JP2005526589A - ニトロ芳香族化合物を水素化するための担持触媒 - Google Patents
ニトロ芳香族化合物を水素化するための担持触媒 Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims abstract description 75
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 36
- 150000001875 compounds Chemical class 0.000 title claims abstract description 11
- 229910000510 noble metal Inorganic materials 0.000 claims abstract description 82
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000843 powder Substances 0.000 claims abstract description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 11
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 claims description 10
- 239000006229 carbon black Substances 0.000 claims description 10
- 229910052703 rhodium Inorganic materials 0.000 claims description 10
- 229910052707 ruthenium Inorganic materials 0.000 claims description 10
- 229910052684 Cerium Inorganic materials 0.000 claims description 9
- 229910052742 iron Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052720 vanadium Inorganic materials 0.000 claims description 7
- 229910052748 manganese Inorganic materials 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 150000002828 nitro derivatives Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 2
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 26
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 229910052763 palladium Inorganic materials 0.000 description 10
- 229910052697 platinum Inorganic materials 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- KGYLMXMMQNTWEM-UHFFFAOYSA-J tetrachloropalladium Chemical compound Cl[Pd](Cl)(Cl)Cl KGYLMXMMQNTWEM-UHFFFAOYSA-J 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- -1 aromatic nitro compounds Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- RMBFBMJGBANMMK-UHFFFAOYSA-N 2,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RMBFBMJGBANMMK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- 239000010970 precious metal Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 150000000703 Cerium Chemical class 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- SZQUEWJRBJDHSM-UHFFFAOYSA-N iron(3+);trinitrate;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O SZQUEWJRBJDHSM-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRTYPQGPARWINR-UHFFFAOYSA-N palladium platinum Chemical compound [Pd].[Pt] JRTYPQGPARWINR-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- KPZSTOVTJYRDIO-UHFFFAOYSA-K trichlorocerium;heptahydrate Chemical compound O.O.O.O.O.O.O.Cl[Ce](Cl)Cl KPZSTOVTJYRDIO-UHFFFAOYSA-K 0.000 description 1
Classifications
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- 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
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- 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
- B01J23/63—Platinum group metals with rare earths or actinides
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- 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
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/648—Vanadium, niobium or tantalum or polonium
- B01J23/6482—Vanadium
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- 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
