DE69821622T2 - Verfahren zur herstellung von phosphinverbindungen - Google Patents
Verfahren zur herstellung von phosphinverbindungen Download PDFInfo
- Publication number
- DE69821622T2 DE69821622T2 DE69821622T DE69821622T DE69821622T2 DE 69821622 T2 DE69821622 T2 DE 69821622T2 DE 69821622 T DE69821622 T DE 69821622T DE 69821622 T DE69821622 T DE 69821622T DE 69821622 T2 DE69821622 T2 DE 69821622T2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- group
- optionally substituted
- formula
- reaction
- 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.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical class P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 238000000034 method Methods 0.000 claims abstract description 13
- 229910052751 metal Inorganic materials 0.000 claims abstract description 12
- 239000002184 metal Substances 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000004437 phosphorous atom Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000000962 organic group Chemical group 0.000 claims abstract description 7
- 125000005647 linker group Chemical group 0.000 claims abstract description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
- -1 di-tert-butylphosphino Chemical group 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 11
- 239000011777 magnesium Substances 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- HGKVWUCWXIMWCZ-UHFFFAOYSA-N ditert-butyl(naphthalen-1-yl)phosphane Chemical compound C1=CC=C2C(P(C(C)(C)C)C(C)(C)C)=CC=CC2=C1 HGKVWUCWXIMWCZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 13
- 125000002947 alkylene group Chemical group 0.000 abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000003446 ligand Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- IJJURYQDEVNZCW-UHFFFAOYSA-N bromophosphane Chemical compound BrP IJJURYQDEVNZCW-UHFFFAOYSA-N 0.000 description 4
- 238000003747 Grignard reaction Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 230000006315 carbonylation Effects 0.000 description 3
- 238000005810 carbonylation reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- MCRSZLVSRGTMIH-UHFFFAOYSA-N ditert-butyl(chloro)phosphane Chemical compound CC(C)(C)P(Cl)C(C)(C)C MCRSZLVSRGTMIH-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- KGKAYWMGPDWLQZ-UHFFFAOYSA-N 1,2-bis(bromomethyl)benzene Chemical group BrCC1=CC=CC=C1CBr KGKAYWMGPDWLQZ-UHFFFAOYSA-N 0.000 description 1
- FMGGHNGKHRCJLL-UHFFFAOYSA-N 1,2-bis(chloromethyl)benzene Chemical group ClCC1=CC=CC=C1CCl FMGGHNGKHRCJLL-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FBBYITNAWIWFGV-UHFFFAOYSA-N 2-di(propan-2-yl)phosphanylethynyl-di(propan-2-yl)phosphane Chemical compound CC(C)P(C(C)C)C#CP(C(C)C)C(C)C FBBYITNAWIWFGV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 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
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- DFXVHMWBGFOKIQ-UHFFFAOYSA-N bromo(ditert-butyl)phosphane Chemical compound CC(C)(C)P(Br)C(C)(C)C DFXVHMWBGFOKIQ-UHFFFAOYSA-N 0.000 description 1
- NXXRXPHOTKKBCZ-UHFFFAOYSA-N butyl(chloro)phosphane Chemical compound CCCCPCl NXXRXPHOTKKBCZ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- JZPDBTOWHLZQFC-UHFFFAOYSA-N chloro-di(propan-2-yl)phosphane Chemical compound CC(C)P(Cl)C(C)C JZPDBTOWHLZQFC-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- SFCNPIUDAIFHRD-UHFFFAOYSA-N ditert-butyl-[[2-(ditert-butylphosphanylmethyl)phenyl]methyl]phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CC1=CC=CC=C1CP(C(C)(C)C)C(C)(C)C SFCNPIUDAIFHRD-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- B01J31/2447—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 substituents on a ring of the condensed system or on a further attached ring
