FI60215C - Vid framstaellningen av en optiskt aktiv katalysator anvaendbar optiskt aktiv 1,2-bis(o-anisylfosfino)etan - Google Patents
Vid framstaellningen av en optiskt aktiv katalysator anvaendbar optiskt aktiv 1,2-bis(o-anisylfosfino)etan Download PDFInfo
- Publication number
- FI60215C FI60215C FI3487/74A FI348774A FI60215C FI 60215 C FI60215 C FI 60215C FI 3487/74 A FI3487/74 A FI 3487/74A FI 348774 A FI348774 A FI 348774A FI 60215 C FI60215 C FI 60215C
- Authority
- FI
- Finland
- Prior art keywords
- bis
- optiskt
- aktiv
- ethane
- catalyst
- Prior art date
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- 239000003054 catalyst Substances 0.000 title description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 230000003287 optical effect Effects 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- RIMMHDSDDRRHDT-UHFFFAOYSA-N (2-methoxyphenyl)methyl-[2-[(2-methoxyphenyl)methylphosphanyl]ethyl]phosphane Chemical compound COC1=CC=CC=C1CPCCPCC1=CC=CC=C1OC RIMMHDSDDRRHDT-UHFFFAOYSA-N 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000010948 rhodium Substances 0.000 description 9
- QFVPRARVHGWMOB-UHFFFAOYSA-N 1-methoxy-2-[[2-[(2-methoxyphenyl)methyl-phenylphosphoryl]ethyl-phenylphosphoryl]methyl]benzene Chemical compound COC1=CC=CC=C1CP(=O)(C=1C=CC=CC=1)CCP(=O)(C=1C=CC=CC=1)CC1=CC=CC=C1OC QFVPRARVHGWMOB-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 229910052703 rhodium Inorganic materials 0.000 description 7
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 7
- GKZIPAQOHJQRTP-UHFFFAOYSA-N (2-methoxyphenyl)methyl-[2-[(2-methoxyphenyl)methyl-phenylphosphanyl]ethyl]-phenylphosphane Chemical compound COC1=CC=CC=C1CP(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)CC1=CC=CC=C1OC GKZIPAQOHJQRTP-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- -1 sodium tetrafluoroborate Chemical compound 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical group CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QRBWWOWIHDNJFU-UHFFFAOYSA-N COC1=CC=CC=C1CCP(=O)C1=CC=CC=C1 Chemical compound COC1=CC=CC=C1CCP(=O)C1=CC=CC=C1 QRBWWOWIHDNJFU-UHFFFAOYSA-N 0.000 description 3
- CBQJSKKFNMDLON-JTQLQIEISA-M N-acetyl-L-phenylalaninate Chemical compound CC(=O)N[C@H](C([O-])=O)CC1=CC=CC=C1 CBQJSKKFNMDLON-JTQLQIEISA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- 239000005052 trichlorosilane Substances 0.000 description 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-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
- OVIINTUWRZTCLC-UHFFFAOYSA-N 1-[[cyclohexyl-[2-[cyclohexyl-[(2-methoxyphenyl)methyl]phosphoryl]ethyl]phosphoryl]methyl]-2-methoxybenzene Chemical compound COC1=CC=CC=C1CP(=O)(C1CCCCC1)CCP(=O)(C1CCCCC1)CC1=CC=CC=C1OC OVIINTUWRZTCLC-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- XODAOBAZOQSFDS-UHFFFAOYSA-N 2-acetamido-3-phenylprop-2-enoic acid Chemical compound CC(=O)NC(C(O)=O)=CC1=CC=CC=C1 XODAOBAZOQSFDS-UHFFFAOYSA-N 0.000 description 1
- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 description 1
- QQBDEJVYLGPZKS-UHFFFAOYSA-N 3-acetamido-3-phenylprop-2-enoic acid Chemical compound CC(=O)NC(=CC(O)=O)C1=CC=CC=C1 QQBDEJVYLGPZKS-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ADMWVBXCJSMQLF-UHFFFAOYSA-N C(C)O.[Si] Chemical compound C(C)O.[Si] ADMWVBXCJSMQLF-UHFFFAOYSA-N 0.000 description 1
