CA2612435C - Catalyst and method for hydrogenating organic compounds containing hydrogenable groups - Google Patents
Catalyst and method for hydrogenating organic compounds containing hydrogenable groups Download PDFInfo
- Publication number
- CA2612435C CA2612435C CA2612435A CA2612435A CA2612435C CA 2612435 C CA2612435 C CA 2612435C CA 2612435 A CA2612435 A CA 2612435A CA 2612435 A CA2612435 A CA 2612435A CA 2612435 C CA2612435 C CA 2612435C
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- Prior art keywords
- catalyst
- weight
- ruthenium
- substituted
- solution
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- 239000003054 catalyst Substances 0.000 title claims abstract description 302
- 238000000034 method Methods 0.000 title claims abstract description 96
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 25
- 229910052751 metal Inorganic materials 0.000 claims abstract description 114
- 239000002184 metal Substances 0.000 claims abstract description 114
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 100
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 96
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 27
- 235000012239 silicon dioxide Nutrition 0.000 claims abstract description 23
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 15
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 14
- 150000001298 alcohols Chemical class 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 214
- 238000005984 hydrogenation reaction Methods 0.000 claims description 134
- 239000000463 material Substances 0.000 claims description 65
- -1 amino, hydroxyl Chemical group 0.000 claims description 61
- 230000008569 process Effects 0.000 claims description 45
- 238000005470 impregnation Methods 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 31
- OJLCQGGSMYKWEK-UHFFFAOYSA-K ruthenium(3+);triacetate Chemical compound [Ru+3].CC([O-])=O.CC([O-])=O.CC([O-])=O OJLCQGGSMYKWEK-UHFFFAOYSA-K 0.000 claims description 30
- 150000002739 metals Chemical class 0.000 claims description 25
- 230000000737 periodic effect Effects 0.000 claims description 24
- 230000007704 transition Effects 0.000 claims description 24
- 238000001035 drying Methods 0.000 claims description 23
- 239000011248 coating agent Substances 0.000 claims description 22
- 238000000576 coating method Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 230000035515 penetration Effects 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 230000009467 reduction Effects 0.000 claims description 17
- 239000011593 sulfur Substances 0.000 claims description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 9
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 238000004453 electron probe microanalysis Methods 0.000 claims description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 238000004255 ion exchange chromatography Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 5
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 5
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 4
- 150000001448 anilines Chemical class 0.000 claims description 4
- 150000002016 disaccharides Chemical class 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000002772 monosaccharides Chemical class 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 3
- KMKJEJNILQYGCU-UHFFFAOYSA-N 3-[(5-amino-2-methylphenyl)methyl]-4-methylaniline Chemical compound CC1=CC=C(N)C=C1CC1=CC(N)=CC=C1C KMKJEJNILQYGCU-UHFFFAOYSA-N 0.000 claims description 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 3
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000005846 sugar alcohols Chemical class 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 abstract description 9
- 239000012876 carrier material Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 85
- 238000002474 experimental method Methods 0.000 description 42
- 229910052681 coesite Inorganic materials 0.000 description 41
- 229910052906 cristobalite Inorganic materials 0.000 description 41
- 229910052682 stishovite Inorganic materials 0.000 description 41
- 229910052905 tridymite Inorganic materials 0.000 description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 40
- 239000001257 hydrogen Substances 0.000 description 40
