JP5956470B2 - チオ抵抗性触媒、製造方法および選択的水素化における使用 - Google Patents
チオ抵抗性触媒、製造方法および選択的水素化における使用 Download PDFInfo
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- JP5956470B2 JP5956470B2 JP2013552239A JP2013552239A JP5956470B2 JP 5956470 B2 JP5956470 B2 JP 5956470B2 JP 2013552239 A JP2013552239 A JP 2013552239A JP 2013552239 A JP2013552239 A JP 2013552239A JP 5956470 B2 JP5956470 B2 JP 5956470B2
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- catalyst
- copper
- range
- palladium
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- 239000003054 catalyst Substances 0.000 title claims description 103
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title description 2
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 title 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 45
- 239000007864 aqueous solution Substances 0.000 claims description 34
- 229910052751 metal Inorganic materials 0.000 claims description 25
- 239000002184 metal Substances 0.000 claims description 25
- 229910000510 noble metal Inorganic materials 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 23
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 21
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 239000002243 precursor Substances 0.000 claims description 20
- 229910052763 palladium Inorganic materials 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- 150000004706 metal oxides Chemical class 0.000 claims description 16
- 229910044991 metal oxide Inorganic materials 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 230000002829 reductive effect Effects 0.000 claims description 11
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 10
- 239000012702 metal oxide precursor Substances 0.000 claims description 9
- 239000005751 Copper oxide Substances 0.000 claims description 8
- 229910000431 copper oxide Inorganic materials 0.000 claims description 8
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
- 150000002739 metals Chemical class 0.000 claims description 6
- 238000001354 calcination Methods 0.000 claims description 5
- 239000004927 clay Substances 0.000 claims description 5
- 239000003610 charcoal Substances 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 3
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims description 3
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 3
- 239000005750 Copper hydroxide Substances 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 229910052776 Thorium Inorganic materials 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229940116318 copper carbonate Drugs 0.000 claims description 3
- 229910001956 copper hydroxide Inorganic materials 0.000 claims description 3
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 3
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 claims description 3
- 125000002897 diene group Chemical group 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 150000003839 salts Chemical group 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- KLFRPGNCEJNEKU-FDGPNNRMSA-L (z)-4-oxopent-2-en-2-olate;platinum(2+) Chemical compound [Pt+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O KLFRPGNCEJNEKU-FDGPNNRMSA-L 0.000 claims description 2
- CTUFHBVSYAEMLM-UHFFFAOYSA-N acetic acid;platinum Chemical compound [Pt].CC(O)=O.CC(O)=O CTUFHBVSYAEMLM-UHFFFAOYSA-N 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- LHQLJMJLROMYRN-UHFFFAOYSA-L cadmium acetate Chemical compound [Cd+2].CC([O-])=O.CC([O-])=O LHQLJMJLROMYRN-UHFFFAOYSA-L 0.000 claims description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910000011 cadmium carbonate Inorganic materials 0.000 claims description 2
- PLLZRTNVEXYBNA-UHFFFAOYSA-L cadmium hydroxide Chemical compound [OH-].[OH-].[Cd+2] PLLZRTNVEXYBNA-UHFFFAOYSA-L 0.000 claims description 2
- XIEPJMXMMWZAAV-UHFFFAOYSA-N cadmium nitrate Inorganic materials [Cd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XIEPJMXMMWZAAV-UHFFFAOYSA-N 0.000 claims description 2
- CXKCTMHTOKXKQT-UHFFFAOYSA-N cadmium oxide Inorganic materials [Cd]=O CXKCTMHTOKXKQT-UHFFFAOYSA-N 0.000 claims description 2
