EP2013194A2 - Procédé de production d'oxyde d'éthylène dans un réacteur à microcanaux - Google Patents
Procédé de production d'oxyde d'éthylène dans un réacteur à microcanauxInfo
- Publication number
- EP2013194A2 EP2013194A2 EP07727831A EP07727831A EP2013194A2 EP 2013194 A2 EP2013194 A2 EP 2013194A2 EP 07727831 A EP07727831 A EP 07727831A EP 07727831 A EP07727831 A EP 07727831A EP 2013194 A2 EP2013194 A2 EP 2013194A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- microchannel reactor
- reactor
- ethylene oxide
- microchannel
- ethylene
- 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.)
- Withdrawn
Links
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 46
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000005977 Ethylene Substances 0.000 claims abstract description 38
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 38
- 239000000463 material Substances 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims description 40
- 230000008569 process Effects 0.000 claims description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 11
- 229910052709 silver Inorganic materials 0.000 claims description 11
- 239000004332 silver Substances 0.000 claims description 11
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 230000018044 dehydration Effects 0.000 claims description 7
- 238000006297 dehydration reaction Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- -1 nitrogen-containing compound Chemical class 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000002739 metals Chemical class 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052702 rhenium Inorganic materials 0.000 claims description 5
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 239000011733 molybdenum Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 239000010937 tungsten Substances 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052776 Thorium Inorganic materials 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 229960003750 ethyl chloride Drugs 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052733 gallium Inorganic materials 0.000 claims description 3
- 229910052732 germanium Inorganic materials 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052735 hafnium Inorganic materials 0.000 claims description 3
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052758 niobium Inorganic materials 0.000 claims description 3
- 239000010955 niobium Substances 0.000 claims description 3
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052715 tantalum Inorganic materials 0.000 claims description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052716 thallium Inorganic materials 0.000 claims description 3
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 230000003647 oxidation Effects 0.000 description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 229910017464 nitrogen compound Inorganic materials 0.000 description 10
- 150000002830 nitrogen compounds Chemical class 0.000 description 10
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 238000006735 epoxidation reaction Methods 0.000 description 4
- 238000004880 explosion Methods 0.000 description 4
- 230000008092 positive effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 3
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 238000006057 reforming reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000004230 steam cracking Methods 0.000 description 2
- 229910001868 water Inorganic materials 0.000 description 2
- JUZHDRZOQVECPH-UHFFFAOYSA-N 1-nitropropane Chemical compound [CH2]CC[N+]([O-])=O JUZHDRZOQVECPH-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
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001963 alkali metal nitrate Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 235000013844 butane Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 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
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000000629 steam reforming Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000010457 zeolite Substances 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
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
Definitions
- the present invention relates to an improved process for the production of ethylene oxide (EO) in a microchannel reactor, wherein an ethylene-containing material stream and an oxygen or oxygen source-containing material stream fed to the microchannel reactor and in the catalyst-containing microchannel reactor, the reaction takes place to ethylene oxide.
- EO ethylene oxide
- ethylene oxide from ethylene is assigned in principle to the reaction class of the epoxidations, which is to be understood as a subclass of the oxidations. Furthermore, a distinction between these terms is not made, which is to be understood by the term oxidation of ethylene, the epoxidation of ethylene.
- US 2006/0036106 describes the preparation of ethylene oxide by reaction in a microchannel reactor. In general, this procedure may be advantageous, e.g. an improved heat dissipation and an intensified contact of the educt molecules (ethylene and oxygen source) possible.
- a process for the production of ethylene oxide has been found in a microchannel reactor, wherein an ethylene-containing stream and an oxygen or oxygen source-containing material stream fed to the microchannel reactor and in the catalyst-containing microchannel reactor, the reaction takes place to ethylene oxide, which characterized characterized is that continuously fed to the microchannel reactor alkyl halides in a total concentration of 0.3 to 50 volume ppm, based on the total volume flow of all introduced into the reactor streams.
