JP4101803B2 - リン原子に結合したsp2混成炭素原子を含む架橋基を有する二座ジホスフィン組成物を用いてエチレン性不飽和化合物をヒドロホルミル化する方法 - Google Patents
リン原子に結合したsp2混成炭素原子を含む架橋基を有する二座ジホスフィン組成物を用いてエチレン性不飽和化合物をヒドロホルミル化する方法 Download PDFInfo
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- JP4101803B2 JP4101803B2 JP2004539074A JP2004539074A JP4101803B2 JP 4101803 B2 JP4101803 B2 JP 4101803B2 JP 2004539074 A JP2004539074 A JP 2004539074A JP 2004539074 A JP2004539074 A JP 2004539074A JP 4101803 B2 JP4101803 B2 JP 4101803B2
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- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 74
- 125000004432 carbon atom Chemical group C* 0.000 title claims abstract description 52
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 125000004437 phosphorous atom Chemical group 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 36
- 150000001875 compounds Chemical class 0.000 title claims abstract description 31
- 229910052799 carbon Inorganic materials 0.000 title claims abstract description 15
- 239000000203 mixture Substances 0.000 title description 13
- 125000006413 ring segment Chemical group 0.000 claims abstract description 37
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 24
- -1 halide anions Chemical class 0.000 claims abstract description 23
- 239000003446 ligand Substances 0.000 claims abstract description 22
- 229910052751 metal Inorganic materials 0.000 claims abstract description 21
- 239000002184 metal Substances 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 18
- 150000001768 cations Chemical class 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
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- 230000002378 acidificating effect Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000004820 halides Chemical group 0.000 description 4
- NFHFRUOZVGFOOS-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.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 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 238000011010 flushing procedure Methods 0.000 description 3
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- MBAHGFJTIVZLFB-UHFFFAOYSA-N methyl pent-2-enoate Chemical compound CCC=CC(=O)OC MBAHGFJTIVZLFB-UHFFFAOYSA-N 0.000 description 3
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- 239000001301 oxygen Chemical group 0.000 description 3
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- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
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- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
