JP2011522696A - 有機化合物を水素化するための触媒および方法 - Google Patents
有機化合物を水素化するための触媒および方法 Download PDFInfo
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- JP2011522696A JP2011522696A JP2011512867A JP2011512867A JP2011522696A JP 2011522696 A JP2011522696 A JP 2011522696A JP 2011512867 A JP2011512867 A JP 2011512867A JP 2011512867 A JP2011512867 A JP 2011512867A JP 2011522696 A JP2011522696 A JP 2011522696A
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- 239000003054 catalyst Substances 0.000 title claims abstract description 79
- 238000000034 method Methods 0.000 title claims abstract description 45
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 29
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 99
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 95
- 239000002041 carbon nanotube Substances 0.000 claims description 85
- 229910021393 carbon nanotube Inorganic materials 0.000 claims description 85
- 229910052757 nitrogen Inorganic materials 0.000 claims description 55
- 238000005984 hydrogenation reaction Methods 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 18
- DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical compound N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 230000003197 catalytic effect Effects 0.000 claims description 12
- 239000010439 graphite Substances 0.000 claims description 8
- 229910002804 graphite Inorganic materials 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 239000007791 liquid phase Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 3
- QALQXPDXOWOWLD-UHFFFAOYSA-N [N][N+]([O-])=O Chemical compound [N][N+]([O-])=O QALQXPDXOWOWLD-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- 229910000510 noble metal Inorganic materials 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229910018134 Al-Mg Inorganic materials 0.000 description 3
- 229910018467 Al—Mg Inorganic materials 0.000 description 3
- -1 C—C double bonds Chemical group 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- KMAQZIILEGKYQZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1 KMAQZIILEGKYQZ-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 241001330002 Bambuseae Species 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
-
- 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
- B01J21/185—Carbon nanotubes
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nanotechnology (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Composite Materials (AREA)
- Crystallography & Structural Chemistry (AREA)
- Physics & Mathematics (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
72gのCo−Mn−Al−Mg混合酸化物触媒(Mn:Co:Al2O3:MgO 17:18:44:22)を、例えばWO2007/093337、実施例2に記載の通り製造し、350gの従来法によるカーボンナノチューブ凝集体(Baytubes(登録商標)、Bayer MaterialScience AG)の初期投入をガス流および温度の均一な分布を流動床中に得るために予め存在させた流動床反応器中に設置した。
これは、アセトニトリルを、反応器中に19g/分の供給速度で供給したことを除いて、実施例1の通り製造した。生産性は、5.9窒素ドープカーボンナノチューブのg/触媒のgであった。
これは、導入した触媒の量が48gであること、およびアセトニトリルの代わりにピリジンを、反応器中に26g/分の供給速度で供給したことを除いて、実施例1の通り製造した。生産性は、10.1窒素ドープカーボンナノチューブのg/触媒のgであった。
これは、導入した触媒の量が104gであることを除いて、実施例3の通り製造した。生産性は、13.8窒素ドープカーボンナノチューブのg/触媒のgであった。
これは、導入した触媒の量が80gであること、ピリジンの代わりにジメチルホルムアルデヒドを、反応器中に31.5g/分の供給速度で供給したこと、および水素を導入しなかったことを除いて、実施例3の通り製造した。
これらは、供給速度を10.1g/分に設定したことを除いて、実施例5の通り製造した。生産性は、5.0窒素ドープカーボンナノチューブのg/触媒のgであった。このようにして製造した窒素ドープカーボンナノチューブを、3.5重量%の窒素含量および1.52mol/molの第4級窒素に対するピリジン窒素の比率を有した。