- a process for the production of ethylene oxide has been found in a microchannel reactor, wherein an ethylene-containing stream and an oxygen or oxygen source-containing material stream fed to the microchannel reactor and in the catalyst-containing microchannel reactor, the reaction is carried out to ethylene oxide, which is characterized in that nitrogen-containing compounds in a total concentration of 0.3 to 50 ppm by volume, based on the total volume flow of all material streams introduced into the reactor, are continuously fed to the microchannel reactor.
- the total volume flow to which the concentrations of alkyl halides or nitrogen-containing compounds according to the invention refer here is to be understood as meaning the total volume flow of all material streams introduced into the reactor, in particular O 2, ethylene and optionally contained inert gas components, for example N 2, methane, and If necessary, further existing impurities such as CO2, CO, Ar and H 2 O.
- the proportion of CO2 possibly present in the total flow of material supplied to the microchannel reactor is suitably kept low. It has been found that a CO 2 concentration of less than 2% by volume, in particular less than 1% by volume, in the microchannel reactor is particularly advantageous for the effectiveness of the inventive production process of ethylene oxide by oxidation of ethylene.
- both alkyl halides and nitrogen-containing compounds can be fed, the total concentration of these two additional added streams is 0.6-100 ppm by volume, based on the total volume flow of all introduced into the reactor streams, the proportion of alkyl halides prefers about between see 0.1 and 1, more preferably between 0.3 and 1 based on the two supplied streams is.
- the targeted, continuous addition of alkyl halides and / or nitrogen-containing compounds in the concentration range according to the invention substantially improves the selectivity of the catalyst.
- the feed of alkyl halides and / or nitrogen-containing compounds according to the invention reduces the formation of CO.sub.2 by total oxidation of ethylene. This advantageously achieves an increase in selectivity of 0.1-10% compared to a process for the oxidation of ethylene to ethylene oxide in the microchannel reactor without the introduction of alkyl halides and / or nitrogen-containing compounds.
- the activity of the catalyst can be influenced or adjusted by the feed, since it can lead to the formation of a catalyst phase favorable for the oxidation of ethylene.
- EP 266015 page 11, Table 2 it is disclosed to feed 0.3 to 20 ppm by volume of an alkyl halide as a reaction moderator.
- Examples which are mentioned in EP 266015, page 11, line 3 1, 2-dichloroethane, vinyl chloride or chlorinated polyphenyl compounds.
- the concentration range according to the invention proves to be particularly advantageous in the production process for ethylene oxide in a microchannel reactor.
- concentration of alkyl halide and / or nitrogen-containing compound depends on the specific conditions.
- the material stream to be supplied according to the invention to alkyl halides or nitrogen-containing compounds depends on the temperature, composition of the feed gas, type of catalysts used and the molecular structure of the alkyl halide or the nitrogen-containing compound.
- microchannel reactors are suitable for carrying out the process according to the invention.
- Tube (bundle) or fluidized bed reactors offer microchannel reactors inherent safety, i.e., due to the very small dimensions of the reaction channels (dimension in at least one spatial direction ⁇ 3mm, preferably 1mm). a spread of flames or explosions is not possible (falling below the minimum quench diameter).
- a reactor design for maximum explosion pressures is eliminated.
- microchannel reactors allow for more precise temperature control such that e.g. suppresses the formation of hot spots and a driving style with an optimally selected axial temperature profile can be made possible. The passage of the reactor is effectively prevented.
- Microchannel reactors or microreactors are generally understood to mean reactors whose characteristic dimensions of the reaction channels, i. the dimensions in at least one spatial direction, e.g. Height or width or diameter, in the range of a few microns to a few millimeters, preferably ⁇ 3 mm.
- microchannel reactors are in principle suitable for reactions with fast kinetics (removal of diffusion limitations), strong heat of reaction (better temperature control) and explosive substances (blown through reactions or explosions not possible). Possibly.
- microchannel reactors By using microchannel reactors a process intensification (higher space-time yields, product yields, selectivities) is possible. As a result both investment costs (smaller, more compact devices) and variable costs (raw material costs) can be reduced.