- 229910052739 hydrogen Inorganic materials 0.000 description 40
- 238000004458 analytical method Methods 0.000 description 31
- 125000004432 carbon atom Chemical group C* 0.000 description 30
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 230000035484 reaction time Effects 0.000 description 27
- 230000000694 effects Effects 0.000 description 25
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 23
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 239000000523 sample Substances 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- 239000002243 precursor Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 230000007423 decrease Effects 0.000 description 16
- 238000006722 reduction reaction Methods 0.000 description 16
- 102100035474 DNA polymerase kappa Human genes 0.000 description 15
- 101710108091 DNA polymerase kappa Proteins 0.000 description 15
- 238000011156 evaluation Methods 0.000 description 15
- 238000004817 gas chromatography Methods 0.000 description 15
- 239000007789 gas Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 239000012535 impurity Substances 0.000 description 10
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000007791 liquid phase Substances 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 8
- GGLHXZYMYYBBHT-UHFFFAOYSA-N dinonyl cyclohexane-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCCCC GGLHXZYMYYBBHT-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 239000002923 metal particle Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 238000004626 scanning electron microscopy Methods 0.000 description 7
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 6
- AWGBKZRMLNVLAF-UHFFFAOYSA-N 3,5-dibromo-n,2-dihydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=CC(Br)=C1O AWGBKZRMLNVLAF-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 150000005840 aryl radicals Chemical class 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- GXRDMEGSBKPONF-UHFFFAOYSA-N bis(2-methyloctyl) benzene-1,2-dicarboxylate Chemical compound CCCCCCC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)CCCCCC GXRDMEGSBKPONF-UHFFFAOYSA-N 0.000 description 5
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229910000510 noble metal Inorganic materials 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000004611 spectroscopical analysis Methods 0.000 description 5
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- WOSOOWIGVAKGOC-UHFFFAOYSA-N azanylidyneoxidanium;ruthenium(2+);trinitrate Chemical compound [Ru+2].[O+]#N.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O WOSOOWIGVAKGOC-UHFFFAOYSA-N 0.000 description 4
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000012159 carrier gas Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000005229 chemical vapour deposition Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical class OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 4
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 4
- 229960001826 dimethylphthalate Drugs 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 238000002149 energy-dispersive X-ray emission spectroscopy Methods 0.000 description 4
- 239000001307 helium Substances 0.000 description 4
- 229910052734 helium Inorganic materials 0.000 description 4
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- 229910021486 amorphous silicon dioxide Inorganic materials 0.000 description 3
- CMCJNODIWQEOAI-UHFFFAOYSA-N bis(2-butoxyethyl)phthalate Chemical compound CCCCOCCOC(=O)C1=CC=CC=C1C(=O)OCCOCCCC CMCJNODIWQEOAI-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 238000009434 installation Methods 0.000 description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 238000002161 passivation Methods 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical compound CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 description 2
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 2
- 238000000408 29Si solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- BDDNYDPRCCDQQJ-UHFFFAOYSA-N 3'-(3-hydroxyphenyl)-4-methylspiro[1h-1,4-benzodiazepine-3,2'-oxirane]-2,5-dione Chemical compound CN1C(=O)C2=CC=CC=C2NC(=O)C11OC1C1=CC=CC(O)=C1 BDDNYDPRCCDQQJ-UHFFFAOYSA-N 0.000 description 2