イソプロパノール中のニトロベンゼンの30%濃度溶液から構成される5gの反応混合物を、撹拌圧反応器中に設置した。実施例1〜6からの窒素ドープカーボンナノチューブまたは非ドープカーボンナノチューブ(Baytubes(登録商標)、Bayer MaterialScience AG製)を、いずれの場合にも、カーボンナノチューブが懸濁液の3重量%になるような量でそこに添加した。
Claims (15)
- 有機化合物を水素化するための触媒であって、窒素ドープカーボンナノチューブを触媒活性成分として含み、該窒素ドープカーボンナノチューブ中における窒素の割合が、黒鉛相において0.05〜20重量%の範囲であること、および該窒素がピリジン配置中に少なくとも部分的に存在することを特徴とする、触媒。
- 窒素は、ピリジン窒素の少なくとも一部に加えて、第4級窒素および/またはニトロ窒素および/またはニトロソ窒素および/またはアミン窒素の形態で存在することを特徴とする、請求項1に記載の触媒。
- ピリジン窒素の割合は、本発明の触媒中において、窒素ドープカーボンナノチューブ中に存在する窒素の少なくとも20mol%であり、好ましくは30mol%を越えることを特徴とする、請求項1または2に記載の触媒。
- 第4級窒素に対するピリジン窒素の比率は、少なくとも1.25mol/mol、好ましくは少なくとも1.3mol/molであることを特徴とする、請求項2または3に記載の触媒。
- 水素により有機化合物を水素化するための方法であって、該水素化を、窒素ドープカーボンナノチューブを触媒活性成分として含む触媒の存在下で行い、該窒素ドープカーボンナノチューブ中における窒素の割合が、黒鉛層中において0.05〜20重量%の範囲であり、該窒素が、ピリジン配置中に少なくとも部分的に存在することを特徴とする、前記方法。
- 有機化合物を液相中に存在させ、水素をガス形態で存在させることを特徴とする、請求項5に記載の方法。
- 有機化合物を、液体溶媒中に存在させることを特徴とする、請求項6に記載の方法。
- 溶媒は、任意の水素化活性官能基を含まない有機溶媒であるか、または該有機溶媒の混合物であることを特徴とする、請求項7に記載の方法。
- 20℃〜350℃の範囲、好ましくは40℃〜300℃の範囲の温度で行うことを特徴とする、請求項6〜8のいずれかに記載の方法。
- 有機化合物および水素を、ガス形態で存在させることを特徴とする、請求項5に記載の方法。
- 120〜750℃、好ましくは140〜650℃、特に好ましくは200〜600℃の温度で行うことを特徴とする、請求項5に記載の方法。
- 複数の段階で、好ましくは2〜10、特に好ましくは2〜6、極めて特に好ましくは2〜5、とりわけ2または3の直列に接続した反応帯域で行うことを特徴とする、請求項5〜11のいずれかに記載の方法。
- 触媒を、少なくとも50重量%、好ましくは少なくとも80重量%、特に好ましくは少なくとも95重量%の窒素ドープカーボンナノチューブを含有させることを特徴とする、請求項5〜12のいずれかに記載の方法。
- 触媒を、固定床として存在させることを特徴とする、請求項5〜13のいずれかに記載の方法。
- 固定床を、触媒活性を反応帯域において主流方向に増加させる構造化床の形態で存在させることを特徴とする、請求項14に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102008028070A DE102008028070A1 (de) | 2008-06-12 | 2008-06-12 | Katalysator und Verfahren zur Hydrierung von organischen Verbindungen |
DE102008028070.4 | 2008-06-12 | ||
PCT/EP2009/003950 WO2009149849A1 (de) | 2008-06-12 | 2009-06-03 | Katalysator und verfahren zur hydrierung von organischen verbindungen |
Publications (3)
Publication Number | Publication Date |
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JP2011522696A true JP2011522696A (ja) | 2011-08-04 |
JP2011522696A5 JP2011522696A5 (ja) | 2012-07-19 |
JP5430653B2 JP5430653B2 (ja) | 2014-03-05 |
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JP2011512867A Expired - Fee Related JP5430653B2 (ja) | 2008-06-12 | 2009-06-03 | 有機化合物を水素化するための触媒および方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US8614355B2 (ja) |
EP (1) | EP2285768B1 (ja) |
JP (1) | JP5430653B2 (ja) |
KR (1) | KR20110016445A (ja) |
CN (1) | CN102056888A (ja) |
DE (1) | DE102008028070A1 (ja) |
ES (1) | ES2462744T3 (ja) |
WO (1) | WO2009149849A1 (ja) |
Cited By (1)
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JP2020528199A (ja) * | 2017-07-18 | 2020-09-17 | ピーエイチ マター、エルエルシー | 多機能電極添加剤 |
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DE102007062421A1 (de) * | 2007-12-20 | 2009-06-25 | Bayer Technology Services Gmbh | Verfahren zur Herstellung von Stickstoff-dotierten Kohlenstoffnanoröhrchen |
DE102009058833A1 (de) * | 2009-12-18 | 2011-06-22 | Bayer Technology Services GmbH, 51373 | Stickstoff-dotierte Kohlenstoffnanoröhrchen mit Metall-Nanopartikeln |
DE102012209634A1 (de) * | 2012-06-08 | 2013-12-12 | Leibniz-Institut Für Katalyse E.V. An Der Universität Rostock | Verwendung von thermisch behandelten geträgerten Kobaltkatalysatoren zur Hydrierung von Nitroaromaten |