- the inventive design of the production process of ethylene oxide using microchannel reactors advantageously a process intensification can be achieved. This leads u.a. to an increased productivity of the catalyst, i. In the microchannel reactor, an increased space-time yield is achieved compared to conventional tubular reactors at a defined temperature with the same catalyst.
- the alkyl halides used in the microchannel reactor are preferably vinyl chloride, ethyl chloride, ethylene dichloride or mixtures thereof as reaction moderators. Particularly preferred is ethyl chloride.
- an increase in the alkyl halide concentration during operation for performance optimization makes sense.
- nitrogen-containing compounds are NH3, NO, NO2, N2O, N2O3, N2O3, organic nitro compounds such as e.g. Nitromethane, nitroethane, 1- or 2-nitropropane. Particularly preferred is the use of NO.
- the feeding of nitrogen-containing compounds takes place in particular in combination with a nitrate or nitrite promotion, e.g. Alkali metal nitrate promotion, preferably KNO3, the catalytically active material.
- a nitrogen-containing compound in a total concentration of 0.3 to 50 ppm by volume, based on the total volume of all introduced into the reactor reactants in particular O2, ethylene and optionally inert gas, such as N2, methane, and if necessary further (in cycle gas) contaminants such as CO2, CO, Ar and H2O.
- ethylene and optionally inert gas such as N2, methane
- further (in cycle gas) contaminants such as CO2, CO, Ar and H2O.
- an increase in the selectivity of 0.1-5% is advantageously achieved in comparison with a process for the oxidation of ethylene to ethylene oxide in the microchannel reactor without feeding nitrogen-containing compound.
- higher alkanes in the feed such as ethane, propane, butanes and even higher alkanes suppress the positive effect of the alkyl halides fed in.
- the concentration of the sum of higher alkanes in the feed is therefore preferably less than 5% by volume, more preferably less than 1% by volume. Particularly preferred is a concentration of the sum of higher alkanes in the feed less than 500 ppm by volume.
- the performance enhancement of the EO catalysts according to the invention by feeding in alkyl halides and / or nitrogen compounds requires precise, continuous metering.
- the metering is usually carried out by feeding the alkyl halides and / or the nitrogen compounds through the inlet gas at the reactor inlet.
- decomposition or oxidation of the alkyl halides and / or the nitrogen compounds can occur, so that the effective concentration of the metered alkyl halides and / or the nitrogen compounds can vary over the reactor length.
- accumulation of the alkyl halides and / or the nitrogen compounds on the catalyst by e.g. Overdose due to excessive input concentration, come, which can lead to a reduced catalyst performance.
- the optimum concentration of the fed alkyl halides and / or nitrogen compounds over the entire reactor length is then possibly no longer guaranteed.
- the alkyl halides or the alkyl halides and / or the nitrogen compounds are passed in a stepped manner over the reactor length in the reaction space.
- a very accurate, partial metering of the alkyl halides and / or the nitrogen compounds is possible.
- a favorable for the / the catalyst (s) and / or operating point (e) concentration profile over the reactor length (concentration falling, constant or increasing) set and a further improved performance of the EO catalysts can be achieved.
- the gradual addition can be ensured, for example, by dividing the total amount of alkyl halides and / or nitrogen compounds to be metered into equal or different partial streams, wherein a partial stream is metered into the reactor inlet via the input gas and at least one further partial stream is metered at a metering point or is metered in more than two streams several dosing points after the reactor inlet into the reactor.
- the arrangement of the metering points for the partial streams after the reactor inlet is advantageously carried out along the reactor length so that optimum catalyst performance, ie in particular maximum selectivity, is achieved over the entire catalyst mass.
- the total flow can be divided into four partial flows, the reactor length LR being divided into four sections, for example the length LR / 4.
- the first partial stream is metered into the first reactor section via the reactor inlet.
- the further three partial streams are then metered into the three reactor sections following the first reactor section after a reactor length of L R / 4 or 2 * L R / 4 or 3 * L R / 4.
- the exothermic oxidation of ethylene to ethylene oxide according to the invention in the microchannel reactor is coupled with an endothermic reaction in order to be able to use or remove the heat released in the EO synthesis.