- VSFLHLFFNNDRLJ-UHFFFAOYSA-N COC1=CC=CC=C1CCCP(=O)CCP(=O)CCCC1=CC=CC=C1OC Chemical compound COC1=CC=CC=C1CCCP(=O)CCP(=O)CCCC1=CC=CC=C1OC VSFLHLFFNNDRLJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 229960003767 alanine Drugs 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 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 1
- PJXFVEDMOFFYNO-UHFFFAOYSA-N cyclohexyl-[2-[cyclohexyl-[(2-methoxyphenyl)methyl]phosphanyl]ethyl]-[(2-methoxyphenyl)methyl]phosphane Chemical compound COC1=CC=CC=C1CP(C1CCCCC1)CCP(C1CCCCC1)CC1=CC=CC=C1OC PJXFVEDMOFFYNO-UHFFFAOYSA-N 0.000 description 1
- PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MHRHSILWNGSOBL-UHFFFAOYSA-N ethyl-[(2-methoxyphenyl)methyl]-phenylphosphane Chemical compound C=1C=CC=CC=1P(CC)CC1=CC=CC=C1OC MHRHSILWNGSOBL-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
-
- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
-
- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
- B01J31/2414—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
- C07F15/008—Rhodium compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5027—Polyphosphines
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/827—Iridium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI802271A FI63216C (fi) | 1973-12-03 | 1980-07-17 | Foerfarande foer framstaellning av optiskt aktiva beta-substituerade alfa-acylamidosyror samt den i foerfarandet anvaenda katalysatorn |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US42146373A | 1973-12-03 | 1973-12-03 | |
US42146373 | 1973-12-03 | ||
US51498774 | 1974-10-15 | ||
US05/514,987 US4008281A (en) | 1973-12-03 | 1974-10-15 | Asymmetric catalysis |
Publications (3)
Publication Number | Publication Date |
---|---|
FI348774A FI348774A (no) | 1975-06-04 |
FI60215B FI60215B (fi) | 1981-08-31 |
FI60215C true FI60215C (fi) | 1981-12-10 |
Family
ID=27025254
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI3487/74A FI60215C (fi) | 1973-12-03 | 1974-12-02 | Vid framstaellningen av en optiskt aktiv katalysator anvaendbar optiskt aktiv 1,2-bis(o-anisylfosfino)etan |
FI802271A FI63216C (fi) | 1973-12-03 | 1980-07-17 | Foerfarande foer framstaellning av optiskt aktiva beta-substituerade alfa-acylamidosyror samt den i foerfarandet anvaenda katalysatorn |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI802271A FI63216C (fi) | 1973-12-03 | 1980-07-17 | Foerfarande foer framstaellning av optiskt aktiva beta-substituerade alfa-acylamidosyror samt den i foerfarandet anvaenda katalysatorn |
Country Status (23)
Country | Link |
---|---|
US (2) | US4008281A (no) |
JP (1) | JPS5410352B2 (no) |
BE (1) | BE822848A (no) |
BR (1) | BR7410074A (no) |
CA (1) | CA1051912A (no) |
CH (1) | CH601142A5 (no) |
DE (2) | DE2463010C2 (no) |
DK (3) | DK139873B (no) |
FI (2) | FI60215C (no) |
FR (1) | FR2253026B1 (no) |
GB (1) | GB1466803A (no) |
HU (1) | HU172991B (no) |
IL (1) | IL46108A (no) |
IN (2) | IN145550B (no) |
IT (1) | IT1026717B (no) |
MX (3) | MX148257A (no) |
NL (1) | NL166692C (no) |
NO (2) | NO744324L (no) |
PL (1) | PL107722B1 (no) |
RO (1) | RO72485A (no) |
SE (2) | SE421316B (no) |
SU (1) | SU663273A3 (no) |
YU (1) | YU318874A (no) |