- QCUOBSQYDGUHHT-UHFFFAOYSA-L cadmium sulfate Chemical compound [Cd+2].[O-]S([O-])(=O)=O QCUOBSQYDGUHHT-UHFFFAOYSA-L 0.000 claims description 2
- GKDXQAKPHKQZSC-UHFFFAOYSA-L cadmium(2+);carbonate Chemical compound [Cd+2].[O-]C([O-])=O GKDXQAKPHKQZSC-UHFFFAOYSA-L 0.000 claims description 2
- CFEAAQFZALKQPA-UHFFFAOYSA-N cadmium(2+);oxygen(2-) Chemical compound [O-2].[Cd+2] CFEAAQFZALKQPA-UHFFFAOYSA-N 0.000 claims description 2
- ZKXWKVVCCTZOLD-UHFFFAOYSA-N copper;4-hydroxypent-3-en-2-one Chemical compound [Cu].CC(O)=CC(C)=O.CC(O)=CC(C)=O ZKXWKVVCCTZOLD-UHFFFAOYSA-N 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 2
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 claims description 2
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- NWAHZABTSDUXMJ-UHFFFAOYSA-N platinum(2+);dinitrate Chemical compound [Pt+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O NWAHZABTSDUXMJ-UHFFFAOYSA-N 0.000 claims description 2
- PQTLYDQECILMMB-UHFFFAOYSA-L platinum(2+);sulfate Chemical compound [Pt+2].[O-]S([O-])(=O)=O PQTLYDQECILMMB-UHFFFAOYSA-L 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 239000011148 porous material Substances 0.000 description 19
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 14
- 229910052717 sulfur Inorganic materials 0.000 description 14
- 239000011593 sulfur Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 12
- 239000003502 gasoline Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000012535 impurity Substances 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 9
- 229910017604 nitric acid Inorganic materials 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000011787 zinc oxide Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000005470 impregnation Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 238000000197 pyrolysis Methods 0.000 description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 238000010304 firing Methods 0.000 description 6
- ZRKMQKLGEQPLNS-UHFFFAOYSA-N 1-Pentanethiol Chemical compound CCCCCS ZRKMQKLGEQPLNS-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 238000007865 diluting Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 239000012696 Pd precursors Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical group [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- -1 alkenyl aromatic compounds Chemical class 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000002923 metal particle Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 238000002459 porosimetry Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 2
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 2
- 229940007718 zinc hydroxide Drugs 0.000 description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 description 2
- 229960001763 zinc sulfate Drugs 0.000 description 2
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 description 2
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 2
- ROGIWVXWXZRRMZ-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1 ROGIWVXWXZRRMZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- KWXSMVPUXACIJE-UHFFFAOYSA-N [N+](=O)([O-])[O-].[Zn+2].O.[Zn+2].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-] Chemical compound [N+](=O)([O-])[O-].[Zn+2].O.[Zn+2].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-] KWXSMVPUXACIJE-UHFFFAOYSA-N 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000331 cadmium sulfate Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- HCRZXNOSPPHATK-UHFFFAOYSA-L copper;3-oxobutanoate Chemical compound [Cu+2].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O HCRZXNOSPPHATK-UHFFFAOYSA-L 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000004817 gas chromatography 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
- 238000000227 grinding Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical group O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000012694 precious metal precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000003716 rejuvenation Effects 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- JGPSMWXKRPZZRG-UHFFFAOYSA-N zinc;dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O JGPSMWXKRPZZRG-UHFFFAOYSA-N 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