- Coupling in this context means a thermal coupling.
- both the exothermic reaction for producing the ethylene oxide and the thermally coupled endothermic reaction in the microchannel reactor preferably take place in adjacent reaction channels. The fact that these two reactions take place within the microchannel reactor in possibly adjacent reaction channels, a good heat exchange over the walls of the reaction channels is ensured, whereby the effectiveness of the overall process is further improved.
- reaction channels for the coupling of exothermic and endothermic reaction in a microchannel reactor is known in the art. Information on this can be found, for example, in US 2006/0036106 A1, page 16, paragraph 143. Therein it is disclosed that for the heat removal of the exothermic ethylene epoxidation to ethylene oxide can either use a suitable and well-known heat transfer medium or thermally coupled the reaction with endothermic reactions. As examples, steam reforming reactions and dehydrogenation reaction are generally mentioned.
- the thermal coupling is achieved by a reforming reaction of an alcohol, since this reaction proceeds in the same temperature range as the production of ethylene oxide.
- the product of the reforming reaction comprises H2 and CO, but these substances can not be used in the process for producing ethylene oxide.
- US 2006/0036106 A1 page 4, paragraph 68, proposes to precede the ethylene oxide production in the microchannel reactor by an oxidative dehydrogenation of ethane ("upstream"), the ethylene thus formed together with an oxygen source via the EO catalyst
- this above-mentioned reaction proves to be disadvantageous in the course of its use with the production of ethylene oxide according to the invention
- the ethylene obtained in the oxidative dehydrogenation of ethane can be used as starting material for the production of ethylene oxide
- the exothermic production of ethylene oxide is thermally coupled with the endothermic reaction of the dehydration of ethanol in the manner described above.
- This proves to be particularly advantageous because it can be obtained as a product ethylene with very high yields.
- the ethylene formed can be fed to the ethylene oxide synthesis.
- the formed ethylene is separated after separation by e.g. Condensation of the water formed in the dehydration and / or other resulting products fed to the ethylene oxide synthesis.
- ethylene can be made by steam cracking of oil or naphtha or by steam cracking of ethane.
- Ethylene can also be prepared by catalytic, oxidative or autothermal dehydrogenation of ethane.
- Other methods of making ethylene are the oxidative coupling of methane or metathesis reactions, higher olefins such as e.g. Propene.
- the major disadvantage of all these methods is the dependence on fossil resources such as e.g. Oil and natural gas.
- ethylene can also be prepared by catalytic dehydration of ethanol in addition to the methods mentioned.
- the catalytic dehydration of ethanol is an endothermic reaction.
- oxidic catalysts eg Al 2 O 3 , ZrO 2 (BuII.Soc.Chem.Jpn. 1975, 48, 3377
- salts sulfates (J.Cal. 1971, 22, 23)
- phosphates Kinet 1964, 5, 347
- hetero polyphosphoric acids
- ion exchange resins or supported mineral acids in the temperature range up to 400 ° C are used.
- Particularly preferred catalysts for the dehydration of ethanol are zeolites which can be used in the temperature range from 200 to 300 ° C. (eg ZSM-5 (J. Catal. 1978, 53, 40), selectivity: 98%, conversion: 100% ).
- the synthesis of EO on silver catalysts usually takes place in the temperature range of 200-300 ° C. It is therefore a particularly advantageous embodiment of the inventive method to couple the exothermic synthesis of ethylene oxide from ethylene in the microchannel reactor with an endothermic, catalytic dehydration of ethanol to ethylene.
- coupling is again to be understood as meaning the above-described thermal coupling in preferably adjacent microchannels.
- silver-containing catalysts As catalysts in microchannel reactors all for the production of ethylene oxide from ethylene and oxygen generally suitable silver-containing catalysts, optionally with a suitable support material can be used.
- a suitable support material As examples of common and promoter-doped silver catalysts suitable for our process, e.g. the silver catalysts of DE-A 23 00 512, DE-A 25 21 906, EP-A 14 457, DE-A 24 54 972, EP-A 172 565, EP-A 357 293, EP-A 1 1 356, EP A 85 237, DE-A 25 60 684, DE-A 27 53 359 and EP 266015 may be mentioned.