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- PPDFQRAASCRJAH-UHFFFAOYSA-N 2-methylthiolane 1,1-dioxide Chemical compound CC1CCCS1(=O)=O PPDFQRAASCRJAH-UHFFFAOYSA-N 0.000 description 1
- NGDNVOAEIVQRFH-UHFFFAOYSA-N 2-nonanol Chemical compound CCCCCCCC(C)O NGDNVOAEIVQRFH-UHFFFAOYSA-N 0.000 description 1
- VGKLVWTVCUDISO-UHFFFAOYSA-N 3,4-dibromothiophene Chemical compound BrC1=CSC=C1Br VGKLVWTVCUDISO-UHFFFAOYSA-N 0.000 description 1
- BZKWXJNGYJCFRO-UHFFFAOYSA-N 3-(hydroxymethyl)-2-methylpentanoic acid Chemical compound CCC(CO)C(C)C(O)=O BZKWXJNGYJCFRO-UHFFFAOYSA-N 0.000 description 1
- GYSCXPVAKHVAAY-UHFFFAOYSA-N 3-Nonanol Chemical compound CCCCCCC(O)CC GYSCXPVAKHVAAY-UHFFFAOYSA-N 0.000 description 1
- RRZPCBLAZBRYCL-UHFFFAOYSA-N 4-ethyl-2-methylthiolane 1,1-dioxide Chemical compound CCC1CC(C)S(=O)(=O)C1 RRZPCBLAZBRYCL-UHFFFAOYSA-N 0.000 description 1
- ACQSGULVVCVHTP-UHFFFAOYSA-N 5-[2-(9-phosphabicyclo[3.3.1]nonan-5-yl)phenyl]-9-phosphabicyclo[3.3.1]nonane Chemical compound C1CCC(P2)CCCC12C1=CC=CC=C1C1(P2)CCCC2CCC1 ACQSGULVVCVHTP-UHFFFAOYSA-N 0.000 description 1
- YGACOUREDJBMCB-UHFFFAOYSA-N 5-butyl-9-phosphabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1(CCCC)P2 YGACOUREDJBMCB-UHFFFAOYSA-N 0.000 description 1
- AUBHPOIVWXGTQX-UHFFFAOYSA-N 5-ethyl-9-phosphabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1(CC)P2 AUBHPOIVWXGTQX-UHFFFAOYSA-N 0.000 description 1
- UVTCMBXPJIUSFK-UHFFFAOYSA-N 5-hydroxy-2,4-dimethylpentanoic acid Chemical compound OCC(C)CC(C)C(O)=O UVTCMBXPJIUSFK-UHFFFAOYSA-N 0.000 description 1
- WZNXBMDGFRTUOZ-UHFFFAOYSA-N 6-hydroxy-2-methylhexanoic acid Chemical compound OC(=O)C(C)CCCCO WZNXBMDGFRTUOZ-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- PNAJBOZYCFSQDJ-UHFFFAOYSA-N 7-hydroxyheptanoic acid Chemical compound OCCCCCCC(O)=O PNAJBOZYCFSQDJ-UHFFFAOYSA-N 0.000 description 1
- HRSBWHHVKVUGCM-UHFFFAOYSA-N C12(CCCC(CCC1)P2)C2=C(C=C(C(=C2)F)F)C21CCCC(CCC2)P1 Chemical compound C12(CCCC(CCC1)P2)C2=C(C=C(C(=C2)F)F)C21CCCC(CCC2)P1 HRSBWHHVKVUGCM-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- WDTSWRQKFJCUPR-UHFFFAOYSA-N butane;2-cyclononylphosphonane Chemical compound CCCC.C1CCCCCCCC1C1PCCCCCCC1 WDTSWRQKFJCUPR-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 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
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- BTZNPZMHENLISZ-UHFFFAOYSA-N fluoromethanesulfonic acid Chemical compound OS(=O)(=O)CF BTZNPZMHENLISZ-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- KBAHHKPJCXUMAP-UHFFFAOYSA-N hept-1-ene oct-1-ene Chemical compound CCCCCC=C.CCCCCCC=C KBAHHKPJCXUMAP-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- CETWDUZRCINIHU-UHFFFAOYSA-N methyl-n-amyl-carbinol Natural products CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 1
