JP4334338B2 - 超臨界相におけるコロイド−触媒作用によるガス移動 - Google Patents
超臨界相におけるコロイド−触媒作用によるガス移動 Download PDFInfo
- Publication number
- JP4334338B2 JP4334338B2 JP2003502045A JP2003502045A JP4334338B2 JP 4334338 B2 JP4334338 B2 JP 4334338B2 JP 2003502045 A JP2003502045 A JP 2003502045A JP 2003502045 A JP2003502045 A JP 2003502045A JP 4334338 B2 JP4334338 B2 JP 4334338B2
- Authority
- JP
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- Prior art keywords
- supercritical
- catalyst
- reaction
- metal
- hydrogen
- 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
- 238000012546 transfer Methods 0.000 title abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 230000008569 process Effects 0.000 claims abstract description 13
- 229910052751 metal Inorganic materials 0.000 claims description 52
- 239000002184 metal Substances 0.000 claims description 52
- 239000000084 colloidal system Substances 0.000 claims description 35
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 34
- 239000003054 catalyst Substances 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 238000005984 hydrogenation reaction Methods 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 17
- 239000001569 carbon dioxide Substances 0.000 claims description 17
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 17
- 229920001400 block copolymer Polymers 0.000 claims description 12
- 150000002894 organic compounds Chemical class 0.000 claims description 11
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical compound C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 claims description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical group [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 6
- CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical compound CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 claims description 5
- PPWNCLVNXGCGAF-UHFFFAOYSA-N 3,3-dimethylbut-1-yne Chemical compound CC(C)(C)C#C PPWNCLVNXGCGAF-UHFFFAOYSA-N 0.000 claims description 5
- NGKSKVYWPINGLI-UHFFFAOYSA-N prop-2-ynylbenzene Chemical compound C#CCC1=CC=CC=C1 NGKSKVYWPINGLI-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 239000002923 metal particle Substances 0.000 abstract description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 description 21
- 150000002431 hydrogen Chemical class 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 16
- 239000012530 fluid Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 238000006276 transfer reaction Methods 0.000 description 11
- 150000002739 metals Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- -1 polysiloxanes Polymers 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000007037 hydroformylation reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000001345 alkine derivatives Chemical class 0.000 description 5
- 239000002815 homogeneous catalyst Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000002638 heterogeneous catalyst Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229910002065 alloy metal Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- QXLPXWSKPNOQLE-UHFFFAOYSA-N methylpentynol Chemical compound CCC(C)(O)C#C QXLPXWSKPNOQLE-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910001111 Fine metal Inorganic materials 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 244000089486 Phragmites australis subsp australis Species 0.000 description 1
- 229920000361 Poly(styrene)-block-poly(ethylene glycol) Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- MLADTXSZMSOWIM-UHFFFAOYSA-N butane;carbon dioxide Chemical compound O=C=O.CCCC MLADTXSZMSOWIM-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002366 time-of-flight method Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B35/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving a change in the type of bonding between two carbon atoms already directly linked
- C07B35/02—Reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds
-
- 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
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10125613A DE10125613A1 (de) | 2001-05-25 | 2001-05-25 | Kolloidkatalysierte Wasserstoffübertragung in überkritischer Phase |
| PCT/EP2002/005719 WO2002098925A2 (de) | 2001-05-25 | 2002-05-24 | Kolloidkatalysierte gasübertragung in überkritischer phase |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004527584A JP2004527584A (ja) | 2004-09-09 |
| JP2004527584A5 JP2004527584A5 (enExample) | 2006-01-05 |
| JP4334338B2 true JP4334338B2 (ja) | 2009-09-30 |
Family
ID=7686184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003502045A Expired - Fee Related JP4334338B2 (ja) | 2001-05-25 | 2002-05-25 | 超臨界相におけるコロイド−触媒作用によるガス移動 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7193120B2 (enExample) |