- Particularly suitable promoters for EO catalysts are the elements nitrogen, sulfur, phosphorus, boron, fluorine, Group IA metals, Group IIA metals, rhenium, molybdenum, tungsten, chromium, nickel, copper, platinum, palladium, titanium, hafnium , Zirconium, vanadium, thallium, thorium, tantalum, niobium, gallium, indium, tin and germanium and mixtures thereof.
- examples are silver catalysts having a silver content of 5 to 50 wt .-%, in particular from 6 to 30 wt.%, Based on the total catalyst composition, a content of the light alkali metals lithium and / or sodium from 1 to 5000 ppm by weight, the content of the heavy alkali metals rubidium and / or cesium from 1 to 5000 ppm by weight, a content of tungsten from 1 to 5000 ppm by weight, a content of molybdenum from 1 to 3000 ppm by weight and / or a content of rhenium of 1 to 10,000 ppm by weight and a content of sulfur and / or phosphorus and / or boron of 1 to 3000 ppm by weight, based on the total catalyst mass called.
- any porous material which is stable under the conditions of the ethylene oxide synthesis for example activated carbon, aluminum oxides, titanium, zirconium or silicon dioxides or other ceramic compositions or corresponding mixtures, can be used as the carrier material.
- activated carbon aluminum oxides, titanium, zirconium or silicon dioxides or other ceramic compositions or corresponding mixtures
- silver in the form of, for example, a film or a mesh or felt can be used as a catalyst in the microchannel reactor.
- the inventive method provides an effective and procedurally simple way of producing ethylene oxide in a microchannel reactor.
- the targeted, continuous addition of alkyl halides and / or nitrogen-containing compounds in the claimed range a particularly high increase in the effectiveness is achieved. These advantages are further increased in the case of a gradual addition.
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- Epoxy Compounds (AREA)
Abstract
Procédé de production d'oxyde d'éthylène dans un réacteur à microcanaux, consistant à introduire dans le réacteur à microcanaux un courant de substances renfermant de l'éthylène et un courant de substances renfermant de l'oxygène ou une source d'oxygène, et à effectuer la transformation en oxyde d'éthylène dans le réacteur à microcanaux renfermant un catalyseur, procédé caractérisé en ce qu'on introduit en continu dans le réacteur à microcanaux, un halogénure d'alkyle à une concentration de 0,3 à 50 volumes ppm, par rapport au flux volumique total de tous les courants de substances introduits dans le réacteur.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07727831A EP2013194A2 (fr) | 2006-04-21 | 2007-04-05 | Procédé de production d'oxyde d'éthylène dans un réacteur à microcanaux |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06112890 | 2006-04-21 | ||
| EP07727831A EP2013194A2 (fr) | 2006-04-21 | 2007-04-05 | Procédé de production d'oxyde d'éthylène dans un réacteur à microcanaux |
| PCT/EP2007/053363 WO2007122090A2 (fr) | 2006-04-21 | 2007-04-05 | Procédé de production d'oxyde d'éthylène dans un réacteur à microcanaux |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2013194A2 true EP2013194A2 (fr) | 2009-01-14 |
Family