EP2837612A1 (en) | 2013-08-13 | 2015-02-18 | Bayer Technology Services GmbH | Nitrogen-doped carbon nanotubes as high selective noble metal-free catalysts for hydrogenation of functionalized nitroaromatics |
CN106807426A (zh) * | 2015-11-30 | 2017-06-09 | 北京化工大学 | 一种无金属加氢催化剂及应用 |
CN105753717B (zh) * | 2016-04-01 | 2018-06-01 | 湘潭大学 | 一种无金属加氢催化剂在催化1-硝基萘加氢反应中的应用 |
CN105749954B (zh) * | 2016-04-01 | 2018-07-20 | 湘潭大学 | 一种无金属加氢催化剂及其催化1,5-二硝基萘加氢反应的应用 |
CN105669464B (zh) * | 2016-04-01 | 2018-07-27 | 湘潭大学 | 一种无金属加氢催化剂在催化硝基苯及其衍生物加氢反应中的应用 |
CN105777577B (zh) * | 2016-04-01 | 2018-01-02 | 湘潭大学 | 一种无金属加氢催化剂在催化硝基环己烷加氢反应中的应用 |
CN105921164B (zh) * | 2016-05-20 | 2018-08-31 | 湘潭大学 | 一种掺氮活性炭负载碱金属改性的镍基催化剂的制备方法和应用 |
DE102017204322A1 (de) * | 2017-03-15 | 2018-09-20 | Rheinisch-Westfälische Technische Hochschule (Rwth) Aachen | Verfahren zur chemischen Umsetzung von Zuckern oder Zuckeralkoholen zu Glykolen |
DE102018215394A1 (de) * | 2018-09-11 | 2020-03-12 | Rheinisch-Westfälische Technische Hochschule Aachen | Verfahren zur chemischen Umsetzung von Zuckern oder Zuckeralkoholen zu Glykolen |
US11597652B2 (en) * | 2018-11-21 | 2023-03-07 | Cence, Inc. | Carbon nanofiber having embedded carbon nanotubes, and method of manufacture |
CN111470982A (zh) * | 2019-01-23 | 2020-07-31 | 中国石油化工股份有限公司 | 一种苯胺类化合物的合成方法 |
CN111470979A (zh) * | 2019-01-23 | 2020-07-31 | 中国石油化工股份有限公司 | 一种苯胺类化合物的合成方法 |
CN111468123A (zh) * | 2019-01-23 | 2020-07-31 | 中国石油化工股份有限公司 | 一种苯胺类化合物的合成方法 |
CN111470975A (zh) * | 2019-01-23 | 2020-07-31 | 中国石油化工股份有限公司 | 一种苯胺类化合物的合成方法 |
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JP3903365B2 (ja) * | 2001-03-29 | 2007-04-11 | 株式会社東芝 | 光アシスト磁気記録ヘッド及び光アシスト磁気記録装置 |
US20070275160A1 (en) * | 2003-10-10 | 2007-11-29 | Stephen Maldonado | Carbon Nanostructure-Based Electrocatalytic Electrodes |
DE602005026167D1 (de) * | 2004-11-16 | 2011-03-10 | Hyperion Catalysis Internat Inc | Verfahren zur herstellung von trägerkatalysatoren aus metallbeladenen kohlenstoffnanoröhrchen |
JP4635607B2 (ja) * | 2004-12-28 | 2011-02-23 | Tdk株式会社 | 熱アシスト磁気記録ヘッド及び熱アシスト磁気記録装置 |
DE102006007147A1 (de) | 2006-02-16 | 2007-08-23 | Bayer Technology Services Gmbh | Verfahren zur kontinuierlichen Herstellung von Katalysatoren |
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JPN6013023973; Stefan van DOMMELE, et al.: 'Nitrogen-containing carbon nanotubes as solid base catalysts' Chemical Communications Volume 2006, Issue 46, 2006, pages 4859-4861 * |
JPN6013023978; S. van DOMMELE, et al.: 'Tuning nitrogen functionalities in catalytically grown nitrogen-containing carbon nanotubes' Carbon Volume 46, Issue 1, 2008, Pages 138-148 * |
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Cited By (2)
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JP2020528199A (ja) * | 2017-07-18 | 2020-09-17 | ピーエイチ マター、エルエルシー | 多機能電極添加剤 |
JP7368853B2 (ja) | 2017-07-18 | 2023-10-25 | ピーエイチ マター、エルエルシー | 多機能電極添加剤 |
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US20110130592A1 (en) | 2011-06-02 |
WO2009149849A1 (de) | 2009-12-17 |
JP5430653B2 (ja) | 2014-03-05 |
EP2285768A1 (de) | 2011-02-23 |
CN102056888A (zh) | 2011-05-11 |
EP2285768B1 (de) | 2014-03-19 |
KR20110016445A (ko) | 2011-02-17 |
US8614355B2 (en) | 2013-12-24 |
DE102008028070A1 (de) | 2009-12-17 |
ES2462744T3 (es) | 2014-05-26 |
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