- B01J31/2452—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 substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom
-
- 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
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/5063—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds
- C07F9/5068—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds from starting materials having the structure >P-Hal
-
- 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
- B01J2231/30—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
-
- 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
-
- 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
- B01J2531/824—Palladium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9717059.1A GB9717059D0 (en) | 1997-08-13 | 1997-08-13 | Method of manufacturing phosphine compound |
| GB9717059 | 1997-08-13 | ||
| US6162797P | 1997-10-09 | 1997-10-09 | |
| US61627P | 1997-10-09 | ||
| PCT/GB1998/002392 WO1999009040A1 (en) | 1997-08-13 | 1998-08-07 | Method of manufacturing phosphine compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69821622D1 DE69821622D1 (de) | 2004-03-18 |
| DE69821622T2 true DE69821622T2 (de) | 2005-01-05 |
Family
ID=26312052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69821622T Expired - Lifetime DE69821622T2 (de) | 1997-08-13 | 1998-08-07 | Verfahren zur herstellung von phosphinverbindungen |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6335471B1 (enExample) |
| EP (1) | EP1003754B1 (enExample) |
| JP (1) | JP4283436B2 (enExample) |
| KR (1) | KR100581624B1 (enExample) |
| CN (1) | CN1140531C (enExample) |
| AT (1) | ATE259370T1 (enExample) |
| AU (1) | AU741245B2 (enExample) |
| CA (1) | CA2297838C (enExample) |
| DE (1) | DE69821622T2 (enExample) |
| ES (1) | ES2212329T3 (enExample) |
| GB (1) | GB9717059D0 (enExample) |
| MY (1) | MY121701A (enExample) |
| TW (1) | TW480265B (enExample) |
| WO (1) | WO1999009040A1 (enExample) |
| ZA (1) | ZA987218B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9805348D0 (en) * | 1998-03-16 | 1998-05-06 | Ici Plc | Compound |
| MY133839A (en) † | 2000-03-14 | 2007-11-30 | Shell Int Research | Process for the carbonylation of pentenenitrile |
| JP2003007823A (ja) * | 2001-06-20 | 2003-01-10 | Mitsubishi Electric Corp | 信号バス配置 |
| DE60329658D1 (de) | 2002-02-04 | 2009-11-26 | Hokko Chem Ind Co | Verfahren zur herstellung eines tertiären phosphins mit daran gebundener sperriger kohlenwasserstoff gruppe |
| DE10217517A1 (de) | 2002-04-19 | 2003-11-06 | Bayer Ag | Verfahren zur Herstellung tertiärer Phosphane |
| TWI301481B (en) * | 2002-08-10 | 2008-10-01 | Lucite Int Uk Ltd | A catalyst system |
| EP1651587A1 (en) * | 2003-07-03 | 2006-05-03 | Lucite International UK Limited | Process for the hydroformylation of ethylenically unsaturated compounds |
| GB0403592D0 (en) | 2004-02-18 | 2004-03-24 | Lucite Int Uk Ltd | A catalyst system |
| GB0411951D0 (en) * | 2004-05-28 | 2004-06-30 | Lucite Int Uk Ltd | Carbonylation of ester |
| KR20060086178A (ko) | 2005-01-26 | 2006-07-31 | 삼성전자주식회사 | 액정 표시 장치 |
| GB0516556D0 (en) * | 2005-08-12 | 2005-09-21 | Lucite Int Uk Ltd | Improved catalyst system |
| ES2700427T3 (es) | 2005-11-17 | 2019-02-15 | Lucite Int Uk Ltd | Carbonilación de compuestos etilénicamente insaturados |
| GB0607494D0 (en) | 2006-04-13 | 2006-05-24 | Lucite Int Uk Ltd | Metal complexes |
| WO2008065448A1 (en) * | 2006-12-02 | 2008-06-05 | Lucite International Uk Limited | Novel carbonylation ligands and their use in the carbonylation of ethylenically unsaturated compounds |