- QXLPXWSKPNOQLE-UHFFFAOYSA-N methylpentynol Chemical compound CCC(C)(O)C#C QXLPXWSKPNOQLE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- NZLCAHVLJPDRBL-UHFFFAOYSA-N octa-2,4-diene Chemical compound CCCC=CC=CC NZLCAHVLJPDRBL-UHFFFAOYSA-N 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- VYGSFTVYZHNGBU-UHFFFAOYSA-N trichloromethanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)(Cl)Cl VYGSFTVYZHNGBU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- 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
- B01J31/2419—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
- B01J31/2428—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom
- B01J31/2433—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
-
- 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
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2461—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring
- B01J31/2471—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring with more than one complexing phosphine-P atom
- B01J31/2476—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
-
- 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
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2461—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring
- B01J31/248—Bridged ring systems, e.g. 9-phosphabicyclononane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
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- 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
- B01J2531/824—Palladium
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
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Description
(a)VIII族金属カチオン源と、
(b)ジホスフィン配位子と、
(c)アニオン源と
を含む触媒系の存在下で、エチレン性不飽和化合物を一酸化炭素および水素と反応させることによってヒドロホルミル化する方法に関する。
(a)VIII族金属カチオン源と、
(b)一般式I
X1−R−X2(I)
を有するジホスフィン配位子(式中、X1およびX2はそれぞれ独立に置換されていてもよい少なくとも5つの環原子を有する環状基を表し、環原子の1つはリン原子であり、Rは、sp2混成炭素原子によって各リン原子に結合した、置換されていてもよい二価の架橋基を表す)と、
(c)18℃の水溶液中で測定してpKa<3の酸、またはそれから誘導された塩と、
(d)ハロゲン化物アニオン源と
を含む触媒系の存在下で、置換されていてもよいエチレン性不飽和化合物を一酸化炭素および水素と反応させることによってヒドロホルミル化する方法を提供する。
1,2−P,P’ビス(9−ホスファビシクロノニル)ベンゼン、
1,2−P,P’ビス(9−ホスファビシクロノニル)4−メチルベンゼン、
3,4−P,P’ビス(9−ホスファビシクロノニル)チオフェン、
1,2−P,P’ビス(9−ホスファビシクロノニル)シクロペンテン、
1,2−P,P’ビス(9−ホスファビシクロノニル)シクロヘキセン
の全ての異性体構造が含まれる。
X1−R2−X2(II)(式中、X1およびX2はそれぞれ独立に置換されていてもよい少なくとも5つの環原子を有する環状基を表し、その1つはリン原子であり、R2は、各リン原子にsp2混成炭素原子によって結合した置換されていてもよい二価の架橋基を表す。)を有するジホスフィン配位子も提供する。
一般式III、
X1−R3−X2(III)(式中、X1およびX2はそれぞれ独立に置換されていてもよい少なくとも5つの環原子を有する環状基を表し、その1つはリン原子であり、R3は、各リン原子にsp2混成炭素原子によって結合した二価のシクロアルケン基を表す。)を有するジホスフィン配位子も提供する。
一般式IV、