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/652—Chromium, molybdenum or tungsten
- B01J23/6522—Chromium
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- 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
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/656—Manganese, technetium or rhenium
- B01J23/6562—Manganese
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- 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
- B01J23/8906—Iron and noble metals
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- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
本発明による触媒および基準触媒が製造され、ニトロ芳香族化合物の水素化における前記触媒の触媒特性が比較される。
一次貴金属成分としてのPd、二次貴金属成分としてのPtおよび刊行物に記載の非貴金属成分を有するPd−Pt−Fe/SB3金属原子性触媒(trimetallic catalyst)(Pd1.6%+Pt0.2%+Fe4.0%)の製造。Chevron社の製品Shawinigan Black(この触媒Shawinigan BlackをSBと略記した)をカーボンブラック担体として使用する。米国特許第3127356号明細書、実施例VIIに開示されたようなPd−Pt−Fe/SB(Pd1.6%+Pt0.2%+Fe4.0%)触媒を製造する。
Shawinigan Black22.06g(Chevron社の市販製品、この触媒Shawinigan BlackをSBと略記した)を脱イオン水2000ml中に懸濁させ、この懸濁液を炭酸ナトリウム溶液を用いて10のpHに設定する。テトラクロロパラジウム(II)酸2g(20%)、ヘキサクロロ白金(IV)酸0.2g(25%)および脱イオン水200ml中の塩化セリウム(III)七水和物の溶液を、前記懸濁液に添加する。80℃への加熱後、炭酸ナトリウム溶液を用いてpHを6.4に設定し、懸濁液を攪拌し、濾過する。無水触媒100gは、Pd1.6%、Pt0.2%およびCe10.5%を含有する。この触媒は、Pd−Pt−Ce/SB(1.6、0.2、10.5)と略記される。
触媒Pd−Pt/SB(Pd1.6%、Pt0.2%)を実施例1の記載と同様に製造するが、しかし、実施例1に記載の量の代わりに、Shawinigan Black24.69gを使用し、セリウム塩は使用しない。無水触媒100gは、Pd1.6%およびPt0.2%を含有する。
活性炭98.21gを脱イオン水500ml中に懸濁させ、この懸濁液を炭酸ナトリウム溶液を用いて10のpHに設定する。テトラクロロパラジウム(II)酸8g(20%)、ヘキサクロロ白金(IV)酸0.8g(25%)および脱イオン水200ml中の硝酸鉄(III)九水和物の溶液を、前記懸濁液に添加する。80℃への加熱後、炭酸ナトリウム溶液を用いてpHを6.4に設定し、懸濁液を攪拌し、ホルムアルデヒドで還元し、濾過する。無水触媒100gは、Pd1.6%、Pt0.2%およびFe4.2%を含有する。この触媒は、Pd−Pt−Fe/AC(1.6、0.2、4.2)と略記される。
活性炭を脱イオン水500ml中に懸濁させ、この懸濁液を炭酸ナトリウム溶液を用いて10のpHに設定する。テトラクロロパラジウム(II)酸8g(20%)、二次貴金属成分および脱イオン水200ml中の非貴金属成分の塩の溶液を、前記懸濁液に添加する。80℃への加熱後、炭酸ナトリウム溶液を用いてpHを6.4に設定し、懸濁液を攪拌し、ホルムアルデヒドで還元し、濾過する。量は、第1表中に記載されている。
活性炭を脱イオン水500ml中に懸濁させ、この懸濁液を炭酸ナトリウム溶液を用いて10のpHに設定する。ヘキサクロロ白金(IV)酸11.6g(25%)、それぞれ脱イオン水200ml中溶解された二次貴金属成分および非貴金属成分の塩の溶液を、前記懸濁液に添加する。80℃への加熱後、炭酸ナトリウム溶液を用いてpHを6.4に設定し、懸濁液を攪拌し、ホルムアルデヒドで還元し、濾過する。量は、第2表中に記載されている。
Claims (10)
- 触媒活性成分として一次貴金属成分、二次貴金属成分および1つ以上の非貴金属成分の混合物を含有する、粉末の形の担持水素化触媒において、Ptが一次貴金属成分として、二次貴金属成分としてのPd、Ru、Rhおよび非貴金属成分としてのV、Fe、Mn、Ceおよび/またはCrと一緒に使用されていてもよいか、またはPdが一次貴金属成分として、二次貴金属成分としてのRu、Rhおよび非貴金属成分としてのV、Fe、Mn、Ceおよび/またはCrと一緒に使用されていてもよいか、またはPdが一次貴金属成分として、二次貴金属成分としてのPtおよび非貴金属成分としてのCeおよび/またはCrと一緒に使用されていてもよいことを特徴とする、粉末の形の担持水素化触媒。
- 物理的に活性化された炭素、化学的に活性化された炭素、カーボンブラック、酸化アルミニウムまたは酸化珪素は、粉末の形の担体として使用されている、請求項1記載の粉末の形の担持水素化触媒。
- 無水水素化触媒100gが一次貴金属成分10〜50mmol、一次貴金属成分に対して1〜60モル%の二次貴金属成分および一次貴金属成分に対して1〜700モル%の非貴金属成分を含有する、請求項1記載の水素化触媒。
- 無水水素化触媒100gが一次貴金属成分15〜20mmol、一次貴金属成分に対して8〜12モル%の二次貴金属成分および一次貴金属成分に対して1〜600モル%のセリウムを含有する、請求項1記載の水素化触媒。
- 請求項1から4までのいずれか1項に記載の水素化触媒の製造法において、一次貴金属成分、二次貴金属成分および非貴金属成分を溶解された形で含有する水溶液を、水中の粉末の形の担体の懸濁液に添加し、一次貴金属成分および二次貴金属成分ならびに非貴金属成分を塩基を用いて粉末の形の担体材料上に付着させ、場合によっては還元剤を用いて還元を実施することを特徴とする、請求項1から4までのいずれか1項に記載の水素化触媒の製造法。
- アミノ芳香族化合物へのニトロ芳香族化合物の水素化のための請求項1から4までのいずれか1項に記載の触媒の使用。
- アニリンへのニトロベンゼンの水素化のための請求項1から4までのいずれか1項に記載の触媒の使用。
- トルエンジアミンへのジニトロトルエンの水素化のための請求項1から4までのいずれか1項に記載の触媒の使用。
- アニリンの製造法において、相応するニトロ化合物の接触水素化を液相中で連続的または非連続的に操作される方法として1〜100バールの圧力および0℃〜200℃の温度で請求項1から4までのいずれか1項に記載の触媒の存在で実施することを特徴とする、アニリンの製造法。
