JP5223195B2 - 新規触媒 - Google Patents
新規触媒 Download PDFInfo
- Publication number
- JP5223195B2 JP5223195B2 JP2006546629A JP2006546629A JP5223195B2 JP 5223195 B2 JP5223195 B2 JP 5223195B2 JP 2006546629 A JP2006546629 A JP 2006546629A JP 2006546629 A JP2006546629 A JP 2006546629A JP 5223195 B2 JP5223195 B2 JP 5223195B2
- Authority
- JP
- Japan
- Prior art keywords
- palladium
- alkyne
- polyethyleneimine
- compound
- alkene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 239000003054 catalyst Substances 0.000 title claims description 31
- 229920002873 Polyethylenimine Polymers 0.000 claims description 81
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 72
- 150000001345 alkine derivatives Chemical class 0.000 claims description 66
- 150000001336 alkenes Chemical class 0.000 claims description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 30
- 150000002941 palladium compounds Chemical class 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 239000011261 inert gas Substances 0.000 claims description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000007872 degassing Methods 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 32
- 238000004519 manufacturing process Methods 0.000 description 32
- 238000006722 reduction reaction Methods 0.000 description 25
- 150000001335 aliphatic alkanes Chemical class 0.000 description 17
- 229910052763 palladium Inorganic materials 0.000 description 17
- 239000000758 substrate Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 8
- -1 palladium halide Chemical class 0.000 description 8
- 239000011981 lindlar catalyst Substances 0.000 description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 4
- KSLSOBUAIFEGLT-UHFFFAOYSA-N 2-phenylbut-3-yn-2-ol Chemical compound C#CC(O)(C)C1=CC=CC=C1 KSLSOBUAIFEGLT-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 235000002597 Solanum melongena Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002940 palladium Chemical class 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 230000010757 Reduction Activity Effects 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229940046892 lead acetate Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 2
- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 231100000167 toxic agent Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- LRYWJUOPPCVNFT-UHFFFAOYSA-N 2-phenylbut-3-en-2-ol Chemical compound C=CC(O)(C)C1=CC=CC=C1 LRYWJUOPPCVNFT-UHFFFAOYSA-N 0.000 description 1