X1−R4−X2(IV)(式中、X1およびX2はそれぞれ独立に置換されていてもよい少なくとも5つの環原子を有する環状基を表し、その1つはリン原子であり、R4は二価の芳香族基を表し、芳香族環は環原子として1個または複数のヘテロ原子を含み、その芳香族基は各リン原子にsp2混成炭素原子によって結合している。)を有するジホスフィン配位子も提供する。
(a)VIII族金属カチオン源と、
(b)上述のジホスフィン配位子と
を含む触媒をさらに提供する。
白金またはパラジウムと炭素原子12までのカルボン酸との塩、パラジウム−または白金の、例えば、一酸化炭素またはアセチルアセトナートとの錯体、またはイオン交換樹脂などの固体材料と結合したパラジウムまたは白金などの白金またはパラジウム化合物である。パラジウム(II)アセタートおよび白金(II)アセチルアセトナートは好ましい金属源の例である。
(1,2−PP’ビス(9−ホスファビシクロ[3.3.1]ノニル)ベンゼンの調製)
窒素雰囲気下の300mlのシュレンク容器に、9.44g(40ミリモル)の1,2−ジブロモベンゼン、22.4g(200ミリモル)の1,4−ジアザビシクロ[2,2,2]オクタン、13g(91ミリモル)の9−ホスファビシクロ[3.3.1]ノナン、2.32g(2ミリモル)のテトラキス(トリフェニルホスフィン)パラジウム(0)、および150mlのキシレン(溶媒)を装填する。混合物を140℃で一夜攪拌し、その間に臭酸1,4−ジアザビシクロ[2,2,2]オクタンの沈殿物が形成される。混合物を100℃に冷却したのち、熱濾過する。キシレン溶液を冷却した後、1,2−ビス−([3.3.1]−9−ホスファビシクロノナン)ベンゼンの結晶が形成される。液体をデカンテーションし、生成物を100mlの熱トルエンから再結晶化する。
(1,2−PP’ビス(9−ホスファビシクロ[3.3.1]ノニル)シクロペンテンの調製)
窒素雰囲気下の200mlのシュレンク容器に、5.0g(22ミリモル)の1,2−ジブロモシクロペンテン、9.0g(80ミリモル)の1,4−ジアザビシクロ[2,2,2]オクタン、8.0g(56ミリモル)の9−ホスファビシクロ[3.3.1]ノナン、1.16g(1ミリモル)のテトラキス(トリフェニルホスフィン)パラジウム(0)、および60mlのキシレンを装填する。混合物を140℃で一夜攪拌し、その間に臭酸1,4−ジアザビシクロ[2,2,2]オクタンの沈殿物が形成される。混合物を100℃に冷却したのち、熱濾過する。キシレン溶液を冷却した後、1,2−PP’ビス(9−ホスファビシクロ[3.3.1]ノニル)−シクロペンテンベンゼンの沈殿物が形成される。さらに−35℃まで冷却した後、液体をデカンテーションし、残渣を熱メタノールで攪拌することによって精製する。1,2−PP‘ビス(9−ホスファビシクロ[3.3.1]ノニル)−シクロペンテンが4.3g(12.4ミリモル、56%)の収率で得られ、31pおよび1H NMRによれば純粋である。31P NMR(CD2Cl2):−25.9ppm、1H NMR(CD2Cl2):2.60ppm(m、4H)、2.26ppm(m、4H)、1.4〜2.1ppm(m、24H)。
(3,4−PP’ビス(9−ホスファビシクロ[3.3.1]ノニル)チオフェンの調製)
3,4−PP’ビス(9−ホスファビシクロ[3.3.1]ノニル)チオフェンは、1,2−PP’ビス(9−ホスファビシクロ[3.3.1]ノニル)シクロペンテンを1,2−ジブロモペンテンから調製するのと同じようにして、3,4−ジブロモチオフェンから調製する。3,4−PP’ビス(9−ホスファビシクロ[3.3.1]ノニル)チオフェンは、40%の収率で得られ、31p NMR(CD2Cl2):−24.4ppm、1H NMR(CD2Cl2):7.08ppm(s、2H)、2.46ppm(s、4H)、1.4〜2.2ppm(m、24H)によって純粋である。
BPBE=1,2−PP’ビス(9−ホスファビシクロ[3.3.1]ノニル)ベンゼン
BPCP=1,2−PP’ビス(9−ホスファビシクロ[3.3.1]ノニル)シクロペンテン
BPTH=3,4−PP’ビス(9−ホスファビシクロ[3.3.1]ノニル)チオフェン
BPET=1,2−PP’ビス(9−ホスファビシクロ[3.3.1]ノニル)エタン
BPPT=1−P(9−ホスファビシクロ[3.3.1]ノニル),2−P(9−ホスファビシクロ[3.3.1]ノニル−メチル)ベンゼン
BPFB=1,2−PP’ビス(9−ホスファビシクロ[3.3.1]ノニル)4,5−ジフルオロ−ベンゼン
BPBU=2,3−PP’ビス(9−ホスファビシクロ[3.3.1]ノニル)ブタン
BPCH=1,2−PP’ビス(9−ホスファビシクロ[3.3.1]ノニル)シクロヘキサン
MSA=メタンスルホン酸
FSA=トリフルオロメタンスルホン酸
実施例4〜8および比較実施例A〜Dは、350mlの磁石で攪拌したオートクレーブ中で行った。オートクレーブに、表Iに示した基質、30mlのエチルヘキサノール、10mlのスルホラン、および0.5mlの水、0.25ミリモル(56mg)の酢酸パラジウムII、表Iに示した量の二座ジホスフィン、および表Iに示した量の酸を装填した。窒素でフラッシュした後、オートクレーブを分圧20バールの一酸化炭素と分圧40バールの水素で加圧した。続いて、反応器を封止し、内容物を表Iに示した温度に加熱し、その温度で5時間保った。表Iに、カルボニル化の初期速度を示す(反応速度で)。カルボニル化の初期速度は、最初の30%の基質変換に対する一酸化炭素の平均消費量で定義される。冷却の後、サンプルを反応器の内容物から取り出し、ガス液体クロマトグラフィーで分析した。生成物全体の重量に対するアルカノール生成物のパーセントを表Iに示す。アルカノール生成物全体の重量に対する直鎖アルカノール生成物のパーセントも表Iに示す。残部は、主としてアルデヒド、ケトン、およびアセタールを含み、これらはアルカノールの中間生成物である。さらに、いくらかの水素化副生成物が得られた。水素化副生成物の量を表Iに示す。表Iの実験は、本発明による触媒が、いくつかの従来技術の触媒よりもヒドロホルミル化生成物を得るうえでより活性が高いことを示している。