- トルエンジアミンの製造法において、相応するニトロ化合物の接触水素化を液相中で連続的または非連続的に操作される方法として1〜100バールの圧力および0℃〜200℃の温度で請求項1から4までのいずれか1項に記載の触媒の存在で実施することを特徴とする、トルエンジアミンの製造法。
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DE10154811 | 2001-11-08 | ||
US33315301P | 2001-11-27 | 2001-11-27 | |
DE10216108A DE10216108A1 (de) | 2001-11-08 | 2002-04-12 | Pulverförmiger geträgerter Hydrierkatalysator |
PCT/EP2002/009874 WO2003039743A1 (en) | 2001-11-08 | 2002-09-04 | Supported catalyst for hydrogenation of nitroaromatics |
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JP2005526589A true JP2005526589A (ja) | 2005-09-08 |
JP4523275B2 JP4523275B2 (ja) | 2010-08-11 |
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JP (1) | JP4523275B2 (ja) |
CN (1) | CN100479916C (ja) |
BR (1) | BR0213928A (ja) |
HU (1) | HUP0402102A3 (ja) |
PL (1) | PL368203A1 (ja) |
WO (1) | WO2003039743A1 (ja) |
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ES2294075T3 (es) * | 2001-12-07 | 2008-04-01 | Basf Se | Procedimiento para la obtencion de catalizadores de rutenio/hierro sobre soportes de carbono. |
DE10349095A1 (de) | 2003-10-17 | 2005-05-19 | Basf Ag | Verfahren zur Herstellung von Aminen |
CN1898229B (zh) * | 2003-12-19 | 2012-05-30 | 宇部兴产株式会社 | 四氢吡喃-4-酮以及吡喃-4-酮的制备方法 |
DE102005041532A1 (de) | 2005-08-31 | 2007-03-01 | Basf Ag | Verfahren zur Herstellung von Aminen |
CN101429453B (zh) * | 2008-03-19 | 2010-05-12 | 中国石油天然气股份有限公司 | 裂解汽油馏分一段选择性加氢方法 |
CN102000568B (zh) * | 2010-11-11 | 2012-08-15 | 厦门大学 | 一种硝基芳香烃的还原方法 |
CN102952022B (zh) * | 2012-09-13 | 2014-04-09 | 赛鼎工程有限公司 | 二硝基甲苯连续制备二胺基甲苯的方法及使用的催化剂和催化剂的制备方法 |
CN105080567B (zh) * | 2014-04-22 | 2017-09-29 | 中国科学院长春应用化学研究所 | 催化剂以及芳香氨基化合物的制备方法 |
CN105435808A (zh) * | 2014-08-20 | 2016-03-30 | 中国石油化工股份有限公司 | 一种炭黑贵金属催化剂的制备方法 |
CN104971738B (zh) * | 2015-07-07 | 2017-06-27 | 淮阴工学院 | 磁性纳米钯催化剂的制备方法 |
WO2017163680A1 (ja) * | 2016-03-23 | 2017-09-28 | エヌ・イー ケムキャット株式会社 | 反応組成物及びこれを用いた反応システム |
US10322992B2 (en) | 2016-12-13 | 2019-06-18 | King Abdulaziz University | Methods of making cerium oxide polyaniline composite nanospheres and methods of use |
CN109225258A (zh) * | 2018-10-19 | 2019-01-18 | 郴州高鑫铂业有限公司 | 一种Pt-Fe/C催化剂及其制备方法和应用 |
CN111013561A (zh) * | 2019-12-31 | 2020-04-17 | 贵研工业催化剂(云南)有限公司 | 一种用于硝基苯液相加氢制苯胺的催化剂的制备方法 |
CN114534733B (zh) * | 2020-11-24 | 2024-04-12 | 万华化学集团股份有限公司 | 一种硝基化合物加氢制芳胺催化剂的制备方法 |
CN113145112B (zh) * | 2021-04-30 | 2023-03-24 | 福州大学 | 一种用于二硝基甲苯选择性加氢的Pd-Pt/C催化剂的制备方法 |
CN114289034B (zh) * | 2021-12-27 | 2024-02-02 | 万华化学集团股份有限公司 | 一种贵金属催化剂和制备方法及其在催化二硝基甲苯加氢制备甲苯二胺应用 |
CN114471544A (zh) * | 2022-02-25 | 2022-05-13 | 天脊煤化工集团股份有限公司 | 一种催化剂及其在苯胺制备中的应用 |
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- 2002-09-04 EP EP02779300A patent/EP1441850A1/en not_active Withdrawn
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CN100479916C (zh) | 2009-04-22 |
JP4523275B2 (ja) | 2010-08-11 |
HUP0402102A2 (hu) | 2005-01-28 |
WO2003039743A1 (en) | 2003-05-15 |
EP1441850A1 (en) | 2004-08-04 |
CN1582199A (zh) | 2005-02-16 |
HUP0402102A3 (en) | 2010-07-28 |
BR0213928A (pt) | 2004-08-31 |
PL368203A1 (en) | 2005-03-21 |
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