- B01J23/70—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
- B01J23/8926—Copper and 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
- B01J23/54—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
- B01J23/60—Platinum group metals with zinc, cadmium or mercury
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
- B01J35/635—0.5-1.0 ml/g
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/16—Reducing
- B01J37/18—Reducing with gases containing free hydrogen
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
- C10G45/34—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used
- C10G45/40—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used containing platinum group metals or compounds thereof
-
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/44—Hydrogenation of the aromatic hydrocarbons
- C10G45/46—Hydrogenation of the aromatic hydrocarbons characterised by the catalyst used
- C10G45/52—Hydrogenation of the aromatic hydrocarbons characterised by the catalyst used containing platinum group metals or compounds thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
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- B01J23/48—Silver or gold
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
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Description
1) 第IB族または第IIB族からの金属の金属酸化物の前駆体の水溶液を調製する工程であって、前記前駆体は、イオンの形態である、工程;
2) 先行する工程において得られた前記溶液を、耐火性酸化物、炭、粘土、シリカ−アルミナおよび/またはそれらの混合物によって形成される群から選択される担体上に組み入れる、工程;
3) 先行する工程において得られた、促進された担体を、乾燥させおよび焼成する、工程;
4) 第VIIIB族からの貴金属の前駆体の水溶液を調製する、工程;
5) 第VIIIB族からの貴金属の前駆体の前記溶液を、促進され、乾燥させられ、および焼成された担体中に組み入れる、工程;
6) 先行する工程において得られた担体を、乾燥させ、焼成する、工程;
7) 工程6)において得られた触媒を還元する、工程;
を含む。
以下の実施例において、担体の比表面積は、BET法(ASTM標準D3663)を用いて計測された。細孔容積は、ASTM標準D4284−92による水銀ポロシメトリによって、140°の濡れ角で計測された。
硝酸パラジウムPd(NO3)2の水溶液の調製は、10重量%の硝酸パラジウムおよび10重量%の硝酸を含有する硝酸パラジウムPd(NO3)2水溶液(Aldrich)6.51gを脱塩水で希釈することによって行った。調製された水溶液の全体積は、担体の細孔容積に相当していた。
硝酸銅Cu(NO3)2の水溶液の調製は、水和された硝酸銅(Aldrich)3.75gおよび1×10−3モル/Lの硝酸溶液5mLを脱塩水で希釈することによって行った。調製された水溶液の全体積は、担体の細孔容積に相当していた。
硝酸亜鉛Zn(NO3)2の水溶液の調製は、六水和硝酸亜鉛(Aldrich)8.92gおよび1×10−4モル/Lの硝酸溶液5mLを脱塩水で希釈することにより行った。調製された水溶液の全体積は、担体の細孔容積に相当していた。
硝酸亜鉛Zn(NO3)2の水溶液の調製は、六水和硝酸亜鉛(Aldrich)39.20gおよび1×10−4モル/Lの硝酸溶液5mLを脱塩水で希釈することにより行った。調製された水溶液の全体積は、担体の細孔容積に相当していた。
硝酸銅Cu(NO3)2の水溶液の調製は、水和硝酸銅(Aldrich)30.70gおよび1×10−3モル/Lの硝酸溶液5mLを脱塩水で希釈することにより行った。調製された水溶液の全体積は、担体の細孔容積に相当していた。
触媒試験の前に、触媒A、B、C、DおよびEの処理を、時間当たりかつ触媒の重量(g)当たり水素1リットルの流れ中、300℃/hの昇温勾配および2時間にわたる150℃の一定温度段階により行い、パラジウムのみを金属形態に還元した。このようにして、触媒B、C、DおよびEが得られ、金属の形態のパラジウム、並びに、酸化亜鉛または酸化銅によって促進された。
選択性=%C5オレフィン/(%C5オレフィン+%C5パラフィン)×100
選択性は、高い活性で、すなわち、イソプレンの99.8%が転化させられた時に、ペンタンチオール含有率32ppmを有する供給原料について測定された。結果は、表1に示される。
Claims (9)
- 活性相を担体上に沈着させられて含むチオ抵抗性触媒であって、前記活性相は、第VIIIB族からの少なくとも1種の貴金属と、全触媒重量に対して少なくとも2〜50重量%の第IB族または第IIB族からの金属酸化物とからなり、該貴金属は、還元された形態にあり、白金およびパラジウムから選択され、該金属酸化物は、酸化銅および酸化カドミウムによって形成される群から選択され、前記担体は、耐火性酸化物、炭、粘土、シリカ−アルミナおよび/またはそれらの混合物によって形成される群から選択され、前記担体の比表面積は、110〜300m2/gの範囲である、触媒。
- 最終担持触媒の全質量に対する、第IB族または第IIB族からの金属酸化物の重量による量は、2.1〜45重量%の範囲である、請求項1に記載の触媒。
- 最終担持触媒の全質量に対する、第VIIIB族からの貴金属の重量による量は、0.01〜2重量%の範囲である、請求項1または2に記載の触媒。
- 耐火性酸化物は、マグネシウム、アルミニウム、ケイ素、ジルコニウム、トリウム、チタンおよび/またはそれらの混合の酸化物によって形成される群から選択される、請求項1〜3のいずれか1つに記載の触媒。
- 請求項1〜4のいずれか1つに記載のチオ抵抗性触媒の調製方法であって、以下の工程:
1) 第IB族または第IIB族からの金属の酸化物の前駆体の水溶液を調製する工程であって、前記前駆体は、イオンの形態である、工程;
2) 先行する工程において得られた前記溶液を、耐火性酸化物、炭、粘土、シリカ−アルミナおよび/またはそれらの混合物によって形成される群から選択される担体上に組み入れる、工程;
3) 先行する工程において得られた促進された担体を、乾燥させおよび焼成する、工程;
4) 第VIIIB族からの貴金属の前駆体の水溶液を調製する、工程;
5) 第VIIIB族からの貴金属の前駆体の前記溶液を、促進され、乾燥させられおよび焼成された担体中に組み入れる、工程;
6) 先行する工程において得られた担体を、乾燥させおよび焼成する、工程;
7) 工程6)において得られた触媒を還元する、工程であって、該還元工程は、80〜160℃の範囲の温度で還元ガスの存在下に現場内で行われる、工程;
を含む、方法。 - 第IB族または第IIB族からの金属の酸化物の前駆体は、酢酸銅、銅アセチルアセトナート、炭酸銅、水酸化銅、硝酸銅、硫酸銅、酢酸カドミウム、カドミウムアセチルアセトナート、炭酸カドミウム、水酸化カドミウム、硝酸カドミウムおよび硫酸カドミウムから選択される、請求項5に記載の方法。
- 第VIIIB族からの貴金属の前駆体は、硝酸パラジウム、硫酸パラジウム、酢酸パラジウム、パラジウムアセチルアセトナート、硝酸白金、硫酸白金、酢酸白金および白金アセチルアセトナートによって構成される群から選択される塩である、請求項5または6に記載の方法。