- XGLHYBVJPSZXIF-UHFFFAOYSA-N 2-phenylbutan-2-ol Chemical compound CCC(C)(O)C1=CC=CC=C1 XGLHYBVJPSZXIF-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- GFUIMFAJKPSCLA-UHFFFAOYSA-N CC(C)NCCN(CCC(C)(C)C)CCNC Chemical compound CC(C)NCCN(CCC(C)(C)C)CCNC GFUIMFAJKPSCLA-UHFFFAOYSA-N 0.000 description 1
- BFPYWIDHMRZLRN-UHFFFAOYSA-N CC(CC1)(C(CC2)C(CCc3c4)C1c3ccc4O)C2(C#C)O Chemical compound CC(CC1)(C(CC2)C(CCc3c4)C1c3ccc4O)C2(C#C)O BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 208000005156 Dehydration Diseases 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- OHQLYLRYQSZVLV-UHFFFAOYSA-N dioxopalladium Chemical compound O=[Pd]=O OHQLYLRYQSZVLV-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 229910002094 inorganic tetrachloropalladate Inorganic materials 0.000 description 1
- 229910052743 krypton Inorganic materials 0.000 description 1
- DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 229910052704 radon Inorganic materials 0.000 description 1
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- ABKQFSYGIHQQLS-UHFFFAOYSA-J sodium tetrachloropalladate Chemical compound [Na+].[Na+].Cl[Pd+2](Cl)(Cl)Cl ABKQFSYGIHQQLS-UHFFFAOYSA-J 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
-
- C—CHEMISTRY; METALLURGY
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Description
(式中、x及びyは、それぞれ独立して0又は正の自然数を表す。但し、xとyが共に0の場合を除く。)が挙げられる。本発明に係るポリエレンイミンの分子量は、通常100〜10,000,000、好ましくは800〜750,000、より好ましくは10,000〜100,000、更に好ましくは20,000〜30,000である。
等が挙げられ、一置換アルキンの具体例としては、例えば
ポリエチレンイミン2.11 g(シグマアルドリッチジャパン(株)製)を200 mLナスフラスコに入れ、真空ポンプによる減圧下で48時間脱気した。その後、該ナスフラスコにメタノール100 mL (HPLCグレード,和光純薬工業(株)製)を加え、ポリエチレンイミンを均一に溶解した。次いで、得られた溶液を、酢酸パラジウム200mg(1mmol)を入れた後アルゴンを充填した200 mLナスフラスコに移し、酢酸パラジウムをポリエチレンイミンのメタノール溶液中で完全に溶解した。その後、アルゴンを水素ガスに置換し、室温下で24時間撹拌反応させた。更に、減圧下でメタノールを乾燥した後、残渣を真空ポンプによる減圧下で24時間乾燥し、黒色の粘性固体(本発明のシロップ状Pd-PEI触媒)を得た。
ポリエチレンイミン12.66g(シグマアルドリッチジャパン(株)製)を200 mL三角フラスコに入れ、メタノール60 mLを加え溶解した。そこに酢酸パラジウム1.2g (6 mmol)を加え、アルゴン置換を行い、室温下で26時間撹拌した。その後、減圧下でメタノールを乾燥し、黒色のガム状固体(ガム状Pd-PEI触媒)を得た。
基質としての3-フェニル-1-ブチン-3-オール146mg (1 mmol)と実施例1で得たシロップ状Pd-PEI触媒15mgを、表1記載の各種溶媒(表1記載の溶媒量)に加え、水素雰囲気下室温で24時間撹拌、反応させた。反応後、酢酸エチル20 mLと水20 mLを添加混合し、静置後酢酸エチル層を分取した。得られた酢酸エチル層に飽和食塩水20 mLを添加混合し、静置後酢酸エチル層を分取した。次いで、無水硫酸マグネシウムで乾燥した後、溶媒を減圧留去した。
得られた物質を1H-NMRスペクトルで測定し、基質の残存率、対応のアルケン及び対応のアルカンの生成率を求めた。得られた結果を表1に示す。尚、表1中の1:2:3は、基質(3-フェニル-1-ブチン-3-オール)の残存率:対応のアルケン(3-フェニル-1-ブテン-3-オール)の生成率:対応のアルカン(2-フェニル-2-ブタノール)の生成率(重量比率)を表す。
基質としての3-フェニル-1-ブチン-3-オール 146mg(1 mmol)と比較例1で得たガム状Pd-PEI触媒15mgを、水1.25mLとアセトニトリル1.25mLの混合溶媒に加え、水素雰囲気下室温で48時間撹拌、反応させた。反応後、酢酸エチル20 mLと水20 mLを添加混合し、静置後酢酸エチル層を分取した。得られた酢酸エチル層に飽和食塩水20 mLを添加混合し、静置後酢酸エチル層を分取した。次いで、無水硫酸マグネシウムで乾燥後、溶媒を減圧留去した。