| EP (1) | EP1404725B1 (enExample) |
| JP (1) | JP4334338B2 (enExample) |
| AT (1) | ATE310024T1 (enExample) |
| AU (1) | AU2002325219A1 (enExample) |
| DE (2) | DE10125613A1 (enExample) |
| WO (1) | WO2002098925A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060188436A1 (en) * | 2005-02-18 | 2006-08-24 | Linnard Griffin | Apparatus and method for the production of hydrogen |
| US20060180464A1 (en) * | 2003-08-19 | 2006-08-17 | Linnard Griffin | Apparatus and method for the controllable production of hydrogen at an accelerated rate |
| US20050042150A1 (en) * | 2003-08-19 | 2005-02-24 | Linnard Griffin | Apparatus and method for the production of hydrogen |
| US20050109162A1 (en) * | 2003-11-24 | 2005-05-26 | Linnard Griffin | Apparatus and method for the reduction of metals |
| US20090228397A1 (en) * | 2008-03-07 | 2009-09-10 | Blue Kai, Lnc. | Exchange for tagged user information with scarcity control |
| JP5936027B2 (ja) * | 2011-07-20 | 2016-06-15 | Jnc株式会社 | 基質と水素との反応生成物の製造方法 |
| JP7280596B2 (ja) * | 2019-02-25 | 2023-05-24 | 大学共同利用機関法人自然科学研究機構 | 銀ナノ粒子樹脂複合体及び水素化触媒 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1028143A (en) * | 1910-07-29 | 1912-06-04 | William B Shepard | Aeroplane. |
| US5238607A (en) * | 1992-02-28 | 1993-08-24 | E. I. Du Pont De Nemours And Company | Photoconductive polymer compositions and their use |
| AU4957193A (en) * | 1992-09-14 | 1994-04-12 | Unichema Chemie Bv | Process for the production of alcohols |
| DE4319909C2 (de) * | 1993-06-16 | 1996-11-07 | Solvay Deutschland | Palladium, Platin, Nickel, Kobalt und/oder Kupfer umfassender Aerogel-Trägerkatalysator, Verfahren zu seiner Herstellung und Verwendung eines Palladium-Aerogel-Trägerkatalysators |
| DK0791041T3 (da) * | 1994-07-01 | 2001-08-06 | Magnus Haerroed | Hydrogenering af et substrat med substrat og hydrogen i en i det væsentlige superkritisk eller nær-kritisk opløsning |
| DE19506113A1 (de) | 1995-02-22 | 1996-08-29 | Max Planck Gesellschaft | Kolloidale Metallzubereitung und Verfahren zu ihrer Herstellung |
| DE19538872C2 (de) * | 1995-10-19 | 1997-12-18 | Karlsruhe Forschzent | Verfahren zur Behandlung einer organischen Verbindung mit einem im überkritischen Zustand vorliegenden Lösungsmittel |
| GB9607917D0 (en) * | 1996-04-17 | 1996-06-19 | Swan Thomas & Co Ltd | Supercritical hydrogenation |
| ID18866A (id) * | 1996-11-11 | 1998-05-14 | Hoffmann La Roche | Hidrogenasi katalitik |
| DE19745904A1 (de) | 1997-10-17 | 1999-04-22 | Hoechst Ag | Polymerstabilisierte Metallkolloid-Lösungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Katalysatoren für Brennstoffzellen |
| RU2144020C1 (ru) | 1998-06-24 | 2000-01-10 | Институт элементоорганических соединений им.А.Н.Несмеянова РАН | Способ гидрирования ацетиленовых спиртов |
| GB2336363B (en) * | 1998-08-13 | 2000-03-15 | English Hop Products Limited | Hydrogenation of hop acids |
| JP2980899B1 (ja) * | 1998-09-01 | 1999-11-22 | 科学技術振興事業団 | 列状に配置された金属超微粒子を含有する金属・有機ポリマー複合構造体とその製造方法 |
| DE19913395A1 (de) * | 1999-03-24 | 2000-09-28 | Wolfgang Hoelderich | Einschlußverbindungen mit zeolithischem Wirtsgitter, deren Herstellung und Einsatz |
| US6747179B1 (en) * | 1999-08-20 | 2004-06-08 | North Carolina State University | Carbon dioxide-soluble polymers and swellable polymers for carbon dioxide applications |
| EP1210306A2 (en) * | 1999-08-20 | 2002-06-05 | North Carolina State University | Polymer-bound catalysts for use in carbon dioxide |
-
2001
- 2001-05-25 DE DE10125613A patent/DE10125613A1/de not_active Withdrawn
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2002
- 2002-05-24 DE DE50204954T patent/DE50204954D1/de not_active Expired - Lifetime
- 2002-05-24 EP EP02758203A patent/EP1404725B1/de not_active Expired - Lifetime
- 2002-05-24 AU AU2002325219A patent/AU2002325219A1/en not_active Abandoned
- 2002-05-24 AT AT02758203T patent/ATE310024T1/de not_active IP Right Cessation
- 2002-05-24 WO PCT/EP2002/005719 patent/WO2002098925A2/de not_active Ceased
- 2002-05-25 US US10/478,597 patent/US7193120B2/en not_active Expired - Fee Related
- 2002-05-25 JP JP2003502045A patent/JP4334338B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004527584A (ja) | 2004-09-09 |
| DE10125613A1 (de) | 2002-11-28 |
| EP1404725B1 (de) | 2005-11-16 |
| WO2002098925A3 (de) | 2003-09-12 |
| US7193120B2 (en) | 2007-03-20 |
| US20040162377A1 (en) | 2004-08-19 |
| ATE310024T1 (de) | 2005-12-15 |
| WO2002098925A2 (de) | 2002-12-12 |
| DE50204954D1 (de) | 2005-12-22 |
| EP1404725A2 (de) | 2004-04-07 |
| WO2002098925A8 (de) | 2003-12-24 |
| AU2002325219A1 (en) | 2002-12-16 |
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