- 前記第VIIIB族からの貴金属の前駆体の水溶液は、アルカリ水酸化物およびアルカリ土類水酸化物によって構成される群から選択される無機塩基によって中和される、請求項5〜7のいずれか1つに記載の方法。
- 少なくとも1つのアセチレン基、ジエン基および/またはアルケニル芳香族基を含む化合物の選択的水素化のための、請求項1〜4のいずれか1つに記載の触媒の使用。
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FR11/00288 | 2011-01-31 | ||
FR1100288A FR2970881B1 (fr) | 2011-01-31 | 2011-01-31 | Catalyseur thioresistant, procede de fabrication et utilisation en hydrogenation selective |
PCT/FR2012/000017 WO2012104498A2 (fr) | 2011-01-31 | 2012-01-10 | Catalyseur thioresistant, procede de fabrication et utilisation en hydrogenation selective |
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CN105521778B (zh) * | 2014-09-28 | 2017-11-28 | 中国石油化工股份有限公司 | 一种含铂和钯的双金属催化剂及其制备方法与应用以及芳烃饱和方法 |
CN112718012B (zh) * | 2019-10-28 | 2023-10-10 | 中国石油化工股份有限公司 | 一种蒽醌法生产双氧水的催化剂及其制备方法 |
FR3132646A1 (fr) * | 2022-02-14 | 2023-08-18 | IFP Energies Nouvelles | Catalyseur comprenant une phase active de palladium et de cuivre |
FR3132647A1 (fr) * | 2022-02-14 | 2023-08-18 | IFP Energies Nouvelles | Procede de preparation d’un catalyseur comprenant une phase active de palladium et de cuivre |
FR3134015A1 (fr) * | 2022-03-31 | 2023-10-06 | IFP Energies Nouvelles | Catalyseur a base de palladium et de zinc sur un support d’alumine |
WO2024030039A2 (en) * | 2022-08-05 | 2024-02-08 | Qatar Foundation For Education, Science And Community Development | Functionalized limestone with antimicrobial properties and for heavy metals and phosphate removal for wastewater treatment applications |
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US3218268A (en) * | 1962-07-18 | 1965-11-16 | Chemetron Corp | Selective hydrogenation catalyst |
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FR2413127A1 (fr) | 1978-01-02 | 1979-07-27 | Inst Francais Du Petrole | Procede de preparation d'un catalyseur de metal noble du groupe viii presentant une resistance amelioree au soufre, catalyseur obtenu et son utilisation pour l'hydrogenation d'hydrocarbures aromatiques |
US4280930A (en) * | 1979-03-05 | 1981-07-28 | Uop Inc. | Nonacidic multimetallic catalytic composite |
US4231897A (en) * | 1979-05-04 | 1980-11-04 | Uop Inc. | Attenuated superactive multimetallic catalytic composite |
US4312791A (en) * | 1979-08-16 | 1982-01-26 | Uop Inc. | Nonacidic multimetallic catalytic composite |
FR2523149A1 (fr) | 1982-03-15 | 1983-09-16 | Catalyse Soc Prod Francais | Nouveau catalyseur supporte palladium-or, sa preparation et son utilisation dans les reactions d'hydrogenation selective d'hydrocarbures diolefiniques et/ou acetyleniques |
DE3830319C1 (ja) * | 1988-09-07 | 1989-07-20 | Degussa Ag, 6000 Frankfurt, De | |
FR2670400B1 (fr) * | 1990-12-13 | 1993-04-02 | Inst Francais Du Petrole | Procede de preparation de catalyseurs multimetalliques. |
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FR2729090A1 (fr) * | 1995-01-11 | 1996-07-12 | Inst Francais Du Petrole | Catalyseurs de reduction selective des oxydes d'azote en azote en milieu oxydant, procede de preparation et utilisation |
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FR2773087B1 (fr) * | 1997-12-26 | 2000-02-11 | Inst Francais Du Petrole | Catalyseurs de reduction des oxydes d'azote dans un milieu oxydant, preparation et utilisation |
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FR2874837B1 (fr) * | 2004-09-08 | 2007-02-23 | Inst Francais Du Petrole | Catalyseur dope et procede ameliore de traitement de charges hydrocarbonees |
FR2882531B1 (fr) * | 2005-02-25 | 2007-04-27 | Inst Francais Du Petrole | Procede de preparation de catalyseurs multimetalliques utilisables dans des reactions de transformation des hydrocarbures |
JP5336234B2 (ja) * | 2009-03-19 | 2013-11-06 | 旭化成ケミカルズ株式会社 | 複合粒子担持物及びその製造方法並びにカルボン酸エステルの製造方法 |
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JP2014511261A (ja) | 2014-05-15 |
WO2012104498A3 (fr) | 2012-12-27 |
EP2670822B1 (fr) | 2016-04-27 |
FR2970881B1 (fr) | 2015-03-20 |
WO2012104498A2 (fr) | 2012-08-09 |
US20130338413A1 (en) | 2013-12-19 |
EP2670822A2 (fr) | 2013-12-11 |
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