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CWZIYUKYRFDSAR-UHFFFAOYSA-N CCCCCCO.CCCCCCO.CCCCCCO Chemical compound CCCCCCO.CCCCCCO.CCCCCCO CWZIYUKYRFDSAR-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
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- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 125000005495 pyridazyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- BPEVHDGLPIIAGH-UHFFFAOYSA-N ruthenium(3+) Chemical compound [Ru+3] BPEVHDGLPIIAGH-UHFFFAOYSA-N 0.000 description 1
- BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 description 1
- GTCKPGDAPXUISX-UHFFFAOYSA-N ruthenium(3+);trinitrate Chemical compound [Ru+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O GTCKPGDAPXUISX-UHFFFAOYSA-N 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
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- 238000001179 sorption measurement Methods 0.000 description 1
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- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 239000006228 supernatant Substances 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000004627 transmission electron microscopy Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000008207 working material Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/08—Silica
-
- 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
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/462—Ruthenium
-
- 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
- B01J23/46—Ruthenium, rhodium, osmium or iridium
-
- 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
-
- 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
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0205—Impregnation in several steps
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B35/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving a change in the type of bonding between two carbon atoms already directly linked
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005029200.3 | 2005-06-22 | ||
| DE102005029200A DE102005029200A1 (de) | 2005-06-22 | 2005-06-22 | Katalysator und Verfahren zur Hydrierung von hydrierbare Gruppen enthaltenden organischen Verbindungen |
| PCT/EP2006/063323 WO2006136541A2 (de) | 2005-06-22 | 2006-06-20 | Ru-katalysator und verfahren zur hydrierung von hydrierbare gruppen enthaltenden organischen verbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2612435A1 CA2612435A1 (en) | 2006-12-28 |
| CA2612435C true CA2612435C (en) | 2015-02-24 |
Family
ID=37433856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2612435A Expired - Fee Related CA2612435C (en) | 2005-06-22 | 2006-06-20 | Catalyst and method for hydrogenating organic compounds containing hydrogenable groups |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8207327B2 (enExample) |
| EP (1) | EP1899051A2 (enExample) |
| JP (1) | JP2008543550A (enExample) |
| KR (1) | KR101354236B1 (enExample) |
| CN (1) | CN101242895B (enExample) |
| CA (1) | CA2612435C (enExample) |
| DE (1) | DE102005029200A1 (enExample) |
| WO (1) | WO2006136541A2 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005049568A1 (de) | 2005-10-17 | 2007-04-19 | Basf Ag | Verfahren zur kontinuierlichen Hydrierung oder hydrierenden Aminierung |
| EP2049254B1 (de) | 2006-07-31 | 2010-12-15 | Basf Se | Verfahren zur regenerierung von rutheniumkatalysatoren für die kernhydrierung von phthalaten |
| US8889936B2 (en) | 2006-07-31 | 2014-11-18 | Basf Se | Method of regenerating ruthenium catalysts for the hydrogenation of benzene |
| ES2759627T3 (es) | 2006-07-31 | 2020-05-11 | Basf Se | Procedimiento integrado consistente en la hidrogenación con catalizadores de rutenio y regeneración de los mismos |
| DE102007025223A1 (de) | 2007-05-31 | 2008-12-04 | Süd-Chemie AG | Zirkoniumoxid-dotierter VAM-Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung |
| DE102007025362A1 (de) | 2007-05-31 | 2008-12-11 | Süd-Chemie AG | Dotierter Pd/Au-Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung |
| DE102007025315A1 (de) * | 2007-05-31 | 2008-12-11 | Süd-Chemie AG | Katalysator zur selektiven Hydrierung acetylenischer Kohlenwasserstoffe und Verfahren zu seiner Herstellung |
| DE102007025443A1 (de) | 2007-05-31 | 2008-12-04 | Süd-Chemie AG | Pd/Au-Schalenkatalysator enthaltend HfO2, Verfahren zu dessen Herstellung sowie dessen Verwendung |