実施例10および比較実施例Eは350mlの磁石で攪拌したオートクレーブ中で行った。オートクレーブに、30mlの内部C11とC12オレフィンの混合物(基質として)、30mlのエチルヘキサノール、10mlのスルホラン、0.5mlの水、0.25ミリモル(56mg)の酢酸パラジウムII、表Iに示した量の二座ジホスフィン、0.2ミリモルのHCl、および表IIに示した量のスルホン酸を装填した。
実施例11〜14、比較実施例FおよびGは、350mlの磁石で攪拌したオートクレーブ中で行った。オートクレーブに、15mlのメチルペンテノアート、0.25ミリモル(56mg)の酢酸パラジウムII、10mlのスルホラン、表IIIに示した量のメタノール、表IIIに示した量の二座ジホスフィン、表IIIに示した量の塩酸(HCl)、表IIIに示した量のスルホン酸を装填した。窒素でフラッシュした後、オートクレーブを分圧20バールの一酸化炭素と分圧40バールの水素で加圧した。続いて、反応器を封止し、内容物を表IIIに示した温度に加熱し、その温度で5時間保った。冷却の後、サンプルを反応器の内容物から取り出し、ガス液体クロマトグラフィーで分析した。ヒドロホルミル化生成物に向けての反応速度を表IIIに示す。この反応速度は、形成したヒドロホルミル化生成物のガス液ガスクロマトグラフで求めたモルをパラジウムのモルおよび100%変換に必要な時間で除して計算される。
Claims (24)
- (a)VIII族金属カチオン源と、
(b)一般式I
X1−R−X2(I)
を有するジホスフィン配位子(式中、X1およびX2はそれぞれ独立に少なくとも5つの環原子を有する置換されていてもよい環状基を表し、環原子の1つはリン原子であり、Rは、sp2混成炭素原子によって各リン原子に結合した、置換されていてもよい二価のシクロアルケン架橋基である)と、
(c)18℃の水溶液中で測定してpKa<3の酸、またはそれから誘導された塩と、
(d)ハロゲン化物アニオン源とを含む触媒系の存在下で、置換されていてもよいエチレン性不飽和化合物を一酸化炭素および水素と反応させることによってヒドロホルミル化する方法。 - 前記リン原子に結合したシクロアルケン架橋基の炭素原子が不飽和結合を介して他の原子に結合している請求項1に記載の方法。
- X1および/またはX2が、少なくとも6個の環原子を有する置換されていてもよいホスファ−ビシクロアルキル基を表す請求項1または2に記載の方法。
- 前記ジホスフィン配位子(b)が、
1,2−P,P’ビス(9−ホスファビシクロノニル)シクロペンテン、および
1,2−P,P’ビス(9−ホスファビシクロノニル)シクロヘキセンから選択される請求項1から3のいずれか一項に記載の方法。 - 前記VIII族金属カチオン源がPdカチオン源である請求項1から4のいずれか一項に記載の方法。
- 前記エチレン性不飽和化合物が、少なくとも4個の炭素原子を含むアルケンである請求項1から5のいずれか一項に記載の方法。
- 一般式III
X1−R3−X2(III)
(式中、X1およびX2はそれぞれ独立に置換されていてもよい少なくとも5つの環原子を有する環状基を表し、環原子の1つはリン原子であり、R3は、sp2混成炭素原子によって各リン原子に結合した二価のシクロアルケン基を表す。)を有するジホスフィン配位子。 - (a)VIII族金属カチオン源と、
(b)請求項7に記載のジホスフィン配位子とを含む触媒系。 - (a)VIII族金属カチオン源と、
(b)一般式I
X1−R−X2(I)
を有するジホスフィン配位子(式中、X1およびX2はそれぞれ独立に少なくとも5つの環原子を有する置換されていてもよい環状基を表し、環原子の1つはリン原子であり、Rは、sp2混成炭素原子によって各リン原子に結合した、1個または複数のヘテロ原子を環原子として含む、置換されていてもよい二価の芳香族架橋基である)と、
(c)18℃の水溶液中で測定してpKa<3の酸、またはそれから誘導された塩と、
(d)ハロゲン化物アニオン源とを含む触媒系の存在下で、置換されていてもよいエチレン性不飽和化合物を一酸化炭素および水素と反応させることによってヒドロホルミル化する方法。 - 前記リン原子に結合した芳香族架橋基の炭素原子が不飽和結合を介して他の原子に結合している請求項9に記載の方法。
- 両方のリン原子が前記芳香族架橋基の隣接する位置で結合している請求項9または10に記載の方法。
- X1および/またはX2が、少なくとも6個の環原子を有する置換されていてもよいホスファ−ビシクロアルキル基を表す請求項9から11のいずれか一項に記載の方法。
- 前記ジホスフィン配位子(b)が、
3,4−P,P’ビス(9−ホスファビシクロノニル)チオフェンである請求項9から12のいずれか一項に記載の方法。 - 前記VIII族金属カチオン源がPdカチオン源である請求項9から13のいずれか一項に記載の方法。
- 前記エチレン性不飽和化合物が、少なくとも4個の炭素原子を含むアルケンである請求項9から14のいずれか一項に記載の方法。
- 一般式IV
X1−R4−X2(IV)
(式中、X1およびX2はそれぞれ独立に置換されていてもよい少なくとも5つの環原子を有する環状基を表し、環原子の1つはリン原子であり、R4は二価の芳香族基を表し、芳香族環は1個または複数のヘテロ原子を環原子として含み、その芳香族基はsp2混成炭素原子によって各リン原子に結合している。)を有するジホスフィン配位子。 - (a)VIII族金属カチオン源と、
(b)請求項16に記載のジホスフィン配位子とを含む触媒系。 - (a)VIII族金属カチオン源と、
(b)一般式I
X1−R−X2(I)
を有するジホスフィン配位子(式中、X1およびX2はそれぞれ独立に少なくとも5つの環原子を有する置換されていてもよい環状基を表し、環原子の1つはリン原子であり、Rは、sp2混成炭素原子によって各リン原子に結合した、炭素原子のみを環原子として含む、置換されていてもよい二価の芳香族架橋基である)と、
