014-12-23 | 2018-03-13 | Saint-Gobain Ceramics & Plastics, Inc. | Shaped abrasive particles and method of forming same |
| EP3277459B1 (en) | 2015-03-31 | 2023-08-16 | Saint-Gobain Abrasives, Inc. | Fixed abrasive articles and methods of forming same |
| TWI634200B (zh) | 2015-03-31 | 2018-09-01 | 聖高拜磨料有限公司 | 固定磨料物品及其形成方法 |
| RU2017144427A (ru) * | 2015-06-02 | 2019-07-09 | Сайентифик Дизайн Компани, Инк. | Пористые тела с улучшенной архитектурой пор |
| CN115781499A (zh) | 2015-06-11 | 2023-03-14 | 圣戈本陶瓷及塑料股份有限公司 | 包括经成形研磨颗粒的研磨制品 |
| KR102243356B1 (ko) | 2016-05-10 | 2021-04-23 | 생-고뱅 세라믹스 앤드 플라스틱스, 인코포레이티드 | 연마 입자 및 이의 형성 방법 |
| CN109462993A (zh) | 2016-05-10 | 2019-03-12 | 圣戈本陶瓷及塑料股份有限公司 | 磨料颗粒及其形成方法 |
| EP3519134B1 (en) | 2016-09-29 | 2024-01-17 | Saint-Gobain Abrasives, Inc. | Fixed abrasive articles and methods of forming same |
| JP7107934B2 (ja) | 2016-12-02 | 2022-07-27 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | エチレンエポキシ化触媒のコンディショニング方法およびエチレンオキシドの生成の関連方法 |
| US10563105B2 (en) | 2017-01-31 | 2020-02-18 | Saint-Gobain Ceramics & Plastics, Inc. | Abrasive article including shaped abrasive particles |
| CN110719946B (zh) | 2017-06-21 | 2022-07-15 | 圣戈本陶瓷及塑料股份有限公司 | 颗粒材料及其形成方法 |
| WO2019055773A1 (en) | 2017-09-15 | 2019-03-21 | MultiPhase Solutions, Inc. | GAS PHASE CHROMATOGRAPHY OF SELECTIVE HALOGEN DETECTION FOR ONLINE ANALYSIS AND CONTROL OF SELECTIVE OXIDATION CHEMICAL PRODUCTION PROCESSES |
| US20210039074A1 (en) * | 2018-02-07 | 2021-02-11 | Basf Se | Method for preparing a silver impregnation solution |
| EP4081370A4 (en) | 2019-12-27 | 2024-04-24 | Saint-Gobain Ceramics & Plastics Inc. | ABRASIVE ARTICLES AND THEIR FORMATION PROCESSES |
| CN119238386A (zh) | 2019-12-27 | 2025-01-03 | 圣戈本陶瓷及塑料股份有限公司 | 磨料制品及其形成方法 |
| CN114846112A (zh) | 2019-12-27 | 2022-08-02 | 圣戈本陶瓷及塑料股份有限公司 | 磨料制品及其形成方法 |
| CN113121474A (zh) * | 2019-12-30 | 2021-07-16 | 中国石油化工股份有限公司 | 乙烯环氧化银催化剂的开车方法 |
| CN114057669B (zh) * | 2020-07-29 | 2023-12-08 | 中国石油化工股份有限公司 | 一种乙烯环氧化恒温开车方法 |
| CN114436998A (zh) * | 2020-11-05 | 2022-05-06 | 中国石油化工股份有限公司 | 一种乙烯环氧化开车方法 |
| CN118541241A (zh) | 2021-12-30 | 2024-08-23 | 圣戈班磨料磨具有限公司 | 磨料制品及其形成方法 |
| WO2023130053A1 (en) | 2021-12-30 | 2023-07-06 | Saint-Gobain Abrasives, Inc. | Abrasive articles and methods of forming same |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1170663A (en) | 1967-03-22 | 1969-11-12 | Shell Int Research | Process for preparing Silver Catalysts |
| US3702259A (en) | 1970-12-02 | 1972-11-07 | Shell Oil Co | Chemical production of metallic silver deposits |
| 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 |
| US4908343A (en) | 1987-02-20 | 1990-03-13 | Union Carbide Chemicals And Plastics Company Inc. | Catalyst composition for oxidation of ethylene to ethylene oxide |
| US5057481A (en) | 1987-02-20 | 1991-10-15 | Union Carbide Chemicals And Plastics Technology Corporation | 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 |
| 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 |
| US5155242A (en) | 1991-12-05 | 1992-10-13 | Shell Oil Company | Process for starting-up an ethylene oxide reactor |
| US5407888A (en) | 1992-05-12 | 1995-04-18 | Basf Aktiengesellschaft | Silver catalyst |
| US5856534A (en) * | 1997-12-18 | 1999-01-05 | Arco Chemical Technology, L.P. | Epoxidation process using supported silver catalysts treated with carbon dioxide |
| JP4042332B2 (ja) | 2001-02-27 | 2008-02-06 | 三菱化学株式会社 | レニウム含有触媒を用いるオレフィンオキシドの製造方法 |
| AU2003243757A1 (en) | 2002-06-28 | 2004-01-19 | Shell Oil Company | A method for improving the selectivity of a catalyst and a process for the epoxidation of an olefin |
| CA2494767C (en) * | 2002-06-28 | 2012-07-17 | John Robert Lockemeyer | A method for the start-up of an epoxidation process and a process for the epoxidation of an olefin |
| CN100376561C (zh) * | 2002-06-28 | 2008-03-26 | 国际壳牌研究有限公司 | 环氧化方法的开车方法、烯烃环氧化的催化剂和方法 |