Families Citing this family (47)
Publication number | Priority date | Publication date | Assignee | Title |
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US4124533A (en) * | 1971-03-08 | 1978-11-07 | Monsanto Company | Metal coordination complexes containing optically active phosphine or arsine ligands |
HU177239B (hu) * | 1974-10-15 | 1981-08-28 | Monsanto Co | Eljárás N-acetamido-L-alanin-származékok előállítására α-acetamido-akrilsav-származékok aszimmetrikus katalitikus hídrogénezésével |
US4515731A (en) * | 1975-08-25 | 1985-05-07 | Monsanto Company | Asymmetric catalysis |
US4115417A (en) * | 1975-10-16 | 1978-09-19 | Hoffmann-La Roche Inc. | Asymmetric hydrogenation catalyzed by rhodium complexes of chiral tertiary phosphines |
US4166824A (en) * | 1977-06-14 | 1979-09-04 | American Cyanamid Company | Chiral rhodium-diphosphine catalyst capable of catalytic reduction of a tetramisole precursor to give a significant excess of the desired S-(-)isomer, levamisole |
US4120870A (en) * | 1977-07-18 | 1978-10-17 | Hoffmann-La Roche Inc. | Metal phosphine complex |
IT1087963B (it) * | 1977-10-17 | 1985-06-04 | Snam Progetti | Idrogenazione asimmetrica di olefine prochirali mediante complessi di metalli di transazione immobilizzati in minerali argillosi. |
ZA793744B (en) * | 1978-07-24 | 1981-02-25 | Merck & Co Inc | Z-2-acylamino-3-monsosubstituted propenoates |
US5147868A (en) * | 1978-07-24 | 1992-09-15 | Merck & Co., Inc. | Thienamycin renal peptidase inhibitors |
US4880793A (en) * | 1978-07-24 | 1989-11-14 | Merck & Co., Inc. | Combination of thienamycin-type antibiotics with dipeptidase inhibitors |
US4616038A (en) * | 1978-07-24 | 1986-10-07 | Merck & Co., Inc. | Combination of thienamycin-type antibiotics with dipeptidase inhibitors |
US4302401A (en) * | 1980-01-23 | 1981-11-24 | Exxon Research & Engineering Co. | Tetraalkyl phosphonium substituted phosphine and amine transition metal complexes |
DE3034353A1 (de) * | 1979-02-12 | 1981-03-26 | Exxon Research Engineering Co | Tetraalkyl phosphonium substituted transition metal complexes |
US4204997A (en) * | 1979-03-19 | 1980-05-27 | Monsanto Company | Asymmetric amination of 1,3-dienes |
US4539208A (en) * | 1980-09-17 | 1985-09-03 | Merck & Co., Inc. | Combination of thienamycin-type antibiotics with dipeptidase inhibitors |
DE3000445C2 (de) * | 1980-01-08 | 1982-12-02 | Degussa Ag, 6000 Frankfurt | Rhodiumkomplexe und deren Verwendung |
US4473505A (en) * | 1980-02-12 | 1984-09-25 | Exxon Research And Engineering Co. | Phosphine and phosphonium compounds and catalysts |
US4331818A (en) * | 1980-03-19 | 1982-05-25 | The Procter & Gamble Company | Chiral phospine ligand |
DE3018388A1 (de) * | 1980-05-14 | 1981-11-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von optisch aktiven verbindungen und deren verwendung zur herstellung von vitamin e |
DE3039053C2 (de) * | 1980-10-16 | 1984-05-24 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Dipeptiden |
US4376870A (en) * | 1980-12-05 | 1983-03-15 | Monsanto Company | Optically active phosphine compounds |
US4343741A (en) * | 1981-04-22 | 1982-08-10 | Hoffmann-La Roche Inc. | Chiral phosphines |
US4393240A (en) * | 1981-07-06 | 1983-07-12 | Stille John K | Optically active phosphines |
