KR20040044943A - 개선된, 탈벤질화용 귀금속 촉매 - Google Patents
개선된, 탈벤질화용 귀금속 촉매 Download PDFInfo
- Publication number
- KR20040044943A KR20040044943A KR10-2004-7003941A KR20047003941A KR20040044943A KR 20040044943 A KR20040044943 A KR 20040044943A KR 20047003941 A KR20047003941 A KR 20047003941A KR 20040044943 A KR20040044943 A KR 20040044943A
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- KR
- South Korea
- Prior art keywords
- palladium
- platinum
- catalyst
- less
- carbon support
- Prior art date
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- 239000003054 catalyst Substances 0.000 title claims abstract description 124
- 238000006264 debenzylation reaction Methods 0.000 title description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 123
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 100
- 239000011148 porous material Substances 0.000 claims abstract description 70
- 239000003575 carbonaceous material Substances 0.000 claims abstract description 57
- 239000002131 composite material Substances 0.000 claims abstract description 52
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 16
- 239000011574 phosphorus Substances 0.000 claims abstract description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 155
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 128
- 229910052763 palladium Inorganic materials 0.000 claims description 78
- 229910052697 platinum Inorganic materials 0.000 claims description 64
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 28
- 125000000524 functional group Chemical group 0.000 claims description 18
- 229910000510 noble metal Inorganic materials 0.000 claims description 17
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 15
- 229910052759 nickel Inorganic materials 0.000 claims description 15
- 125000006239 protecting group Chemical group 0.000 claims description 15
- 239000010948 rhodium Substances 0.000 claims description 15
- 229910052703 rhodium Inorganic materials 0.000 claims description 15
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 15
- 229910052707 ruthenium Inorganic materials 0.000 claims description 15
- 150000002894 organic compounds Chemical class 0.000 claims description 14
- 239000011133 lead Substances 0.000 claims description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 229910052802 copper Inorganic materials 0.000 claims description 10
- 239000010949 copper Substances 0.000 claims description 10
- 229910052732 germanium Inorganic materials 0.000 claims description 10
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 10
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- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 10
- 229910052718 tin Inorganic materials 0.000 claims description 10
- 239000011135 tin Substances 0.000 claims description 10
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 10
- 239000010937 tungsten Substances 0.000 claims description 10
- 229910052721 tungsten Inorganic materials 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052741 iridium Inorganic materials 0.000 claims description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052762 osmium Inorganic materials 0.000 claims description 5
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- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims description 5
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 150000001720 carbohydrates Chemical class 0.000 claims description 2
- 235000014633 carbohydrates Nutrition 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 19
- 239000002184 metal Substances 0.000 abstract description 19
- 238000004519 manufacturing process Methods 0.000 abstract description 2
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- 239000000654 additive Substances 0.000 description 20
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- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
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- 125000004429 atom Chemical group 0.000 description 3
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
-
- B01J35/617—
-
- B01J35/618—
-
- B01J35/635—
-
- B01J35/66—
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Carbon And Carbon Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/954,235 US6992037B2 (en) | 2001-09-17 | 2001-09-17 | Precious metal catalyst for debenzylation |
| US09/954,235 | 2001-09-17 | ||
| PCT/US2002/026880 WO2003024592A2 (en) | 2001-09-17 | 2002-08-23 | Improved precious metal catalyst for debenzylation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20040044943A true KR20040044943A (ko) | 2004-05-31 |
Family
ID=25495136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2004-7003941A KR20040044943A (ko) | 2001-09-17 | 2002-08-23 | 개선된, 탈벤질화용 귀금속 촉매 |
Country Status (13)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7659225B2 (en) * | 2001-09-17 | 2010-02-09 | Basf Catalysts Llc | Precious metal catalyst for debenzylation |
| US6706658B2 (en) * | 2001-12-21 | 2004-03-16 | Engelhard Corporation | Catalyst for purification of aromatic acids |
| US6720283B2 (en) * | 2002-01-03 | 2004-04-13 | Dalian Institute Of Chemical Physics | Activated carbon supported cobalt based catalyst for direct conversion of synthesis gas to diesel fuels |
| US7237260B2 (en) * | 2003-07-08 | 2007-06-26 | Matsushita Electric Industrial Co., Ltd. | Method for dynamic selection for secure and firewall friendly communication protocols between multiple distributed modules |
| DE102007017182A1 (de) * | 2007-04-12 | 2008-10-16 | Evonik Degussa Gmbh | Geträgerter Edelmetall-Katalysator |
| US8828903B2 (en) * | 2008-11-10 | 2014-09-09 | Basf Corporation | Copper catalyst for dehydrogenation application |
| US20100310441A1 (en) * | 2009-06-05 | 2010-12-09 | Basf Corporation | Catalytic Article for Removal of Volatile Organic Compounds in Low Temperature Applications |
| WO2012074841A2 (en) | 2010-11-30 | 2012-06-07 | Basf Corporation | Copper chromite hydrogenation catalysts for production of fatty alcohols |
| GB201116713D0 (en) | 2011-09-28 | 2011-11-09 | Johnson Matthey Plc | Catalyst |
| US11253839B2 (en) | 2014-04-29 | 2022-02-22 | Archer-Daniels-Midland Company | Shaped porous carbon products |
| CN115178255A (zh) * | 2014-04-29 | 2022-10-14 | 阿彻丹尼尔斯米德兰公司 | 炭黑基成型多孔产物 |
| US9468922B1 (en) * | 2015-06-11 | 2016-10-18 | The United States Of America As Represented By The Secretary Of The Navy | Carbon monolith supported nanoparticle catalysts |
| US10722867B2 (en) | 2015-10-28 | 2020-07-28 | Archer-Daniels-Midland Company | Porous shaped carbon products |
| US10464048B2 (en) | 2015-10-28 | 2019-11-05 | Archer-Daniels-Midland Company | Porous shaped metal-carbon products |
| JP7094954B2 (ja) * | 2017-06-06 | 2022-07-04 | エヌ・イーケムキャット株式会社 | 脱ベンジル反応用触媒 |
| CN115591544A (zh) * | 2021-06-28 | 2023-01-13 | 中国科学院大连化学物理研究所（Cn） | 一种氢解催化剂的制备及应用 |
| CN113745552B (zh) * | 2021-08-17 | 2024-04-09 | 西安交通大学 | 用于直接乙醇和甲醇燃料电池的碳载钯锡氮化钽纳米电催化剂及其制备方法 |
| CN113769736B (zh) * | 2021-09-06 | 2024-02-27 | 陕西瑞科新材料股份有限公司 | 一种氢氧化钯炭载体催化剂的制备方法 |
Family Cites Families (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2409494A (en) | 1944-02-11 | 1946-10-15 | Texas Co | Catalyst manufacture |
| US2556616A (en) | 1948-03-25 | 1951-06-12 | Corning Glass Works | Method of making electrically conducting glass and articles made therefrom |
| US2611750A (en) | 1950-02-07 | 1952-09-23 | Sun Oil Co | Thermally hardened porous solid |
| GB901848A (en) | 1957-12-05 | 1962-07-25 | Atomic Energy Authority Uk | Process for manufacturing carbon articles |
| GB962634A (en) | 1959-11-20 | 1964-07-01 | Secr Aviation | Carbon articles |
| US3109712A (en) | 1960-01-11 | 1963-11-05 | Plessey Co Ltd | Bodies and shapes of carbonaceous materials and processes for their production |
| FR82269E (fr) | 1962-06-06 | 1964-01-17 | Joint Francais | Joint torique d'étanchéité |
| US3235346A (en) | 1960-11-22 | 1966-02-15 | Valley Co Inc | Composite bodies comprising a continuous framework and an impregnated metallic material and methods of their production |
| FR1317683A (US06992037-20060131-C00002.png) | 1961-03-23 | 1963-05-10 | ||
| US3342555A (en) | 1961-06-19 | 1967-09-19 | Dow Chemical Co | Process for the preparation of light weight porous carbon |
| US3171720A (en) | 1961-06-23 | 1965-03-02 | Great Lakes Carbon Corp | Carbonaceous bodies useful for thermal insulation and processes for preparing same |
| US3348967A (en) | 1962-12-27 | 1967-10-24 | Valley Co Inc | Process of making an article having a hard carbide, boride or silicide outer region |
| US3387940A (en) | 1963-08-29 | 1968-06-11 | Union Carbide Corp | High-strength carbon foam |
| US3310611A (en) | 1964-07-15 | 1967-03-21 | Aerojet General Co | Method of producing an artificial graphite body |
| US3446593A (en) | 1965-01-07 | 1969-05-27 | Lorraine Carbone | Process for the manufacture of macroporous vitreous carbon |
| NL6608613A (US06992037-20060131-C00002.png) | 1965-06-21 | 1966-12-22 | ||
| US3345440A (en) | 1965-06-29 | 1967-10-03 | John M Googin | Method for manufacturing foam carbon products |
| US3352788A (en) | 1965-08-26 | 1967-11-14 | Atlas Chem Ind | Activated carbon compositions |
| SE307704B (US06992037-20060131-C00002.png) | 1968-01-31 | 1969-01-13 | Ehrenreich & Cie A | |
| US3544502A (en) | 1968-05-23 | 1970-12-01 | Sun Oil Co | Latex stabilized with salts of polymethylated muconic acids |
| US3628984A (en) | 1968-05-27 | 1971-12-21 | Nippon Carbon Co Ltd | Method for the manufacture of heat-resistant carbonaceous products having low permeability |
| GB1266685A (US06992037-20060131-C00002.png) | 1968-07-12 | 1972-03-15 | ||
| US3634569A (en) | 1969-01-08 | 1972-01-11 | United Aircraft Corp | Method of manufacture of dense graphite structures |
| US3608170A (en) | 1969-04-14 | 1971-09-28 | Abex Corp | Metal impregnated composite casting method |
| US3574548A (en) | 1969-08-11 | 1971-04-13 | Atomic Energy Commission | Process for manufacturing a cellular carbon body |
| GB1260034A (en) | 1969-08-12 | 1972-01-12 | Coal Industry Patents Ltd | Method of manufacturing unitary porous carbon bodies |
| US3657166A (en) | 1969-10-08 | 1972-04-18 | Phillips Petroleum Co | Production of foamed thermoplastic with carbonized cellular structure |
| US3635676A (en) | 1969-11-05 | 1972-01-18 | Atomic Energy Commission | Method for increasing the strength of carbon foam |
| US3859421A (en) | 1969-12-05 | 1975-01-07 | Edward E Hucke | Methods of producing carbonaceous bodies and the products thereof |
| US3775078A (en) | 1972-05-22 | 1973-11-27 | Corning Glass Works | Process for making carbon-containing ceramics |
| US3964933A (en) | 1974-04-08 | 1976-06-22 | Exxon Research And Engineering Company | Carbon article including electrodes and methods of making the same |
| US4076873A (en) | 1974-07-29 | 1978-02-28 | Shea Lawrence E | Resorcinol-aldehyde resins used to bind reinforcing materials such as glass fibers in shaped object form |
| US4061596A (en) | 1974-12-02 | 1977-12-06 | Mitsubishi Chemical Industries Ltd. | Process for preparing titanium oxide shaped carrier |
| NL7502968A (nl) | 1975-03-13 | 1976-09-15 | Stamicarbon | Werkwijze voor het bereiden van edelmetaal- katalysatoren. |
| US3978000A (en) * | 1975-03-19 | 1976-08-31 | American Cyanamid Company | Catalysts based on carbon supports |
| US4082694A (en) | 1975-12-24 | 1978-04-04 | Standard Oil Company (Indiana) | Active carbon process and composition |
| US4026078A (en) | 1976-02-09 | 1977-05-31 | Geometrics | Spherical structural arrangement |
| US4029567A (en) | 1976-04-20 | 1977-06-14 | Canadian Patents And Development Limited | Solids recovery from coal liquefaction slurry |
| US4532227A (en) * | 1976-12-27 | 1985-07-30 | Texaco Development Corporation | Low ash pelleted carbon and process of preparation |
| US4090978A (en) | 1976-12-28 | 1978-05-23 | Uop Inc. | Electrocatalysts and a method for the preparation thereof |
| US4269737A (en) | 1978-07-25 | 1981-05-26 | Exxon Research & Engineering Company | Method for preparing a group IVB, VB or VIB metal oxide on inorganic refractory oxide support catalyst and the product prepared by said method |
| US4263268A (en) | 1978-11-21 | 1981-04-21 | Shandon Southern Products Limited | Preparation of porous carbon |
| US4329260A (en) | 1979-09-24 | 1982-05-11 | Uop Inc. | Integral shaped replication supports |
| DE3017812A1 (de) * | 1980-05-09 | 1981-11-12 | Merck Patent Gmbh, 6100 Darmstadt | Cyclopropanderivate, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
| US4431820A (en) * | 1980-11-18 | 1984-02-14 | The Upjohn Company | 6-Methoxy indoline acetate and its 5-nitro and 5-amino derivatives |
| US4416804A (en) * | 1981-11-23 | 1983-11-22 | Uop Inc. | Acidic multimetallic catalytic composite |
| US4595765A (en) * | 1983-09-19 | 1986-06-17 | Clairol Incorporated | Process for preparing 5,6-dihydroxyindole |
| DE3418150A1 (de) | 1984-05-16 | 1985-11-21 | Degussa Ag, 6000 Frankfurt | Aktivkohle und das verfahren zu ihrer herstellung |
| US4668496A (en) | 1984-11-05 | 1987-05-26 | Plastics Engineering Company | Vitreous carbon |
| US4598060A (en) | 1985-01-28 | 1986-07-01 | Shell Oil Company | Process for the preparation of wide pore catalysts |
| US4892972A (en) | 1985-10-07 | 1990-01-09 | Amoco Corporation | Purification of crude terephthalic acid |
| US4954469A (en) | 1988-08-01 | 1990-09-04 | Robinson Ken K | Granulated activated carbon for water treatment |
| DE3834743A1 (de) | 1988-10-12 | 1990-04-19 | Degussa | Verfahren zur herstellung einer grobporigen formkohle |
| US5166437A (en) * | 1989-03-03 | 1992-11-24 | Orion-Yhtyma Oy | Process for the preparation of fluoxetine |
| US5108597A (en) | 1990-03-22 | 1992-04-28 | Regents Of The University Of Minnesota | Carbon-clad zirconium oxide particles |
| DE69114145T2 (de) * | 1990-12-26 | 1996-05-30 | Du Pont | Katalytische hydrogenolyse. |
| WO1993009755A1 (es) * | 1991-11-13 | 1993-05-27 | Consejo Superior Investigaciones Científicas | Oligosacaridos utilizables para inhibir la mitosis de astrocitos y celulas tumorales del sistema nervioso. su procedimiento de obtencion |
| US5362908A (en) | 1993-03-10 | 1994-11-08 | Amoco Corporation | Catalyst and method for purifying crude terephthalic acid, isophthalic acid or naphthalene dicarboxylic acid |
| DE4308101C1 (de) * | 1993-03-15 | 1994-07-28 | Degussa | Verfahren zur Herstellung platingruppenmetallhaltiger Hydrierkatalysatoren auf Aktivkohle |
| US5432284A (en) * | 1993-09-08 | 1995-07-11 | G. D. Searle & Co. | Process for the preparation of heterocyclic alkylamide derivatives |
| US5462651A (en) * | 1994-08-09 | 1995-10-31 | Texaco Inc. | Hydrodearomatization of hydrocarbon oils using novel "phosphorus treated carbon" supported metal sulfide catalysts |
| EP0821620A1 (en) | 1995-04-17 | 1998-02-04 | Engelhard Corporation | Formed compositions |
| WO1997016424A1 (en) * | 1995-11-02 | 1997-05-09 | Schering Corporation | Process for preparing 1-(4-fluorophenyl)-3(r)-(3(s)-hydroxy-3-([phenyl or 4-fluorophenyl])-propyl)-4(s)-(4-hydroxyphenyl)-2-azetidinone |
| US5756833A (en) | 1996-02-01 | 1998-05-26 | Amoco Corporation | Catalytic purification and recovery of dicarboxylic aromatic acids |
| US5616792A (en) | 1996-02-01 | 1997-04-01 | Amoco Corporation | Catalytic purification of dicarboxylic aromatic acid |
| JPH105586A (ja) | 1996-06-20 | 1998-01-13 | Jgc Corp | 粒状活性炭成型体、担体および触媒 |
| US6040344A (en) * | 1996-11-11 | 2000-03-21 | Sepracor Inc. | Formoterol process |
| US5977409A (en) * | 1997-04-15 | 1999-11-02 | University Of Toledo | Method of using α-substituted benzylamine chiral auxiliary synthetic reagents |
| ITMI971161A1 (it) * | 1997-05-19 | 1998-11-19 | Montecatini Tecnologie Srl | Catalizzatori di idrogenazione |
| AU7318900A (en) | 1999-09-21 | 2001-04-24 | Asahi Kasei Kabushiki Kaisha | Catalysts for hydrogenation of carboxylic acid |
| US6706658B2 (en) * | 2001-12-21 | 2004-03-16 | Engelhard Corporation | Catalyst for purification of aromatic acids |
| US6720283B2 (en) * | 2002-01-03 | 2004-04-13 | Dalian Institute Of Chemical Physics | Activated carbon supported cobalt based catalyst for direct conversion of synthesis gas to diesel fuels |
-
2001
- 2001-09-17 US US09/954,235 patent/US6992037B2/en not_active Expired - Lifetime
-
2002
- 2002-08-23 MX MXPA04002485A patent/MXPA04002485A/es active IP Right Grant
- 2002-08-23 EP EP02798921A patent/EP1436079A2/en not_active Withdrawn
- 2002-08-23 PL PL02374277A patent/PL374277A1/xx not_active Application Discontinuation
- 2002-08-23 RU RU2004111662/04A patent/RU2004111662A/ru not_active Application Discontinuation
- 2002-08-23 IL IL16091002A patent/IL160910A0/xx active IP Right Grant
- 2002-08-23 KR KR10-2004-7003941A patent/KR20040044943A/ko not_active Application Discontinuation
- 2002-08-23 JP JP2003528680A patent/JP4328618B2/ja not_active Expired - Lifetime
- 2002-08-23 CA CA002460852A patent/CA2460852A1/en not_active Abandoned
- 2002-08-23 BR BRPI0212571-4A patent/BR0212571A/pt not_active IP Right Cessation
- 2002-08-23 CN CNB028205197A patent/CN100443166C/zh not_active Expired - Lifetime
- 2002-08-23 WO PCT/US2002/026880 patent/WO2003024592A2/en active Application Filing
-
2004
- 2004-03-17 IL IL160910A patent/IL160910A/en not_active IP Right Cessation
- 2004-03-17 HR HRP20040268 patent/HRP20040268A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP4328618B2 (ja) | 2009-09-09 |
| WO2003024592A2 (en) | 2003-03-27 |
| PL374277A1 (en) | 2005-10-03 |
| CA2460852A1 (en) | 2003-03-27 |
| HRP20040268A2 (en) | 2004-12-31 |
| CN100443166C (zh) | 2008-12-17 |
| BR0212571A (pt) | 2006-08-29 |
| US20030060361A1 (en) | 2003-03-27 |
| IL160910A (en) | 2007-12-03 |
| MXPA04002485A (es) | 2004-05-31 |
| RU2004111662A (ru) | 2005-09-10 |
| WO2003024592A3 (en) | 2003-11-20 |
| IL160910A0 (en) | 2004-08-31 |
| EP1436079A2 (en) | 2004-07-14 |
| CN1571699A (zh) | 2005-01-26 |
| JP2005526588A (ja) | 2005-09-08 |
| US6992037B2 (en) | 2006-01-31 |
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