| DE102007025444A1 (de) * | 2007-05-31 | 2008-12-11 | Süd-Chemie AG | VAM-Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung |
| DE102007025356A1 (de) * | 2007-05-31 | 2009-01-08 | Süd-Chemie AG | Verfahren zur Herstellung eines Schalenkatalysators und Schalenkatalysator |
| DE102007025442B4 (de) | 2007-05-31 | 2023-03-02 | Clariant International Ltd. | Verwendung einer Vorrichtung zur Herstellung eines Schalenkatalysators und Schalenkatalysator |
| DE202008017277U1 (de) | 2008-11-30 | 2009-04-30 | Süd-Chemie AG | Katalysatorträger |
| ES2602116T3 (es) | 2008-12-17 | 2017-02-17 | Basf Se | Procedimiento continuo de producción de ciclohexilmetanoles sustituidos |
| US20110144398A1 (en) | 2009-12-11 | 2011-06-16 | Basf Se | Process for regenerating a ruthenium-containing supported hydrogenation catalyst |
| WO2011072992A1 (en) | 2009-12-15 | 2011-06-23 | Exxonmobil Chemical Patents Inc. | Temperature control of an oligomerisation process and reactor |
| KR101833077B1 (ko) | 2009-12-15 | 2018-02-27 | 바스프 에스이 | 방향족 화합물의 수소화를 위한 촉매 및 방법 |
| EP2534281B1 (de) | 2010-02-12 | 2019-01-09 | Basf Se | Verfahren zur herstellung von 4-isopropylcyclohexylmethanol |
| US8889920B2 (en) | 2010-02-12 | 2014-11-18 | Basf Se | Process for preparing 4-isopropylcyclohexylmethanol |
| MX2012010715A (es) | 2010-03-24 | 2012-10-05 | Basf Se | Proceso para la preparacion de 4 - ciclohexil - 2 - metil - 2- butanol. |
| US8450534B2 (en) | 2010-03-24 | 2013-05-28 | Basf Se | Process for preparing 4-cyclohexyl-2-methyl-2-butanol |
| DE102010026462A1 (de) * | 2010-07-08 | 2012-01-12 | Süd-Chemie AG | Verfahren zur Herstellung eines Schalenkatalysators und Schalenkatalysator |
| US9056812B2 (en) | 2011-09-16 | 2015-06-16 | Basf Se | Process for preparing 4-cyclohexyl-2-methyl-2-butanol |
| CN103796980B (zh) | 2011-09-16 | 2016-08-31 | 巴斯夫欧洲公司 | 制备4-环己基-2-甲基-2-丁醇的方法 |
| US9340754B2 (en) | 2012-11-27 | 2016-05-17 | Basf Se | Process for the preparation of cyclohexyl-substituted tertiary alkanols |
| CN106338551B (zh) * | 2015-07-07 | 2019-03-08 | 中国石油化工股份有限公司 | 重整催化剂中不同形态硫元素含量的分析方法 |
| EP3359290B1 (de) * | 2015-10-05 | 2025-01-01 | Basf Se | Verfahren zur herstellung von ruthenium/eisen/kohlenstoffträger-katalysatoren |
| JP6131370B1 (ja) * | 2016-06-10 | 2017-05-17 | 千代田化工建設株式会社 | 合成ガス製造触媒用担体及びその製造方法、合成ガス製造触媒及びその製造方法、並びに合成ガスの製造方法 |
| CN109790101A (zh) * | 2016-09-09 | 2019-05-21 | 埃克森美孚化学专利公司 | 邻苯二甲酸酯的氢化方法 |
| KR102324239B1 (ko) * | 2017-11-06 | 2021-11-08 | 한화솔루션 주식회사 | 방향족 화합물의 수소화 반응용 촉매 및 이의 제조방법 |
| GB2613281B (en) * | 2020-09-29 | 2025-01-29 | Resonac Corp | Method for producing ethyl acetate production catalyst |
| ES3014723T3 (en) | 2020-12-18 | 2025-04-24 | Evonik Oxeno Gmbh & Co Kg | Method for regenerating hydrogenation catalysts |
| US11918989B2 (en) * | 2020-12-18 | 2024-03-05 | Evonik Operations Gmbh | Process for regeneration of hydrogenation catalysts |
| CN114602463B (zh) * | 2022-04-13 | 2023-12-05 | 宏业生物科技股份有限公司 | 一种对羟基苯甲酸乙酯加氢催化剂及其制备方法 |
| GB2630272B (en) | 2023-05-15 | 2025-07-02 | Johnson Matthey Plc | Ruthenium eggshell catalyst |
| CN117101676A (zh) * | 2023-07-12 | 2023-11-24 | 安徽香枫新材料股份有限公司 | 催化剂、制备工艺以及dinp制备dinch的工艺 |
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| US4072628A (en) | 1974-11-05 | 1978-02-07 | Ici Americas Inc. | Regeneration of supported ruthenium catalyst |
| BE882279A (fr) | 1980-03-18 | 1980-07-16 | Raffinerie Tirlemontoise Sa | Procede de reactivation d'un catalyseur, a base de metaux du groupe du platine, pour l'hydrogenation des sucres |
| US4431750A (en) | 1982-05-19 | 1984-02-14 | Phillips Petroleum Company | Platinum group metal catalyst on the surface of a support and a process for preparing same |
| ATE89260T1 (de) * | 1988-01-14 | 1993-05-15 | Huels Chemische Werke Ag | Verfahren zur produktion von 4,4'diaminodicyclohexylmethan mit niedrigem transtrans-isomergehalt durch katalytische hydrogenierung von 4,4'-diaminodiphenylmethan. |
| US4923842A (en) * | 1988-10-11 | 1990-05-08 | Allied-Signal Inc. | Lanthanum containing catalyst for treating automotive exhaust |
| US5102850A (en) * | 1990-10-17 | 1992-04-07 | W. R. Grace & Co. - Conn. | Catalyst supports having promoter oxide gradient, resulting catalyst and method of making the supports |