US4359596A (en) * | 1981-08-03 | 1982-11-16 | Exxon Research And Engineering Co. | Liquid salt extraction of aromatics from process feed streams |
US4440634A (en) * | 1981-08-03 | 1984-04-03 | Exxon Research And Engineering Co. | Organic salt compositions in extraction processes |
US4422975A (en) * | 1981-08-03 | 1983-12-27 | Exxon Research And Engineering Co. | Organic salt compositions in extraction processes |
JPS5849179A (ja) * | 1981-09-17 | 1983-03-23 | ブラザー工業株式会社 | 2本針ミシンの制御装置 |
JPS6061587A (ja) * | 1983-09-16 | 1985-04-09 | Takasago Corp | ロジウム−ホスフイン錯体 |
US4766226A (en) * | 1984-02-01 | 1988-08-23 | Smithkline Beckman Corporation | Antitumor pharmaceutical compositions and methods for treating tumors employing α,ω-bis(disubstitutedphosphino)hydrocarbon derivatives or [α, ω-bis(disubstitutedphosphino)hydrocarbon] di |
US4857549A (en) * | 1984-02-01 | 1989-08-15 | Smithkline Beckman Corporation | Antitumor compounds |
JPS6163690A (ja) * | 1984-09-04 | 1986-04-01 | Takasago Corp | ルテニウム−ホスフイン錯体 |
US5011995A (en) * | 1987-07-28 | 1991-04-30 | Ciba-Geigy Corporation | Process for the preparation of optically active secondary amines |
US4912221A (en) * | 1988-10-27 | 1990-03-27 | Occidental Chemical Corporation | Chiral 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and precursors and preparation thereof |
JPH0623150B2 (ja) * | 1988-11-15 | 1994-03-30 | 高砂香料工業株式会社 | 光学活性3−ヒドロキシブタン酸類の製造方法 |
US5202474A (en) * | 1989-06-22 | 1993-04-13 | Monsanto Company | Asymmetric catalytic hydrogenation of α-arylpropenoic acids |
US5198561A (en) * | 1989-06-22 | 1993-03-30 | Monsanto Company | Ruthenium-BINAP asymmetric hydrogenation catalyst |
US5233084A (en) * | 1989-06-22 | 1993-08-03 | Monsanto Company | Method for preparing α-arylpropionic acids |
EP0512415B1 (de) * | 1991-05-03 | 1997-08-06 | Hoechst Aktiengesellschaft | Verfahren zur enantioselektiven Synthese von 2(R)-Benzylbernsteinsäuremonoamid-Derivaten |
US5744655A (en) * | 1996-06-19 | 1998-04-28 | The Dow Chemical Company | Process to make 2,3-dihalopropanols |
JP2972887B1 (ja) * | 1998-10-29 | 1999-11-08 | 千葉大学長 | 光学活性ビスホスフィノメタン並びにそれらのロジウム又は銅錯体を用いる不斉合成 |
GB9823716D0 (en) | 1998-10-29 | 1998-12-23 | Isis Innovation | Diphosphines |
US6350922B1 (en) | 1998-12-18 | 2002-02-26 | The Dow Chemical Company | Process for making 2,3-dihalopropanols |
GB0004297D0 (en) | 2000-02-23 | 2000-04-12 | Ucb Sa | 2-oxo-1 pyrrolidine derivatives process for preparing them and their uses |
FR2887253A1 (fr) * | 2005-06-20 | 2006-12-22 | Phosphoenix Sarl | Nouvelles arylphosphines p chirales ortho-fonctionnalisees et derives: leur preparation et utilisation en catalyse asymetrique |
GB0707379D0 (en) * | 2007-03-28 | 2007-05-23 | Celtic Catalysts Ltd | Chiral phosphorus compounds |
US20210291156A1 (en) * | 2018-06-08 | 2021-09-23 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Catalyst compositions for hydroformylation and methods of use thereof |
CN110396072B (zh) * | 2019-09-02 | 2022-09-13 | 上海欣海健伟实业有限公司 | (s)-3-羟基四氢呋喃的制备方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL134180C (no) * | 1961-03-29 | 1900-01-01 | ||
US3145227A (en) * | 1961-06-14 | 1964-08-18 | American Cyanamid Co | Organic phosphine oxides and methods of preparing same |