ID=38625356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP07727831A Withdrawn EP2013194A2 (fr) | 2006-04-21 | 2007-04-05 | Procédé de production d'oxyde d'éthylène dans un réacteur à microcanaux |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20090270640A1 (fr) |
| EP (1) | EP2013194A2 (fr) |
| CN (1) | CN101448804A (fr) |
| WO (1) | WO2007122090A2 (fr) |
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| EP2024351B1 (fr) * | 2006-05-19 | 2011-03-09 | Basf Se | Production d'anhydride phtalique par oxydation en phase gazeuse d'o-xylol |
| WO2007135102A2 (fr) * | 2006-05-19 | 2007-11-29 | Basf Se | Production d'anhydride phtalique par oxydation en phase gazeuse d'o-xylol dans un réacteur principal et un réacteur secondaire |
| EP2106290B1 (fr) | 2006-12-21 | 2016-04-13 | Basf Se | Système catalytique et procédé d'oxydation en phase gazeuse en utilisant une pré-couche |
| CA2686825C (fr) * | 2007-05-09 | 2016-09-13 | Shell Internationale Research Maatschappij B.V. | Catalyseur d'epoxydation, procede de preparation de ce catalyseur, et procede de production d'un oxyde d'olefine, d'un 1,2-diol, d'un ether de 1,2-diol, d'un 1,2-carbonate ou d'une alcanolamine |
| CA2685512C (fr) | 2007-05-09 | 2016-12-06 | Shell Internationale Research Maatschappij B.V. | Catalyseur d'epoxydation, procede de preparation de ce catalyseur, et procede de production d'un oxyde d'olefine, d'un 1,2-diol, d'un ether de 1,2-diol, d'un 1,2-carbonate ou d'une alcanolamine |
| US20110028740A1 (en) * | 2008-04-07 | 2011-02-03 | Basf Se | Method for starting a gas phase oxidation reactor that contains a catalytically active silver-vanadium oxide bronze |
| US8492566B2 (en) | 2008-04-07 | 2013-07-23 | Basf Se | Method for starting a gas-phase oxidation reactor |
| WO2009137427A2 (fr) | 2008-05-07 | 2009-11-12 | Shell Oil Company | Procédé pour le démarrage d'un procédé d'époxydation, procédé pour la fabrication d'oxyde d'éthylène, d'un 1,2-diol, d'un éther de 1,2-diol, d'un 1,2-carbonate ou d'une alcanolamine |
| KR101629038B1 (ko) | 2008-05-07 | 2016-06-09 | 셀 인터나쵸나아레 레사아치 마아츠샤피 비이부이 | 산화올레핀, 1,2-디올, 1,2-디올 에테르, 1,2-카보네이트 또는 알칸올아민의 생산방법 |
| EP2313385A2 (fr) * | 2008-07-14 | 2011-04-27 | Velocys Inc. | Processus de fabrication d oxyde d éthylène au moyen de la technologie de processus en microcanal |
| BRPI0915854A2 (pt) | 2008-07-14 | 2015-08-04 | Basf Se | Processo para preparar óxido de etileno |
| US8524927B2 (en) | 2009-07-13 | 2013-09-03 | Velocys, Inc. | Process for making ethylene oxide using microchannel process technology |
| US9079154B2 (en) | 2012-05-04 | 2015-07-14 | Basf Se | Catalyst for the epoxidation of alkenes |
| KR20150013704A (ko) | 2012-05-04 | 2015-02-05 | 바스프 에스이 | 알켄의 에폭시화용 촉매 |
| US9714227B2 (en) | 2013-12-09 | 2017-07-25 | Basf Se | Catalyst for the epoxidation of alkenes |
| 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 |
| CN104292187B (zh) * | 2014-10-10 | 2016-05-18 | 南京工业大学 | 一种制备高品质环氧大豆油的方法 |
| CN106311228B (zh) * | 2015-07-02 | 2019-06-28 | 中国石油化工股份有限公司 | 银催化剂、其制备方法及应用 |
| CN108368080B (zh) * | 2015-12-15 | 2022-04-15 | 国际壳牌研究有限公司 | 从环氧乙烷制造中的循环气体流去除乙烯基碘杂质的方法和系统 |
| BR112018012058B1 (pt) | 2015-12-15 | 2021-01-05 | Shell Internationale Research Maatschappij B.V. | processo para operar um sistema de leito de guarda |