(c)18℃の水溶液中で測定してpKa<3の酸、またはそれから誘導された塩と、
(d)ハロゲン化物アニオン源とを含む触媒系の存在下で、置換されていてもよいエチレン性不飽和化合物を一酸化炭素および水素と反応させることによってヒドロホルミル化する方法。 - 前記リン原子に結合した芳香族架橋基の炭素原子が不飽和結合を介して他の原子に結合している請求項18に記載の方法。
- 両方のリン原子が前記芳香族架橋基の隣接する位置で結合している請求項18または19に記載の方法。
- X1および/またはX2が、少なくとも6個の環原子を有する置換されていてもよいホスファ−ビシクロアルキル基を表す請求項18から20のいずれか一項に記載の方法。
- 前記ジホスフィン配位子(b)が、
1,2−P,P’ビス(9−ホスファビシクロノニル)ベンゼン、および
1,2−P,P’ビス(9−ホスファビシクロノニル)4−メチルベンゼンから選択される請求項18から21のいずれか一項に記載の方法。 - 前記VIII族金属カチオン源がPdカチオン源である請求項18から22のいずれか一項に記載の方法。
- 前記エチレン性不飽和化合物が、少なくとも4個の炭素原子を含むアルケンである請求項18から23のいずれか一項に記載の方法。
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JP2004517901A (ja) * | 2001-01-19 | 2004-06-17 | カイロテック・テクノロジー・リミテッド | 配位子およびその使用 |
WO2002064250A2 (en) * | 2001-01-31 | 2002-08-22 | Shell Internationale Research Maatschappij B.V. | Process for the carbonylation of ethylenically unsaturated compounds, bidentate diphosphine composition used in this process and processes for preparation of this bidentate diphosphine composition |
DE10106348A1 (de) | 2001-02-09 | 2002-08-14 | Basf Ag | Als Katalysator oder zur Herstellung eines Katalysatorsystems geeignete Verbindung |
CN1308337C (zh) * | 2001-11-09 | 2007-04-04 | 国际壳牌研究有限公司 | 用于不饱和化合物羰基化的双齿配位体 |
US6743921B2 (en) * | 2002-01-24 | 2004-06-01 | Dsm Catalytica Pharmaceuticals, Inc. | Process for the preparation of nonracemic syn-1-(4-hydroxy-phenyl)-2-(4-hydroxy-4-phenyl-piperidin-1-yl)-1-propanol compounds |
US6806391B2 (en) * | 2002-07-31 | 2004-10-19 | Shell Oil Company | Process for the carbonylation of ethylenically unsaturated compounds and bidentate diphosphine composition used in this process |
CN1684931A (zh) * | 2002-09-26 | 2005-10-19 | 国际壳牌研究有限公司 | 伯醇的制备方法 |
US7265242B2 (en) * | 2004-02-26 | 2007-09-04 | Shell Oil Company | Process for the carbonylation of ethylenically or acetylenically unsaturated compounds |
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AU2003299066A1 (en) | 2004-04-19 |
CA2500095C (en) | 2011-10-18 |
CA2500095A1 (en) | 2004-04-08 |
DE60317533T2 (de) | 2008-09-18 |
ATE378109T1 (de) | 2007-11-15 |
US20040167362A1 (en) | 2004-08-26 |
US7414155B2 (en) | 2008-08-19 |
CN100363319C (zh) | 2008-01-23 |
WO2004028689A3 (en) | 2004-07-29 |
US20070238892A1 (en) | 2007-10-11 |
ZA200502080B (en) | 2005-11-30 |
EP1542798A2 (en) | 2005-06-22 |
CN1684769A (zh) | 2005-10-19 |
WO2004028689A2 (en) | 2004-04-08 |
US7250538B2 (en) | 2007-07-31 |
DE60317533D1 (de) | 2007-12-27 |
JP2006500415A (ja) | 2006-01-05 |
AU2003299066A8 (en) | 2004-04-19 |
EP1542798B1 (en) | 2007-11-14 |
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