得られた物質を1H-NMRスペクトルで測定し、基質の残存率、並びに対応のアルケン及び対応のアルカンの生成率を求めた。得られた結果を表2に示す。また、実施例2の溶媒として酢酸エチル(2mL)+ピリジン(0.5mL)を用いた場合の結果を併せて示す。尚、表1中の1:2:3は、基質の残存率:対応のアルケンの生成率:対応のアルカンの生成率(重量比率)を表す。
表3に記載の各種アルキンを基質とし、用いる溶媒を、酢酸エチル 2mLとピリジン0.5mLの混合溶媒から表3に記載の溶媒(溶媒量)とした以外は、実施例2と同様に実験を行った。得られた物質を1H-NMRスペクトルで測定し、基質の残存率、並びに対応のシス型アルケン、トランス型アルケン及び対応のアルカンの生成率を求めた。得られた結果を表3にそれぞれ示す。尚、表中の1:2:3:4は、基質の残存率:対応のシス型アルケンの生成率:トランス型アルケンの生成率:対応のアルカンの生成率(重量比率)を表す。
表4に記載の各種一置換アルキンを基質とし、用いる混合溶媒を、酢酸エチル 2mLとピリジン0.5mLの混合溶媒から表4に記載の溶媒(溶媒量)とした以外は、実施例2と同様に実験を行った。得られた物質を1H-NMRスペクトルで測定し、基質の残存率、並びに対応のアルケン及び対応のアルカンの生成率を求めた。得られた結果を表4にそれぞれ示す。尚、表中の1:2:3は、基質の残存率:対応のアルケンの生成率:対応のアルカンの生成率(重量比率)を表す。
基質として表5に記載の各種一置換アルキン1 mmolと、基質の10重量%のリンドラー触媒(パラジウム/炭酸カルシウム/酢酸鉛)とを、シクロヘキサン2 mLとキノリン117 μlの混合溶媒に加え、水素雰囲気下室温で24時間撹拌し、反応させた。得られた反応溶液をメンブランフィルター(Millex-LG, 0.20 μm、日本ミリポア社製)を用いてろ過した後、酢酸エチル20 mL、水20 mL及び10 %硫酸水素ナトリウム適量を加え、攪拌した。静置して2層に分離後、酢酸エチル層を分取した。更に、得られた酢酸エチルに飽和食塩水20 mLを添加して攪拌し、静置して2層に分離後酢酸エチル層を分取した。得られた酢酸エチルを無水硫酸マグネシウムで乾燥後、溶媒を減圧留去した。
Claims (5)
- 反応系内の空気を、不活性ガス、水素ガス又は両者の混合ガスで置換した状態、或いは反応系内の空気を脱気して得られる無酸素状態で、ポリエチレンイミンとパラジウム化合物と水素ガスとを反応させることにより得られる、パラジウム担持ポリエチレンイミン化合物を含んでなる、アルキンからアルケンへの還元用触媒。
- 反応系内の空気を、不活性ガス、水素ガス又は両者の混合ガスで置換した状態、或いは反応系内の空気を脱気して得られる無酸素状態で、ポリエチレンイミンとパラジウム化合物と水素ガスとを反応させることにより得られる、パラジウム担持ポリエチレンイミンの存在下、アルキンと水素とを接触させることを特徴とする、アルキンからアルケンへの還元方法。
- パラジウム担持ポリエチレンイミンの存在下アルキンと水素とを、有機溶媒中で接触させる、請求項2に記載の還元方法。
- 有機溶媒が、アセトニトリル、酢酸エチル、ジオキサン、メタノール、ベンゼン、トルエン、ピリジン、テトラヒドロフラン、ヘキサン及びジエチルエーテルから選ばれる1種又は2種以上の混合溶液である、請求項3に記載の還元方法。
- アルキンが一置換アルキンである請求項4に記載の還元方法。
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US20090018301A1 (en) * | 2006-03-10 | 2009-01-15 | Thomas Stephen J | Heterogeneous hydrosilylation catalysts, polymers formed therewith, and related coating compositions |
JP5255215B2 (ja) * | 2007-02-28 | 2013-08-07 | 一般財団法人川村理化学研究所 | 遷移金属固定化リアクター、及びその製造方法 |
JP5598910B2 (ja) * | 2010-06-14 | 2014-10-01 | 独立行政法人産業技術総合研究所 | フッ素化合物の製造方法 |
JP5786621B2 (ja) * | 2010-12-24 | 2015-09-30 | エヌ・イーケムキャット株式会社 | 選択的水素化用触媒、その製造方法及びそれを用いる選択的水素化法。 |
JP7180440B2 (ja) * | 2018-02-23 | 2022-11-30 | 三菱ケミカル株式会社 | 貴金属触媒、還元方法及び化合物の製造方法 |
CN109928873A (zh) * | 2019-04-09 | 2019-06-25 | 大连理工大学 | 一种水相催化炔酸选择性加氢还原制备烯酸的方法 |
US20220134323A1 (en) * | 2019-09-30 | 2022-05-05 | Lg Chem, Ltd. | Catalyst for hydrogenation reaction and method for producing same |
CN113563150B (zh) * | 2021-07-15 | 2022-09-02 | 南通大学 | 水供氢钯催化炔烃半还原选择性合成顺、反式烯烃的方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS5547147A (en) * | 1978-08-17 | 1980-04-03 | Heyl & Co | Hydrogenated catalyst and its preparation and its hydrogenating method |