| FR2689517B1 (fr) * | 1992-04-02 | 1995-07-28 | Inst Francais Du Petrole | Procede d'hydrogenation selective des hydrocarbures. |
| US5399535A (en) * | 1993-08-17 | 1995-03-21 | Rohm And Haas Company | Reticulated ceramic products |
| DE4328007A1 (de) * | 1993-08-20 | 1995-02-23 | Huels Chemische Werke Ag | Katalysator zur Herstellung von Bis-Para-aminocyclohexylmethan mit niedrigem Anteil an trans-trans-Isomer durch Hydrierung von Methylendiamin |
| EP0813906A3 (de) * | 1996-06-19 | 1998-11-18 | Basf Aktiengesellschaft | Verfahren zur Umsetzung einer organischen Verbindung in Gegenwart eines geträgerten Rutheniumkatalysators |
| US6248924B1 (en) * | 1996-06-19 | 2001-06-19 | Basf Aktiengesellschaft | Process for reacting an organic compound in the presence of a supported ruthenium catalyst |
| US6852667B2 (en) * | 1998-02-16 | 2005-02-08 | Sumitomo Chemical Company Limited | Process for producing chlorine |
| JPH11222447A (ja) * | 1998-02-04 | 1999-08-17 | Mitsubishi Chemical Corp | 芳香族化合物の部分水素添加によるシクロオレフィン類の製造方法 |
| DE19827844A1 (de) | 1998-06-23 | 1999-12-30 | Aventis Res & Tech Gmbh & Co | Verfahren zur Herstellung von Schalenkatalysatoren durch CVD-Beschichtung |
| DE19832087A1 (de) * | 1998-07-16 | 2000-01-20 | Basf Ag | Verfahren zur Umsetzung von organischen Verbindungen mit boroxidhaltigen, makroporösen Trägerkatalysatoren |
| CN1117623C (zh) * | 2000-11-23 | 2003-08-13 | 中国科学院生态环境研究中心 | 汽车尾气净化三效催化剂及其制备方法 |
| DE10128242A1 (de) | 2001-06-11 | 2002-12-12 | Basf Ag | Verfahren zur Hydrierung organischer Verbindungen |
| DE10128204A1 (de) | 2001-06-11 | 2002-12-12 | Basf Ag | Verfahren zur Herstellung von cycloaliphatischen Verbindungen I, die Seitenketten mit Epoxidgruppen aufweisen |
| DE10128205A1 (de) | 2001-06-11 | 2002-12-12 | Basf Ag | Ruthenium-Katalysatoren |
| ATE422962T1 (de) * | 2002-05-31 | 2009-03-15 | Evonik Degussa Gmbh | Geträgerter rutheniumkatalysator und verfahren zur hydrierung eines aromatischen amins in gegenwart dieses katalysators |
| DE10253803A1 (de) | 2002-11-18 | 2004-05-27 | Degussa Ag | Verfahren zur Herstellung von aliphatischen Isocyanaten aus aromatischen Isocyanaten |
| DE10253802A1 (de) * | 2002-11-18 | 2004-06-03 | Degussa Ag | Verfahren zur Hydrierung von aromatischen Urethanen in Gegenwart eines geträgerten Rutheniumkatalysators |
| US7230035B2 (en) | 2002-12-30 | 2007-06-12 | Conocophillips Company | Catalysts for the conversion of methane to synthesis gas |
| DE10361157A1 (de) | 2003-12-22 | 2005-07-21 | Basf Ag | Ruthenium-Heterogenkatalysator und Verfahren zur Herstellung eines Bisglycidylethers der Formel I |
| WO2005061106A1 (de) | 2003-12-22 | 2005-07-07 | Basf Aktiengesellschaft | Ruthenium-heterogenkatalysator, verfahren zur hydrierung einer carbocyclischen aromatischen gruppe und kernhydrierte bisglycidylether der bisphenole a und f |
| DE10361151A1 (de) | 2003-12-22 | 2005-07-14 | Basf Ag | Ruthenium-Heterogenkatalysator und Verfahren zur Hydrierung einer carbocyclischen aromatischen Gruppe, insbesondere zur Herstellung eines Bisglycidylethers der Formel I |
-
2005
- 2005-06-22 DE DE102005029200A patent/DE102005029200A1/de not_active Withdrawn
-
2006
- 2006-06-20 KR KR1020087001732A patent/KR101354236B1/ko not_active Expired - Fee Related
- 2006-06-20 CN CN2006800305342A patent/CN101242895B/zh not_active Expired - Fee Related
- 2006-06-20 JP JP2008517476A patent/JP2008543550A/ja active Pending
- 2006-06-20 WO PCT/EP2006/063323 patent/WO2006136541A2/de not_active Ceased
- 2006-06-20 EP EP06777365A patent/EP1899051A2/de not_active Withdrawn
- 2006-06-20 US US11/993,777 patent/US8207327B2/en not_active Expired - Fee Related
- 2006-06-20 CA CA2612435A patent/CA2612435C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1899051A2 (de) | 2008-03-19 |
| KR101354236B1 (ko) | 2014-01-22 |
| KR20080027871A (ko) | 2008-03-28 |
| DE102005029200A1 (de) | 2006-12-28 |
| WO2006136541A3 (de) | 2007-04-12 |
| CA2612435A1 (en) | 2006-12-28 |
| WO2006136541A2 (de) | 2006-12-28 |
| US20100152436A1 (en) | 2010-06-17 |
| CN101242895A (zh) | 2008-08-13 |
| US8207327B2 (en) | 2012-06-26 |
| CN101242895B (zh) | 2012-01-11 |
| JP2008543550A (ja) | 2008-12-04 |
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