| US7615655B2 (en) * | 2003-09-29 | 2009-11-10 | Dow Global Technologies, Inc. | Process for the production of alkylene oxide using a gas-phase promoter system |
| US8791280B2 (en) | 2005-08-10 | 2014-07-29 | Sd Lizenzverwertungsgesellschaft Mbh & Co. Kg | Process for preparation of catalyst carrier and its use in catalyst preparation |
| KR101485955B1 (ko) * | 2007-05-11 | 2015-01-22 | 베리 제이. 빌릭 | 산화올레핀 제조 공장에서의 고선택성 촉매의 개시 방법 |
| US7553980B2 (en) * | 2007-09-26 | 2009-06-30 | Sd Lizenzverwertungsgesellschaft Mbh & Co. Kg | Process for initiating a highly selective ethylene oxide catalyst |
| KR101629037B1 (ko) * | 2008-05-07 | 2016-06-09 | 셀 인터나쵸나아레 레사아치 마아츠샤피 비이부이 | 에폭시화 방법의 스타트업 방법, 산화에틸렌, 1,2-디올, 1,2-디올 에테르, 1,2-카보네이트 또는 알칸올아민의 생산방법 |
| BR112012014695A2 (pt) * | 2009-12-17 | 2015-09-15 | Scient Design Co | processo para start-up de epoxidação |
| US20110152073A1 (en) * | 2009-12-23 | 2011-06-23 | Scientific Design Company, Inc. | Epoxidation process and microstructure |
-
2010
- 2010-12-16 BR BR112012014695A patent/BR112012014695A2/pt not_active IP Right Cessation
- 2010-12-16 RU RU2012130065/04A patent/RU2542978C2/ru not_active IP Right Cessation
- 2010-12-16 IN IN5178DEN2012 patent/IN2012DN05178A/en unknown
- 2010-12-16 TW TW099144226A patent/TWI485141B/zh not_active IP Right Cessation
- 2010-12-16 EP EP20140171850 patent/EP2778157A1/en not_active Withdrawn
- 2010-12-16 EP EP10842602.4A patent/EP2513077B1/en not_active Revoked
- 2010-12-16 MX MX2012007043A patent/MX2012007043A/es active IP Right Grant
- 2010-12-16 JP JP2012544826A patent/JP5946772B2/ja not_active Expired - Fee Related
- 2010-12-16 CN CN201080057763.XA patent/CN102666514B/zh not_active Expired - Fee Related
- 2010-12-16 KR KR1020127018627A patent/KR101790254B1/ko not_active Expired - Fee Related
- 2010-12-16 CA CA2783604A patent/CA2783604C/en not_active Expired - Fee Related
- 2010-12-16 US US12/970,392 patent/US8530682B2/en not_active Expired - Fee Related
- 2010-12-16 WO PCT/US2010/060769 patent/WO2011084600A2/en not_active Ceased
- 2010-12-16 MY MYPI2012002389A patent/MY157612A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN2012DN05178A (show.php) | 2015-10-23 |
| MX2012007043A (es) | 2012-07-20 |
| KR101790254B1 (ko) | 2017-10-26 |
| RU2012130065A (ru) | 2014-01-27 |
| MY157612A (en) | 2016-06-30 |
| CN102666514A (zh) | 2012-09-12 |
| WO2011084600A3 (en) | 2011-11-17 |
| CN102666514B (zh) | 2015-11-25 |
| TW201136906A (en) | 2011-11-01 |
| RU2542978C2 (ru) | 2015-02-27 |
| TWI485141B (zh) | 2015-05-21 |
| EP2513077A4 (en) | 2013-05-22 |
| US8530682B2 (en) | 2013-09-10 |
| EP2513077A2 (en) | 2012-10-24 |
| CA2783604A1 (en) | 2011-07-14 |
| WO2011084600A2 (en) | 2011-07-14 |
| BR112012014695A2 (pt) | 2015-09-15 |
| EP2778157A1 (en) | 2014-09-17 |
| JP2013514387A (ja) | 2013-04-25 |
| KR20120106809A (ko) | 2012-09-26 |
| CA2783604C (en) | 2018-05-01 |
| US20110152548A1 (en) | 2011-06-23 |
| EP2513077B1 (en) | 2014-06-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5946772B2 (ja) | エポキシ化始動工程 | |
| KR102155068B1 (ko) | 고 선택성 산화에틸렌 촉매를 위한 스타트-업 공정 | |
| EP1893331A1 (en) | Calcination in an inert gas in the presence of a small concentration of an oxidizing component | |
| CN102665898B (zh) | 环氧化方法和显微结构 | |
| CN102892503B (zh) | 用于制造高选择性环氧乙烷催化剂的方法 | |
| KR102155073B1 (ko) | 후-컨디셔닝 단계를 이용하는 에폭시화 공정 | |
| US8624045B2 (en) | Process for olefin oxide production | |
| CN104203931A (zh) | 具有添加缓和剂的环氧化方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20131018 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20141202 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150302 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150908 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20151207 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160510 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160601 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5946772 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |