CA2460852A1 - Improved precious metal catalyst for debenzylation - Google Patents
Improved precious metal catalyst for debenzylation Download PDFInfo
- Publication number
- CA2460852A1 CA2460852A1 CA002460852A CA2460852A CA2460852A1 CA 2460852 A1 CA2460852 A1 CA 2460852A1 CA 002460852 A CA002460852 A CA 002460852A CA 2460852 A CA2460852 A CA 2460852A CA 2460852 A1 CA2460852 A1 CA 2460852A1
- Authority
- CA
- Canada
- Prior art keywords
- palladium
- platinum
- less
- carbon support
- catalyst
- 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.)
- Abandoned
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 126
- 239000010970 precious metal Substances 0.000 title claims description 21
- 238000006264 debenzylation reaction Methods 0.000 title description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 127
- 239000011148 porous material Substances 0.000 claims abstract description 116
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 103
- 239000002131 composite material Substances 0.000 claims abstract description 67
- 239000003575 carbonaceous material Substances 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 29
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 19
- 239000011574 phosphorus Substances 0.000 claims abstract description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 154
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 128
- 229910052763 palladium Inorganic materials 0.000 claims description 75
- 229910052697 platinum Inorganic materials 0.000 claims description 64
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 30
- 125000000524 functional group Chemical group 0.000 claims description 20
- 125000006239 protecting group Chemical group 0.000 claims description 20
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 15
- 229910052759 nickel Inorganic materials 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 239000011133 lead Substances 0.000 claims description 11
- 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
- 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
- 229910052702 rhenium Inorganic materials 0.000 claims description 10
- 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
- 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
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 229910052762 osmium Inorganic materials 0.000 claims description 5
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 5
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
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- 108090000765 processed proteins & peptides Proteins 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 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
- 230000002363 herbicidal effect Effects 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 19
- 239000002184 metal Substances 0.000 abstract description 19
- 239000000243 solution Substances 0.000 description 21
- 239000000654 additive Substances 0.000 description 20
- 238000010438 heat treatment Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000463 material Substances 0.000 description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 13
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 229910021641 deionized water Inorganic materials 0.000 description 7
- -1 nutshells Substances 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000007327 hydrogenolysis reaction Methods 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000009826 distribution Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- 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 4
- 230000008901 benefit Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 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
- 238000000518 rheometry Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229920003091 Methocel™ Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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- 230000000996 additive effect Effects 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 229920003086 cellulose ether Polymers 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
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- 239000001569 carbon dioxide Substances 0.000 description 2
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- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 102220487426 Actin-related protein 2/3 complex subunit 3_K15M_mutation Human genes 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
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- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
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- VMRJECJWGHKSMH-UHFFFAOYSA-L [Na].[Pt](Cl)Cl Chemical compound [Na].[Pt](Cl)Cl VMRJECJWGHKSMH-UHFFFAOYSA-L 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
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- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 229910001617 alkaline earth metal chloride Inorganic materials 0.000 description 1
- 229910000316 alkaline earth metal phosphate Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
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- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
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- 229910052743 krypton Inorganic materials 0.000 description 1
- DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 1
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- JRTYPQGPARWINR-UHFFFAOYSA-N palladium platinum Chemical compound [Pd].[Pt] JRTYPQGPARWINR-UHFFFAOYSA-N 0.000 description 1
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- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
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- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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- 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—
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 |
|---|---|
| CA2460852A1 true CA2460852A1 (en) | 2003-03-27 |
Family
ID=25495136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002460852A Abandoned CA2460852A1 (en) | 2001-09-17 | 2002-08-23 | Improved precious metal catalyst for debenzylation |
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 |
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-
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 |
| KR20040044943A (ko) | 2004-05-31 |
| WO2003024592A2 (en) | 2003-03-27 |
| PL374277A1 (en) | 2005-10-03 |
| 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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| EEER | Examination request | ||
| FZDE | Discontinued |