| GB0625518D0 (en) * | 2006-12-21 | 2007-01-31 | Lucite Int Uk Ltd | Carbonylation of conjugated dienes |
| GB0812297D0 (en) * | 2008-07-04 | 2008-08-13 | Lucite Int Uk Ltd | Novel carbonylation ligand sand thier use of in the carbonylation of ethylenically unsaturated compounds |
| GB201000078D0 (en) | 2010-01-05 | 2010-02-17 | Lucite Int Uk Ltd | Process for the carbonylation of ethylenically unsaturated compounds, novel carbonylation ligands and catalyst systems incorporatng such ligands |
| JP6714459B2 (ja) | 2015-07-23 | 2020-06-24 | エボニック オペレーションズ ゲーエムベーハー | アルコキシカルボニル化のためのベンゼン系ジホスフィンリガンド |
| EP3272729B1 (de) | 2016-07-19 | 2019-09-04 | Evonik Degussa GmbH | Verfahren zur herstellung von estern durch carbonylierung von ethern |
| ES2722052T3 (es) | 2016-07-19 | 2019-08-07 | Evonik Degussa Gmbh | Procedimiento para la alcoxicarbonilación de olefinas en un medio con baja concentración de ácidos de Brønsted |
| EP3272730B1 (de) | 2016-07-19 | 2019-01-02 | Evonik Degussa GmbH | Verfahren zur alkoxycarbonylierung von ethern |
| EP3527576B1 (de) | 2018-02-14 | 2020-11-18 | Evonik Operations GmbH | Propyl-verbrückte diphosphinliganden für die alkoxycarbonylierung |
| CN113912646B (zh) * | 2021-11-18 | 2024-05-17 | 浙江新化化工股份有限公司 | 一种双齿膦配体的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4774362A (en) * | 1987-04-24 | 1988-09-27 | Eastmank Kodak Company | Chelating ligands and catalysts and processes employing the same |
| GB9425911D0 (en) * | 1994-12-22 | 1995-02-22 | Ici Plc | Process for the carbonylation of olefins and catalyst system for use therein |
-
1997
- 1997-08-13 GB GBGB9717059.1A patent/GB9717059D0/en active Pending
-
1998
- 1998-08-07 AU AU87376/98A patent/AU741245B2/en not_active Ceased
- 1998-08-07 AT AT98938770T patent/ATE259370T1/de not_active IP Right Cessation
- 1998-08-07 ES ES98938770T patent/ES2212329T3/es not_active Expired - Lifetime
- 1998-08-07 CA CA002297838A patent/CA2297838C/en not_active Expired - Fee Related
- 1998-08-07 EP EP98938770A patent/EP1003754B1/en not_active Expired - Lifetime
- 1998-08-07 WO PCT/GB1998/002392 patent/WO1999009040A1/en not_active Ceased
- 1998-08-07 KR KR1020007001443A patent/KR100581624B1/ko not_active Expired - Fee Related
- 1998-08-07 DE DE69821622T patent/DE69821622T2/de not_active Expired - Lifetime
- 1998-08-07 US US09/485,470 patent/US6335471B1/en not_active Expired - Lifetime
- 1998-08-07 CN CNB988080192A patent/CN1140531C/zh not_active Expired - Fee Related
- 1998-08-07 JP JP2000509719A patent/JP4283436B2/ja not_active Expired - Fee Related
- 1998-08-11 MY MYPI98003642A patent/MY121701A/en unknown
- 1998-08-12 ZA ZA987218A patent/ZA987218B/xx unknown
- 1998-08-13 TW TW087113302A patent/TW480265B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001515085A (ja) | 2001-09-18 |
| CA2297838C (en) | 2008-06-10 |
| EP1003754A1 (en) | 2000-05-31 |
| CN1140531C (zh) | 2004-03-03 |
| MY121701A (en) | 2006-02-28 |
| ZA987218B (en) | 1999-02-15 |
| US6335471B1 (en) | 2002-01-01 |
| EP1003754B1 (en) | 2004-02-11 |
| AU8737698A (en) | 1999-03-08 |
| AU741245B2 (en) | 2001-11-29 |
| DE69821622D1 (de) | 2004-03-18 |
| ES2212329T3 (es) | 2004-07-16 |
| JP4283436B2 (ja) | 2009-06-24 |
| KR100581624B1 (ko) | 2006-05-23 |
| CN1266436A (zh) | 2000-09-13 |
| KR20010022841A (ko) | 2001-03-26 |
| WO1999009040A1 (en) | 1999-02-25 |
| CA2297838A1 (en) | 1999-02-25 |
| ATE259370T1 (de) | 2004-02-15 |
| GB9717059D0 (en) | 1997-10-15 |
| TW480265B (en) | 2002-03-21 |
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