JPS61138591A (ja) * | 1984-12-12 | 1986-06-26 | Sumitomo Chem Co Ltd | 溶存酸素の除去方法 |
JPS6272639A (ja) * | 1985-09-24 | 1987-04-03 | ゾルファイ インテロックス ゲゼルシャフト ミット ベシュレンクテル ハフツング | アルキル−5,6,7,8−テトラヒドロアントラヒドロキノンの製造法 |
JPS6470596A (en) * | 1987-08-19 | 1989-03-16 | Heyl Chem Pharm | Use of soluble porous hydrogenating catalyst in position selective hydrogenation of oils and fats |
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Publication number | Priority date | Publication date | Assignee | Title |
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EP0008407B1 (de) * | 1978-08-17 | 1983-10-26 | Heyl Chemisch-pharmazeutische Fabrik GmbH & Co. KG | Polymere Hydrierkatalysatoren, Verfahren zur Herstellung dieser Katalysatoren und ihre Verwendung für katalytische Hydrierungen |
US4323698A (en) * | 1978-12-04 | 1982-04-06 | Mobil Oil Corporation | Resin-metal compound complex for catalyzing chemical reactions |
US4252677A (en) * | 1979-12-04 | 1981-02-24 | Xerox Corporation | Preparation of colloidal dispersion of nickel, palladium and platinum by the polymer-catalyzed decomposition of carbonyl compounds thereof |
AU696631B2 (en) * | 1996-10-30 | 1998-09-17 | Phillips Petroleum Company | Catalyst composition useful for hydrogenating unsaturated hydrocarbons |
GB9918229D0 (en) * | 1999-08-04 | 1999-10-06 | Ici Plc | Improvements relating to metal-compound catalysed processes |
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2005
- 2005-12-02 WO PCT/JP2005/022151 patent/WO2006059703A1/ja active Application Filing
- 2005-12-02 EP EP05811579A patent/EP1829610A4/en not_active Withdrawn
- 2005-12-02 US US11/720,720 patent/US20080269425A1/en not_active Abandoned
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5547147A (en) * | 1978-08-17 | 1980-04-03 | Heyl & Co | Hydrogenated catalyst and its preparation and its hydrogenating method |
JPS61138591A (ja) * | 1984-12-12 | 1986-06-26 | Sumitomo Chem Co Ltd | 溶存酸素の除去方法 |
JPS6272639A (ja) * | 1985-09-24 | 1987-04-03 | ゾルファイ インテロックス ゲゼルシャフト ミット ベシュレンクテル ハフツング | アルキル−5,6,7,8−テトラヒドロアントラヒドロキノンの製造法 |
JPS6470596A (en) * | 1987-08-19 | 1989-03-16 | Heyl Chem Pharm | Use of soluble porous hydrogenating catalyst in position selective hydrogenation of oils and fats |
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JPWO2006059703A1 (ja) | 2008-06-05 |
US20080269425A1 (en) | 2008-10-30 |
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