| EP3390356B1 (fr) * | 2015-12-15 | 2019-11-13 | Shell International Research Maatschappij B.V. | Procédés et systèmes permettant d'éliminer les impuretés d'iodure à partir d'un flux de gaz de recyclage dans la production d'oxyde d'éthylène |
| CN107216296B (zh) * | 2016-03-22 | 2020-07-17 | 中国石油化工股份有限公司 | 在微通道反应器内制备环氧丙烷的方法 |
| WO2018029189A1 (fr) | 2016-08-08 | 2018-02-15 | Basf Se | Catalyseur pour l'oxydation de l'éthylène en oxyde d'éthylène |
| 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 |
| JP6887284B2 (ja) * | 2017-03-30 | 2021-06-16 | 日立Astemo株式会社 | 排ガス浄化システム |
| WO2019020793A1 (fr) | 2017-07-28 | 2019-01-31 | Basf Se | Procédé de production d'un corps moulé de catalyseur comprenant de l'argent appliqué sur un support d'alumine |
| US12629664B2 (en) | 2018-02-07 | 2026-05-19 | Basf Se | Method for preparing a silver impregnation solution |
| TWI808125B (zh) | 2018-02-07 | 2023-07-11 | 德商巴斯夫歐洲公司 | 有效地將乙烯氧化轉化為環氧乙烷之催化劑 |
| CN110201487B (zh) * | 2019-06-24 | 2021-06-25 | 浙江天采云集科技股份有限公司 | 一种乙烯法制环氧乙烷中高纯度高收率甲烷致稳气净化与再利用方法 |
| EP3858820A1 (fr) * | 2020-01-29 | 2021-08-04 | Clariant International Ltd | Concept de réacteur et procédé de préparation d'oxyde d'éthylène à partir d'éthanol |
| US20240408585A1 (en) | 2021-01-26 | 2024-12-12 | Basf Se | Epoxidation catalyst |
| EP4082996B1 (fr) * | 2021-04-29 | 2023-10-11 | TotalEnergies OneTech | Couplage oxydatif non catalytique de méthane |
| CN120051334A (zh) | 2022-10-12 | 2025-05-27 | 巴斯夫欧洲公司 | 环氧化催化剂 |
| CN120129671A (zh) | 2022-10-28 | 2025-06-10 | 巴斯夫欧洲公司 | 由可再生来源的乙醇制造异壬醇的方法 |
| EP4638400A1 (fr) | 2022-12-20 | 2025-10-29 | Basf Se | Fabrication d'un produit chimique d'intérêt dérivé de l'éthylène, en particulier de l'acide acrylique, en combinaison avec la génération de vapeur chauffée |
| WO2025078359A1 (fr) | 2023-10-09 | 2025-04-17 | Basf Se | Fabrication de produits chimiques dérivés d'éthylène ayant une teneur en carbone d'origine biologique à partir de bio-naphta |
| CN121969593A (zh) | 2023-10-09 | 2026-05-01 | 巴斯夫欧洲公司 | 由热解油制造具有生物基碳含量的乙烯衍生的化学品 |
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| DE3414717A1 (de) * | 1984-04-18 | 1985-10-31 | Linde Ag, 6200 Wiesbaden | Verfahren und reaktor zur durchfuehrung exothermer katalytischer reaktionen |
| IL84232A (en) * | 1986-10-31 | 1992-06-21 | Shell Int Research | Catalyst and process for the catalytic production of ethylene oxide |
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| AU2003278999A1 (en) * | 2002-09-30 | 2004-04-23 | Shell Oil Company | Calcium carbonate carrier for making silver based epoxidation catalysts |
| EP1786797B1 (fr) * | 2004-08-12 | 2014-11-26 | Velocys, Inc. | Procédé de conversion de l' éthylène en oxyde d'éthylène en utilisant une technologie de procédé par microcanaux |
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- 2007-04-05 EP EP07727831A patent/EP2013194A2/fr not_active Withdrawn
- 2007-04-05 US US12/297,895 patent/US20090270640A1/en not_active Abandoned
- 2007-04-05 WO PCT/EP2007/053363 patent/WO2007122090A2/fr not_active Ceased
- 2007-04-05 CN CNA2007800186282A patent/CN101448804A/zh active Pending
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Also Published As
| Publication number | Publication date |
|---|---|
| CN101448804A (zh) | 2009-06-03 |
| WO2007122090A3 (fr) | 2008-02-07 |
| WO2007122090A2 (fr) | 2007-11-01 |
| US20090270640A1 (en) | 2009-10-29 |
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