US3849480A (en) * | 1968-09-09 | 1974-11-19 | Monsanto Co | Catalytic asymmetric hydrogenation |
US3657298A (en) * | 1970-01-06 | 1972-04-18 | Pressure Chemical Co | Arsenic and phosphorus containing polydentates |
NL155004B (nl) | 1970-05-11 | 1977-11-15 | Monsanto Co | Werkwijze voor het asymmetrisch hydrogeneren van een eventieel beta-gesubstitueerd alfa-acylaminoacrylzuur en/of een zout daarvan, alsmede werkwijze voor de bereiding van een katalysatoroplossing. |
FR2116905A5 (fr) * | 1970-12-10 | 1972-07-21 | Inst Francais Du Petrole | Nouveaux coordinats bidentes,leur fabrication et leurs applications |
US4124533A (en) * | 1971-03-08 | 1978-11-07 | Monsanto Company | Metal coordination complexes containing optically active phosphine or arsine ligands |
US3780112A (en) * | 1972-08-09 | 1973-12-18 | Union Carbide Corp | Substituted ethylene bis(phosphine oxides) |
FR2230654B1 (no) * | 1973-05-21 | 1975-11-21 | Rhone Poulenc Ind |
-
1974
- 1974-10-15 US US05/514,987 patent/US4008281A/en not_active Expired - Lifetime
- 1974-11-22 IL IL7446108A patent/IL46108A/xx unknown
- 1974-11-29 NL NL7415583.A patent/NL166692C/xx not_active IP Right Cessation
- 1974-12-02 DE DE2463010A patent/DE2463010C2/de not_active Expired
- 1974-12-02 MX MX170590A patent/MX148257A/es unknown
- 1974-12-02 JP JP13708774A patent/JPS5410352B2/ja not_active Expired
- 1974-12-02 FR FR7439420A patent/FR2253026B1/fr not_active Expired
- 1974-12-02 RO RO7480666A patent/RO72485A/ro unknown
- 1974-12-02 BR BR10074/74A patent/BR7410074A/pt unknown
- 1974-12-02 IT IT3008774A patent/IT1026717B/it active
- 1974-12-02 BE BE151066A patent/BE822848A/xx not_active IP Right Cessation
- 1974-12-02 CH CH1593974A patent/CH601142A5/xx not_active IP Right Cessation
- 1974-12-02 CA CA215,181A patent/CA1051912A/en not_active Expired
- 1974-12-02 HU HU74MO00000927A patent/HU172991B/hu unknown
- 1974-12-02 NO NO744324A patent/NO744324L/no unknown
- 1974-12-02 DE DE2456937A patent/DE2456937C3/de not_active Expired
- 1974-12-02 SE SE7415029A patent/SE421316B/xx unknown
- 1974-12-02 YU YU03188/74A patent/YU318874A/xx unknown
- 1974-12-02 MX MX742888U patent/MX5144E/es unknown
- 1974-12-02 DK DK625274AA patent/DK139873B/da not_active IP Right Cessation
- 1974-12-02 PL PL1974176129A patent/PL107722B1/pl unknown
- 1974-12-02 FI FI3487/74A patent/FI60215C/fi active
- 1974-12-02 GB GB5201774A patent/GB1466803A/en not_active Expired
- 1974-12-02 MX MX170589A patent/MX149399A/es unknown
-
1975
- 1975-08-21 SU SU752163234A patent/SU663273A3/ru active
-
1976
- 1976-06-03 DK DK245376A patent/DK245376A/da not_active Application Discontinuation
- 1976-06-03 DK DK245476A patent/DK245476A/da not_active Application Discontinuation
-
1977
- 1977-06-27 IN IN958/CAL/77A patent/IN145550B/en unknown
- 1977-06-27 IN IN957/CAL/77A patent/IN145549B/en unknown
-
1978
- 1978-07-31 US US05/929,635 patent/US4220590A/en not_active Expired - Lifetime
-
1980
- 1980-07-03 NO NO802008A patent/NO802008L/no unknown
- 1980-07-17 FI FI802271A patent/FI63216C/fi not_active IP Right Cessation
-
1981
- 1981-08-21 SE SE8104949A patent/SE8104949L/sv not_active Application Discontinuation
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